Looking for Chicago date ideas that you actually want to do? You’ve come to the right place.
Whether you're planning a first date or looking to rekindle the romance in a long-term relationship, the Windy City is brimming with unique and exciting opportunities to create unforgettable memories.
From scenic strolls in serene parks to adventurous outings on Lake Michigan, Chicago offers a rich palette of experiences that cater to every couple's taste.
Dive into this guide to discover how you can enjoy everything from cozy cafe dates to thrilling nights out in one of America's most vibrant cities.
And just so you know - nobody pays us to include these date ideas on our list. They’re just places we’ve been to or experiences we’ve loved that we want to recommend, so you can find the best things to do in Chicago.
The Best Date Ideas in Chicago
Explore The Loop Together with a Romantic Scavenger Hunt
Where? The Loop
Whether you were born and raised in Chicago or you’ve arrived here looking for great date ideas, I can almost guarantee you’ve never tried something like this before.
Here’s the deal. Scavenger hunts like these are one of the best date ideas in Chicago, regardless of how long you’ve been together.
The concept is simple (but genius): you and your date receive clues, puzzles and riddles to your phones, you have to solve them to unlock cool places and interesting spots in the city, and you learn a bunch of stuff along the way.
Basically, you two lovebirds become the main characters in your own urban adventure, giving you a cool activity to get to know each other or bond while you explore the city in a totally new and unique way.
Practical information: All you need is WhatsApp, mobile data, comfortable shoes and each other. You can stop and start the game whenever you want. This is a great choice if you’re going double-dating or hanging out with other couples.
See an Improv Show at The iO Theater
Where? The iO Theater, North Kingsbury Street
Looking for Chicago date ideas that will impress a literature fan or a culture vulture? Check this out.
If you’ve never been before, The iO is an awesome improv comedy club that hosts some truly incredible shows - and my favorites have always been the ones with literary influences.
A few years back, they had a Jane Austen improv show that spoke straight to my Emma-loving heart, but I have a special soft spot for the Shakespeare improv shows. Theater and the written word are two of my favorite things, but don’t worry - this isn’t high brow comedy or folks sitting around thinking about how clever they are. It’s a hilarious, creative night out - just give it a try!
Practical information: Check showtimes and purchase tickets at ioimprov.com.
Escape Into Nature at Montrose Point Bird Sanctuary
Where? Montrose, about a 15 minute drive north of Chicago
Cites are awesome places, but sometimes, it’s nature that does the best job of handling romance.
Honestly, given that this place is only located a stone’s throw away in Uptown you’d kinda expect this place to be on more people’s radars, but for some reason, it’s highly underrated. If you have a car, it’s super easy to get to - and truly, it’s one of the most beautiful and peaceful places near the city.
Once you get there, take a peaceful walk together, see some vibrant birdlife, take pictures of what you see and each other, the options are endless. There’s a walking path that you can follow that takes you to the shore of Lake Michigan, and the view of the Chicago skyline is to die for.
Practical information: Visit for more information on visitor guidelines and the best times to observe wildlife.
Get Your Minds Blown at The Magic Parlour
Where? 50 West Randolph
You might not know you’re into magic yet, but believe me – you’ll know once you’ve visited this place.
The Magic Parlour is a performing arts venue in Chicago where people go to see out of this world magic happen right in front of their eyes. The star of the show is Dennis Watkins, whose father and grandfather were also magicians, and he really knows how to impress!
More than just a show of swift “magic tricks” or optical illusions, performances here are truly wowing and incredibly funny! Prepare to laugh, learn and have your eyes pop in this intimate venue that adds that splash of magic we all want on our date night.
Practical information: Dress code, showtimes, and ticket prices can be found at themagicparlourchicago.com.
Check Out Chicago’s Iconic (and Lesser-Known) Museums, Galleries and Gardens
Where? Various
(Maybe) a hot take? Museum dates are way cooler than dinner dates. There, I’ve said it.
If it’s your first date together or you’re still in that “getting to know each other” phase, museums, galleries or gardens are the perfect place to generate conversation and find out what the other person is into. Plus, it’s nice to meet up during daylight hours - it feels more casual and there’s more room to show your personality.
Luckily, we’re spoiled for choice when it comes to finding awesome museum choices in Chicago. Here are some of my favorites, in no particular order:
- Art Institute of Chicago: World-famous art gallery that is expensive but worth it imo. If you’re not into art, you’ll recognize many of the names inside, and if you are into art, you’ll love it!
- Garfield Park Conservatory: The cutest date spot in town. Basically a huge greenhouse full of incredible flowers, and it has an adorable picnic spot too.
- Museum of Contemporary Art Chicago: Not usually as crowded as other museums and full of amazing art pieces. They also have sensory-friendly mornings occasionally if you prefer a quieter, more relaxed vibe.
- Peggy Notebaert Nature Museum: Ok, this one might be my favorite. Free for residents on Thursdays, this place is an homage to the wonders of nature - whether that’s animal or plant life. Try to get inside at 2pm when the butterflies are released into the incredible green atrium, it’s an incredible sight to behold (and warm, so if you’re planning a winter date, this is how to get some warm, summer vibes going!).
