Looking for great date ideas in Chicago? I have put together the ultimate list of the best Chicago date ideas 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
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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: A Tribute to Adele
Candlelight: A Tribute to Taylor Swift
You can find the full list of current candlelight concerts in Chicago here.
Listen to Concerts Under The Stars
Enjoy classical music concerts on a rooftop or a beautiful garden oasis this summer. Upcoming Concerts Under The Stars include:
Sinatra Under the Stars at AIRE
ABBA Under the Stars at AIRE
Amy Winehouse: Jazz Under the Stars
You can find the full list of Concerts Under The Stars 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.
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.
Take an Architecture River Cruise
An architecture river cruise is a must on any Chicago bucket list for locals and visitors alike.
Take a Lake Cruise
A lake cruise is perfect for a romantic date in the summer. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views and a refreshing lake breeze.
A sunset cruise or a fireworks cruise is perfect for a date night.
If your time is short, you can do a combination river and lake cruise.
Hold and Feed a Bunny
Looking for a unique indoor thing to do in Chicago? Visit the Cuddle Bunny (2901 N Clark St) where visitors can pet and feed bunnies. Cuddle Bunny also hosts special events like yoga and story time. You can read more about the experience here.
Fun Chicago Date Ideas
Play Indoor Mini Golf
Play mini golf with drinks at one of the several indoor miniature golf courses in the Chicago area.
Play Outdoor Mini Golf
There are a few outdoor miniature golf courses in Chicago including City Mini Golf at Maggie Daley Park and Diversey Miniature Golf.
Pixar Putt at Navy Pier is a pop-up, open-air 18-hole mini-golf course featuring characters from some of Pixar’s most beloved films. There also have After Dark sessions available for adults 18+ on Thursday, Friday and Saturday which are perfect for a date night.
Have Fun at Navy Pier
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).
Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises:
Museum of Ice Cream
Chicago’s newest attraction, 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.
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.
Go Indoor Skydiving
Go indoor skydiving at iFLY Chicago – Lincoln Park (800 W Scott St).
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.
Most Romantic Chicago Date Ideas
These romantic date ideas are perfect for an anniversary date, birthday, Valentine’s Day or other special date.
Join a Fireworks Cruise
Enjoy fireworks on Wednesday and Saturday night in the summer from the water on a fireworks lake or river cruise.
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.
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 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 the Fireworks
Navy Pier puts on free fireworks shows every Wednesday (at 9 pm) and Saturday night (at 10 pm) from Memorial Day weekend to Labor Day weekend.
You can see watch the firework shows for free from Navy Pier and various points along the lakefront.
Walk 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.
There are numerous beaches along the way if you want to stop for a picnic 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.
Visit Lincoln Park Zoo
Lincoln Park Zoo (2400 N. Cannon Drive) is another good date spot for a daytime date. During the Christmas holiday season, you can visit the zoo during Zoolights after hours in the evening.
Watch Free Outdoor Movies
There are several places you can watch free outdoor movies in Chicago including Gallagher Way in Wrigleyville and Millennium Park.
Listen to Free Outdoor Music Concerts at Millennium Park
One of the best things to do in Chicago during a nice summer day is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.
Grant Park Music Festival runs on Wednesdays, Fridays and Saturdays and the Millennium Park Summer Music Series, runs on Mondays & Thursdays in the summer.
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 an upscale restaurant on the 95th floor named the The Signature Room at the 95th, and a bar on the 96th floor called The Signature Lounge at the 96th which are 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 Kayaking in the River
Active couples might enjoy kayaking in the Chicago River. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders.
There are several kayak tours to choose from including sunset tours, moonlight tours and fireworks tours.
Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
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.
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.
What are your favorite date spots in Chicago?
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
- Weekend in Chicago: 3 Day Itinerary (According to a Local)
- The Perfect Itinerary for One Day in Chicago
- Most Instagrammable Places in Chicago
- Best Free Things to Do in Chicago
