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

Hype Park
See this picturesque South Side neighborhood 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, visit the Chicago Riverwalk

Riverwalk seating

Like 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, like Art on theMART, when a large-scale lighting installation that projects art on to the Merchandise Mart building’s three-acre facade.

Best Large City in the U.S.

If you like Goose Island, do a neighborhood beer crawl

With more than 160 breweries all across the city, Chicago is more than ready to serve you a cold one. We created neighborhood brewery crawls that explore some of the city’s vibrant brewing districts. 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

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.

Bellemore, Proxi, Girl & the Goat, and Beatrix are all popular (and tasty) options that are 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

Boutique shopping in Chicago neighborhoods

The 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, grab seats at a storefront theatre

Broadway in Chicago brings some of the hottest shows and biggest hits to the Loop’s bustling theatre district. But if you’re looking for something a bit more under-the-radar, head to our diverse neighborhoods to experience Chicago’s thriving storefront theatre scene.

These independent theatres present original works and cutting-edge performances that give you a glimpse of the fearless soul of the city. There are tons to choose from, including The Den Theatre in Wicker Park, Theatre Wit in Lakeview, A Red Orchid Theatre in Old Town, and more.

Insider tip: Check out HotTix for discounted ticket prices at theatre around the city.