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If Summertime Chi’s bajillion festivals, concerts and patios are leaving you in a state of decision paralysis, you’re not alone. That’s why we’ve planned five perfect summer dates. Now’s your chance to get in some QT with your S.O.—admit it, it feels like you’ve barely seen him since the onslaught of wedding season began.

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Feeling nostalgic? We suggest an old-fashioned soda shop and drive-in movie. Drive west on I-290 and make a stop in Oak Park for an ice cream to share (or not) from historic Petersen’s Ice Cream. Then it’s back on the highway to finish your night with an 8:30 showing at Cascade Drive-In in West Chicago. There’s a throwback snack bar with hot dogs and nachos, but you’re also welcome to pack your own picnic.

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Spend an evening soaking up Pilsen’s lively arts scene. Pick the second Friday of the month, when galleries open their doors to the public (and dole out free cups of wine). Just strolling from gallery to gallery, taking in the art and the artists themselves is fun, but make the most of your evening by planning dinner at Dusek’s followed by a show at the adjoining Thalia Hall. If you’re not ready to head home, finish things up with drinks at downstairs Punch House.

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OK, so the Chicago River isn’t exactly the wilderness, but a three-hour fireworks kayak tour with Kayak Chicago can still be pretty majestic. Before your tour, enjoy a quick bite on the river deck at Whole Foods Lincoln Park—just watch how many craft beers or wines you have, since getting tipsy can take on new meaning in a kayak. Tours depart just around the corner at 8 p.m. and will take you through downtown’s canyons of glass and steel before finishing with a massive fireworks display at Navy Pier. Now, if only you could figure out how to get a good iPhone shot of those fireworks.

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MCA Chicago


The best things in life are free, right? The Museum of Contemporary Art proves just that with its weekly free Tuesdays on the Terrace. Take in the current exhibitions, then settle out in the garden to hear a live, rotating jazz ensemble. Bring a blanket to relax on the lawn and grab some nosh and cocktails from the MCA Café.


The way to our hearts? Definitely through our stomachs, which is why a date in Restaurant Row sounds perfect. Start with a refreshing Show Pony (vodka, melon, hibiscus, grapefruit, lime and soda) on the patio at City Mouse, Jason Vincent’s restaurant at the new Ace Hotel in the West Loop. From there, it’s time to stroll and take in the scene along Fulton Market before you make your reservation at RM Champagne Salon. Champagne plus oysters plus an oh-so-charming patio equals true love forever.

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