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Best First Date Ideas in Chicago | 5 Places She'll Love

August 23, 2012

You've finally got a date with the Chicago girl you'd like to take home to the family. But you don't know where to take her: what are you supposed to do for your first date?

Olive Garden isn't going to work for all its class and Italian spirit, despite its fantastic reviews lately.  The restaurant down the street your cousins own is a no-go, in case they mention your clingy, desperate side. In that case, you might like to check out our list of the absolute best places to take a girl in Chicago on a first date that will impress her, please her, and hopefully get you that second call back.

Millennium Park

Take your date for a casual, elegant stroll through the most beautiful park in Chicago, where you'll have time to find her soft side, figure out what she likes and dislikes, and see if there really is a spark in between you too. You can have a reflective moment at the Bean, marvel at the Crown Fountain, and finish off the night with dinner at a classy but suave restaurant on nearby Michigan Avenue. This works twice as well if your date has never been in Chicago before, as you'll see Chicago's most beautiful and visitor-friendly sites.

The House of Blues

For an entertaining and delicious evening, go on a first date at the House of Blues, a combination event venue, music concert hall, and excellent restaurant featuring major bands from around the U.S.A. Just in the next week, you'll find the best Gospel Brunch in the nation, Seether, and Tesla performing, as well as many more excellent musicians arriving nonstop. The food is pretty great, too.

Café Ba-Ba-Reeba

A creative and uncommon place to take a date in Chicago, this excellent cafe is known for its amazing Spanish Tapas and top-notch sangria that will blow you out of the water. If you don't know what either of those words mean, all the better: it'll be a first-time experience for both of you. Rest assured, trying the dozens of small dishes in Tapas is a great way to spark conversation, and even if she decides that she's not particularly fond of it (she'll love it, trust us), you'll have a unique shared memory to look back upon when you're old and married together.

Art Institute of Chicago

Chicago's premier art museum is chock-full of opportunities to display your incredible intellectual skills, care for the high arts and unique ability to make any painting into a mildly interesting story about yourself. You'll find famous Impressionist and Post-Impressionist paintings such as Edward Hopper's Nighthawks and over 30 genuine Monets. You'll see van Gogh's Bedroom in Arles and Renoir. Just be sure to brush up on your painter's terminology to appear informed and cultivated.

Navy Pier

There's no better place to go than the Navy Pier for a first date in Chicago. Ride on the massive Ferris Wheel and admire the Chicago scenery. Win her a stuffed elephant from the ring-tossing carnival game. Go for a long, romantic, introspective walk down the side of the pier. Watch a movie at the IMAX theater. Race through the Funhouse Maze for a healthy dose of competition, adrenaline, and absolute confusion. You'll have no shortage of things to do, even for the most seasoned Chicago resident.

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