Romantic Date Night Ideas in Chicago
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The Most Romantic Date Ideas For Valentine’s Day in Chicago in 2023

ByUmesh Kumar

What to do if you’re looking for romantic date ideas in Chicago. You’ll find everything from interesting date ideas to the most romantic date ideas for Valentine’s Day in Chicago.

Chicago has everything you’re searching for, whether you’re native seeking new date ideas or a visitor having a romantic getaway.

The ideal location to win over that particular someone in your life is a city with a vibrant culture, beautiful historic buildings, and exciting adventures. There are interesting sites to see in Chicago in any season. You won’t run out of things to do even if the weather wrecks your plans.

Your date night will be a romantic and enthralling experience thanks to the abundance of attractions to visit, the various cuisine to try, the comfortable surroundings, and the exciting activities.

In Chicagoland, treat your date to a fun-filled day of exercise or a classic dinner and drink date. These 69 Chicago date ideas can help you make the most of your time together.

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69 Romantic Date Night Ideas in Chicago

69 Romantic Date Night Ideas in Chicago
69 Romantic Date Night Ideas in Chicago

Spread Out A Picnic In The Park

A fine assortment of wine and gourmet snacks wrapped inside a basket may dress up the custom of bringing meals to attractive locations. In one of Chicago’s numerous parks, sprawl out with your significant other and enjoy your favorite spread while you watch the sunset behind the city’s famous skyline.

For instance, the historic Humboldt Park has lagoons, boathouses, an inland beach, and more. What was once a prairie community that developed into a hub for leisure activities is now a charming location for spreading out your picnic blanket. While chatting with your special someone, order caviar and other treats from the neighboring Heritage Restaurant and Caviar Bar.

Burnham Park also has Promontory Point, which provides a breathtaking perspective of the skyline. Beginning with this artificial peninsula, architect Daniel H. Burnham envisioned a vast park including islands, a boat harbor, beaches, play spaces, and other features. Even though Burnham’s vision for the park was never fully realized, the location is nevertheless a lovely spot to take in Chicago and the splendor of Lake Michigan.

Either of these places is perfect for a romantic day out, but to make the picnic-in-the-park experience even more special, surprise your significant other with a stunning bouquet of flowers.

Dinner And A Movie — With A Twist

The standard date option of dinner and a movie is spiced up by Chicago’s distinctive alternatives. Bring a bunch of garden roses to your date’s door to begin the evening.

Try Music Box Theatre if you and your date want to explore independent films or if box office smashes are not your thing. The theatre was viewed as a scaled-down imitation of Chicago’s thriving movie palaces when it first debuted in 1929.

These days, this theatre draws sizable people because of its unusual film selection. It frequently screens international movies, and if you can attend it on a special night, you can see the world premiere of an independent movie. To sample the greatest steak in Argentina, stop by Tango Sur first.

At AMC Dine-in Block 37, it is possible to see a movie while eating. From your seat, you and your significant other may choose what to eat. Your options for food, including sushi, flatbread, and more, are served straight to you so you can watch the big screen in more comfort. You are no longer confined to buttery popcorn.

Take A Stroll On The Pier

The iconic Chicago landmark Navy Pier is a buzzing hub of entertainment and gastronomic variety. The pier also provides culinary excursions, allowing you and your date to explore a variety of eateries without being limited to just one. Or, if you’re craving pizza, treat yourself to Giordano’s, a favorite in Chicago for its deep dish.

With your date, you may have fun at the pier with games and rides, and the extensive list of attractions offers an endless itinerary. Ride the coasters or use the remote control boats to satisfy your competitive side.

Draw your special someone close on the renowned Centennial Wheel to cap off your evening at the pier. The sparkling city lights from the top of the Ferris wheel provide the ideal ambiance.

Take In The Music At A Jazz Lounge

Jazz’s impromptu and mellow melodies offer a seductive environment for dates. The jazz clubs in Chicago transport you back to the early 1900s when rhythmic music first emerged. To make your jazzy date night even more special, you may both wear the part.

Live music may be heard at Green Mill Cocktail Lounge, which also has décor similar to Clark Monroe’s Uptown House in Harlem. Grab a classic drink with your date and enjoy a relaxing night of talk and music.

A live magazine act called “Paper Machete” is also frequently presented at this club. Seating cannot be booked, so keep an eye on the schedule of performances for the most well-known artists and arrive early to get a place.

The River North neighborhood’s Andy’s Jazz Club and Restaurant were originally popular among journalists and other media employees. Jazz was embraced by the society around the middle of the 1970s.

Laugh Along At A Comedy Night

One of the finest ways to start a date night is with laughter, which is also the best medicine. Attend a comedy club to start your date off on a lighthearted and romantic note; Chicago offers several great spots to laugh.

A renowned comedy venue and a training ground for comics, Second City. The Second City has hosted a number of well-known comedians, including Steve Carell and Tina Fey. You may see improvised performances, comedy, and musical numbers. A branch of Second City called Up Comedy Club presents stand-up comedy performances.

Another venue for stand-up comedy is The Comedy Bar, which also has a brewery and a restaurant. As the comedians create a fun backdrop for your night out, enjoy comfort cuisine with your significant other.

Every night, Zanies brings in top-tier performers for their nonstop jokes and belly-laugh-inducing antics. This comedy club has been successful for 40 years, and if you want to learn how to tell jokes well, it also provides comedy lessons.

