Hey there romantics, we’ve caught you trying to find things to do in Chicago for couples!
Well that’s alright, because that’s what we’re here to give you. Or at least, a few ideas of what you could get up to in the Windy City.
Whether you call it “date night” or hanging out together just the two of you, you can never have too many ideas of activities or fun things to do.
Take it from us - we’ve already put a guide together on date ideas in Chicago, but we understand that you might be looking for something a little different than your traditional date ideas. By all means, take a look at it if you need more ideas – otherwise, read on to find out our top 12 things to do in Chicago for couples, no matter how long you’ve been together!
And just so you know, nobody pays us to be featured on this list. They’re just experiences we’ve had or places we’d recommend visiting so you can find the best things to do in Chicago!
Best Things to Do in Chicago for Couples
Do a Scavenger Hunt Through The Loop
Location: 📍Chicago Loop
Ok, a couple of questions: Did you and your partner meet here in Chicago? Are you visiting us from another state or overseas? Have both or either of you lived here all your lives?
If you answered yes to any of the above, this is for you.
Scavenger hunts like these bring out your inner detectives and get you both scurrying around Chicago on the hunt for hidden gems, iconic landmarks, and quirky trivia while enjoying some friendly competition.
All you need is a phone, WhatsApp, comfortable walking shoes and each other, and each ticket (which only costs 20 bucks each, by the way) also includes recommended refreshment stops.
Practical information: Start and stop your game whenever you want. Prices and booking details can be found at CityDays.
Check Out Some Cool Museums Together
Location: 📍Various
Looking for things to do in Chicago for couples that enrich your minds? Well, maybe or maybe not - but a little more brain power is never a bad idea.
Dive into Chicago's rich culture and history by visiting some of its coolest museums. I’m not just talking about all the big dogs (although, they are awesome), but straying off the beaten path and checking out somewhere you’ve never been together is a super cute and fun activity to do together.
I could sit here typing out a bunch of recommendations but I’ll just give you my top 5 for some inspiration:
- 📍Art Institute of Chicago: There’s no WAY you’ve seen all the art in here, it’d take forever. But it’s got everything you could possibly want or need under one roof. My partner and I are obsessed.
- 📍The Field Museum: One of the biggest natural history museums in the world and full of awesome (and some kinda creepy) exhibits including dinosaurs!
- 📍Museum of Science and Industry: One of my faves. It’s the perfect size, has interactive exhibits and it’s just fascinating walking around.
- 📍Chicago Cultural Center: Oh my gosh the ceilings in here! And it’s free to enter! There’s just something super romantic about this place. Doesn’t take long to walk around but I just love it.
- 📍National Museum of Mexican Art: Another free option, this is a little way outside of Chicago (Pilsen, to be exact) but the bright colors and incredible art is just amazing.
Practical information: Check individual museum websites for opening hours and ticket prices. Many museums offer discounted or free admission days.
Take a Romantic River Cruise Together
Location: 📍Chicago River
If you’ve seen this before, it’s because Chicagoans will recommend this to everyone–but with very good reason.
It’s like this. Here in Chicago, we’re proud of our architecture. It sets us apart from other cities, and it just so happens that one of the best views you can get of the city is aboard a boat. We don’t make the rules!
Of course, if you’re a Chicagoan yourself, there’s a strong chance you’ve already done this. But then you’ll know how awesome it is, and hey, if it reminds both of you why you fell in love in this great city, that’s a win in my book.
Practical information: Cruises operate daily, with tickets starting at around $40 per person. Check local tour providers for schedules.
Go For a Walk Along the Navy Pier
Location: 📍Navy Pier
Looking for things to do in Chicago for couples that get you immersed in the city? Head to Navy Pier.
People seem to have branded Navy Pier as “too touristy” which I think is unfair. Why do tourists like going there? Because it’s awesome and we take it for granted!
