BEST Date Ideas in Chicago for Date Nights + Day Dates (2023)

Looking for great date ideas in Chicago? I have put together the ultimate list of the best Chicago date ideas in 2023 whether looking for the most romantic things to do in Chicago for couples on a date night or unique and fun first or second date ideas. From free and cheap date ideas for those on a budget to special date ideas for those looking to impress, you will find the perfect spot for every type of date.

Best Date Ideas in Chicago (2023)

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Unique Date Ideas in Chicago

Listen to Music at an Intimate Candlelight Concert

Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some upcoming concerts include:

Candlelight: Romantic Jazz featuring Billie Holiday, Frank Sinatra, & Ella Fitzgerald
Candlelight: Holiday Jazz and Soul Classics feat. Ella Fitzgerald
Candlelight: A Tribute to Adele
Candlelight: A Tribute to Bad Bunny
Candlelight: A Tribute to Rihanna

You can find the full list of current candlelight concerts in Chicago here.

Spray Paint ‘n’ Sip Urban Art Workshop

Grab some spray paint and unleash your inner street artist at a Spray Paint ‘n’ Sip Urban Art Workshop. This interactive spray paint workshop will teach you the ins and outs of working with spray paint and other elements of graffiti and street art as you create your own painted mural.

Where: Studio W.I.P. at The Chicago Kedzie Plaza, 800 North Kedzie Avenue, Unit 208

Cost:  $40 per person for adults. Click here to purchase tickets.

Take a Pottery Class

Discover the art of wheel-throwing potter with this course tailored for beginners. You can learn the basics of clay preparation, centering, and shaping and create your own unique pieces, from mugs to bowls and plates.

Where: 917 w 18th St, Chicago

Cost:  $35 per person.

Dine in the Dark While Blindfolded

Looking for a unique dining experience? Dining in the Dark (Hubbard Inn, 110 W Hubbard) is a gastronomical experience that invites you to explore the full potential of your taste buds in a uniquely entertaining atmosphere. While blindfolded, you’ll enjoy delectable surprise dishes and feast on an entire meal without using your sight, thereby enhancing your other senses. There are three menus to choose from including a vegan option.

Fun Chicago Date Ideas

Disney100: The Exhibition

The Disney100: The Exhibition will only be in Chicago for a few weeks. The Walt Disney Archives opens its vault of historical and special treasures, works of art, artifacts, costumes, and memorabilia with the launch of Disney100: The Exhibition. This exhibition celebrates the magic of Disney, which is capturing the hearts of audiences of all ages around the globe. Wonder at more than 250 artifacts and props, see costumes from some of your favorite Disney classics, and explore enchanting galleries that bring the magic of Disney to life. Featuring the latest members of the Disney family (Pixar, Star Wars, and MARVEL) along with renowned classics like Snow White and the Seven Dwarfs (1937) and recent releases such as Encanto.

Where: Exhibition Hub Art Center Chicago, 2367 W Logan Blvd, Chicago, IL 60647

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

Play Games at a Barcade

Chicago has several arcade bars where you can have drinks while playing arcade games including Logan Arcade (2410 W Fullerton Ave), Emporium Logan Square (2363 N Milwaukee Ave), Emporium Wicker Park (1366 N Milwaukee Ave), Headquarters Beercade (213 W Institute Pl) and Replay Lincoln Park (2833 N Sheffield Ave).

Play Indoor Mini Golf

Play mini golf with drinks at one of the several indoor miniature golf courses in the Chicago area.

Have Fun at Navy Pier

outdoor rides at Navy Pier fun date idea in Chicago

Navy Pier has several fun outdoor activities at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line).

Watch a Drunk Shakespeare Play

Join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry. Set within a speakeasy, five actors attempt to perform a Shakespearean play after one of them downs multiple shots of various alcohols. Every show is different depending on who is drinking and what they’re drinking. Must be 21+ with valid ID.

Where: The Lounge At The Lion, 182 North Wabash Avenue

Cost:  Prices start at $29 per person. Click here to purchase tickets.

See a Magic Show

Take your date to a magic show. Chicago Magic Lounge (5050 North Clark Street) gets rave reviews. Another great magic shows is Trickery Chicago Magic Show (3453 N Halsted Street).

