City Guides

21 Sure-Fire First Date Ideas in Chicago for 2024

Published on Dec 12th 2024
first date ideas in Chicago

If you’ve faced your fears and asked someone out, you want to make sure it’s one of the more memorable first date ideas in Chicago that they’ve been on. A bit of research and planning will ensure they know that you put some effort into it. Those grand gestures that you see in dating shows are actually the opposite of what you want to do. 

Psychology Today mentions that the scene selection for your first date (like a bowling alley or white tablecloth dinner) is important in creating comfort so you and your date can see if you have chemistry. Ideally, you want something that’s more relaxed than formal because it gives both of you a chance to relax and be yourselves. 

Planning a first date idea in Chicago can be nerve-wracking, so just imagine you’re the one showing up on a blind date or meeting your online pen pal for the first time. Thankfully, you’re in a city that’s bursting with opportunities for fun and connection. From live sports to great food and some seasonal outdoor activities, you’re set up for success with any of these first-date ideas in Chicago. 

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Unique First Date Ideas in Chicago

1. Explore Your Artistic Side

Women in Paint and Sip Class for First Date Idea in Chicago
Doing a paint and sip will help to break the ice (via Classpop!)

This could mean heading to a museum or gallery which works as a nice and quiet first date idea in Chicago. Or, you can try some creative practices firsthand with a paint and sip in Chicago. Activities like these help to break the ice and get you talking.

2. Take a Speakeasy Tour

The Windy City has a long history with prohibition and secret speakeasies, and a guided tour of this way of life will be one of the most unique first-date ideas in Chicago you will ever experience. Under a blanket of darkness, make your way to several original speakeasies and learn about their history from your expert guide. You can even sip a few adult beverages, legally. 

3. Savor Beer and Chocolate Cake

While the combination might sound a little outlandish, they are both immensely popular at Moody Tongue, a brewery with two Michelin stars. You don’t have to enjoy them at the same time, but after a flight of some of their specialty beers like the juiced lychee IPA or caramelized chocolate churro porter, save some room to split a piece of 12-layer chocolate cake. For a couple of foodies, this is one of the most unique first date ideas in Chicago.

4. Enjoy the Architecture By Boat

An architectural boat tour is not only a unique first-date idea in Chicago but also one of the best ways to take in so many of the city’s incredible sites and skyscrapers. Make it a little more romantic by taking the cruise at night so you can see everything all lit up and magical with a cocktail in hand. You’ll enjoy your company (along with the view) while also learning about Chicago’s history.

5. Order Drinks at Milk Room

Milk Room Bar
Milk Room is a microbar with a history (via Milk Room)

There are about a million bars and restaurants to choose from when you’re planning a unique first date idea in Chicago, but Milk Room is an experience you’ll never forget. This tiny bar only seats eight people, so you’ll need to plan ahead. All the drinks are made with rare, vintage spirits for a one-of-a-kind sip. 

Best First Date Ideas in Chicago

6. Ride the Ferris Wheel at Navy Pier

While Navy Pier is pretty touristy, you can still enjoy one of the best first date ideas in Chicago here with the Ferris wheel. Enjoy a little adrenaline rush paired with some quiet time just the two of you as the wheel slowly circles around, showing different views of the city along the way. Each little gondola is enclosed so you can enjoy this attraction all year round. 

7. Drive-In at Superdawg

Skip the fancy dinner reservation and keep it classic with one of the best first-date ideas in Chicago. Enjoy Chicago-style hot dogs, fries and maybe a supershake or supermalt at this funky retro drive-in. The business has been around since 1948 and was opened by two high school sweethearts. Maybe that’s good juju for your new relationship? Either way, you can’t go wrong starting off with one of the most iconic Chicago foods

8. Walk (or Bike) the North Shore Channel Trail

Get out and enjoy some fresh air and exercise with plenty to see and do on this first date idea in Chicago. The North Shore Channel Trail follows the Chicago River up to Evanston and there are plenty of sites and attractions worth stopping at on your way. You’ll get farther on a bike than on foot and could even make your way up to Lincolnwood Town Center or the Skokie Northshore Sculpture Park.

9. Appreciate the Arts at AIC

Art Institute of Chicago First Date Idea in Chicago
Lose yourselves in the Art Institute of Chicago (via Canva)

The Art Institute of Chicago proudly displays Van Gogh and Picasso pieces on their crisp white walls, but there’s plenty more to take in here. Head down to the basement for a giant room filled to the brim with miniature dioramas, 68 to be exact, each crafted by an artisan so they are beautiful and authentic. It’s the perfect quiet place to get to know someone and discuss art with one of the best first-date ideas in Chicago. 

10. Grab a Seat at Guthrie’s Tavern

This cozy old tavern is perfect for first-date ideas in Chicago because it’s laid-back while also offering a great selection of beer and tasty bites. Even better, they have an impressive selection of board games you can use while you dine there, the perfect thing to keep that first date conversation flowing and take your mind off your nerves. Not into board games? Check out Tuesday night trivia or free donuts on the weekends. 

Romantic Date Ideas in Chicago

11. Take a Swan Boat Cruise

Just like a scene out of The Notebook, a private swan boat ride for two is an ultra-romantic date idea in Chicago for lovers. From May until September, you can rent one of these majestic paddle boats in Humboldt Park Lagoon. 

