Looking for unique and fun date ideas in Chicago? Whether this is your first date or a couple on a weekly date night, here are 23 fun things to do and romantic places to go on a date in Chicago that are sure to impress that special someone!
1. Take a cooking class
Taking a cooking class together can be one of the most fun first dates in Chicago. Since there will be other people in the class, you and your date won’t feel any pressure that can accompany first dates. You’ll get to know each other in a light-hearted atmosphere and have a great time laughing off any food mishaps you may make together. Plus, you will already have a plan for that second date -- cooking a meal together from the recipes you learned. The Chopping Block has lots of classes to choose from: Spanish Tapas, Parisian cuisine, Neapolitan Pizza, and more. They even offer vegetarian and gluten-free cooking classes!
2. Play an escape room
Put your love to the test on a date at The Escape Game Chicago. See how well you can work together under pressure with just 60 minutes to escape a ‘locked’ room. You’ve got to solve riddles, puzzles, and clues quickly to escape one of the uniquely themed rooms.
Do you like art? Play The Heist and attempt to recover a stolen priceless Monet painting. If you are sci-fi fans, play Mission: Mars. Like the hardest challenges, then Prison Break is for you, where you must escape from a 1950s jail cell! Playing an escape room will create a bond like no other! With the last game starting just after midnight, The Escape Game Chicago is a great idea for a late-night date.
3. Discover Chicago’s street art
For a fun and free date idea in Chicago, take a stroll along the 16th Street Mural wall in Pilsen, one of Chicago’s coolest neighborhoods. This two-mile embankment runs along 16th Street from Halsted Street to Western Avenue. Here you’ll see murals by Chicago’s top muralists. These thought-provoking pieces of art will have you and your date talking for the rest of the night. If you plan your date in advance, go for the Chicago Arts District Second Friday evening when galleries and studios are open for free to visitors.
4. Make your own art
Instead of seeing art, why not make some of your own? At Spray Paint N Sip’s Urban Art Workshop, you and your date will get down and dirty…well, dirty for sure as you learn the art of graffiti! This 90-minute interactive workshop includes instruction on working with spray paint and stencil application. Then you both get to create original works of art to bring home as a memento of the time you spent together learning something new and creative! The workshop is BYOB so bring your sparkling water, soda, or bottle of wine!
5. Relax at a spa
One of Chicago’s best activities for couples to enjoy together is to be pampered at a spa. AIRE Ancient Baths is a one-of-a-kind spa inspired by the tradition of thermal baths from ancient Roman, Greek, and Ottoman civilizations. From the minute you walk into the candlelit AIRE, you will feel a sense of tranquility wash over you. The experience includes thermal baths of different temperatures, an aromatherapy steam room, and a heated indoor/outdoor pool.
AIRE has couples’ packages, such as the Love Constellations where you’ll have a 45-minute massage for two plus access to all the other amenities. Undoubtedly, AIRE is one of the most romantic places in Chicago.
If you're date is with your besties for a Girls' Night Out, AIRE will pamper you the way you deserve to be!
6. Get spooked on a ghost tour
A date night spent taking a scary Chicago ghost tour is one way to ensure that you and your date will end up holding hands at some point! Tour guides tell true, spine-tingling stories about the lost souls that linger around Chicago. The 3-hour Original Chicago Hauntings Ghost Tour takes you via bus to the sites of mass tragedies like the Iroquois Theater Fire and to the death site of Chicago’s most famous ghost, “Resurrection Mary”. If you prefer a walking tour (and to save some money!), take this free Chicago Haunted History & Ghost Tour. If you like ghosts and gangsters, try this 2-hour Chicago Gangster and Ghost Tour.
7. Take a donut tour
If your sweetheart has a sweet tooth, take the Underground Donut Tour! This two-mile tour passes through Downtown Chicago, parts of River North, and finishes near Magnificent Mile. The tour stops at four shops to try the most delicious donut shops in the city. You can also take a DIY donut tour. Do some research and map out your route. Better yet, use this Self-Guided Walking Tour for Donuts in Chicago for a super sweet date!
If your sitter cancels at the last minute, and your romantic time together suddenly includes the kids, this donut tour is just right as a family-friendly activity in Chicago!
