Downtown Chicago’s iconic skyline is rightly the first image that comes to mind for many when the city is mentioned, but the U.S.’s third most populous city is so much more. That’s not to say there isn’t excellent food and fun to be had downtown, but Chicago’s real beating heart is in its neighborhoods, and a complete visit should include a wider sampling of all the Windy City has to offer. Here, 13 places you need to experience in the Chicago.
Entertainment Venues
Green Mill
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This legendary Uptown jazz club feels relatively unchanged from the days when it was a noted hangout of Al Capone, but don’t ask to see the secret escape tunnels underneath the bar. They don’t let anyone down there. Just enjoy the reliably excellent live jazz.
Lincoln Hall
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This renovated former movie theater is known for booking talented musical acts of all types and having some of the finest sound quality in the city—the Lincoln Hall’s ownership group also runs longtime favorite Schubas Tavern, a fine venue in its own right.
The Second City
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The list of comedy legends who’ve graced The Second City’s main stage is too long to get into—just note the endless photos of them performing to small crowds before they were household names, then catch a future star on stage at this comedy institution.
Thalia Hall
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This landmark venue, built in 1892, hosts concerts by well-known musical acts year-round. It adjoins three renowned bars and restaurants, including the Michelin-starred Dusek’s Board & Beer.
Wrigley Field
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Wrigley Field is famous for its ivy-covered outfield walls, manual scoreboard, and lively atmosphere. It’s also home to the Chicago Cubs, renowned for their 108-year journey from lovable losers to 2016 World Series Champions.
Museums
Art Institute of Chicago
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From the well-known bronze lion sculptures guarding the façade to iconic works like American Gothic, the Art Institute of Chicago has few peers among American art museums. Following the 2009 opening of the Renzo Piano-designed modern wing, only New York’s Metropolitan Museum of Art is larger.
Field Museum
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Chicago’s heralded natural history museum has a staggering depth and breadth of exhibitions, headlined by SUE, famously the largest and most complete Tyrannosaurus Rex skeleton ever discovered.
Museum of Science and Industry
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The interactive exhibitions at this Chicago institution enthrall children and adults alike, but none are quite as memorable as the opportunity to walk through an actual German U-boat captured by the Allies during World War II.
Parks and Trails
The 606
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Formally known as “The Bloomingdale Line,” Chicago’s answer to New York City’s High Line took a defunct 2.7-mile stretch of railroad and converted it into an elevated, landscaped bike and pedestrian trail that links four Chicago neighborhoods—Wicker Park, Bucktown, Logan Square and Humboldt Park.
Lakefront Trail
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The 18-mile paved pathway that traces Chicago’s shoreline connects the North and South sides, links numerous parks and beaches, and provides the unmatched experience of having the endless expanse of Lake Michigan to one side and the towering skyline to the other.
Morton Arboretum
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Head to suburban Lisle for this 1,700-acre public garden founded in 1922 by Joy Morton, best known as the man who started Morton Salt. Today Morton Arboretum is home to more than 4,000 plant species, numerous tranquil trails for hiking and biking, and outdoor art exhibitions.
Places to Shop
The Magnificent Mile
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If you only know a few areas of Chicago, The Magnificent Mile is likely one of them, but that doesn’t make the collection of luxury retail any less impressive, not to mention the opportunity to take in architectural treasures like Tribune Tower and the Wrigley Building in between stores.
Wicker Park/Bucktown
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These adjacent, eminently walkable neighborhoods may have lost a bit of the hipster edge that defined them in the early aughts, but they still represent a more eclectic shopping experience to the more staid Magnificent Mile, with a combination of independent boutiques and chain retail, plus a diverse array of dining options.
Next Up: The Hemispheres Guide to Chicago
