Looking for great date ideas in Chicago? I have put together the ultimate list of the best Chicago date ideas in 2024 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 (2024)
Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.
Most Romantic Chicago Date Ideas
These romantic date ideas are perfect for an anniversary date, birthday, Valentine’s Day or other special date.
Watch Free Fireworks
Navy Pier puts on a free fireworks show twice a week between Memorial Day weekend and Labor Day weekend. While you can watch the fireworks from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.
You can see the fireworks on a tour like this fireworks and evening segway tour.
A romantic way to watch the fireworks is on a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.
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 Candle Making Class
Looking for a unique and romantic date night during the weekend? Join this Couples Candle Making Class at Above Average Candle Studio (3414 West Foster Avenue) where you and your date can create a signature scented candle together or this candlemaking class in downtown Chicago at Reggie Hathorn (900 North Michigan Avenue, Level 6).
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 also a fun date idea. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views especially around sunset.
If your time is short, you can do a combination river and lake cruise.
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:
A Tribute to Taylor Swift
A Tribute to Beyoncé at Music Box Theatre
Featuring Mozart, Bach, and Timeless Composers
Neo-Soul & Hip-Hop Favorites
A Tribute to Coldplay on Strings
The Best of Hans Zimmer
You can find the full list of current candlelight concerts in Chicago here.
Listen to Concerts Under The Stars
Enjoy a music concert on a beautiful rooftop with city views. Upcoming Concerts Under The Stars include:
ABBA Under The Stars at AIRE
Sinatra Under the Stars at AIRE
Amy Winehouse Under The Stars
You can find the full list of Concerts Under The Stars here.
Ride the Ferris Wheel at Navy Pier
If you are visiting Navy Pier to check out the fireworks on a Wednesday or Saturday night, head there before sunset to ride the large Ferris wheel and enjoy the beautiful skyline views (click here to purchase a fast pass ticket and skip the long line).
Navy Pier offers other fun date activities including the new Flyover Chicago, an immersive flyover experience.
Unique Date Ideas in Chicago
Titanic: The Exhibition
Titanic: The Exhibition is a unique date idea in the Chicago suburbs. This interactive experience allows you to step inside recreations of the Titanic’s interior. Immerse yourself in the stories of its passengers, see hundreds of artifacts, and discover the tale of the design, creation, launch, maiden voyage, and tragedy of the historic ship.
Where: 4963 Old Orchard Shopping Center, Skokie, IL 60077 (about 17 miles from downtown Chicago)
Cost: Price varies. Click here for full prices and to purchase tickets in advance.
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
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.
Hold and Feed a Bunny
Looking for a unique thing to do in Chicago? Visit the Cuddle Bunny in Chicago, where visitors can pet and feed bunnies. Cuddle Bunny also hosts special events like yoga and story time.
Where: Cuddle Bunny, 2901 N Clark St, Chicago, IL 60657
Where: 917 W 18th St, Chicago
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
Visit an Escape Room
An escape room is a fun date activity. You and your date will work together to find clues, solve puzzles, and complete a mission with this thrilling escape room adventure in Chicago.
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.
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.
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 nightly. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
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.
You can rent 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.
Take a Water Taxi to Chinatown
A great cheap date idea is to take a water taxi to Chinatown. In addition to eating and walking around Chinatown, you can relax and enjoy Ping Tom Memorial Park, which has unique skyline views.
Visit Lincoln Park Zoo
Lincoln Park Zoo is one of a few free admission zoos in the United States.
Where: 2400 N. Cannon Drive
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.
Listen to Free Outdoor Music Concerts
A free date activity during a warm summer evening is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.
The annual Grant Park Music Festival (through August 17, 2024) is the only free outdoor classical-music concert series in the US. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors.
The Millennium Park Summer Music Series (Mondays & Thursdays through August 8, 2024) features a wide variety of music from established and emerging artists at the iconic Jay Pritzker Pavilion.
Watch Free Outdoor Movies
Take your date to watch an outdoor movie for free. You can watch outdoor movies at Gallagher Way in Wrigleyville on select Wednesdays through the end of September. Seating on the grass is free but you can also purchase VIP seating. You can find the full schedule of movies at Gallagher Way here.
This summer you can also watch free movies on Tuesday evenings through August 20, 2024 at Millennium Park. Guests can sit at the Jay Pritzker Pavilion or lounge on the Great Lawn as movies are presented on the state-of- the-art, 40-foot LED screen. You can find the full schedule for the Millennium Park Summer Film Series here.
You can also watch free outdoor movies at various public parks throughout the city
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.
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).
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.
– Tango Sur (3763 N Southport Ave) – Argentinian steakhouse that is dark and candlelight.
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:
View this post on Instagram
– 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
