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Dating in Chicago
You have a hot date and are looking for fun Chicago date ideas ! Sure, you could do dinner and drinks, but why not try something different or unexpected? Sharing a new experience is a great way to get to know someone better. Below, you’ll find creative ideas for dates in Chicago! (Props to my Instagram fam for submitting ideas for this article!)
Plus, at the end of this post, I will also share my first three dates with my husband, whom I met on a dating app, by the way!
16 Fun Chicago Date Ideas
1. Museum Hack
Museum Hack offers unconventional, “not your grandma’s” guided tours through some of the country’s top museums including the Art Institute in Chicago. You’ll experience an interactive tour where you’ll learn some of the wildest, sexiest, strangest stories about the artists and the exhibits. You’ll have plenty of interesting stories for a good debriefing session with your date. Get the full scoop on Museum Hack in this review on Lizzyfay.com.
2. Free outdoor concert
Check out a free concert series where you can spread open a blanket, open a bottle of wine and enjoy some live music. Outdoor concerts have a laid-back feel, so you can bounce between conversation, listening to the entertainment and people watching. Perhaps you’ll even get a little cozy if all goes well. You can find free concerts through the Grant Park Music Festival.
3. Get Active Together
Go rock climbing at Brooklyn Boulders’ huge indoor wall or try a workout class neither of you has tried before such as Solidcore. One of Kam’s and my go-to activities together when the weather is nice is to walk! Seriously, we will put on comfy shoes and walk from River North to Lakeview and try a new restaurant when we get there. You can also walk or jog along the Lakefront Trail, the Rivewalk or the 606. It’s a great way to explore the city and chat with your date.
4. Escape Room
In these game rooms, you will get “locked” inside a room with your date and you’ll have to solve a series of puzzles using clues and strategy to escape. On this date you’ll find out if your date is a team player and see his/her problem-solving skills in action! There are several of escape rooms in Chicago and surrounding suburbs and they are popping up across the country, so there might be one in your area. I completed the Escape Room’s “Mission to Mars” in Chicago’s River North, and had a great time.
5. Visit an Arboretum or Zoo
You can walk and talk while taking in the scenery and wildlife. A visit to Lincoln Park Zoo (free) followed by a rooftop drink at J Parker, is always a good afternoon. Kam and I walked through the zoo on our third date and it was a memorable day.
6. Dine at a BYOB
I love the vibe of a good BYOB. There are tons of great BYOB restaurants in Chicago. One of our favorites is Irazu in Wicker Park. The portions are generous and the Costa Rican cuisine is delicious.
7. Laugh Your Booty off at a Comedy Club
Take advantage of the world-famous comedy clubs in the Windy City. Zanies offers free admission on Tuesday nights for Chicagoans (bring your ID), the iO Theater does an improv show called Whirled News Tonight every Saturday, and of course, you can’t go wrong with Second City.
8. Learn Improv Together at Second City
If you prefer to participate rather than watch, you and your date can try an interactive, improv comedy class at Second City. My husband and I did the two-hour “Improve Test Drive” together. We had a blast learning some the basic rules of improvisation in a fun and supportive environment. The class takes place every Friday at 5:30pm and Sunday at 7pm. It costs $20.
There’s something special about watching a movie among hundreds of people outdoors with an incredible skyline as the backdrop. During the summer, bring some snacks, a blanket and a bottle of wine and watch a movie at Millennium Park. Here’s the film series lineup for 2019.
10. Take a Massage Class
Why not train your partner to give you the perfect massage? 🙂 Kam and I took a class at The Love Institute, where we learned techniques for better, stronger, and longer massages. It was awesome! The price for two is $175 but we used this Groupon for a 55% off a couples massage class for two.
11. Eat Along Restaurant Row
Randolph Street is jam packed with incredible restaurants, so make a reservation at a hot spot! Even if its a month away, you’ll have something to look forward to it. A couple of places like Au Cheval have first-come first served tables, so put your name on the list and grab a cocktail next door at Lone Wolf or a latte nearby at Sawada Coffee while you wait. Au Cheval will text you when your table is ready.
12. Take a Helicopter Tour of Chicago
Surprise your date with a splurge-worthy experience! Helicopter rides are an incredible way to see the city and make for an unforgettable date. I wrote an entire post and made a video with everything you need to know about booking a helicopter tour in Chicago.
13. Get Drinks at a Speakeasy
Chicago has a storied history when it comes to speakeasies. There are several speakeasy-inspired bars in Chicago to choose from. Some of them have live entertainment, and others have a dark, cozy atmosphere which sets a sexy tone for date night!
14. Do something seasonal
Seasonal activities are special because there’s only a limited time to enjoy them and they can also be nostalgic. In the summer you can visit a farmers market for breakfast crepes (this one is my favorite). In the winter you can go to Christkindlmarket or try something fun from my list of things to do in the Winter.
15. Go to the Dog Park
Do either of you have a dog? Dogs are known to put people in good moods, so hanging out at a dog park is bound to be a fun experience, especially if you are animal lovers. The casual setting is great to get to know each other, and with all the dogs around, awkward silences are nearly impossible.
16. Cooking Class
Learning something new together always makes for a great date. When it involves food and wine, it’s a bonus! Kam and I did a pasta making class through AirBnb. It was an intimate class with only 8 participants taught in the home of a Chicago chef who appeared on MasterChefs!
Our First Few Chicago Dates
I hope that list of Chicago date ideas inspired you to plan a night out with your s/o! I thought I’d share the first few dates I had in Chicago with my now-husband, Kam.
For my first date with Kam, we did the usual – met up for a drink. We were supposed to go to, Drumbar, a chic speakeasy-inspired rooftop bar inside the Rafaello Hotel, but that was closed for a private event, so we ended up across the street chatting over caipirinhas at the The Ritz Carlton hotel bar. He made me laugh on several occasions and left me interested, but it was our second date that got me hooked!
For date number two, he invited me to dinner at Celeste in River North, but what happened next was completely unexpected. Over dinner we discovered we both loved old-school hip hop and rap music, so we decided to wrap up dinner and go to Sub 51 where we danced to our favorite songs all night. Totally unexpected and by far the best second date I ever had.
For our third date, we met up at Lincoln Park Zoo and spent all day talking and walking around the city. It was a great start to our relationship!
Did you have an amazing date idea in Chicago? Let’s hear it in the comments below!
A big thank you to my instagram fam for submitting ideas for this article including: @barbermogul, @mhansen0408, @jjjjohnnnn, @amandafriedman513, @jessicajoy87, @thesocialchicagoan, @carolinecascio.
Be sure to check out my list of Fun Things to Do on a Wednesday in Chicago!
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