Take In The Views At The Conservatory

Although the skyline, architecture, and brilliant lights of the city are all stunning, there is also something special about green regions.

In the glass-enclosed Garfield Park Conservatory, there are luxuriant indoor gardens as well as outdoor gardens that close in the winter. You may bring your date to this verdant retreat at any time of year to unwind.

There are eight indoor sections to the enormous floral refuge known as the Garfield Park Conservatory. Examine the fern and palm chambers as well as the water lily pond. The public dining area and event space in Horticulture Hall allow for an even closer examination of the plant life.

Before the date, send your date some lovely flowers or a blossoming plant to provide a hint about your location.

Visit The Zoo

Go to the Lincoln Park Zoo with your date if you both appreciate nature. Since you don’t see giraffes or monkeys every day, the range of unusual creatures encourages lively discourse. Take advantage of the opportunity to enjoy the variety of the animal kingdom with your favorite pet.

This establishment is the fourth-oldest zoo in the United States, having been in operation for more than 150 years. Year-round, the Lincoln Park Zoo is accessible to everyone for free thanks mostly to the proceeds from its gift shops and fundraising efforts.

Browse An Art Gallery Arm-in-arm

Consider taking your significant other on a date when you explore Chicago’s art museums or galleries and talk about the artworks you see. There are many venues to choose from because Chicago is a city with an abundance of art collections.

The unique works of art throughout Chicago’s Museum of Contemporary Art may be appreciated without much historical understanding. This museum’s architecture also showcases ground-breaking works of art by Josef Paul Kleihues. You and your date may admire the optical beauty created by his north staircase as you stroll through it.

The Art Institute of Chicago features a wide range of civilizations, historical periods, and artistic genres for history enthusiasts. You may enjoy several types of art together, including paintings, sculptures, textiles, and photography.

You and your date may enjoy either, depending on your mood and interests, because Chicago’s art galleries showcase upcoming artists and its museums honor former artists. As you tour the galleries with your date, ask them about their preferences to learn more about them and the art world.

Meet For Drinks

Visit the chicest bars and breweries that Chicago has to offer with your sweetheart. Try different wines or visit themed pubs with entertaining settings. Many old bars in Chicago can keep you entertained with amazing music and a speakeasy atmosphere.

The Violet Hour is a bar with a Wicker Park address that models its decor and libations after the years shortly before Prohibition began to restrict alcohol use in the country in 1920.

An often-changing mural is lighted by a single light bulb at the entryway to this upscale location, creating a deliciously dramatic impression. A beautiful ambiance is created inside with candles, blue leather high-backed chairs, crystal chandeliers, and other elements.

Another famous tavern that plays jazz and country music is The California Clipper. This pub combines the music of today with its musical heritage from the 1930s, and it still has a jukebox with current songs. Any date will be attractive in the interior’s crimson tint.

It’s a great idea to try something new on a date, and Chicago’s bars have a tonne of creative cocktails and unique surroundings. Chicago’s many taprooms may satisfy every fancy, whether you want to sample the newest adult beverage creation or are mesmerized by the scenery.

The Aviary is a bar with a focus on inventive alcoholic cocktails that redefine the term “innovation.” Whether your beverage arrives in the form of a vapor-filled teapot or an orb in a glass, this experience will add excitement to your special night.

The Signature Lounge is housed in a contemporary, tall building with a clear, mesmerizing view of the setting sun. Watch the light grow golden while enjoying an Old Fashioned with your date. The view of the metropolis and skyscrapers at nightfall is as picturesque as a date in Chicago can be.

Sculpt A Masterpiece Together

Enroll in a pottery class with your significant someone to experience new and personal ways to connect. Your creative side will come out in this practical exercise.

Beginner and more experienced clay students are both welcome at Penguin Foot Pottery. This Logan Square facility provides several levels of hand development as well as wheel throwing for novices.

Although you and your companion might buy a series of lessons, drop-in sessions are also offered for a short period of time. For shorter, one-time classes, just drop by during their designated drop-in hours; Penguin Foot does not require appointments.

A different place to express yourself creatively is Park West Ceramics. Beginner workshops are used for lessons at this Lincoln Park facility. The student-to-instructor ratio in these courses is low, and at the end of the program, each participant will have created one piece of art.

Just keep in mind that creating pottery is messy, so make sure your date is wearing clothes that can get filthy!

Climb The Willis Tower And Skydeck Ledge

Willis Tower, which was once known as the Sears Tower and rises 110 floors, is a striking structure. Four states—Illinois, Indiana, Wisconsin, and Michigan—can be seen from the summit perspective.

To give you and your date a burst of energy before climbing the tower—even if the elevator is one of the quickest functioning elevators in the world—visit a nearby coffee shop.

Before you set out for the tower, you can get a smooth dark roast from the nearby New Zealand coffee roaster Mojo Coffee. Another café with a bakery that takes pleasure in using organic food is called Floriole.

Visitors may go outside and enjoy a recognizable view of Chicago from the Skydeck, also known as the observation deck, which is located close to the top of the structure. A glass viewing area on the Skydeck’s ledge gives you the impression that you are hanging in midair.

The Chicago skyline may be seen in all its glory from there, directly beneath your feet! It’s an experience that both you and your date won’t soon forget.

