The top 11 date ideas in Chicago

Planning the perfect date can be a tall order, it's not always easy to strike the perfect balance between fun, romantic, and memorable. Whether you're in a long-term relationship or just getting to know eachother, we've got you covered! Here are 11 ideas for the best dates in the Windy City. 

1. Navy Pier

A true gem that stands the test of time for both locals and tourists. Indulge in all the rides and games that are sure to keep your inner child thoroughly amused, and go for a spin on the iconic Ferris wheel! Take in the cityscape and lakeside views from on top of the city (or at least what feels like it).

Don't forget to check out the fireworks schedule and enjoy the amazing show to cap off a romantic evening.

2. Wrigley Field

If you're looking to score an epic date, head to a Cubs game at the iconic Wrigley Field. There’s no better way to spend a day than sharing Cracker Jacks and peanuts, and belting “Take Me Out to the Ballgame” in a crowd of Cubs fans. Sports fanatics or not, this is definitely a home-run date.

Alternatively, if you're not in town during baseball season hit up a Bulls game! 

3. Lincoln Park Zoo

Level up your generic “coffee and a walk” date and take a walk on the wild side... well a walk through the Lincoln Park Zoo. Perfect for a  first date, there's plenty of time for get-to-know-you chat, and the wildlife offers an easy ice breaker in case of any awkward silences. 

Bonus: This date is totally free (Read: money for post-zoo drinks at a nearby cocktail bar!)

4. Comedy Club

Chicago's comedy scene is seriously no joke (pun intended). Hit up The Second City for world-famous improv show, or venture out to one of the city’s many comedy clubs for some knee-slapping stand-up. The comedy game is strong here, so you’re sure to find something that will tickle your funny bone!

5. Food Truck Festival

Chicago's food scene is absolutely drool-worthy. If you're looking for a unique culinary experience, look no further than a food truck festival! Explore the world of rolling restaurants and the various cuisines they have to offer. Remember, a couple who eats together stays together (at least until dessert).

6. Art Institute of Chicago

If you and your date prefer something a little more artsy, look no further! You can't go wrong with a visit to the Chicago Art Institute, one of the countries oldest and largest museums in the world, so you can get totally lost in the art for hours! If inspiration strikes (and the date goes well), get creative and give it a go yourselves. Try some erotic body painting or life drawing (Titanic, anyone?).

7. Picnic in Millenium Park

Head out for a walk in another one of Chicago’s iconic parks, Millennium Park. Home to Cloud Gate (aka “The Bean”), Millennium Park is also host to many free summer concerts! So pack your picnic basket and head our for an evening of live music and romantic vibes in the park.

If you're looking for a winter date, try the park's skating rink!

8. Kayaking on the Chicago River

For a totally unique perspective of the city, hop in a kayak and paddle down the Chicago River. This is a unique advendure that takes you right through the heart of the city - without the Michigan Ave traffic. If being on the actual river is not your vibe (super fair), take a stroll along the Riverwalk promenade instead. 

For an extra festive date, do this on St. Paddy's Day when the river is bright green! The streets are too packed to get anywhere so the river is honestly the most chill place to be. 

9. Garfield Park Conservatory

If getting in touch with nature is your thing (but maybe touching the river isn’t) the Garfield Park Conservatory is the tropical escape for you! Wander through the lush gardens and be sure to check out their calendar for special events, like a romantic evening of Music Under Glass!

10. Beach Day at North Avenue Beach

A hot day in Chicago, calls for a date at North Avenue Beach. Whether you're relaxing by the lake, playing some competitive beach volleyball, or simply strolling hand in hand along the shore, this fun date is sure to make a splash! 

11. Cook County Forest Preserves

Ecape the urban hustle and bustle for the afternoon and head out to Cook County Forest Preserves. If you're the outdoorsy type, this is the perfect setting for a couples hike or bike ride. Enjoy a break from the city and connect with nature... Maybe even get a little naughty in the woods.