Practical information: Visit the websites for current exhibits, opening hours, and ticket information.
Fun Date Ideas in Chicago
Sip Drinks Looking at The Best Views in Chicago at Awesome Rooftop Bars
Where? Various
You’re probably getting the picture that I’m not a huge fan of dinner dates, but that’s not actually true. I’m just fussy - and that means I’ve got a pretty high bar when it comes to finding good places to eat or drink in the city.
Obviously, your idea of a good time might be different from mine, but I’m of the belief that you can’t go wrong with a nice rooftop bar - bonus points for places with good food. Beautiful views, delicious food and drinks, nice atmosphere - sign me up.
Here’s where I recommend:
- The Up Room at the Robey Hotel: Located on the 13th floor of the Robey Hotel. Incredible views, amazing Art Deco-inspired décor and a great cocktail menu.
- Hancock's bar (360 CHICAGO Observation Deck): Located on the 94th floor of the John Hancock Center, this bar is actually part of the 360 CHICAGO Observation Deck and has breathtaking views of the city and Lake Michigan.
- Cindy's Rooftop: Incredible panoramic views of Millennium Park and Lake Michigan, has super creative cocktails and has a stylish but relaxed vibe.
- The J. Parker at the Hotel Lincoln: The best views of Lincoln Park and the lakefront - this place is great if you want a bite to eat, I love the small sharing plates and the cocktails always look so pretty (and taste good too!).
- LondonHouse Rooftop Bar: A tri-level rooftop bar that (in my opinion) looks best at night. It’s an old, gorgeous, historic building, and I love seeing all the city lights and the terrace that overlooks the Chicago River and Michigan Avenue. I’m all about the Sangria here (but the espresso martinis are top tier as well).
Play Video Games and Cuddle with Cats at Catcade
Where? 624 W Belmont Ave.
Probably the cutest place for date ideas in Chicago, and if you or your partner are cat-lovers, it’s pretty much a no-brainer to visit The Catcade.
The clue is in the name: The Catcade is an arcade that doubles as a cat rescue, so you can play classic video and arcade games surrounded by feline friends - all of whom are adorable and adoptable.
Practical information: Visit thecatcade.org for opening hours, booking, and more about their mission (and just to meet the cats ahead of time - I love ‘em all).
Explore Chicago’s Unique Neighborhoods on an Urban Adventure
Where? Various
Looking for date ideas that turn quality time together into an adventure? Look no further!
Sometimes, your heart says “travel” but your bank account says “maybe just a Metra ride”. But that’s ok, because Chicago is full of cool, quirky and interesting little pockets that feel a million miles away (even if they’re just a few stops away).
The best way to do this imo is to sign up to a self-guided urban adventure like this - directions, clues and puzzles get sent to your phone, you get to interact with the city and all of its quirks, and you get recommended bar and cafe stops along the way.
But if you want to get out of The Loop, pay a visit to some of Chicago’s smaller (but no less interesting) neighborhoods. I’d recommend checking out Pilsen (rich in Latino culture with a thriving arts and culinary scene), Downtown Libertyville (lots of restaurants and cute shops), Geneva (super walkable and pretty)... the list goes on.
Practical information: Use the Metra or CTA to get to your destination, most (if not all) of these areas are super walkable. Once there, maybe do a bar crawl or follow your noses to find great hidden gem restaurants.
Or Go Head-to-Head at HQ Beercade
Where? 213 W Institute Pl
If you’re looking for Chicago date ideas that add a competitive twist to your date night, you’ve gotta check out HQ Beercade.
This is easily one of the coolest (and one of my favorite) hangout spots in Chicago, mostly because it’s impossible not to have a good time there. As the name suggests, this is an arcade bar that serves alcohol, meaning you and your date get to be grown up kids for the night.
It’s nostalgic for gamers, but also super accessible to people who have never played before. And best of all, it’s free to enter, the games are all free except the basketball which only costs $1.
Practical information: Check out the website for game lists and special event nights.
Visit Chicago’s Best (and AWESOME) Board Games Cafes
Where? W Irving Park Road and Milwaukee Ave
Looking for old school date ideas in Chicago that bring out your inner romantic? Give this a try.
There’s something very intimate about playing board games as a couple - maybe it’s because you’re forced to be mindful as you strategize, the lack of screens, or the fact you get so engrossed in what’s in front of you that time just seems to disappear. Whatever it is, I’m here for it - and luckily for me, so is my partner, so we often have board games dates at home and in the city.
If you don’t have any board games at home or you want some new ones to try, I recommend heading over to the Stay and Play Game Cafe (which is actually owned by a lovely couple, they serve incredible Puerto Rican food and have a huge selection of games) or Snakes & Lattes, which has a chilled-out vibe and has incredible oat milk Nutella lattes.
Practical information: This is a great choice if you’re going double-dating or hanging out with other couples. If you want game inspo, my partner and I are super into Cascadia, Codenames, Monikers and Bohnanza right now!