Go On A Hike

With a few neighboring state parks to explore, you and your companion are sure to discover the ideal hiking site. Nature provides one of the most lovely and romantic dates in Chicago. Visit the Waterfall Glen Forest Preserve in DuPage County to spend some time in nature.

This serene outdoor retreat offers magnificent vistas, serene waterfalls, several paths, and picnic areas. This breathtaking spot is ideal for a great date if you enjoy the outdoors and don’t mind traveling a half-hour outside of the city.

Ice Skate Hand-in-hand

During the colder months, grab your ice skates and go to Maggie Daley Park in the heart of Chicago. This mercurial twisting rink provides fantastic views of the city skyline and maximum fun.

What could be more romantic than skating hand-in-hand under the stunning Chicago night sky if you’re looking for things to do in Chicago at night? Make sure you reserve in advance online!

Maggie Daley Park offers entertaining activities all year round, so if you’re planning a spring or summer date and the rink is closed for the season, have no fear! You’re likely to find something you like, whether it’s mini-golf, tennis, the climbing wall, or a leisurely garden stroll.

Treat Your Sweet Tooth

With some scrumptious goodies, what better way to spend a pleasant evening? For your sweetest cravings, JoJo’s Shake Bar in River North has an abundance of loaded milkshakes, vintage cocktails, and other delectable sweets.

The typical ice cream date is given a distinctive twist by this wacky milkshake establishment. If you don’t want to stick with desserts, there are plenty of traditional bar selections on the menu, like onion rings and Buffalo wings.

Kayak On The River

Your list of romantic dates in Chicago should include a serene cruise down the Chicago River. While kayaking in the great outdoors is a timeless date idea, paddling amongst skyscrapers gives the activity a distinctively urban flavor.

You may reserve a kayak excursion with Wateriders that offers stunning city views. When you book your trip on the river, you’ll get to see Chicago from a whole different angle and create wonderful plans for a special date.

Hit The Lanes

Bowling is a pleasant and traditional date night activity, but Chicago gives it an intriguing twist. The best date night in Chicago is at Kings Dining & Entertainment in Lincoln Park, where you can take in a disco-like setting from the ’70s, tasty appetizers, and a friendly bowling battle.

Another fantastic place for a date is Waveland Bowl, which offers 40 lanes of bowling, terrific rates, and delectable Chicago-style cuisine. With Waveland Bowl’s group rental options, you may reserve a lane to add extra couples or make it a double date.

Accent Your Date With Flowers

Bring your date a floral arrangement from Ode à la Rose to complement each of these outings and up the romance. You may choose the ideal bouquet for your significant other, whether it’s a trademark bouquet or an anniversary arrangement for a special occasion.

Delivery of a signature gift box gives your floral selection a classy touch. Set the tone for your evening by giving your date flowers when you pick them up or by sending a bouquet of roses to their office.

Add some rose petals for a romantic touch to your privacy settings as an additional method to complete your date night ideas. You may scatter these rose petals, which are available in pink, crimson, or white, on tables, the floor, and other surfaces to provide a charming appearance.

Stroll Through Millennium Park

Stroll Through Millennium Park - Romantic Date Night Ideas in Chicago
Stroll Through Millennium Park – Romantic Date Night Ideas in Chicago

Visit the renowned Millennium Park for one of the top free date ideas in Chicago. Explore the grounds, take in the fountains, and discover some amazing public art.

This area should be investigated if you’re searching for a place to stay in Chicago while you’re there.

Undoubtedly, you must take a picture in front of the famous Cloudgate sculpture, popularly referred to as the Bean. Share the picture on social media to brag about your fantastic date in Chicago!

Numerous free events and concerts are also held at Millennium Park throughout the year. Every interest may be satisfied. This is a fantastic way to cut costs on your date without sacrificing pleasure!

Put this on your romantic Chicago agenda if you have two days there!

Dine at Alinea

Consider making a reservation at Alinea if you’re seeking the greatest date night restaurants in Chicago. At this premium restaurant, you’ll develop a fresh perspective on what food can be.

This award-winning restaurant will wow you with its inventive and contemporary cuisine, which is distinct to the palate and the sight.

Three Michelin Stars have been awarded to Chef Grant Achatz’s cuisine as a result of his use of molecular gastronomy. There will be several dishes throughout your lunch that features both great dining and exploration.

To ensure a table, be prepared to make a reservation far in advance. Even though this is not an inexpensive dating night, serious foodies will find it worthwhile.

One of the greatest spots to experience Chicago at night is undoubtedly here!

Take a Helicopter Tour

Consider taking a helicopter trip if you’re seeking the ideal adventurous date idea. This is a wonderful way to have an unforgettable time in Chicago.

You will be treated to breathtaking views of the recognizable skyline with its tall skyscrapers and ballparks as you soar overhead. The size of the lake will also be visible to you.

To make the experience even more romantic, sign up for a sunset tour and take in the colorful sky. As night falls, the city’s lights will glisten.

One of the most romantic things to do for an anniversary or other special occasion in Chicago is this. There isn’t a more ideal date concept than this.

If you’re in Chicago during the fall, this is much more striking.

Bike Along the Lake

A bike ride by the river in Chicago is another inexpensive date idea. There are several bike-share stations located all around the city where you may borrow a bike for a reasonable rate.

Grab your bikes and ride them to the Lakefront Trail. Awesome vistas of Lake Michigan and the city can be found on each side of this 18-mile paved cycling trail.

