The 11 Best Date Ideas in Chicago | Aldult Toys Blog

Planning the perfect date can be a difficult task, it’s not always easy to find the perfect balance between fun, romance, and memories. Whether you’re in a long-term relationship or just getting to know each other, 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 entertain your inner child, and take a ride on the iconic Ferris wheel! Admire the cityscape and lake views from the top of the city (or so it seems).

Don’t forget to check out the fireworks program and enjoy the breathtaking spectacle to crown a romantic evening.

2. Wrigley Field

If you’re looking for 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 singing “Take Me Out to the Ballgame” in front of a crowd of Cubs fans. Sports fan or not, this date is sure to be a hit.

Otherwise, if you’re out of town during baseball season, catch a Bulls game!

3. Lincoln Park Zoo

Take your coffee and walk date to the next level and head out into nature…a stroll through Lincoln Park Zoo. Perfect for a first date, you’ll have plenty of time to chat and get to know each other, and the wildlife will help break the ice in case of an awkward silence.

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

4. Comedy Club

Chicago’s comedy scene is no picnic (pun intended). Head to The Second City for a world-class improv show, or venture to one of the city’s many comedy clubs for knee-slapping stand-up. The comedy scene is strong here, so you’re sure to find something that will make you laugh!

5. Food Truck Festival

Chicago’s food scene is absolutely to die for. If you’re looking for a unique culinary experience, look no further than a food truck festival! Explore the world of mobile restaurants and the different cuisines they offer. Remember, a couple that eats together stays together (at least until dessert).

6. Art Institute of Chicago

If you and your partner prefer something a little more artistic, look no further! You can’t go wrong with a visit to the Chicago Art Institute, one of the oldest and largest museums in the world, where you can get totally lost in art for hours! If inspiration strikes (and the date is going well), get creative and give it a try yourself. Try erotic body painting or life drawing (Titanic, anyone?).

7. Picnic at Millennium Park

Take a stroll through one of Chicago’s iconic parks, Millennium Park. Home to Cloud Gate (nicknamed “The Bean”), Millennium Park also hosts many free concerts in the summer! So, pack your picnic basket and head out for an evening of live music and romance in the park.

If you’re looking for a winter getaway, try the park’s ice rink!

8. Kayak on the Chicago River

For a totally unique perspective on the city, hop in a kayak and paddle down the Chicago River. This is a unique adventure that takes you right into the heart of the city, without the traffic of Michigan Avenue. If you don’t feel like walking on the river (and I’m being honest), take a stroll along the Riverwalk instead.

For an even more festive date, do it on St. Patrick’s Day when the river is a vibrant green! The streets are too crowded to walk around, so the river is honestly the most relaxing place to be.

9. Garfield Park Conservatory

If you love getting in touch with nature (but maybe not touching the river), the Garfield Park Conservatory is the tropical getaway for you! Stroll through the lush gardens and don’t forget to check out their calendar for special events, such as a romantic evening Music under glass!

10. Day at North Avenue Beach

A hot day in Chicago means a date at North Avenue Beach. Whether you’re relaxing by the lake, playing beach volleyball, or just strolling hand-in-hand along the shore, this fun date is sure to be a hit!

11. Cook County Forest Preserves

Escape the hustle and bustle of the city for the afternoon and head to the Cook County Forest Preserves. If you enjoy the outdoors, this is the perfect setting for a couple’s hike or bike ride. Enjoy a break from the city and reconnect with nature… you might even indulge in the pleasures of nature in the woods.