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9 Chicago Date Ideas That Never Fail

couple on bp bridge in millennium park in chicago

When it comes to finding great date ideas, Chicago couples have a lot to consider. What season is it? What team does my date root for? Is it ever socially acceptable to lady n’ tramp a slice of deep dish pizza? To help take some of the guesswork out of planning a date night in Chicago, we’ve put together this list of 9 fun date night ideas we think any Chicago native (or newcomer!) would love.

chicago architectural boat tour

1

Cruise Around Town on a Boat Tour

Yes, it’s true that this is very seasonal, but that’s also part of what makes it such a special outdoor Chicago date idea. Book the architecture tour, and you’ll treat your date to one of the very best views of Chicago’s downtown, and, if you book in late afternoon, you might be lucky enough to catch the sunset reflected off the shimmering buildings as well.

karaoke party

2

Belt Out a Tune at Karaoke

There is perhaps no more intimate a moment in a relationship than the one where you realize your SO knows all the words to “Spice Up Your Life”. Take things to the next level by hitting up one of the city’s many karaoke bars, where shots of soju make this knowledge that much easier to bear. We like U Star Karaoke, since it’s a mere hop away from the famed Indian restaurants on Devon (hint, hint).

couple at a cooking class

3

Heat Things Up in a Cooking Class

It’s not surprising that many romant date night ideas in Chicago revolve around food, but this one will let you channel your inner Rick Bayless or Mr. Beef (he’s a real person, right?) by getting your hands dirty in the kitchen. Tip: the classes at Cook Au Vin are some of our favorites.

ComedySportz improv performers

4

Laugh it Up at a Comedy Show

If you’ve never had a date night at a Chicago comedy club, are you even really dating in Chicago? In all seriousness, nothing breaks up the awkwardness of a first date quite like the idea of sharing a few laughs, which is why this is one of our favorite fun date ideas in Chicago. Can’t get in at Second City? Try local favorite ComedySportz, one of the longest-running improv shows in the city.

couple in robes clinking champagne flutes at the spa

5

Get Pampered at the Spa

Is there some tension in your relationship or just tension in your neck and shoulders? Either way, a trip to the spa is the perfect way to relax and enjoy some low-key quality time with the one you love. Feel like putting your love to the test? Try spending a full 24-hours together at local favorite King Spa, where you can wear matching pajamas and try out 9 different themed saunas.

group dance class

6

Cut a Rug at a Dance Class

Admit it: you’ve always wanted to know how to do the merengue or the cha-cha, haven’t you? Well, what better excuse than a fun, active date idea at one of Chicago’s many dance schools (we like Chicago Dance, but really you can’t go wrong!) Plus, once you sharpen your skills, you’ll finally be able to take advantage of all those swing dance parties and tango nights that pop up throughout the city.

man at a magic show

7

Be Captivated By a Magic Show

Magic clubs are all the rage these days, and the Chicago Magic Lounge in Uptown may be the most mesmerizing venue in town, dazzling visitors with large-scale feats performed on stage and slight of hand performed right at your table. For an extra Chicago-ey Chicago date night, go on a Monday where the magic is interspersed with performances from a live jazz band.

aerial acrobat

8

Dig the Theater Scene

Real talk time: Chicago has one of the most vibrant theater scenes in the country. And yet far too many of us are neglecting to take advantage of it. Resolve to do better and surprise your boo with tickets to a play, musical, or opera. Need a suggestion? The Teatro Zinzanni dinner show combines circus-like cabaret acts with a multi-course feast, so no need to make dinner plans for before the show.

woman at American Writers Museum

9

Plan a Day at the Museum

They say knowledge is sexy, so just imagine how alluring you’ll be with a creative, high-brow date idea to one of Chicago’s many excellent museums. Worried about all those potential field trips ruining the romantic vibe? Opt for something a little more low-key, like the much-celebrated American Writers Museum located downtown.

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