12. Jam Out to Music Together

Whether you’re making the most of summertime in Chi with outdoor concerts or cozying up in a small jazz club, experiencing live music together is always a romantic date idea in Chicago. Enjoy a free outdoor concert at Millennium Park Summer Music Series, or head over to The Green Mill for some swanky jazz beats. Tickets to his or her favorite artist make for one of the best experience gifts in Chicago

13. Pamper Yourselves at AIRE Ancient Baths

AIRE Ancient Baths Chicago
AIRE Ancient Baths (via AIRE)

You’ll feel like you’ve been transported out of the city with this luxurious and romantic date idea in Chicago. Spend an afternoon at the AIRE Ancient Baths where you can spend hours soaking in cool, warm and hot baths. Add on something special like a massage to make it extra special. 

14. Sip on Cocktails at Watershed Bar

Make your date feel special when you take them for a special drink at the Watershed Bar. Located in a basement in River North, it’s decked out in Gatsby style and features a fun cocktail menu with names like “Episode 1” and “Episode 2” for the drinks. Or, a staff member will walk by with a beverage cart loaded with rare spirits for you to try. 

15. Eat Dinner at Anelya

Every bite and sip at Anelya is magical with a touch of whimsy, making it the perfect spot for romantic date ideas in Chicago. Mood-lighting is cast by funky neon flower-shaped lamps and your food just might arrive on a shiny zakusky cart. The food is just as enticing and memorable on your first time here as it is for your hundredth. With strong Ukranian influence, it makes for a mouthwatering meal that’s a little different from your usual date night dinners. 

Cheap Date Ideas in Chicago

16. Spend the Day at The Point

Right in the Hyde Park stretch of Burnham Park, you can find this stunning man-made peninsula called Promontory Point or just The Point. On a warm spring or summer day you can hang out here, swimming, paddling and watching the sunset. Pack a picnic and a blanket and make a whole afternoon of this cheap date idea in Chicago. 

17. Plan a Beach Day

Beaches First Date Idea Chicago
Make the most of Chicago's waterfront location (via Canva)

One of the coolest parts about this city is the fact that you have a massive body of water and soft sandy beaches bordering a concrete jungle. When the sun is shining on a summer day, you can sunbathe or stroll along the shoreline for an enjoyable and cheap date idea in Chicago. 

18. Find Peace at Garfield Park Observatory

This stunning indoor sanctuary is free and open 365 days a year, and it just happens to be a great spot for a cheap date idea in Chicago. Admire the hundreds of unique plant species that thrive here as you walk and talk with your date. It’s extra enjoyable when the weather outside is bad because you’re blissfully protected under the glass dome. It’s one of the most enjoyable indoor activities in Chicago because you still feel like you’re outside. 

19. Tour the Lincoln Park Zoo

You don’t have to be a kid to enjoy the zoo, and you just might find it makes for a perfect cheap date idea in Chicago. The zoo itself is massive and well-regarded as a top-notch facility. Two swans were all they had back in 1868, but today the zoo has just about everything from penguins to lions and tropical birds galore. 

20. Ice Skate at Millenium Park

There’s always something happening at Millenium Park, and their winter ice rink is the most romantic cheap date idea in Chicago. Reservations are free, but required, to ensure the rink isn’t too crowded. Soak up the magic of winter then warm up with some hot cocoa.

21. Bird Watch at Northerly Island Park

Northerly Island Park
Northerly Island Park (via Canva)

There’s so much to see in this park situated on the shoreline of Lake Michigan. Follow the walking paths around ponds and prairies where you can observe more than 150 species of flora and tons of wildlife. There are occasional special events here worth checking out, but even on a weekday, it’s a relaxing and beautiful cheap date idea in Chicago. 

First Date Ideas in Chicago FAQs

What is the Best Plan for a First Date?

There’s no formula for planning the best first date idea in Chicago or anywhere for that matter, but there are some key ingredients or things to consider. The whole point of the date is getting to know someone so seeing a movie or some other sort of show is better for later dates. 

You want it to be a place or activity that’s relaxing because first dates can be nerve-wracking. Some things like riding bikes, walking, running or playing mini putt work as a great distraction so you aren’t just staring at your hands trying to think of what to say. 

If you want to go the classic dinner or drinks route, make sure that it’s a good spot that’s not too formal. There are tons of nice Wicker Park restaurants that are trendy and fun, perfect for wooing someone special. One of the most important things you can do is ask questions before picking a spot. 

Maybe he or she mentioned really wanting to try that new Asian restaurant uptown that supposedly has the best ramen in Chicago. Or, they might be vegan! In which case a steakhouse or even a Chicago dog would be a big no-no. 

You want to consider them and their preferences when planning a first date idea in Chicago. Keep it casual and approachable, but not so low-effort that they don’t feel special. 

What Should an Ideal First Date Be?

There’s really no right or wrong way to have a first date, and if you get a little curious before announcing the plan, you’re destined for success. The smallest detail that they shared ahead of time means so much when they notice it in your planning. Dates don’t have to be expensive or extravagant, but they do have to be thoughtful. 

Oh, and they should ideally set you up for conversation and a shared fun experience early on, so that person feels like they’re getting to know you and vice versa. If your first date doesn’t go to plan, that doesn’t mean the relationship is doomed. It’s always good to have a backup plan in place and be flexible to change. 

 

When you’re living in a bustling metropolis like Chicago, dating and picking the perfect first date spots can feel overwhelming. With so many choices, you can find yourself in analysis paralysis pretty quickly. Just come back to these pointers and first-date ideas in Chicago and know that if you’re genuinely trying to plan something nice, it will all work out. 

For even more fun date ideas in Chicago, check out other experiences happening on Classpop!