The path has a lot of attractions. You may stop at some of the parks, museums, and beaches along the way if you become weary of bicycling.

After all that activity, foodies in Chicago may look forward to breakfast if they get hungry.

Watch Fireworks at Navy Pier

Another popular place to go on dates in Chicago is the Navy Pier. And one of the Midwest’s trendiest destinations.

The 3,300-foot-long pier has plenty of entertaining things to fill a fantastic date night.

Visit the Centennial Wheel, look for some interesting statuary, or get something to drink at the Navy Pier Beer Garden. There are several restaurants and retail establishments.

There are fireworks displays every Wednesday and Saturday night from May through August. Kiss each other while the sky above you is illuminated. How love-inducing is that?

Watch the moon reflect on the lake to cap off your romantic evening in Chicago.

Explore the Lincoln Park Conservatory

The Lincoln Park Conservatory is the perfect date-night destination if you enjoy nature and want to save money. This free attraction is located in a stunning late 1800s iron and glass structure.

Take your partner by the hand and take a stroll among the beautiful, tropical vegetation. Since the inside is always open and lush, you may feel some warmth even during the bitter Chicago winters.

The grounds extend outside with fountains and statues. The lovely Alfred Caldwell Lily Pool is another feature you’ll adore. It’s a lovely spot to explore and snap pictures.

Grab a Drink at the Darling

Go to the Darling for a more carefree and laid-back date. This stunning lounge can be found in Fulton Market and is furnished with dark hardwood, leather seats, chandeliers, and floor-to-ceiling bookcases.

As you drink cocktails in the cozy setting, you’ll feel as though you’ve entered an ancient English house. Live music is frequently present, along with various entertainers including dancers, magicians, and others.

The enormous Scrabble board that is mounted on the wall is a neat addition. You may enjoy the pleasant ambiance while playing a game.

Chicago has so many amazing breweries that you should check out!

Take a Pottery Class

Consider taking up pottery if you want to pick up a new pastime with your date. This is a fantastic opportunity to be inventive while still enjoying a fun date night.

If you don’t mind getting a bit dirty, consider signing up for a class at Penguin Foot Pottery in Chicago. Beginners will enjoy learning the fundamentals using the materials offered.

If you are captivated after one lesson, you may practice your craft in a course that lasts a few weeks.

Then you may adorn your house with your new pottery. The memories of the date will stay longer if you have something physical to show for your time together.

Don’t forget to check out Chicago’s many wonderful eateries!

Play Some Arcade Games

Bring your date to Headquarters Beercade if you want some entertaining competition. This is one of the finest things to do in Chicago for couples that are young at heart because it is both a bar and an arcade.

You will have a blast here with the many classic pinball and arcade games available. The menu has pizza, burgers, tacos, and specialty fries in addition to a selection of beers on tap.

Come to one of the trivia evenings and put your pop culture knowledge to the test if you want even more games.

Admire Views At A Rooftop Bar

There are several rooftop pubs dotted across the city that are perfect for a fun night out in Chicago. Every weekend, check out a different location for fresh, breathtaking skyline views from outdoor balconies.

Each bar has unique qualities. They feature a combination of adorable and modern designs, with moods that range from laid-back to party-like. You can locate a great bar to bring your date no matter what you are looking for.

ROOF on the Wit, I|O Urban Roofscape, and Cabra is a some of Chicago’s greatest rooftop bars. One of the nicest things to do for couples in Chicago is to sip beverages outside.

These are some of the top locations in Chicago to see holiday decorations.

Enjoy Happy Hour at the Chicago History Museum

Have you ever wanted to combine drinking with history? With several History Happy Hour events each year, the Chicago History Museum has you covered.

You get two drinks with your event ticket. Additional beverages and snacks are available at the bar.

You and your date will have a more intimate experience at this after-hours event since you will get access to the museum when it is less busy. You’ll get a close-up view of the displays.

Try Playing Whirlyball For An Active Date Night In Chicago!

If Whirlyball is new to you, you’re in for a treat! For a first date or even a double date with friends, this is a fantastic idea.

A novel game that combines basketball, lacrosse, and bumper cars is called a whirly ball. You will navigate the court in a bumper car moving at 4 mph while attempting to toss a Wiffle ball at a hanging target.

This is the date for you if you enjoy having a good time and being active! The only pressure will be to display your athletic prowess because it’s so casual.

Additionally accessible here are bowling and laser tag. Get a bite to eat in the restaurant or bar once you’ve finished playing. After this, date evenings in Chicago will never be the same!

Go Ice Skating at Maggie Daley Park

Ice skating is the ideal option for a winter date night idea! You may test your skating prowess at the Maggie Daley Park Skating Ribbon.

You may travel around and around on this ice ribbon while enjoying views of the buildings. It is the ideal justification to hold hands if you feel wobbly on your skates.

The McCormick Tribune Ice Rink at Millennium Park close to the Bean is another skating rink in the area. This rink is more rectangular and conventional.

Each rink is accessible from November through March. One of the finest holiday activities in Chicago is ice skating.

Sample Drinks at Koval Distiller For A Cool Date Night In Chicago

A visit to the Koval Distillery is one of the nicest dates you can have in Chicago. This location, which has a stunning tasting room, exudes romanticism.

With plush couches and wood accents, the tasting area is decorated in the style of the 1970s. Order a flight of whisky, gin, and cocktails and unwind there. When it’s pleasant outside, a terrace is also available.

