10 Great Casual Date Ideas If You Live In Chicago

Posted by Leticia, 14 Dec 15

Do you live in the Chicago area? Having trouble dreaming up a good casual date idea to impress your new girl? If so, you’re in luck. Below, you’ll find an assortment of great, fun, casual date ideas that will leave your lady wanting more. Read on, and enjoy!

1) Brookfield Zoo

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With more than six thousand animals, there’s always a lot to see at Brookfield. If the weather’s nice, the two of you can make an afternoon of it. Entertainment, lots of exhibits, food, and a fun, casual atmosphere. What’s’ not to like about that? Visits to the zoo usually evoke pleasant childhood memories, too, so your date will have several reasons to smile. If she's an animal lover, give this one some serious consideration.

2) The Museum of Contemporary Art

This is a great casual date venue if your girl has an artistic streak. Featuring one of the largest collections of modern art in the nation, you’ll find enough here to fill up the whole day if you feel so inclined, from the exhibits themselves, to the sculpture garden, a movie theater, and even a restaurant for after you’ve spent the afternoon wandering.

3) Navy Pier

With a good mix of outdoor activities, lots of cafes, bars and assorted shops to wander in and out of, and a lively lake shore ambience, the two of you can have fun in a relaxed atmosphere. Plus, you’ve got the added advantage of getting to know more about her by the types of places she’s drawn to here. If you’re not sure what you want to do, but want to maximize your options for the afternoon, this is a great choice.

4) Water Tower Place

Whether you want to take her shopping, or just go hang out in a place with tons of stuff to do, Water Tower Place should be one of your go-to venues for casual fun. Teeming with people, loaded with a variety of shops and places to eat, there’s never any shortage of fun things to see, do, and experience here. A great, casual place to spend an afternoon or evening together.

5) Wrigley Field

We can’t very well talk about casual fun in Chicago without bringing up the legendary stadium, right? Even if you’re not going for a game, and even if it’s the off season, there’s still plenty to do here, from seasonal tours to ice skating in the rink just outside the field. An area landmark, and not to be missed. It’s even more fun when you get to enjoy it with someone special.

6) Green Mill

What about an evening of live music at the club made famous by the likes of Al Capone? Lively and jumping, there’s always fun to be had at Green Mill. If your girl is a music lover, this might just be the perfect casual date venue. A great choice for a music lover, or anyone who loves to experience the city's night life.

7) North Avenue Beach

Even if you don’t feel like taking a dip in the waters of Lake Michigan, there are still plenty of things to do here. As one of the city’s most popular beaches, you can rent a bike and go for a ride together, grab a snack at any number of places, hit the volleyball courts, and more. It’s all but guaranteed to be a fun filled afternoon.

8) Go On A Pizza Tour

Chicago is famous for lots of things, including Chicago-style pizza. Why not make an adventure of that? Map out a route that takes you past several eateries and try a slice from each to see which you like best. Whether you agree on the winner or not, it’s a great way to spend an afternoon and evening together. Just be sure to bring your appetite and tell her to do the same!

9) Rent a Pair of Harleys

Yes, you really can do that! Just check out EagleRiders. Rent one and ride together, or rent a pair and spend the afternoon exploring on the back of THE quintessential American motorcycle. Not every girl will be into this, but if your girl has a wild, adventurous side, this could be the date she remembers and talks about for years to come.

10) Scavenger Hunt

The City of Chicago has an interesting, innovative way to get to know the area. Using your smartphone, you can go on a “scavenger hunt” that will take you to various parts of the city as you follow clues and look for various landmarks. It’s a casual, fun date that will literally see you cross-crossing the city. Just be sure you’re both wearing comfortable shoes.

As we mentioned, this list barely scratches the surface. There’s so much to see and do in Chicago, that we could probably write a whole book about it. If you want to set a fun, casual tone for you’re a memorable date with the most important person in your life, try one of these on for size!

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