Grab an Ice Cream Together at Chicago's Best Ice Cream Spots
Where? Various locations
Here’s a free tip: finding Chicago date ideas doesn’t have to be all-out, no expenses spared events. Sometimes you just need a cute and sweet activity to start or round off a date nicely – and that’s where these recommendations come in handy.
Cool off and sweeten your date with a visit to some of Chicago's best-loved ice cream spots. And if you ask me, that’s at Lickety Spit (quirky, delicious flavors), the creamy custard of Scooter’s (the best frozen custard I’ve ever had), or the legendary five-flavor Rainbow Cone (been around since 1926 and still going strong, plus I love their cones!).
Practical information: A great date idea if you’re short on time or as an added aside to incorporate into a date nearby. If you go to one of these places as a first date, expect it to become a couples tradition!
Head Out of The City For a Hike
Where? Various locations
Looking for Chicago date ideas that get you burning up a sweat? Gotcha.
Real talk, Illinois isn’t the place to go if you’re looking for difficult or strenuous hikes. It’s pretty flat around here, which means you’re not going to get the crazy, panoramic views that you might in the PNW.
That said, what we lack in vertical height, we more than make up for with pretty views and beautiful preserves. And hey, unless you’re a super avid hiker, you might not want to go all out on a walk anyhow.
Get your walking boots on and take your date for an escape to a scenic sport far away from the hustle and bustle of the city. My favorite spots to take a hike around Chicago are the trails around Maple Lake, the Forest Preserve at Irving and Cumberland which can be accessed by the CTA, or Palos Heights Conservatory.
Practical information: Dress for the weather and bring water with you. As always, hike safely!
Watch a Movie Under The Stars at Fulton Market Rooftop Cinema Club
Where? Fulton Market
If you’ve been together a while and you’re looking for cute date ideas to spice up a date night, get on over to Fulton Market and have a movie night with a twist.
This one doesn’t need too much explanation: you get to watch a movie on a rooftop. Sounds simple, but honestly, this is so much fun and sits in that perfect middle ground of “different” but “exciting”.
One thing worth mentioning is that screenings take place during the day and evening, so plan accordingly (sunscreen, shades when it’s hot, blanket for the evening in case it gets cold) and you wear headphones instead of hearing the movie out loud (perfect for anybody with sensitive hearing + to block out the sounds of snacking!).
Practical information: Screening schedule and ticket purchases can be found at rooftopcinemaclub.com/chicago.
Have a Picnic at Milton Lee Olive Park
Where? Between Ohio Street Beach and Navy Pier
Show your romantic side for your date and plan a picnic date at Chicago’s iconic Milton Lee Olive Park.
Unfortunately, you won’t find Milton Lee Olive Park in many tourist guidebooks - but it’s a massive hit with the locals. Named after the first African-American to receive the Medal of Honor in the Vietnam War, it’s also pretty historical.
In my experience, this park offers some of the best views to be had in Chicago, and for that very reason, it’s a popular place to see couples getting engaged or taking their wedding photos. It’s a great place to people-watch and just hang out with your partner, and the fact it’s free is just another cherry on the cake!
Practical information: There are benches here if you prefer not to sit in the grass, and it’s quite popular with dog owners so by all means bring along your furry pals for the date if you want!
Hit Up Chicago’s Vintage Markets
Ok, so shopping might not be your favorite thing - or your date’s for that matter - but that doesn’t mean you won’t both enjoy this.
I don’t really think of visiting vintage markets as shopping. Mostly because I’m not really keeping an eye out for anything in particular, they’re just fun to walk around and see what you can find – which is why it makes such a great date idea.
Seek out hidden gems, find one-of-a-kind treasures or just show each other the unique finds you come across and then go for a bite to eat together: it’s fun, low-key, good for the environment and hey, it doesn’t have to cost you a dime.
Practical Information: I like Vintage Garage and the Randolph Street Market, but pop up markets appear all over the city at various times of the year. Check Eventbrite to see what’s on.
Hire Rental Canoes and See Chicago From The Water Together
This is for couples who crave a bit of adventure or want to try something new.
If you ask me, canoeing is low-key one of the best water activities out there. It’s fun, pretty easy to learn and doesn’t require thousands of dollars’ worth of investment to get started.
Perfect if you’re an active couple who enjoy working out together, canoeing gives you both the chance to burn off some energy together, but it’s also the perfect opportunity to soak in the stunning views of Chicago from a unique vantage point on the water.
If you don't have your own gear, no worries! You can get a rental pretty cheap at REI (near Ping Tom Park).
Practical Information: You don’t need any prior experience to hire a canoe, but I’d say it definitely helps. Make sure you follow water safety requirements and ask questions if you’re unsure!
Find More Things to Do in Chicago with CityDays
So there you have it! 16+ Chicago date ideas that are sure to shake up your date night, day or weekend!
Remember that no matter what you decide to do on your morning, afternoon or evening out with your date, friends, family, or workmates, 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!