There are so many things to do for date night in Chicago that it can be tough to narrow your choices. Even though the Windy City is full of unique experiences and fun activities, you might find yourself planning the usual dinner and a movie simply because it’s easy.
If you’ve fallen into the trap of boring date nights, use this list to inspire fun date ideas! You’ll find activities that are great for a first date, romantic spots for an anniversary dinner, and out-of-the-box ideas for your next unforgettable Chicago date night!
The Second City hosts improv comedy shows in several locations so there is always something fun to choose from. Interactive shows take the pressure off first dates with lots of chances to break the ice and laugh together. Choose from a variety of improv, stand up, and sketch comedy shows. Just remember not to sit near the front unless you're both open to becoming part of the show!
For one of the most romantic anniversary date ideas in Chicago, book a session at AIRE Ancient Baths in River West. This restored factory houses multiple thermal baths that are modeled after ancient Roman, Greek, and Ottoman bathing experiences. Share a peaceful afternoon moving between the various pools and relaxation areas. Candlelight, luxurious decor, and historic architecture create a memorable setting for couples seeking something beyond the ordinary.
Photo credit: https://beaire.com/
Photo credit: https://beaire.com/
Turn up the heat on date night by learning to make something delicious together. The Chopping Block offers both hands-on cooking classes and virtual demonstrations for all skill levels, from pasta-making to sushi rolling. Working side by side in the kitchen creates plenty of opportunities for conversation, and you'll leave with new skills you can use again during future date nights at home!
If you’re looking for a Chicago date night idea on a week night, Zanies Comedy Club in Old Town hosts performances every night of the week. Established stand-up comedians and rising stars have been performing at Zanies since 1978. Make reservations in advance and arrive early to snag good seats, although the small venue size means there's rarely a bad view.
Plan an adventure to explore dinosaurs and ancient civilizations together at The Field Museum. Take advantage of free admission days for a budget-friendly, daytime date option. You’ll enjoy learning new things together, and the museum's grand architecture and quiet spaces allow for plenty of time for conversation as you explore. 
Special occasions, romantic evenings, and anniversary dates in Chicago are the time to visit stunning locations you wouldn’t go every day, like a rooftop overlooking Millennium Park. Cindy’s is a glass-enclosed rooftop restaurant and bar with gorgeous views of the city skyline and Lake Michigan. Reservations are recommended, especially during peak hours and weekends.
Photo credit: https://www.cindysrooftop.com/
Plan a special date for the foodie in your life with Chicago Food Tours. Choose from several tours that explore different neighborhoods and cultural cuisines. Tours typically include 5-6 stops, mixing well-known spots with hidden gems. You’ll get to experience multiple restaurants in one evening while keeping the conversation flowing naturally.
During warmer months, paddle around the lake in Humboldt Park’s iconic Swan Boats! Consider packing a picnic to enjoy on the shore before or after your boat ride. If being on the water isn’t your thing, rent bikes to explore the beautiful gardens and architecture of the area. It’s an Instagram-worthy date location for couples who love a good selfie. 
Plan a Chicago date day at Chicago Botanic Garden or Garfield Park Conservatory and stroll through nature together! Taking a walk among the beautiful seasonal gardens and tropical greenhouses is a romantic way to spend an afternoon. Visits to the Garfield Park Conservatory are free year-round for Chicago residents.
Taking a stroll along the riverwalk is a fun Chicago date idea for couples who enjoy staying active. Take a long, meandering daytime walk together, or use the riverwalk as the starting point for a night of tasty food and drinks. You’ll enjoy the fresh air and chance to stretch your legs as you walk between various riverfront locations. 
Turn your visit to the Art Institute of Chicago into a fun and engaging date by challenging each other to find your favorite pieces in each gallery. You’ll find city views and contemporary art right around the corner from historical artifacts and architecture from around the world. Be sure to check the upcoming event schedule for special exhibits and programs when you plan your next Chicago date night!
The Lincoln Park Zoo is always free to enter and is full of year-round date possibilities. Summer evenings bring special adults-only events with cocktails and animal encounters, while winter transforms the zoo into a magical light display during ZooLights. Time your visit around animal feeding times for extra entertainment. 
If you're looking for truly unforgettable date night ideas in Chicago, plan a special outing a thousand feet above the Magnificent Mile at 360 CHICAGO. Share panoramic views of the city and Lake Michigan from the 94th floor observation deck before experiencing TILT, the ride that leans you face-first above Chicago from 1,030 feet in the air! Finish the date at CloudBar with craft cocktails and romantic sunset views from the observation deck.
Many fun dates in Chicago start at the beach! Montrose Beach is a popular spot for both active dates on the water and relaxing dates on the sand. You’ll find kayak and volleyball rentals, food stands for tasty treats, and a dog-friendly area for couples who want to bring their furry friends along. In the spring and fall, take a walk along the natural areas to see visiting migratory birds.
