Chicago is such a great city! There’s a lot to do and see, so if you’re planning a visit here are some suggestions to help you get the most of your stay in the Windy City.


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Explore Millennium Park

A visit to Chicago would be incomplete without visiting “The Bean.” But this iconic structure isn’t the only impressive piece of artwork in the park. You can also see the Crown Fountain and 4 large portraits of young girls titled “Jaume Plensa: 10004 Portraits” which tell the story of Chicago’s residents. The park also offers concerts, lectures, and workshops (from beekeeping to kiddie art lessons). It’s also a great place to just kick back, relax, and do some people watching.

Things To Do In Chicago

Buddy The Traveling Monkey Fun Things To Do In Chicago

Buddy The Traveling Monkey Fun Things To Do In Chicago


Willis Tower

Formerly known as the Sears Tower, it is the tallest building in North America. It’s no shock then that from the Skydeck on the 103rd floor you can see some amazing views of the city and surrounding area. On a clear day, you can see 4 states: Illinois, Indiana, Wisconsin and Michigan. Inside there are also displays and exhibits that show the history of the city and tower. But what’s the coolest thing about Willis Tower? The Ledge. In 2009, a series of glass bays were built that extend out from the sides of the building. They allow you to look straight down 1,353 feet to the ground below. Hope you’re not scared of heights!

Willis Tower

View from Willis Tower

Skydeck Willis Tower


Go to the Lincoln Park Zoo

Not only is this zoo huge, it’s also free! And it’s open 365 days a year. There are a lot of animals, tons of interactive activities and demonstrations, beautiful gardens, and even adult-only extravaganzas (yes, they include alcohol!). And another thing that we thought was pretty cool was that you could feel completely surrounded by nature, and yet have an awesome view of the downtown skyline. There are multiple gates so you can enter from any direction and we recommend taking public transportation since you do have to pay for parking.

Lincoln Park Zoo monkey

Lincoln Park Zoo camel

Buddy The Traveling Monkey Fun Things To Do In Chicago


Take a stroll down Navy Pier

There’s so much to do here! There are restaurants, museums, rides, and depending on the season, various events and celebrations. We rode the 150 foot Ferris wheel (some more great views) and the Wave Swinger (flying chairs), ate at the Billy Goat Tavern Grill, checked out a temporary museum, and then walked to the end of the pier. From there we saw the Chicago Harbor Lighthouse and an amazing view of the Chicago skyline.

Navy Pier ferris wheel

navy pier billy goat tavern

lighthouse near navy pier

chicago skyline from navy pier


Take an Architecture Tour on the Chicago River

This tour was one of the highlights of our trip. Chicago is world-renowned for its architecture (it’s known as the birthplace of the skyscraper) and seeing it from the river gives you a really cool perspective. Even if you’re not that into architecture, you still learn a lot about the city itself. There are a few companies that offer tours, but we chose to go with Shoreline Sightseeing. They have the largest touring fleet in Chicago and offered more departure times. The tour lasts 75 minutes and is given by guides that really know their stuff. Although they also have a Night Architecture Tour, I would recommend going on a day tour right before sunset (check sunset times). That way you can clearly see the buildings when you start the tour, but you can also see them impressively lit up by the end of it.

architecture tour

downtown chicago architecture

downtown chicago architecture

chicago architecture at night


Get trapped in a room with a zombie

For something a little different, try getting trapped in a room with a zombie with Room Escape Adventures. We’ve already written about how much fun we had here, but thought it deserved another mention since it was an experience unlike anything we’ve ever had.

chicago escape room


Eat some deep-dish Pizza

This is a no-brainer. If you’re in Chicago, you HAVE to eat some deep-dish. We weighed-in on which restaurants we thought had the best pizza, but I totally encourage you to try as many for yourself as possible. After all, you have to make an informed decision. 😉

Chicago deep dish pizza


Have you been to Chicago? Are there any other fun things to do that you would recommend? Let us know in the comments below! 🙂


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There's a lot to do in Chicago! If you're planning a visit here are some suggestions to help you get the most of your stay in the Windy City.