Just going for a neat little stroll along here will give you incredible views of the city skyline, live entertainment, options for food and drink (I’d especially recommend the beer garden in summertime). It’s also dog friendly, so you can bring along your pup if you have one!
Practical information: Navy Pier is open year-round. Many attractions are free, but some, like the Ferris wheel, have a ticket fee.
Have a Romantic Picnic at Grant Park
Location: 📍Grant Park
Looking for romantic things to do in Chicago for couples? Gotcha.
If you ask me, it doesn’t get more romantic than dining al fresco. It makes me think of trips to Europe and all these cool, casual couples who hang out under trees. Well, that could be you – right here in Chicago!
After all, all you need is a park, and boy do we have those. I like Grant Park (who doesn’t?) because it’s just so pretty. If you haven’t been before, it’s full of fountains, flowers, sculptures and plenty of benches and grassy areas to rest on, so it was basically made for picnicking couples or families.
If you’ve been there and done that, there are tons of other parks to check out:
- Ping Tom (Chinatown)
- Humboldt Park (West Side)
- Loyola Park (North Shore)
Practical information: Grant Park is open daily, and entry is free. Check local listings for event schedules.
Fun Things to Do in Chicago for Couples
Explore the Chicago Botanic Garden
Location: 📍Glencoe, IL
While we’re talking about beautiful flowers, I can’t not mention the Botanic Garden as one of the most romantic things to do in Chicago for couples.
It doesn’t take a genius to understand that flowers, gardens, and all things beautiful instantly qualify as romantic, but you might be wondering what’s so special about this one? I’ll tell ya!
The best thing about the Chicago Botanic Garden is its sheer size. It’s a massive 385 acres of beautifully curated gardens, including a Japanese garden (my favorite) and a butterfly exhibit (it’s like something out of an old Disney movie in there). Go for a stroll, bring a camera and enjoy wandering around nature’s spectacles – did I mention it’s free?
Practical information: Open daily from 8 AM to sunset. Admission is free, but parking fees apply.
Enjoy a Comedy Show at Second City
Location: 📍Various
Ok, that’s enough about how much I rate flowers (for now). Instead, we’ll move onto something more funny than flowery, and what is the universal love language if not laughter?
You probably don’t need reasons why going to comedy clubs is a fun thing to do as a couple, but you might need some pointers on where to go.
In that case, here are my top picks. Oh and, many comedy clubs in Chicago have a two drink minimum spend on top of ticket prices, just so you know!
- 📍Second City: Want to know who’s going to be a future big name? Head here. This place has launched a ton of comedy careers, and for that reason it’s also super popular so book in advance!
- 📍LaughFactory: Pretty much always has a great lineup and it’s open 7 days a week, which is handy.
- 📍The Lincoln Lodge: A cozy, intimate comedy club with reasonably-priced tickets.
Practical information: Showtimes vary; tickets range from $15 to $50. Many places have an 18% gratuity charge for food/drinks. Book in advance to secure good seats.
Go For Drinks at a Rooftop Bar
Location: 📍Various
You might be thinking this idea’s a bit obvious, and you’d be right–except for the fact that you might not know that Chicago’s home to some awesome rooftop bars.
Now, I’m sure this won’t be the first time you grab a beverage with your significant other but if you’re new to Chicago or haven’t explored the bar scene here fully yet, this is your sign.
If you want to know where it's worth visiting, I’d recommend the 📍Up Room or 📍London House.
Practical information: Up Room at the Robey Hotel has no entry fee. London House offers spectacular views. Check their websites for reservations and dress codes.
Attend a Concert at Millennium Park
Location: Millennium Park
During the summer, there’s only one place to be or be seen in Chicago: the Jay Pritzker Pavilion in Millennium Park.
Why? Because between July and August, this place is home to a FREE concert festival. All held outdoors, the Millennium Park Summer Music Series includes concerts from every genre you can think of (classical, contemporary, jazz, house, country…etc).
