7 Chicago Gems You'll Want to Visit on Your Next Trip

Note: All travel is subject to frequently changing governmental restrictions—please check government advisories before scheduling trips. Some attractions and establishments may be closed or providing modified services. We strongly recommend researching any attractions and establishments prior to your visit. This post was update October 20, 2020.

Chicago‘s downtown area offers endless opportunity for exploration with its world class architecture, parks, museums and historic sites. After all, downtown is where you’ll find hits like Cloud Gate (Bean) sculpture, Willis Tower and Navy Pier. But sometimes it’s better to head off the beaten track. On your next visit, instead of following the crowds, check out these top Chicago gems for those looking to explore something new.

1. The 606

The 606 is an elevated multi-use trail that was formerly a railroad track. It runs through the Chicago neighborhoods of Bucktown, Wicker Park, Logan Square and Humboldt Park and features small parks and art installations along the way. Rent a Divvy bike and explore the 2.7-mile trail on wheels or walk it. There are plenty of fun stops nearby. Try Mindy’s Bakery for hot chocolate or Margie’s Candies, a Chicago ice cream shop that has been serving up sweet treats since the 1920s. You can’t go wrong with a pit stop at either.

Photo: Kirsten Maxwell

2. Pilsen

The Pilsen neighborhood is home to Chicago’s largest Hispanic community and the National Museum of Mexican Art. It’s the perfect place to take a stroll and admire street art murals. Don’t miss stopping at taquerias for authentic Mexican cuisine and devouring a paleta (fruit popsicle) at La Michoacana Premium for dessert.

Photo: Kirsten Maxwell

3. Kayaking the Chicago River

The Chicago River runs through the heart of downtown and it is the perfect place to enjoy the city’s architecture from a new perspective. Kayaks can be rented from multiple outfitters along the river and there are many entry and exit points along the way.

4. Chinatown

Chicago visitors are in for a treat when they board a water taxi and head to Chinatown. There are seven water taxi stops downtown and the ride offers beautiful views of Chicago architecture from the water. After disembarking, have a dim sum lunch at Triple Crown and/or take a walking tour of Chinatown. Finish up with a bubble tea from Joy Yee Noodle.

Photo: Kirsten Maxwell

5. Lincoln Park

Located just north of downtown, 1,200-acre Lincoln Park is Chicago’s largest public park. It’s home to the famous Lincoln Park Zoo, one of the oldest in the country (and also free). This is where visitors will also find the Lincoln Park Conservatory, a massive garden offering respite from the elements year round. Nearby is the Peggy Notebaert Nature Museum where families can learn about nature and scientific exploration in a fantastic hands-on environment. The Chicago History Museum also shouldn’t be missed as it takes visitors on an in-depth look at the history of the great city of Chicago. After all this learning, head to Pequod’s for some deep dish pizza and/or Sweet Mandy B’s for delectable treats.

6. Oak Park

Adjacent suburb Oak Park is off the well beaten tourist track, but that doesn’t make it any less interesting. In fact, it’s quite the opposite. The town is home to Frank Lloyd Wright’s home and studio and numerous homes he designed in the Prairie style. Spending the afternoon touring the neighborhoods on a guided or self-paced tour is a perfect way to see the area. It is also home the Ernest Hemingway Birthplace Museum, so literary fans won’t want to miss a chance to take a tour. Down the road is the Garfield Park Conservatory, another beautiful garden space in Chicago and one of the largest in the nation.

Chicago-Gems-Garfield-Park-Conservatory-Travelocity

Photo: Kirsten Maxwell

7. The rooftops

One of the best ways to see Chicago’s signature skyline is at a rooftop restaurant or bar. The views day or night are stellar, and dining al fresco at an altitude is a memorable experience. Some favorite spots include Little Goat and Bernie’s. Many of the downtown hotels also have rooftop restaurants and bars, such as Cindy’s at the Chicago Athletic Association, Loews Streeterville Social at Loews Chicago Hotel, and The J. Parker at Hotel Lincoln. Do as the locals do when the weather warms up, and head outside for a bite to eat.