Additionally, you may take a tour of the distillery to see how the whisky is produced. Check out Koval’s cocktail lessons if you’re looking for further drink-related suggestions for a romantic night in Chicago.

Head To The Theater For Date Night In Chicago

If you want to watch a musical or a movie, Chicago has a tonne of theatres, both large and small. There are nearly 250 theatres available in what is referred to be the “theatre capital of America.”

Of course, the Chicago Theatre is the most well-known theatre in the area. This elegant and historic theatre, which is owned by the Madison Square Garden Company, hosts Broadway musicals, concerts, and other events.

However, there are several smaller theatres to attend if you’re searching for less expensive tickets. Visit the Black Ensemble Theater for presentations about Black life, history, and empowerment that are worthy of a dance.

Court Theater, which innovates on stage by adapting classics, earned the Regional Theatre Tony Award in 2022. You will see incredible performances regardless of the theatre you select.

Purchase a ticket for the Music Box Theatre if a movie showing appeals to you more than a live performance does. In addition to cult classics, independent and international films are also shown here during midnight showings.

The popcorn at this theatre is famous for having actual butter on it. Yum! With this tried-and-true date night in Chicago plan, you can’t go wrong.

Packing List When Having A Date Night In Illinois

Here are some suggestions on how to pack efficiently for your Chicago date night if you’re looking.

One of the most crucial items you should pack when visiting Chicago, Illinois, is a disguised travel bag. You should always secure your personal information. There are a lot of identity thieves.

This lightweight, multicolored unisex hidden travel pouch blocks RFID technology. It is extremely organized to provide you with comfort. To carry your ID securely, tuck it beneath your clothing close to your body.

These RFID sleeves are the ideal answer if, like me, you already own a bag that does not have RFID protection.

You should certainly think about an external charging battery if you want to use your phone to take plenty of images. I always travel with the same high-speed Anker phone charging battery.

I enjoy that it retains its charging capacity across numerous uses, allowing me to travel worry-free. If I forget to recharge it at night, it will still work the next day.

For my birthday, my daughter gave me this FugeTek selfie stick and tripod combo. I adore it so much! It is really simple to operate and composed of lightweight aluminum.

It is simple to use and offers Bluetooth connectivity for selfies that are perfect for Instagram.

Chicago events you go to.

I’ve never been a big fan of packing cubes for trips. Until I gave them a try, that is. I’m addicted now. When I pack for a vacation, I use exactly these cubes to keep organized.

Your own refillable water bottle should be brought along.

My Bobble filtration bottle is something I always bring on vacations from home. The 18.5-ounce weight is ideal for your excursions and fits comfortably in a backpack’s pocket.

Perhaps you are driving a long distance and have limited room in your car or bag for packing. Then you’d benefit from using this set of foldable, collapsible silicone water bottles. Would not occupy a lot of room.

You should have a daypack or backpack with you to carry additional clothing, a phone, food, and water. Regardless of the day or night.

This collapsible, water-resistant backpack is fantastic. And there are several hues available.

Finding romantic activities in Chicago for a memorable date night is so simple! There are several bars and eateries where you may find a quiet spot to talk.

Due to the abundance of parks and lakefront vistas, there are many free or low-cost date night activities in Chicago, such as hiking, bicycling, and picnicking.

Plan a vacation to Chicago if you want to do something special for your anniversary. For couples seeking the trendiest things to do in Illinois, it is one of the top cities in the Midwest.

The Most Interesting Date Ideas in Chicago

Romantic Date Night Ideas in Chicago
The Most Interesting Date Ideas in Chicago

It’s officially summer in Chicago, and we hope your romantic life is becoming hotter by the minute! While there are many romantic restaurants in Chicago where you may wine and dine you’re SO, sometimes it’s great to break the dating mold with something a bit more unique.

This is true whether you’re navigating a flirtatious new affair or wanting to reignite flames in a long-term partnership. Looking for some inspiring love? Please allow us to assist you.

Here are some of our favorite suggestions for inventive dates in Chicago for romantic relationships, platonic connections, and everything in between, ranging from calm afternoons at the city’s top art galleries to exhilarating games of axe throwing.

Get dinner at Time Out Market Chicago

Any stage of a relationship makes it challenging to decide where to dine, so why not streamline date night? Time Out Market Chicago can accommodate your needs if you want sushi and your companion prefers pizza.

There is a cuisine for almost every taste, whether you’re in the mood for tacos, ramen, fried chicken, or ice cream, as some of the top chefs in the city operate 18 restaurants. Place a food order, have a drink, and let the conversation flow.

Glide around in a swan-shaped boat

Swans are known to have lifelong relationships. Even if you aren’t looking to tie the knot, the graceful birds still make for attractive romantic symbols, especially when they are in the shape of boats.

Swan boat tours on the Humboldt Park Lagoon are available from May through September for $30 per hour. After some time spent paddling, take a leisurely stroll to see the old boathouse’s Prairie-style architecture.

Pet some pups at the Montrose Dog Beach

When you can see an endless number of dogs running around the beach for nothing, why attend the Westminster Dog Show? Dogs and their owners have their own section of Montrose Beach that is walled off, but we bet you and your date could pet a few nice dogs with the owners’ permission (and if all else fails, there’s no wrong in dog watching for a bit).

