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If your relationship can survive a clown class, it can survive anything. The Garfield Park Conservatory, which is brimming with lush plant life year-round, is a sight for sore eyes after a winter of staring at gray skies and barren concrete.
Admission is totally free, but leaving a donation at the door can't hurt your chances with your date.
Hit up Geneva for some gorgeous waterfront drinking, New Glarus to enjoy “America’s Little Switzerland” (and lots of yummy beer), or any of a slew of other options.
Not only is a place like Brooklyn Boulders the ideal location to scale fake rocks when you can't get out to the real thing, it also cultivates a fun scene with a regular slate of events including pizza parties, movie nights, yoga, and more. One of the most awesomely weird spaces in the city, Aloft Loft is located in a 110-year-old Logan Square church and offers a variety of circus performances and classes in everything from aerial arts and trapeze to contortion and clowning.
In the wise words of that dashing Casanova Walter Sobchak: “Fuck it, Dude.
Let’s go bowling.” This indoor sport where you're encouraged to drink is one of the great fun equalizers we have on this planet.
The fun part is, Wrigley and Guaranteed Rate couldn’t be more different, so there’s a ballpark experience for everyone.
Since knowing that the mural on Damen in Wicker Park opens up to Violet Hour is no longer considered insider information, Booze Box is a sexy bet, The Office is uber-swank, and East Room is not technically secret but does lack proper signage.For a super-fun time with some cute little furballs, check out The Catcade in Lakeview or Windy Kitty Cafe in Wicker Park.In either location, you and your date can hang out in comfy chairs and get to know each other, or just “ooh” and “aah” over the adorable (and adoptable) cats all around you.If you’re looking to get a bit rowdier, Brew & View is never a bad idea, while a fancy dine-in movie theater like AMC Dine-In Block 37 is the ultimate low-pressure, two birds/one stone lazy afternoon out.There is perhaps no easier summer date than at one of Chicago's fine tiki bars: immediately fun and tropical, the only way you can screw this up is to start talking politics.