Laugh at a Comedy Show

If you want to make your date laugh, take them to one of Chicago’s many comedy clubs. Second City (230 W North Ave) is known for its many famous alums, including Tina Fey, Bill Murray, Chris Farley, Stephen Colbert and Steve Carell.

Other great comedy clubs include iO Chicago (1501 N Kingsbury St) and Laugh Factory Chicago (3175 N Broadway).

Museum of Illusions

The Museum of Illusions Chicago (25 E Washington St) offers an interactive, immersive and fun experience. Visitors can engage in over 80 astonishing and mind-bending exhibits that will teach you about vision, perception, the human brain and science. You can buy a timed entry ticket here.

Visit the Color Factory

Color Factory (320 W Jackson Blvd) is a new interactive art museum located on the lower level of Willis Tower. Named one of the 22 Best New Experiences in the World in 2022 by Time Out, the Color Factory is a sensory celebration of color, with interactive installations, immersive rooms and carefully curated moments inspired by the city of Chicago including its signature ball pit and confetti room.

Museum of Ice Cream

The Museum of Ice Cream (Tribune Tower, 435 North Michigan Ave) is a cute date idea. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles. You can see full prices and purchase tickets in advance here.

Most Romantic Chicago Date Ideas

These romantic date ideas are perfect for an anniversary date, birthday, Valentine’s Day or other special date.

Take a Helicopter Tour

If you are able to splurge, a helicopter tour is the ultimate date night activity.

Relax in Thermal Baths at AIRE Ancient Baths

Relax and enjoy thermal baths, massages and exclusive rituals with your loved one at AIRE Ancient Baths Chicago. Inspired by the tradition of baths from ancient Roman, Greek and Ottoman civilizations, AIRE Chicago is located in a restored historical building lit by candlelight in River West.

Where: AIRE Ancient Baths Chicago, 800 West Superior St., Chicago, IL 60642

Take a Couples Candle Making Class

Looking for a unique and romantic date night during the weekend? Join this Couples Candle Making Class where you and your date can create a signature scented candle together. Click here to see prices and purchase tickets in advance.

Where: Above Average Candle Studio, 3414 West Foster Avenue

Free or Cheap Date Ideas in Chicago

Visit a Conservatory

There are two conservatories in Chicago that make for a great warm escape on a cold or rainy day.

The Garfield Park Conservatory (300 N. Central Park Ave) is one of the largest and most stunning botanical conservatories in the US. Often referred to as “landscape art under glass,” the Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens.

The Lincoln Park Conservatory (2391 N. Stockton Drive) is a public conservatory full of tropical palms and plants.

READ: Best Indoor Things to Do in Chicago for more indoor Chicago attractions.

Look for Street Art

Another fun active date activity is walking around the city looking for street art.

One of the most famous murals in Chicago is Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour.

Relax on the Riverwalk

The Chicago Riverwalk, located along the south bank of the Chicago River from Lake Michigan to west of Franklin Street, is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars and other places to sit and relax along the way. You can find a map of attractions on the Riverwalk here.

Watch Digital Art at Art on theMart

Art on the Mart in the evening is a good free date night idea
Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown twice every night. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Watch Fireworks

Navy Pier puts on free fireworks shows every Wednesday and Saturday night all summer between Memorial Day weekend and Labor Day weekend.

Navy Pier is introducing free winter fireworks shows for the first time this year from 9:00 pm – 9:10 pm every Saturday in December, 2023 (and midnight on Sunday, December 31, 2023).

You don’t have to visit Navy Pier to enjoy the fireworks, you can see them from the lakefront and various restaurants.

Take an Architecture River Cruise

An architecture river cruise is a must on any Chicago bucket list for locals and visitors alike.

Walk the Lakefront Trail

walking and relaxing on the Lakefront Trail

What is more romantic than a walk on the beach? Couples can walk along the Lakefront Trail, a paved path on a 18-mile-long stretch along Lake Michigan.

You can rent SUP paddle boards at North Avenue Beach here and kayaks at Ohio Street Beach here.

There are numerous beaches along the way if you want to stop for a date on the beach. Don’t forget to pack your beach essentials!

Even if the weather is too cold to enjoy the beach, the Lakefront Trail has some of the best spots to sit down, relax and enjoy Chicago skyline views.

Here is a map of the Lakefront Trail as well as its access points.