Steppenwolf Theater is a community-supported ensemble theater with a variety of year-round shows playing Tuesday-Saturdays. Stop at a nearby restaurant or arrive early for a drink from one of the several in-house bars. It’s the perfect date night for local couples looking to support the arts and enjoy a night of theater together. 
The Aviary takes going out for a night of drinks to a whole new level with their signature dining and cocktail experiences. Choose a cocktail progression for drinks only, or make a reservation for a 5 or 7 course meal that engages all your senses. For a more intimate experience, head downstairs and discover The Office, a speakeasy-style bar below the main dining area.
Photo credit: theaviary.com
Photo credit: theaviary.com
The Empty Bottle is a small Chicago music venue with a full bar. You can catch up-and-coming bands with shows most nights of the week. The casual atmosphere, affordable tickets, tasty pizza, and live performances make it a popular spot for first dates and regularly-scheduled date nights alike.
Photo credit: emptybottle.com
The Dawson is a restaurant and bar with a charming outdoor courtyard and several beautiful indoor spaces. The historic building was built in 1888 and renovated in 2013. Be sure to reserve a spot ahead of time since it’s also a popular space for private events and parties.
Photo credit: the-dawson.com
Experience close-up magic in the speakeasy-style Chicago Magic Lounge, hidden behind a laundromat facade. Watch impressive slight-of-hand magic at your table while you eat and enjoy the main stage shows performed by the finest Chicago magicians. Purchase tickets ahead for a romantic date night or special-occassion celebration at this surprisingly sophisticated lounge.
Upgrade your movie night at the historic Music Box Theater, open since 1929. Catch independent films, foreign releases, or cult classics during their midnight screenings. Check the schedule for special events like sing-alongs and director Q&As. The Music Box Lounge + Garden is open to the public and has a rotating menu of cinema-themed cocktails, an extensive collection of VHS films to browse, and board games to play together.
Photo credit: musicboxtheatre.com
Beer lovers can plan a fun date night in Chicago at Revolution Brewing, Illinois’ largest craft brewery. Enjoy food and locally-brewed beers in the Brewpub + Kitchen, or schedule a tour and tasting at the Brewery + Taproom. You’ll find a wide selection of delicious brews at either location.
Photocredit: https://revbrew.com/
Plan a unique date that both locals and visitors will enjoy with Chicago River Boat Architecture Tours. All tours will take you on an informative and engaging journey down the Chicago River where you’ll learn about the city’s iconic architecture. The Cocktail Tour and Navy Pier Fireworks Cruise are especially fun date ideas for couples looking for something out of the ordinary.
Avondale Bowl is a beautifully restored 1930s bowling alley with a cocktail bar and live music on weekends that make it a lively, fun date spot. You’ll share the experience of vintage gaming in a smaller space that’s calmer and quieter than the typical bowling alley. Make sure to book reservations ahead of time since there are limited lanes.
Get your hands dirty together and learn something new at Penguin Foot Pottery. You’ll learn basic techniques and create pieces to take home during one-off pottery workshops. Hands-on activities like this one are fun for early dates or established couples looking to learn something new. Ongoing classes are also available, which works out well for couples who enjoy shared hobbies.
Book a guided tour of the winery, see a live show, or enjoy dinner and drinks at City Winery Chicago. Indulge in a wine flight in the restaurant or book tickets to live shows. Make sure to book your date night tickets ahead of time for winery tours and shows for this popular date night spot.
Bike tours are a fun Chicago date idea for active couples who want to get to know more of the city and spend time outdoors. Explore together on two wheels with a personalized, guided tour from Chicago Bike Adventures, or join a guided neighborhood food tour with Bobby’s Bike Hike Chicago.
Photo credit: bobbysbikehike.com
Create something beautiful together on your next date at a Chicago Glass Collective workshop. Learn basic glass fusing techniques while making custom pieces like small dishes or holiday ornaments. One-day workshops are open to all skill levels, and couples looking to plan regular date nights can sign up for ongoing classes together.
Get ready for some friendly competition on your next date night at Bad Axe Throwing in the West Loop. Trained axe coaches teach proper technique for a safe and fun experience. Walk-ins are welcome, but it’s a good idea to book a lane in advance, especially for weekend dates. Food and drinks are available for those who don’t want to spend their whole night throwing axes. 
Add some spine-tingling excitement to your evening with a walking tour of Chicago's most haunted locations. Chicago Ghost Tours include fascinating historical stories along with spooky legends as you visit haunted houses, cemeteries, and more. What better way to give yourselves a chance to hold on tight to each other’s hands?
Photo credit: ghostcitytours.com
Get close and learn something new together with couples dance lessons from Arthur Murray Dance Centers. Take a one-time class or sign up for ongoing lessons together. Either way, dance lessons will make date night fun and give you the chance to get out of your comfort zone. 
In Chicago, there are endless possibilities for creating memorable moments together, whether you’re planning a first date, regular date nights, or special trips and anniversary dates.
Ready to start planning your next date night in Chicago? Don’t forget to book your visit to 360 CHICAGO, and check out our blog for ideas on even more things to do in the Windy City!
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