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Chicago for Couples

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While Chicago is a city with tremendous history, its contemporary culture, rich arts & music scene, and distinct neighborhoods make it a truly fascinating destination. Sports are also a passion point—catching a game can be a great way to connect with locals!
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58 E Oak St, Chicago, IL 60611, USA
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Inside the newly renovated landmark Esquire Theater in Chicago, the 24,000-sf Del Frisco’s Double Eagle Steak House is one of the largest steak houses in the city, located 15 minutes from the convention center. The 500-seat restaurant opened this...
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20 N Upper Wacker Dr, Chicago, IL 60606, USA
Pass through the beautiful lobby and enter a world where your senses are immersed in soaring vocal art. The Lyric Opera of Chicago is a world-renowned music establishment that features the most famous voices on the globe. There are two on-site...
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60 E Grand Ave, Chicago, IL 60611, USA
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Chicago is known as a steak house town, and lord knows you have plenty from which to choose. But when you want to get both your turf and your surf on, then you simply must head to Joe's. Located in the heart of downtown and bustling with...
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809 W Randolph St, Chicago, IL 60607, USA
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West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above)....
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1551 N Wells St, Chicago, IL 60610, USA
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I've been to most of Chicago's well-known wine bars, but this one surpasses the rest. In the fashionable Old Town neighborhood just north of downtown, Flight 1551 pours more than 250 wines by the glass and by the flight. Burger flights, hummus...
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469 N Racine Ave, Chicago, IL 60642, USA
I took my wife here for a glassmaking course on her birthday, and it was amazing! We were always interested in doing this and I finally decided to look up studios that offered courses. Sharon Gilbert, the artist that owns Talisman Glass, was very...
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5507 N Clark St, Chicago, IL 60640, USA
The goods at Arrin Williams’s year-old Andersonville shop, Haymaker, are mostly handmade by local artisans. Powder-coated-steel side tables by David Greene, hanging plant holders made from reclaimed wood, and coveted leather bags by Chicago-based...
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5547 N Clark St, Chicago, IL 60640, USA
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I wrestled with even posting this highlight, since this is hands down the best sushi joint in Chicago. It's up north, it's BYOB, it plays only music from the 80's, you can get reservations at the drop of a hat, the sushi chefs are personable, they...
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McCormick Blvd, Skokie, IL 60076, USA
Located a bit north of downtown Chicago is the Skokie Northshore Sculpture Park. This two-mile stretch of McCormick Boulevard runs north/south between Touhy Avenue and Dempster Street and features over 60 incredible sculptures. The one featured...
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954 N California Ave, Chicago, IL 60622, USA
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Rootstock crafts great drinks and bites with laid-back style and without pretension. Chef Duncan Biddulph pays attention to the details—he focuses on incorporating locally farmed produce whenever possible and produces their wine and beer in small...
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5491 S Shore Dr, Chicago, IL 60615, USA
With loads of green grass, trees and playgrounds, there is something for everyone at Promontory Point Park. Overlooking the swimmers and sunbathers on the rocks below, one can sit for hours looking at the skyline and Lake Michigan. Locals have...
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1230 W Greenleaf Ave, Chicago, IL 60626, USA
For the most relaxing beach experience, travel a short distance north on Lakeshore Drive and you will find idyllic beaches that you can have almost all to yourself. Here you'll feel free to play, exercise or take a romantic stroll away from the...
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875 N Michigan Ave, Chicago, IL 60611, USA
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Watch the Chicago city lights come up as the sun goes down at the the Signature Lounge. While the Observatory on the 97th floor is a popular spot, you'll have an even more memorable experience lounging, cocktail in hand, overlooking the same...
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175 N State St, Chicago, IL 60601, USA
Chicago has wonderfully rich theater scene ranging from intimate storefront theaters to the famous improv comedians at Second City and any number of Broadway shows. The Cadillac Theatre in the Loop has a beautiful, richly decorated house for large...