14 Unique First Date Ideas In Chicago To Woo Your Potential Boo (2024)

So you’ve landed a date with someone you’re really excited about, and now you’re trying to plan a first date that’ll impress them enough to land you a second one! Luckily, you live in one of the coolest and most beautiful cities in the world, so you have so many options to choose from. To help you wade through this array of choices, we’ve assembled a list of 14 unique first date ideas in Chicago that will help you successfully woo your potential boo (along with your good looks and winning personality, of course!).

Keep reading for our top recommendations, including a few suggestions that use Peerspace venues as their setting!

1. Go on a ghost tour led by Windy City Ghosts

This first date idea in Chicago isn’t going to be for everyone, but if you and your date happen to be the kind of people who love a spooky story and whose favorite holiday is Halloween, Chicago’s most haunted ghost tour from Windy City Ghosts is an awesome option. After all, Chicago has centuries of fascinating history that have led to equally fascinating hauntings around the city: Al Capone, the Great Fire, Prohibition, and so much more. Their standard tour covers eight haunted sights, so you and your date will definitely get your money’s worth! 

2. Cook your date dinner at a Peerspace with a kitchen

If you’re a good cook, one of the most effective ways to impress a first date might be showing off your cooking skills by making the two of you an unbelievably delicious dinner. 

Perhaps you’re not comfortable inviting your date over, for whatever reason, and would rather rent a space with a kitchen. Since we mentioned that Peerspace is the internet’s top marketplace for hourly rentals of event venues and other spaces, you’re probably curious about what the site might have to offer when it comes to Peerspaces with kitchens in Chicago.

Here are a few great examples:

• This warm, sunlit studio with a kitchen and plenty of top-notch cooking equipment. This space is located in Ravenswood and has tons to offer: lots of natural light, 750 square feet of space as well as 10-foot ceilings, and a view of the treetops out the large windows. 
• This one-of-a-kind intimate space, which has been decorated with upcycled lighting, reclaimed wood, and many stunning antiques to create a cozy vibe. 
• This modern Logan Square space with a killer chef’s kitchen is billed as perfect for a private dinner, and we agree—it has two full size ovens, a whopping ten burners, and a full size fridge/freezer and wine fridge, not to mention an inviting ambiance.

There are hundreds more of these kinds of spaces to be found in Chicago, so be sure to run a quick Peerspace search to find more of what’s out there!

3. If you must get coffee, get really good coffee

Chicago has tons of amazing coffee shops to choose from. If you and your date are sticking with coffee for your first meeting, make sure to go to one of the city’s best coffee places to make it extra special.

4. Paddle a swan boat on the Humboldt Park Lagoon

This is pretty much the adventurous opposite of getting coffee for your first date—paddling a swan boat together will require the two of you to work together and may just end up being an effective way to really get to know each other!

Whether you or your date have an upcoming birthday, this list of Chicago’s funnest birthday ideas will provide you even more ways to enjoy the town together!

5. Go mini-golfing at the Big Mini Putt Club

This nine-hole, indoor mini golf course is right next to a full bar, so you’ll have everything you need—entertainment and beverage options—for a successful first date. Plus, getting competitive on a first date is a great way to break the ice and get to know each other a little better. 

6. Go bowling at 10 Pin

Bowling is a classic first date idea, and once again, we think it’s the element of competition breaking the ice that makes it such an appealing activity for two people just getting to know each other. The great thing about 10 Pin is that they offer a tasty, elevated American-inspired gastropub menu, instead of the usual bowling alley fare you’ve come to expect.

7. Play video games at Emporium Arcade Bar

Yet another competitive first date option is Emporium Arcade Bar, which has classic arcade games as well as pinball, an excellent bar, and other entertainment options like live shows, DJs, game tournaments, and more. If you and your date are retro gaming aficionados, it’ll be an especially thrilling way to get to know one another!

8. Go to a Michelin-starred restaurant

As of the most recent Michelin Guide released in 2023, Chicago has a total of 22 restaurants with Michelin stars, with Alinea and Smyth being the only Chicago restaurants with three stars each. Taking your date to any of the restaurants on this list is sure to impress them if you can afford to go out for an extra special meal!

9. Go ice skating at one of Chicago’s best ice rinks

Is your date happening during the frigid months of a Chicago winter? Take advantage of that fact by incorporating a trip to one of the city’s many ice rinks into your first date plans! Then the two of you can warm up over mugs of coffee or hot chocolate, which sounds like the perfect combination of romantic activities to us.

10. Go kayaking on the Chicago River with Kayak Chicago

Did you know that you could go kayaking right in the middle of Chicago? And not only that, but it’s one of the best ways to take in the architecture and the sights of the city. Kayak Chicago offers tours where they’ll lead you through the whole experience from start to finish, and in addition to kayaks, they also have canoes and stand-up paddleboards to choose from.

Be sure to scope out our sick Instagram location ideas in Chicago if you and your date bond over your content creation chemistry!

11. Visit the animals at Lincoln Park Zoo

The 35-acre Lincoln Park Zoo is the fourth oldest zoo in North America, with 200 species on exhibit including big cats, penguins, gorillas, reptiles, polar bears, monkeys, and more! (Plus, it’s free, so this isn’t just one of the great first date ideas in Chicago—it’s an affordable one. You’ll have plenty of money left over for lunch or dinner.)

12. Go on one of the best hikes near Chicago

Depending, of course, on how willing you are to travel, there are tons of beautiful hikes near Chicago, if you and your date are the kind of people to go on a hike for a first date!

13. Show off your ability to pack a picnic at an outdoor Peerspace venue

Assuming that the weather is nice, we’d recommend a picnic as an ideal way to make your date feel special and ensure the two of you have a blast! Be sure to ask your date what they like to eat and make sure you take note of any food allergies/intolerances they may have, or whether they’re vegetarian/vegan. 

There’s no question that Chicago has tons of lovely public parks to choose from—one of the best things about this amazing city—but you might also consider the alternative of renting an outdoor Peerspace venue in Chicago.

Here are just a few examples of the incredible venues waiting to be discovered in Chicago:

• This boutique event garden house in Park Manor, which has a comfortably furnished outdoor area with lots of greenery and an outdoor dining table, not to mention numerous positive reviews that attest to how lovely it is in person!
• This charming inner-city garden and pergola, which comes with a range of amenities that include plenty of seating (including two egg chairs!), tower heating lamps for use in chillier weather, a charcoal BBQ grill, and access to a bathroom. 
• This backyard oasis in nearby Clarendon Hills, where you’ll have access not only to a 4,000-square-foot lawn but also to an in-ground heated pool, a fire pit, two built-in gas grilling stations, and an elevated deck with plenty of seating. It’s easy to imagine spending hours relaxing here!

We’d also recommend doing a Peerspace search yourself so you can use the numerous detailed filters to find spaces that have exactly what you’re looking for.

14. See impressive Chicago-style magic performances at the Chicago Magic Lounge

For a truly unique first date idea in Chicago, how about a trip to see the traditional Chicago-style magic featured at the Chicago Magic Lounge? You and your date might find yourselves genuinely amazed by the close-up magic you’ll see here.

First date ideas in Chicago: conclusion

Having reviewed all 14 of our suggested first date ideas in Chicago, you might now be moving on to the decision-making part of the process: which idea—or ideas, if you’re feeling ambitious!—will you choose? As you decide, don’t forget that you can access tons of amazing and private spaces throughout Chicago by renting them through Peerspace, whether you’re cooking your date dinner, planning a picnic, or some other idea entirely!

Find unique date venues in Chicago on Peerspace