Cuddle up at The Point

Promontory Point, often known as The Point, is a man-made peninsula in Burnham Park’s Hyde Park section that’s ideal for a prolonged date.

Arrive in the afternoon, paddle around in the lake for a bit (the calmer south end is much better for swimming, FYI), then go over to the north end and take a seat on the rocky barrier to take in one of the greatest views of Chicago’s skyline as the sun sets.

Stroll along the 16th Street Murals

A dynamic and ever-evolving outdoor gallery of murals by well-known and up-and-coming painters may be seen on the walls of an old railroad embankment in Pilsen that stretches from the Chicago River to Western Avenue.

As you cross 16th street, make an impression on your date by pointing out some of your favorite pieces of art, whether you like vibrant works by renowned local artists like JC Rivera and Hebru Brantley or the contributions from global street artists like ROA and Sheryo.

Spot lions, tigers, and bears at Lincoln Park Zoo

There aren’t many places better for a first date than Lincoln Park Zoo since A) it’s free to visit and B) it’s packed to the gills with topics to discuss when conversation flags.

While exchanging getting-to-know-you pleasantries, point out pygmy hippos and polar bears; if things go well, you can always continue the night at a neighboring pub.

Get lost inside the Garfield Park Conservatory

In search of an inexpensive date concept? Although reservations are required and gifts are appreciated, the Garfield Park Conservatory is free and open every day of the year.

You and your date may take a stroll around the conservatory’s 10 acres of outdoor gardens or explore the internal chambers that are stuffed to the gills with various plant species, such as palm palms, enormous succulents, and prehistoric ferns.

Tour Chicago Avenue’s best art galleries

Some of the city’s greatest and most inventive galleries are located along the section of Chicago Avenue between Ashland Avenue and Wood Street, making it possible to do a very reasonable (and totally free) walking art tour.

Head west after starting at the Matthew Rachman Gallery, which features modern art and stylish mid-century furniture. Along the road, you’ll see notable galleries such as DOCUMENT, Rhona Hoffman Gallery, Volume, and more. Just be aware that many galleries now demand reservations before visitors.

See an indie movie at the Music Box

You and your date could go to the multiplex to see the newest blockbuster, but we believe it would be a touch more romantic to snuggle up in the Music Box’s historic 750-seat theatre, where you can see everything from international flicks to independent documentaries on the big screen.

Ask for additional (genuine) butter on your bag of popcorn if you truly want to demonstrate how much you care.

Have a beer by the river

Do you want a drink with a view? There’s no need to spend money on costly drinks at a rooftop bar (unless you really want to).

Visit Metropolitan Brewing instead for affordably priced German-style beers and breathtaking views of the Chicago River from its Avondale taproom.

Watch the Neo-Futurists perform 30 plays in 60 minutes

Instead of taking a chance, establish a happy medium between the two at The Neo-Futurist Theater in Andersonville, where the Neo-Futurists have been reinventing the bounds of live theatre for more than 30 years.

Plays may be overly lengthy and stuffy, while comedy acts can fall flat. The Infinite Wrench, the company’s flagship production, crams 30 short plays into a single 60-minute performance, frequently to moving and ludicrous effect.

Explore your shared musical tastes at 606 Records

Although you don’t have to share the same tastes in music with the person you’re dating, it helps to like some of the same bands or genres.

At 606 Records, where you can discover releases from daring local and international labels among vintage rock and soul LPs, stock up on some songs you can listen to together. A Mr. Bongo reissue or a Numero Group collection can be the ideal music for your upcoming supper.

Hit a bullseye while axe throwing

Although axe throwing has become increasingly popular in recent years, don’t rule it out as an interesting (though rather intense) date idea.

Whether you want to test who has the stronger arm, bring some snacks and non-alcoholic drinks along. Also, make sure to check the company’s website to see if one of the two Chicago sites is open for walk-ins.

Share some smoked shrimp at Calumet Fisheries

What could be more romantic than making the trip to Illinois’ border to sample some of this renowned shack’s smoked fish? Catfish, shrimp, and salmon have been available at Calumet Fisheries for more than 70 years.

It’s a takeout-only establishment, so you’ll need to find a place to split your food, whether it’s in your car or on the 95th Street bridge that was prominently featured in The Blues Brothers.

Split a flight of small-batch spirits at Koval Distillery

When ordering drinks starts to seem stale, think about mixing up your date night drinking a bit. You may purchase flights of the distillery’s small-batch spirits to enhance your tasting experience in the hip, ’70s-inspired surroundings of Koval Distillery’s new Ravenswood tasting area.

Select a whisky, gin, or one of the intriguingly flavored liqueurs from the bar’s assortment while relaxing on one of the comfortable leather couches (including rosehip, coffee, chrysanthemum, and honey).

Take a long walk on the North Shore Channel Trail

You might idle away the time with your date while sitting around, or you could go for a walk and enjoy the surroundings. There are several excellent stops along the North Shore Channel Trail as it travels along the Chicago River in the direction of Evanston.

You may stop at Lincolnwood Town Center, enjoy the artwork at Skokie Northshore Sculpture Park, or wind up at the Bahá’ House of Worship in Wilmette, depending on how far you’re willing to travel (you’ll probably get there faster on a bike).

Go bargain hunting at Monarch Thrift Shop

This well-liked secondhand shop in Avondale has everything from new clothes to used books, and the revenues help individuals who are homeless and recovering from addiction.

