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The best fun date ideas in Chicago

Coming up with fun date ideas is often itself not a fun thing to do, but on these dates you won't even have to try

Photograph: Jordan Avery

Until we get better acquainted with our better halves, most dates will likely involve some degree of imbibing. Luckily there are plenty of bars in Chicago to that end. Drinking isn't always necessary to have fun though. The dining scene has produced some pretty great romantic restaurants in Chicago, and we've got loads of romantic places to go, but when you're armed with fun date ideas, you can guarantee a good time.

Go on a thrifting expedition

Before there was Craigslist, there were thrift stores—places where you could find a great gag gift for a friend or a seriously cheap piece of vintage furniture for your own humble abode. Well, Chicago still happens to have a ton of these. Chicago's best thrift stores offer up a great way to browse and get to know someone better without the stress or the hefty price tag shopping can induce.

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Visit Revolution Brewing Taproom

Beyond being just a cool place to hang out with pretty much anyone, the light and airy Revolution Brewing Taproom offers a chance to sample the brewery's latest and freshest beers, as well as an endless supply of its old standards. The tour isn't half bad either. Oh, and there's shuffleboard.

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Enjoy a night at the theater

If you're not already a fan, take all your preconceptions about theater and toss them in Lake Michigan. Chicago has the best of the big and small stage, as well as a helping of Broadway shows that make extended stays in town. Chicago theater is a better date than the movies, or yet another night of "Netflix and chill."

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Try the West Loop sandwich crawl

A tipping point occurs in almost every relationship where eating this much bread and meat in one another's company is not only possible, but an inevitabile. Enter this delicious sandwich crawl through the West Loop, which is currently one of Chicago's best neighborhoods for food and drink at any time of day.

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Board game and a beer

Board games and booze make the perfect companions, and these 12 bars have that relationship on absolute lockdown. If you're more of a Chutes and Ladders kind of gal, or if you prefer the more advanced realm of geekdom in Settlers of Catan, Chicago has something for you—and your date. Geek Bar even offers Dungeons & Dragons for the more stalwart devotees of games sans TV screen. Roll for initiative!

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Go on a Segway tour

Wait, wait, wait. Yes, we are serious! Nobody is too cool to go on a Segway. Scooting around like a dork is actually pretty fun and it'll show your date you know how to put away your pride and have a good time.

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Hang at Chicago Athletic Association

To say the Chicago Athletic Association is beautiful is to put it mildly. From the unparalleled view of Millennium Park and Lake Michigan at Cindy’s rooftop restaurant to more great food and drink at Cherry Circle Room and Shake Shack, there’s no shortage of options. You’ll also love the Game Room, with its private alley entry and bocce, shuffleboard and billiards. Find access to everything you need and more in this wonderfully restored 1890s building.

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The sweet serenade

If you don't want to ride a Segway through the Loop, this is another endearing way to make an ass out of yourself. Who knows? You may even find out you have a pretty good set of pipes. Or maybe you've just been waiting to unleash a Savage Garden serenade on an unsuspecting date. These karaoke bars range from straight-up dive bars to entire establishments dedicated to the amatuer sing-along.

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Cheer on the Sox

Cheering on the White Sox is much less an ordeal than cheering on the Cubs, and it’s so much more the outing. Wrigley Field might have its charms, but the Sox stadium is already nestled in Chicago’s Bridgeport neighborhood, making for a fun day trip, and only a short jaunt away from the culinary and cultural attractions of Pilsen.

To follow and purchase tickets for White Sox games, click here

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