It only takes one trip to Chicago to fall in love. Our skyline, our food, our festivals, museums, neighborhoods and so much more make it a one-of-a-kind city.

You've already seen the classics, so use this guide to discover some of Chicago's hidden gems on your next trip.

If you like Millennium Park, visit Jackson Park. 

Jackson ParkSee these picturesque South Side neighborhoods before the bustle. With the Obama Presidential Library coming to this area in 2020, make your way to Jackson Park before its a hot destination.

The park itself is a scenic escape. Nearby, you'll find Museum Campus South, which boasts seven museums, including the Museum of Science and Industry and the DuSable Museum of African American History


If you like Navy Pier, stop by the Chicago Riverwalk. 

City Winery at Chicago RiverwalkLike Navy Pier, the Chicago Riverwalk is a free attraction that's right on the water. Watch the boats go by (or get on one yourself) while you sip on a drink from one of the restaurants on the water.

Look out for public programming throughout the summer, and this fall, the city is installing a large-scale lighting installation that will project art on to the Merchandise Mart building's three-acre facade. 


If you like Goose Island, make a DIY neighborhood beer crawl. 

Dovetail Brewery ChicagoWith more than 60 breweries in the city, Chicago is more than ready to serve you a cold one. We created six brewery crawls that let you go at your own pace. You can also tour some hoppy hotspots with the Chicago Beer Experience. Don't worry--you can always end up at Goose Island. 

If you're in town on a Friday this summer, join us for a Chicago Friday Night Flights event, which lets you sample several breweries in new neighborhoods each time. 


If you like dining downtown, head to the West Loop. 

West Loop

If you love food, you'll love this part of town. The West Loop is easy to get to via the Green Line, and the restaurants here are known worldwide. 

Within the last year, Bellemore, Proxi, Beatrix and Prairie School are all popular (and tasty) options that have opened in the West Loop and Fulton Market. Create an entire food weekend using our guide to Chicago's top foodie neighborhoods. 


If you like shopping the Magnificent Mile, explore Wicker Park.

Wicker Park-1The labels you find shopping in Wicker Park, Bucktown or Logan Square might not be the big names that dot Michigan Avenue, but there's no shortage of stores out here. It's a blend of boutiques, thrift shops and flagship stores that makes for a great day of bargain-hunting. 

While you're here, try a Bizarre Bucktown tour. 


If you like Broadway in Chicago, belt it out in Boystown. 

SidetrackIt's impossible to have a bad time belting it out during Showtunes at Sidetrack, especially if you've just seen a show in town. Then, go explore the Boystown, Chicago's LGBTQ+ capital, and Lakeview neighborhoods. 

Of course, make sure you see another show while you're here. We always recommend checking HotTix for discounted ticket prices at venues around the city.  

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