If you want to bring along your own chairs, you can do so but you’ve gotta sit on the Great Lawn instead (worth it for the comfort, in my opinion). There’s a concessions tent if you get hungry or thirsty but you can also bring along a picnic if you want to be super romantic.
Practical information: Concerts are held during the summer. Check the Millennium Park website for event schedules.
Walk or Bike the Lakefront Trail
Location: 📍Along Lake Michigan
Looking for things to do in Chicago for couples who love the great outdoors? Time to hit up the Lakefront Trail.
As the name suggests, this activity involves walking or cycling along the perimeter of Lake Michigan. The benefits for this idea are two-fold: you get some exercise under your belt (which is awesome) but it’s also super beautiful. Enjoy the views, stop at one of the beaches and just enjoy being in each other’s company.
Practical information: The trail is open 24/7 and free to use. Bike rentals are available at various points.
Discover the Lincoln Park Zoo
Location: 📍Lincoln Park Zoo
Hey, did you know Chicago is home to one of the oldest zoos in the country? Well, you do now. And you wanna know what’s even better? It’s free to visit!
If I had to rate this place, it’d be way up there with my top 5 fun things to do in Chicago for couples.
Like most other zoos, it’s got all the animals you want to see - penguins, otters, lions, giraffes, macaques, turtles - as well as a bunch of other fauna I’d rather not see (in the wild, at least. I’m looking at you, rattlesnakes!).
There’s also some really beautiful plants and gardens for you both to check out once you’ve said hello to all the creatures great and small.
Practical information: Open daily from 10 AM to 5 PM. Admission is free, but donations are appreciated.
Catch a Game at Wrigley Field
Location: 📍Wrigleyville
If you or your partner is a baseball fan, it’s pretty much a no-brainer: but listen up, even folks who aren’t that into baseball will find something to get out of this place.
First of all, this place is historic – it’s over a hundred years old, and in my opinion, it’s totally iconic. If the Cubs are in town, you might as well grab tickets to a game if you can and soak up all that atmosphere. If they’re away, take a tour of the stadium together, it’s well worth it!
Practical information: Game times and ticket prices vary. Check the Cubs’ official website for details and to purchase tickets.
Relax on North Avenue Beach
Location:📍North Avenue Beach
Don’t let the fact that Chicago is miles away from the ocean crush your dreams of a beach day with your darling.
So we haven’t got miles and miles of coastline on our doorstep, but that doesn’t stop us from making the most of the beach. It might not be a typical “beach”, but Lake Michigan has everything a beach has: soft sand, volleyball courts, and plenty of space to soak up the sun together.
It also has one priceless thing that other beaches don’t have: an incredible view of the skyline.
Practical information: The beach is open daily from 6 AM to 11 PM. Admission is free.
Enjoy a Show at The Chicago Theatre
Location: 📍The Loop
As it’s probably the most iconic landmark on this list of fun things to do in Chicago for couples, I couldn’t forget to mention a visit to The Chicago Theatre.
Opened in the 1920s as a movie theater, Chicago Theatre has seen the evolution of entertainment over the last 100 or so years. From movies to jazz musicians, ballet dancers to comedians, these walls are the secret keepers to some truly incredible stories – stories you won’t wanna miss.
If you’re interested in history, architecture and/or pop culture, you can’t miss out on doing a tour (unfortunately they only run Fridays and Saturdays). But don’t worry if you’re not in town on those days: there’s always something on at this place, just cross your fingers there are tickets left!
Practical information: Showtimes and ticket prices vary. Check the Chicago Theatre’s website for upcoming events and to book tickets.
Visit the Garfield Park Conservatory
Location:📍Garfield Park
Ok, one last mention of where to see beautiful plants in Chicago (there are many, and if you couldn’t tell already, one of my favorite things about Chicago!).
Garfield Park Conservatory is easily one of the most underrated places to visit in Chicago. There aren’t really any words to do this place justice in terms of just how lovely it is, but I’ll do my best.
