So You Want a Perfect Date Night in Chi?

If you’re anything like us, trying to think of what to do with your SO can be a bit of a headache and usually ends with hitting up the same bar spot for the 10th time. Don’t get us wrong, there’s nothing wrong with tradition, especially if your go-to spot is a favorite. BUT if you’re into trying something new and don’t know where to start—look no further! We’ve put together this list of some dates you may not have thought about yourself. Even if you don’t see anything that fits your tastes on this list, hopefully it’ll will get you thinking outside of the box to come up with your perfect summer date night in Chi.


Visit a Conservatory

Perfect for those chilly summer days—take your love to the conservatory to experience all the beauty of nature in a range of climates! Our favorite is Garfield Park Conservatory but if you don’t want to make the trip all the way there Lincoln Park Conservatory is killer too! We go almost weekly and can’t get enough.

Museum Night Out


Take a trip to Museum Campus in the evening for a romantic, evening date. The Adler Planetarium hosts Adler After Dark every third Thursday of the month and the tickets are extremely affordable ($20/person!). You’ll have access to the exhibits, galleries, unlimited shows, and they even serve cocktails and small bites.

Rooftop Dining

A few weeks ago we rounded up some of our favorite rooftop/outdoor spots in the city for this summer. Any of these awesome spots would be perfect for a breezy night out on the town. From The Dawson to Cindy’s, there something for everyone in our list, so why not give them all a try to find your favorite! Here’s a link to everything!

Go to The Magic Lounge


If you’re looking for something a little more different and exciting than your typical date spot, try out The Magic Lounge to be entertained with cocktails and card tricks! Open 5pm every night (except Sunday!) so there’s plenty of opportunities to plan your magical evening!

Trivia Night

Logan Theatre renovations

Are you and your SO movie buffs? If so, try visiting the Logan Square Theater for Movie Trivia Night to test your knowledge! It’s hosted every Tuesday at 8pm in the Lounge and the winning team gets a gift card to the theater. You can bring up to 5 people for your team so why not make it a double date?

Arcade/Game Night

There are plenty of places in the city with arcades or game nights, but out favorites have to be Emporium Arcade Bar and Royal Palms. For more of a laid back, true arcade vibe go for Emporium. It has everything from frogger to pac-man, even air hockey! Royal Palms is the place to be for those who want a more polished (and adorably decorated) atmosphere and out-of-the box games. They’re specialty is shuffle board but they have many others tucked into the corners of their space. Finish it off with some tropical drinks and you’ve got yourself a perfect date!

Kayak/Boat Through the City


Grab your date and head to Wateriders to rent yourselves a kayak! Now you can spend the evening kayaking through the Chicago River. It’s a beautiful way to see your city from a completely new perspective. If kayaking isn’t your thing, don’t worry! Rent a boat or take a guided tour instead. We love the architectural tour as it’s a great way to see all the beautiful buildings as well as learn a few things about the history of some of them.

Check out a Food Festival


If you guys are foodies then Chicago is definitely the city for you. There are countless food fests throughout the summer so depending on your tastes there’s bound to be something that fits. We’d recommend the Tacos y Tamales Festival in Pilsen as it not only has delicious food, but there are art installation, local artisans, and even dance performances. It’s happening July 20th-22nd so be sure to add it to your calendar!

Mini-Golf + Ice Cream

Always a winning combination: old school mini-golf and ice cream! Make your way to Novelty Golf in Lincolnwood (just a little north of the city) to show off your mini-golfing skills and then head over to Dairy Star for a delicious ice cream treat to finish off the night.

Go on a Bike Ride

Rent a set of Divvy Bikes and bike along the lakeshore path for a beautiful view of the city and Lake Michigan. But don’t stop there! Bike along lakeshore until you reach the Shore Club near Lincoln Park and The Gold Coast to some upscale eats and craft cocktails. With a patio a restaurant, and their Oasis, you can decide where you’d like to spend your evening after a relaxing ride along Lake Michigan.