On the Monarch Thrift Shop website, schedule a day for two people, and then show up prepared to get some savings on a variety of gently used products.

Try to hit a strike at Avondale Bowl

Although walk-ins are permitted, you’re best off making an appointment for you and your date to play a few games at this retro-style bowling alley in Avondale because it gets quite busy on the weekends and in the evenings.

There isn’t a digital scorecard in sight here, so you’ll need to do some simple math when you bowl, but the retro atmosphere (and the fully stocked bar in the rear) make it worthwhile.

Find new reads at 57th Street Books

If you have already answered the opening questions (Where are you from? How do you behave? What’s your family like?,” they converse in quiet at Hyde Park’s 57th Street Books.

Browse several books together and secretly determine what you both want to buy at this large yet friendly store, which is praised for its outstanding collection of local writers.

Take advantage of a free museum day

Did you know that visiting the Shedd Aquarium and the Art Institute of Chicago are both free attractions where you can view works of art and tropical fish?

Illinois residents may take advantage of free museum days at some of the city’s major institutions with a little advanced effort and research. Browse future free days or go anytime you like to a museum or zoo that is always free.

Book a tour at The Plant

Trying to win over a green date? Every Sunday, the staff at The Plant, a former meatpacking plant in Back of the Yards that is now home to a group of food companies focusing on sustainability, conduct tours of the building’s facilities to give visitors a behind-the-scenes look at its waste-reduction strategy. Online reservations are required; following, stay for a free tour of the Whiner Beer Company.

Romantic Date Ideas For Valentine’s Day in Chicago

Romantic Date Night Ideas in Chicago
Romantic Date Ideas For Valentine’s Day in Chicago

Valentine’s Day is quickly approaching, and luckily the Windy City offers everything you’ll need to light up the night with romantic riverfront vistas, Michelin-starred restaurants, and spectacular city lights.

Our collection of romantic date ideas includes something for everyone, whether you’re searching for the ideal romantic restaurant, want to spice things up with comedy or a concert, or want something a bit more lowkey.

Is Valentine’s Day this year not your thing? Visit our Bad Blood Break-Up Bar where you may partake in drinking, singing, and dancing to timeless Taylor tunes. Valentine’s Day is a great opportunity to get the team together and treat yourselves to a memorable supper.

Alternatively, go to a dinner party for Galentine’s Day with adorable decorations and fun cocktails. Another option is to gather your friends for a brunch location in Chicago that serves mimosas and bloody marys.

Play Love Pong at SPIN Chicago

SPIN is the original ping pong social club because it combines an uncommon fusion of design, sport, and entertainment.

Go out with your significant other for a night of friendly rivalry that includes DJs, specialty drinks, unexpected acts, and more! Tickets include access to ping pong tables, paddles, limitless balls, DJs, dancing, and more for a 2-hour period.

Where: 344 N. State St., Chicago, IL

Go for a Wine Tasting at Uvae Kitchen & Wine Bar

Uvae Kitchen & Wine Bar in Andersonville is a great place to unwind with a glass of wine. On Saturday, February 11, at 3 p.m., Uvae will host a Valentine’s Day wine tasting showcasing “Sweetheart Wines” at the nearby Fromagerie & Tasting Room. With four 4-ounce wine pours, as well as tiny nibbles like Duck Pâté and a cheese platter, guests may learn about the origins of the celebration.

Uvae will provide a 5-course Valentine’s Day Wine Pairing Dinner that includes Oysters three ways, Lobster Bisque, King Salmon, and a Petite Filet for a more lavish Valentine’s Day experience. A white chocolate soufflé with white chocolate, strawberry crème anglaise, Bischoff, and the meringue will be served for dessert.

Where: 5553 N. Clark St. Chicago, IL

Get Creative at a Couples Spray Paint Workshop

Bring out the street artist inside! You and your significant other will be given the chance to make your very own unique item during this interactive session that is intended for couples. Additionally, you’ll learn the tricks of the trade for using stencils and spray paint.

Not the most artistically inclined individual? Be at ease; Studio W.I.P. artists and staff will be in charge of this session and are eager to assist. Couples who paint together, stay together, always!

Where: The Graff: 3527 W. Grand Ave, Chicago, IL

Experience a Fancy Tasting Menu

A husband and wife team of culinary masters developed the exclusive eatery Esmé, which is situated in Lincoln Park. The Valentine’s Day tasting menu at this exceptional restaurant will highlight opulent dishes and ingredients like white truffles, burned onion consommé, white sweet potato ice cream, osetra caviar return, and more.

Diners may choose from a four-course meal at Bar Esmé (located in the same area) for $150 per person. Duck Ravioli, Monk Fish a la Normandie, Wagyu Au Poivre, and more dishes are available on the menu.

P.S. Esmé, which means “beloved” in French, puts this date night venue off the charts in the romance department. As if the sumptuous food and husband and wife combo aspect weren’t enough, they are married.

Where: 2200 N. Clark St, Chicago, IL

Make and Sip Valentines Cocktails

Check out a unique drink experience with a Valentine’s Day theme. For Valentine’s Day, Gold Coast Social will be adorned, and you and your partner will get to mix two unique celebratory drinks. After you’ve finished blending, savor your beverages with a flatbread with a Valentine’s Day theme.