8. Soar to new heights together
How’s this for a unique date idea -- go skydiving with Skydive Chicago! Get that adrenaline rush you’ve both been seeking when you take that step out into the air and then freefall for 60 seconds at speeds up to 120 miles per hour. First-time skydivers go tandem with an experienced tandem skydiving instructor.
If the forecast says it's going to be a rainy day in Chicago, you can still go skydiving albeit, indoors. You can still have an exhilarating experience at iFLY Chicago. There you can feel the thrill of defying gravity from the safety of a man-made vertical wind tunnel. If things go well, plan that second date for the real thing.
9. Kayak at midnight
Kayaking may not seem like one of the most romantic things to do in Chicago, but it can be depending on when you go! Wateriders has a Moonlight Paddle along the Chicago River that goes through downtown Chicago. You and your date will see the city as it sparkles and reflects off the river, making for a very romantic paddle. Another option is to do a sunset kayak tour which is equally as beautiful. The sunset tours start at 6:30 pm and go until 8 pm so you can grab some dinner afterward.
10. Go to the beach
Is your hot date scheduled for a hot day in Chicago? Head to one of the city's great beaches! The city has over 20 beaches along 26 miles of shoreline along Lake Michigan with great skyline views. In the summer, the water is, on average, 75 degrees making a swim a very comfortable experience.
Lots of beaches have activities like 57th Street Beach where paddleboarding, canoeing, and other non-motorized water sports are allowed at the north end of the beach. The slightly upscale South Shore Beach has a nine-hole golf course and tennis courts. Spend your date building sand castles together and bury your toes in the sand!
Unique Romantic Dinner Dates in Chicago
11. Dinner with a breathtaking view
One of Chicago’s most romantic date ideas is a night visit to one of the city's two skyscraper observation decks. The view of the sparkling city will wow your date! One option is Skydeck, located on the 103rd floor of the Willis Tower, open daily until 10 pm. The other option can include dinner or drinks. The observation deck at 360 Chicago, on the 94th floor of the Hancock Tower, is open until 11 pm.
If you want the same spectacular views over dinner, make reservations at the Signature Room on the 95th floor. It’s open until 9:30 pm on weeknights and 10 pm on weekends. If the date is going well and you want to stay out later, have drinks at the Signature Lounge. It’s open until midnight on weeknights and until 1 am on weekends.
12. Dinner and a movie with a twist
There’s nothing wrong with having dinner and then seeing a movie on date night. But what if you and your date have limited time free? Why not do dinner and a movie at once? Plan an evening at one of Chicago's movie theaters that serve food!
At the Alamo Drafthouse Cinema, you can see a film while eating great food and sipping on handmade cocktails or microbrews. The Alamo plays everything from current blockbusters to independent movies, from classics to foreign films. If you want to bring your own food to a movie, you can in the summer during the free Millennium Park Summer Film Series.
13. Dinner in the Dark
Having dinner blindfolded is an odd but surprisingly great romantic date idea in Chicago. Dining in the Dark offers a three-course gourmet meal that you and your date will enjoy in a romantically warmly lit room. Though once seated, it won't matter what the room looks like because your waiter gently blindfolds you both before your meal begins.
So what’s the purpose of not seeing while dining? The theory is that without your sense of sight, your other sense of taste and smell will be enhanced which makes your meal taste that much better. Plus this unique experience promotes conversation which can be helpful if it's your first date!
Discover Chicago on a date
14. Cheer on the home team
If you‘ve been feeling like you and your partner aren't in sync these days, go see teamwork in action! Spend date night with a Chicago sports team. With sports teams in nearly every professional sport, there’s almost always a game going on. From August through December, see the Chicago Bulls or Chicago Sky play basketball.
You can also attend an ice hockey game with the Blackhawks. Prefer football? Cuddle up under a blanket at a Bears game. Come the warm weather, you can see a baseball game. Choose from the Cubs or the White Sox. Sip on a giant soda together and cheer for the home team!
15. Have a cocktail in a speakeasy
The Library is hands down one of the best hidden romantic spots in Chicago. Located in the basement of the sophisticated Gilt Bar, the Library is behind an unmarked door. Once you enter, you and your date will find yourselves in an intimate, dimly lit bar with candles and plush red velvet booths. Sip on artisanal cocktails or wine from an extensive wine.
On your way out of this secret hideaway, memorialize your evening with a photo from the old-school photo booth. The Library is open Thursday from 6 pm to 10:30 pm and Friday and Saturday from 6 pm to 11 pm. Reservations are a must.
