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A Perfect Day: Chicago

A Perfect Day: Chicago

A Perfect Day: Chicago

Go beyond the bean with this ultimate Chicago guide.

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By Ari Bendersky
People living on the coasts have long considered Chicago part of flyover country, but once they actually, well, stop over, they quickly realize how fantastic this city is and how great our Great Lake is ("It's like an ocean!" so many exclaim upon seeing Lake Michigan). Sure, winters can drag on, but spring through fall? Chicago is the best place to be in America. With a paved lakefront path stretching 18 miles along the city's eastern border, a world-renowned restaurant scene, innovative mixologists, incredible museums, manicured parks and truly hospitable people, Chicago pretty much kicks ass. Here are a handful of favorite things to see/eat/drink/do in the Windy City. 
Any visit to Chicago wouldn't be the same without a stop to the gayborhood to grab a beer at some of our, um, well-worn bars. Since opening in 1987, Roscoe's(3356 N. Halsted St., has stood as a cornerstone (literally, it sits at the corner of Roscoe and Halsted) for the community. Whether you're watching videos up front, having a drink in the garden or doing a twirl on the dance floor, you'll always have a great time. And across the street, Sidetrack(3349 N. Halsted St.,, the grande dame of Boystown, has so much going on in its numerous rooms, it's like you're visiting several different bars at once. Up the street, Halsted's(3441 N. Halsted, 773-348-9696,, with its idyllic backyard patio, is the perfect place to gather for cocktails and bites with your buddies. 
Image via Roscoe's
The Berkshire Room
If you're seeking a perfectly crafted cocktail with small-batch spirits (they have a vast whiskey selection) in a super sexy, art deco masculine space, the Berkshire Room is a top spot. (15 E. Ohio St.,
Image via The Berkshire Room
Mon Ami Gabi
No matter the occasion—birthday, anniversary, Wednesday night whim—this French bistro overlooking Lincoln Park is a go-to spot for me and my husband. Best steak frites in Chicago. (2300 N. Lincoln Park West,
The Lakefront Trail
Either bring your own bike or rent one. The path is one of the best ways to see Chicago for all its beauty and since it traverses so many neighborhoods, you can pop off and explore. Tip: Hit The Dock at Montrose Beach for burgers, tacos, margaritas and live music under the sun.
Image via Wikimedia Commons
Garfield Park Conservatory
No matter when you go, it's always summer inside this glass-domed building on the city's West Side. Lush, floral and fragrant, the conservatory is a perfect respite to winter. (100 N. Central Park Ave.,
Image via Wikimedia Commons
Lickity Split
Forget the froyo. Instead go full fat at this far north side gay-owned old-time frozen custard and candy shop. Want a lighter option? Hit Miko's for Italian ice with all-natural fruit juice. (Lickity Split: 6056 N. Broadway,; Miko's: 1846 N. Damen Ave.,
Image via Google Maps
The Green Mill
Going to this intimate, historic jazz club (where Al Capone used to hang) is in itself an experience, but having nightly jazz shows is an inherent bonus. (4802 N. Broadway,
Argyle Street
Whether you get the duck service and egg rolls (the best in Chicago, in my opinion) at Sun Wah BBQ, pho at Tank Noodle or sweet and savory buns at La Patisserie P, this Asian enclave in uptown offers plenty of flavor and color. 
FirstMerit Bank Pavilion at Northerly Island
Hands down, this is the best outdoor venue to see live music. With the city as your backdrop and the lake behind you, does it really matter who is on stage? (1300 S. Linn White Dr.,

Image via
Modern Wing at the Art Institute
It already housed an incredible collection of modern art, but with the 2015 announcement of a 42-piece gift (worth $400 million) including art by Andy Warhol, Jasper Johns, Cindy Sherman, Roy Lichtenstein and Gerhard Richter, the Modern Wing got even better. (159 E. Monroe St.,
About Ari Bendersky
Ari Bendersky is a Chicago-based lifestyle journalist and content marketer specializing in food, wine, music, travel, and wellness, and is the author of "1000 Food & Art Styling Ideas," published in Dec. 2013. Ari, the former founding editor of Eater Chicago, has been writing for 20 years and his work has appeared in the New York Times, Associated Press, Out,, Wine Enthusiast,, Chicago magazine, Health, Huffington Post, Crain's Chicago Business, and many more publications. 


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