Have a Picnic at the Park

Chicago is full of parks and green spaces that are perfect for a romantic picnic including Lincoln Park, Ping Tom Memorial Park and Milton Lee Olive Park – all of which also have amazing city views.

More Great Date Ideas in Chicago

Still looking for date ideas? Here are more good date ideas in Chicago.

Enjoy the Views from 360 Chicago

360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) has an observatory with great panoramic views of Chicago. The highlight is TILT an enclosed moving platform that tilts you out over Michigan Avenue. Click here to buy a skip the line ticket). You can also visit BAR 94 which has a full 360-degree view of Chicago.

If you prefer to enjoy the same views over a meal or a drink, there is a bar on the 96th floor called The Signature Lounge at the 96th which is open late in the evening.

Art Institute of Chicago

The Art Institute of Chicago (111 S Michigan Ave) is a great choice for a daytime date but it has extended hours (until 8 p.m.) on Thursdays. In addition to its large permanent collection of art from around the world, you can see rotating exhibitions.
Click here to buy a skip the line ticket if you want to avoid long lines.

Adler at Night

The Adler Planetarium is open late every Wednesday night (until 10:00 pm). Experience hands-on, minds-on activities, experiences, and shows about the universe and see their award-winning sky shows. Every Wednesday is free Museum Entry for Illinois residents with proof of residency. Tickets must be purchased online in advance.

Tip:  If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Go Indoor Skydiving

Go indoor skydiving at iFLY Chicago – Lincoln Park (800 W Scott St).

Prohibition Era Speakeasy Experience

Experience a unique Prohibition Era speakeasy and cocktail-tasting experience set during the jazz age of Chicago at The Roar (437 North Rush Street). Grab a delicious 1920s drink and enjoy live music, food, and more.

Live Jazz & Dinner for Two

Have dinner for two with craft cocktails while listening to live music at Le Piano (6970 N Glenwood), a cozy, elegant and romantic venue.

Watch Movies on a Rooftop

Want to watch classic movies against the backdrop of the Chicago skyline? You can watch movies outdoors Rooftop Cinema Club, a rooftop located in Fulton Market.

Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St). This is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks.

Have Dinner at an Intimate Restaurant

Some of the most romantic restaurants in Chicago to take your date include:

North Pond (2610 N Cannon Dr) – Michelin star restaurant inside Lincoln Park with beautiful views.

Bavette’s Bar & Boeuf (218 W Kinzie St) -upscale steakhouse in an ornate, dimly lit wood and brick setting.

Ella Elli (1349 W Cornelia Ave) – Italian-Mediterranean sharing plates and classic cocktails in an intimate setting.

Have Drinks on a Rooftop

Have dinner and drinks at one of the city’s many rooftop bars and restaurants while enjoying amazing views. The best rooftops in Chicago include:


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LH ON 22 (85 East Wacker Drive) – Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

Cindy’s (12 S Michigan Ave) – Restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan.

The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

Kennedy Rooftop (1551 W North Ave) on top of the Hyatt Place Wicker Park, has amazing skyline views.

Chicago Date Ideas During the Holiday Season

Here are a few more date ideas during the Christmas holiday season .

Visit an Authentic German-Style Christmas Market

Christkindlmarket is an authentic German-style outdoor market. Visitors can shop for Christmas ornaments and products from around the world and try various German food and drinks such as roasted nuts, fresh pretzels, bratwurst, and hot spiced wine. The market is in 2 locations: downtown in Daley Plaza and Gallagher Way in Wrigleyville.

ZooLights at Lincoln Park Zoo

ZooLights Presented by ComEd and Invesco QQQ at Lincoln Park Zoo is a cheerful, family-friendly holiday event in the heart of the city. Zoolights features hundreds of luminous LED displays and seasonal experiences, all under the glow of millions of lights.

Jack Frost Christmas Pop Up

Jack Frost Christmas Pop Up is an interactive pop-up outdoor experience located on over 2 acres. In addition to several instagram worthy photo opportunities and a nighttime lights display, there is a full-sized ice rink, bumper cars and axe throwing.

See Holiday Lights

There are many places to see holiday lights in the Chicago area at night even just walking down a random street.

You can also join this BYOB Party Bus Holiday Lights Tour.

Here are the best places to see Christmas and holiday lights in Chicago.

What are your favorite date spots in Chicago?

Planning a trip to Chicago? Check out my Chicago guides and itineraries:




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