Chicago is one of the biggest cities in the United States, and it welcomes millions of visitors every year. The city has a lot of history and is known for its bustling arts and cultural scene. No matter if you’re a sports fan, traveling with kids, enjoying a romantic getaway or want to eat your way through the city, there are dozens of attractions for anyone to enjoy. Before booking your vacation home rental in the Windy City, check out these top 10 places to visit in Chicago.

  1. Wrigley Field
    Richard Cavalleri/

    Wrigley Field is often number one on any list of top 10 places to visit in Chicago. It’s been home to the Chicago Cubs since 1914, and it’s the second oldest MLB park in the U.S. It’s an unforgettable experience for anyone — not just baseball fans. Because it’s a popular spot during baseball season, it might be hard to get tickets to a game at an affordable price. If you’re there to learn the history rather than root for the home team, consider joining one of the 90-minute guided tours. You’ll get to see the ins and outs of the field and get a good dose of history too.

  2. The Second City

    The Second City is an institution in comedy circles. The comedy club first opened its doors in 1959, and it has since churned out dozens of famous comedians. Now-well-known names in comedy such as Tina Fey, Steve Carell and Bill Murray have graced the stage of the improv comedy club. If you stop in for drinks and a show, there’s a good chance the comedian you see on stage will hit it big one day.

  3. Millennium Park
    Creative Family/

    Millennium Park is one of the top places to visit in Chicago downtown. It’s part of the larger Grant Park, which is also worth exploring if you have the time. The big draw to Millennium Park is a giant sculpture named Cloud Gate. It’s a bean-shaped stainless-steel sculpture that towers over 30 feet in the air. While wandering through the park, you can also catch some live music at the outdoor Jay Pritzker Pavilion.

  4. Art Institute of Chicago

    The Art Institute of Chicago is over 400,000 square feet of museum filled with paintings, sculptures, photographs and other pieces. It houses hundreds of thousands of works of art from as far back as the Byzantine Era to as new as just a few years ago. It should be on your list of places to visit in Chicago downtown. Even if you’ve been before, the museum showcases works from traveling exhibitions that change in addition to the permanent collection.

  5. Lake Michigan
    Jake Hukee/

    The city of Chicago sits right up against one of the Great Lakes — Lake Michigan. While there are several places to overlook the water from the land, consider overlooking the city from the water instead. Several boat tours will take you out into the lake where you can get a stunning view of the city skyline. Relax on the water as you watch the sun go down over Chicago.

  6. Field Museum of Natural History

    Another of the popular Chicago places to visit is the Field Museum of Natural History located near Grant Park. It has thousands of artifacts and exhibits that you won’t be able to see anywhere else. These artifacts span multiple eras and were found in locations all around the world. It’s a must-see for any history or archaeology buff.

  7. Lincoln Park Zoo
    Felix Mizioznikov/

    The Lincoln Park Zoo is one of the top 10 places to visit in Chicago, not only because it’s interesting, but also because it has free admission. There is a fee to park, but you can avoid the fee by taking public transportation from your vacation rental home. It’s right on the bus line, so getting there is easy. The Lincoln Park Zoo is one of the oldest in the country, and it exhibits hundreds of animals in their natural habitats.

  8. Superdawg

    You can’t visit Chicago without having a world-famous hot dog. There’s no better place to get one than at the local favorite Superdawg. This drive-in hot dog stand with carhop service follows the same methods that it did when it first opened in 1948. It’s one of the few places serving up a true Chicago-style hot dog.

  9. Navy Pier
    R Scapinello/

    Navy Pier is the ultimate playground for children, but there are tons of attractions for adults to enjoy also. The amusement park covers 50 acres and features rides, gardens, attractions, places to eat and shops. The 150-foot Ferris wheel is one of its biggest attractions. There’s also the children’s museum, concert venue and boat tours departing from the pier.

  10. Green Mill

    When it comes to live music, there’s no shortage of concert venues, lounges and bars to catch a show. However, none are quite as unique as Green Mill. It was a popular spot during the Prohibition Era, and it remains one of the premier spots for catching live jazz performances in the entire country.