Essentially, it’s a giant tropical greenhouse packed with plants and floral displays from all over the world. If you or your partner is into art, this is a great place to get some inspiration (
charge your phone, you’ll wanna take pictures here). If not, just take a romantic walk around and have a peaceful afternoon together, it’s gorgeous!
Practical information: Open daily from 10 AM to 5 PM. Admission is free, but donations are welcome.
Sip Craft Cocktails at a Speakeasy
Location: 📍Various
Prefer to be on the down low rather than up high? No problem!
I get it, rooftop views ain’t for everybody. One of the best things to do in Chicago for couples is to discover all of the many (and there are many) places to eat and drink in the city, and one of the best places to do that is to delve into its more “secret” spaces.
Enjoy craft cocktails in a cozy, intimate setting, perfect for a romantic and adventurous night out with your SO.
Wanna know where to go? Here are my faves:
- 📍The Drifter: If you’re into Burlesque vibes, this is for you.
- 📍Booze Box: I am obsessed with sushi and this bar just so happens to be beneath the main dining area of one of my favorite restaurants in Chicago, so of course it’s on this list. Live DJ sets on weekends which is awesome.
- 📍Blind Barber: Don’t be fooled - you can get a haircut but the bar is concealed behind it. Has a kind of “club” vibe, there’s music and it’s super popular so it gets busy.
- 📍The Library: Oh I love this place but make sure you make a reservation, wait times can be around half an hour if you don’t. More of a place to eat and sip drinks but both are incredible.
Practical information: Hours and entry fees vary by location. Check individual speakeasy websites for details.
Explore the Magnificent Mile
Location: 📍Michigan Avenue
Well with a name like that, it couldn’t not be on our list of things to do in Chicago for couples.
It’s called the Magnificent Mile for a reason, and honestly, it’s great fun. Some people say it’s too touristy and others will even complain that it’s busy sometimes (which I actually think is a good thing, people only flock to places that are good, right?).
Even if you’re not into shopping, just walking around here in the early days of spring puts a spring in my step. Pretty much as soon as the temp tips over 60°, Chicagoans wake from their winter hibernation. Take a look around, stop for a drink or a bite to eat and soak up that energy!
Practical information: Shops and restaurants have varied hours. No admission fee to explore the area.
Attend a Blues Club Together
Location: 📍Various
Last up on our list of things to do in Chicago for couples, an absolute classic: visiting a Blues club together.
If you’re into Blues music, then I won’t waste your time going over why these places are awesome. If you’re yet to discover the beauty of the Blues however, boy oh boy do you have a treat in store.
Blues is the kind of music that almost has to be heard live to truly appreciate it. It’s soulful, deep and yes, has a romantic vibe to it. It’s a little more intimate than a gig or a concert, and it’s also a chance to hang out somewhere mellow with your SO. See for yourself!
Here’s where I’d recommend:
- 📍Kingston Mines: Been around since ‘68 and not going nowhere. Great music, great vibes, amazing cocktails and barbecue food: heaven!
- 📍Buddy Guy’s Legends: Small entry fee of 25 but sooo worth it. The music is incredible and so is the food. A must for lovers of the Blues!
- 📍Rosa’s Lounge: Super chill and welcoming place to listen to live Blues. Also super reasonably priced which is a bonus.
Practical information: Showtimes and cover charges vary by venue. Check individual club websites for details.
Find More Things to Do in Chicago with CityDays
So there you have it! 18+ things to do in Chicago for couples to help you plan some much-needed alone time with your partner.
Remember that no matter what you decide to do on your morning, afternoon or evening out with your date, friends, family, or coworkers, there’s nothing like teamwork to make the dream work.
That’s why we at CityDays create fun, interesting and challenging trails around the world to help you immerse yourself in a city’s culture, history and curios.
Want to find out more?
Check out all our available activities in Chicago here and embark on an adventure in the city you’ll never forget: CityDays awaits!