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Trip Ideas

What to Do in Chicago Now

No city in the world loves (ahem, appreciates) summertime more than Chicago—the sun-soaked riverfront and rooftop bars come to life and appetites ablaze for open-air social hangouts (not to mention the city’s thriving culinary scene). From music to booze, boutiquing and boating, here are the ten best windy city spots to discover right now.

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Cindy’s Rooftop

On the top floor of the Chicago Athletic Association, Cindy’s is a glass-roof restaurant offering some of the city’s best views of Millennium Park and Lake Michigan. Patrons pack onto picnic benches inside the glass atrium to chow on platters of shellfish, scallops and charcuterie, then head outside to imbibe at the new terrace bar, where boozy popsicles, a rotating rose menu, and large-format cocktails (a $300 cocktail serves 20) keep the mood light.

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BYOB Electric Boats

Checked off the architecture tour? Explore the riverfront at your own pace (as long as it’s under five miles an hour) by renting a 10-12 passenger electric pontoon boat, where you can play tunes off your phone and BYOB, so long as there’s a designated driver. (Driving the boat is about as easy as maneuvering a golf cart, but you can also hire a captain for $60 an hour.) Tip: book your trip on a Wednesday or Saturday evening, where you’ll be able to catch the fireworks show going off at Navy Pier.

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The 606

For a breath of fresh air—sans the tourist jams you might run into at the city’s bigger parks—head over to the northwest side’s 2.7-mile elevated park dubbed the ‘606’ (for the zip code prefix locals here share). You’ll find a mix of bikers, runners, and casual strollers amongst the flowers and greenery, and feel free to use the rails-to-trails project as you bounce between city’s Wicker Park, Bucktown, Humboldt Park and Logan Square neighborhoods.

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Luxury Garage Sale

Fashion enthusiasts will get a thrill browsing the impressive—and constantly rotating—inventory this upscale consignment boutique manages at their Gold Coast and Old Town outposts. YSL are aplenty, with some brand new goods (LGS takes extra inventory from a number of designers) and others gently worn (but never musty).

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Fieldhouse Jones

If you’re cool with stepping outside your comfort zone, book a bed, room, or apartment suite at Fieldhouse Jones, a new Airbnb/hotel/hostel hangout that’s recently launched inside an old dairy warehouse near the city’s River North neighborhood. The hotel draws inspiration from the city’s historic Park District Fieldhouses built back the 1850s (meant to serve as inclusive social hubs for when the weather was crummy) and guests are encouraged to mingle and hang at the vintage gymnasium-themed lounge areas, including the Janitor’s Closet speakeasy and DropShot Coffee and Snack Bar.

RELATED: 9 Best Hotels in Chicago

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The Cabana Club

Wicker Park’s Robey Hotel—a buzzy new addition to the hip neighborhood’s iconic six-corner intersection—recently opened up a beachy cocktail lounge and dipping pool on their rooftop. There, guests can take in skyline views and sunbathe on couches while munching on tostadas and sipping on frozen margaritas, mojitos, or buckets of Mexican beer. Note: Right now, the pool is for hotel guests only, but everyone is welcome to hang.

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Duck Duck Goat

One of the toughest reservations in town is, oddly enough, for a takeout staple: Chinese food. Celebrity chef Stephanie Izard (of Top Chef season four, and the brains behind Chicago’s ever-popular The Girl and the Goat restaurant) turned the five-room Duck Duck Goat into a replica of Chinatown (tasseled lanterns, dragons, and crazy patterns included), and the elevated menu boasts hand-pulled noodles, next level dim sum, and—for a limited number of restaurant-goers each night—the city’s juiciest Peking duck. If you can’t catch a rezzy, the restaurant’s got a carryout window (called Duck Duck Ta Go) with a more limited (but equally tasty) menu.

RELATED: The Best Restaurants in Chicago Now

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The Art Institute of Chicago: Un-Highlights Tour

Museum Hack—the unconventional touring company that focuses on the more bizarre, sexy, or secret stories hidden in a museum— has landed at the Art Institute, and for $39 (plus the cost of admission) you can bypass the obligatory impressionist stops and chatter about color for a more immersive, engaging two-hour touring experience. Many of the guides are actors (some from the city’s bustling improv scene) and a few even pass out candy to keep your energy levels up.

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Tapster

Chicago’s first-of-it’s-kind pour-your-own-beer bar has posted up along North Avenue, and with a (fun? dangerous?) swipe card you can access 62 taps serving everything from craft beers to wine, sodas, cold brewed coffees, and draft cocktails. With cozy leather armchairs, bar tables, live music, and a deli counter serving comfort foods like paninis and PBJ’s, Tapster has the makings of an ultimate Saturday afternoon hangout.

RELATED: 20 Ways to Have The Best Summer Ever

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Thalia Hall

Head to Pilsen and catch a comedy show, music, dancing (or even a podcast taping) at the historic Thalia Hall, built back in 1892 and brought back to life thanks to a dust-off a few years back. Within the venue—where shows happen most nights of the week—you’ll find a beer-inspired restaurant called Dusek’s (don’t miss the Juicy Lucy burger), and a basement punch bar called Punch House, where friends can share a super-boozy rum bowl for $66.

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