Where: Gold Coast Social: 7 W Division St, Chicago, IL

Share a Heart Shaped Pizza

There is always the perennial favorite heart-shaped pizza if you want to escape the dinner crowds but still want to spend a romantic evening together. Plan a romantic movie night at home with your significant other, light some lights, and get out the champagne or bubbly to go with your celebratory pizza.

Order Valentine’s Dinner for Two from Sfera, which includes cannoli, a Sfincione in the shape of a heart, appetizers, salads, and cocktail bases for making your own cocktails at home. Alternatively, you could surprise your lover with their preferred pizza from Robert’s in the shape of a heart (you can even get an ice cream heart pizza!).

Bartoli’s, Lou Malnati’s, Giordano’s, Eataly, Homeslice, and Dimo’s are some further eateries that provide heart-shaped pizzas (both in-person and for delivery).

Where: Various locations.

Make Your Own Candles

Create the perfect ambiance by manufacturing your own candles. In an instructor-led session, you may pick from a variety of containers, smells, and additives before measuring, mixing, and pouring your very own candle.

As this activity is BYOB, feel free to have a glass of wine while you wait for your candle to burn down, then take it home and settle in for a romantic evening. Bonus: every time you light it up, you’ll be reminded of your date.

Where: 4999 Old Orchard Center, Unit K11, Skokie, IL 60077

Take a Cooking & Cocktails Class Together

If you want something a bit more engaging than just supper, try attending a cooking class together, where you may learn a new skill and enjoy excellent food. Visit the Fairmont Lodge’s cooking and cocktail classes with your special someone.

Learn how to prepare well-known meals and drinks from Fairmont Chicago’s staff of brilliant chefs and neighborhood mixologists from 6:00 pm to 8:00 pm. Each session will focus on making favorites, such as fresh pappardelle pasta, an innovative drink (with a recipe given so you can make it at home), and a cheese and charcuterie platter.

Where: 200 N Columbus Dr, Chicago, IL

Explore a Museum or Gallery Together

It’s very endearing to explore art in a museum with a friend while also learning something new. The Art Institute is a classic that features top-notch artwork in addition to some romantic locations like the Tiffany window. Explore the many art galleries in River North or head to the Adler Planetarium to discover if you and your date are meant to be.

Where: Various locations.

Sip Champagne at 3 Arts Club Cafe

Don’t allow the fact that this upscale restaurant is located within a Restoration Hardware store to deceive you into believing it lacks romanticism. The gorgeous atmosphere, which is housed in the atrium and surrounded by glass and glowing lights, is the ideal dark setting for a romantic date night. You may have a memorable evening by selecting a bottle from their extensive wine range.

Where: 1300 N Dearborn St., Chicago, IL

Laugh the Night Away at a Stand-Up Comedy Show

Who said love had to be dull? Attend a fun comedy performance with some of today’s top celebrities to laugh off any date night anxieties. A Valentine’s special will be presented by Laugh Factory on February 14; the legendary stage will be decorated to celebrate the occasion. Every taste and humor style will be catered to by these regional comics, many of whom have performed in legendary venues!

Where: Laugh Factory: 3175 N Broadway, Chicago, IL 60657

Share Fondue by the Fire at Geja’s Cafe

There are fancy dinners for two and then there’s Geja’s. The Valentine’s Day special at one of Chicago’s most romantic restaurants includes an appetizer of Swiss Gruyere cheese fondue with a variety of bread, fruits, and vegetables for dipping, as well as an entrée of beef tenderloin, Australian lobster tail, and Gulf shrimp. Geja’s Belgian Chocolate Fondue, flamed tableside and provided with marshmallows for toasting, completes the meal.

Where: 340 W Armitage Ave., Chicago IL 60614

See a Live Show at a Hidden Speakeasy

Slipping into a secret speakeasy is one of the sexiest feelings there is. The sensuous atmosphere of Pigalle and Montmartre in Paris served as the inspiration for Bordel, a cocktail bar, and cabaret. You and your partner will enter the opulent candlelight lounge with pink velvet sofas and draperies, tasseled chandeliers, and intricate bronze sconces after making your way through the secret entrance and up the leopard print stairs.

Enjoy unique beverages together with top-notch jazz musicians, burlesque performers, flamenco artists, magicians, cabaret dancers, and DJ performances every night of the week.

Where: 1721 W Division St., Chicago, IL

Attend a Beauty and the Beast Cocktail Experience

Is there anything more romantic than a true-to-life storybook romance? Give the gift of tickets for this immersive drink experience that combines an escape room, a theatre performance, and an adventure.

Guests are invited to join a 90-minute voyage into the magical and cursed world of Beauty & The Beast, which is based on the Jeanne-Marie Leprince de Beaumont legend. Put on your best exquisite Victorian-inspired attire and take part in making two specialty drinks, resolving puzzles and obstacles, and more!

Where: Esmerelda’s Lounge: 2539 W Division St., Chicago, Illinois 60622

Take a Pizza Making Class and Sip Wine

At this DIY Pizza and Sip class at Millennium Hall, you can spend a special evening cooking homemade Neopolitan pizzas while consuming your preferred beer or wine. Pick from a variety of toppings, sauces, meats, and cheeses before selecting anything from the open bar and taking in some great one-on-one time and conversation. You have the option of eating the pizza together at the restaurant or taking it home when it’s done.

Where: Millennium Hall: 11 N Michigan Ave, Chicago, IL 60602

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