16. Take an architecture river cruise
Any kind of cruise is a nice way to pass time on a date. If you both have always admired Chicago’s stunning architecture, but want to learn a bit more, an architecture cruise along the Chicago River is right for you. On a Chicago Architecture River Tour, you’ll learn about Chicago’s recovery from the devastation of the Great Fire of 1871 and how the city became the birthplace of the nation’s first skyscraper. The cruise covers 40 of the city’s most famous buildings. You’ll come away from an architecture cruise knowing more about Chicago and each other!
17. Stroll along Riverwalk
Whether you are on a first date or the hundredth date, Chicago's Riverwalk will always deliver a nice evening for couples. When the weather is warm enough to spend some time outdoors, this 1.25-mile-long urban path is ideal for walking and talking. There is a lot to see such as public artworks like murals and sculptures.
The river is lined with some of Chicago’s most glorious buildings. Lovely outdoor dining and drinking establishments dot the Riverwalk so you can stop off for a bite or a drink. Riverwalk is open to the public from 6 am to 11 pm every day, making it a popular place to go in Chicago at night.
18. Gaze at the stars
Given Chicago's brightly lit sky at all hours, it isn't the perfect city to seek out the stars. But that's no reason that lovers can’t gaze at the stars! The Adler Planetarium it’s the best bet for seeing stars and constellations within Chicago’s city limits. On select nights, the planetarium’s ‘Scopes at the Adler program invites the public to stargaze through their powerful telescope as educators provide a guided experience.
Even if you don't go to the Adler to see stars, it's a pretty nifty place to visit, especially when you know that it’s open every Wednesday until 10 pm and is free for Illinois residents with proof of residency!
19. See fireworks at Navy Pier
Want some fireworks on your date? Head to Navy Pier for fireworks on Wednesday and Saturday nights in the summer. There’s plenty to do here every night year-round. Walk along the boardwalk holding hands. Grab a drink at the Offshore Rooftop & Bar. Have a meal at one of the fine restaurants. If you like amusement rides, go to Pier Park for the famous Centennial Wheel for beautiful views of the waterfront and skyline.
20. Shedd After Hours
Take your date to meet Chicago’s aquatic creatures at the Shedd Aquarium’s special After Hours series! The Shedd holds regularly scheduled house parties where the over-21 crowd can enjoy food and adult beverages while a DJ spins tunes or live bands play. It's a popular thing to do for adults in Chicago looking for an educational, yet mature event.
Chicago Nightlife Great For Dates
21. Theater and Dance
For a special date night, head to the Chicago Theatre District to see a show. The lavish historic theaters are some of the most beautiful date places in Chicago. Iconic theaters for a wonderful night of entertainment are the James M. Nederlander Theatre and the Cadillac Palace. See what’s playing here.
For incredible plays of the highest caliber see what is on at the Steppenwolf Theatre. Since its inception in the 1970s, it has become the nation’s premier ensemble theatre.
The Joffrey Ballet is well-known throughout the world and seeing a dance performance is a great date idea. This Chicago-based dance company puts on a variety of dance styles from classical masterpieces and cutting-edge contemporary ballets.
22. Live Music
The Chicago Theatre and Riviera Theatre are smaller venues with about 3,600 seats. Both attract well-known performers of varying genres. These historic theaters are lavish and make a gorgeous setting for any date.
Epiphany Center for the Arts is a cultural hub with live music from 5 pm to 8 pm, nearly every day of the week. The performances are free and range from rock, pop, jazz, blues, house, soul, and more.
The Green Mill Cocktail Lounge was a speakeasy in 1907 and still has that atmosphere today. Every night there is some kind of performance going on, be it good music, great comedy, or moving poetry. Note that it is cash only.
The Hideout is a Chicago institution with a bar up front and a stage in the back. There’s an eclectic mix of music during the week. Some nights you can see comedy, dance, or play Bingo!
23. See a comedy show
A dose of laughter can break the ice on a first date and Chicago’s very own Second City is the best you’ll find out there. Several Saturday Night Live cast members found their early success here. The iO Theater also has famous alumni as well. Zanies has a long list of top comedians who have performed here.
Find out about more things to do in Chicago here.
For suggestions on how to plan your time, check out our 2 day Chicago itinerary!
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