10 Very Best Things To Do In Chicago

The US isn’t just the more popular cities of Los Angeles and Nashville, there are so many more Fun US Cities that sometimes get overlooked when planning a trip to the US. This is why I wanted to share some of the very best things to do in Chicago, it’s a city that has so much going for it and is totally fun to boot! 

Now, I know it can be a little difficult to whittle down a few key cities to visit in the US, especially if you’re short on vacation time. After all, the sheer size and diversity of the US mean that one end of the country feels very different from the other. This is exactly why I wanted to share a few key tips on the best things to do in Chicago. 

I loved visiting and I’m already itching to get back to the windy city.

Perched on the banks of Lake Michigan, Chicago has some amazing places to see, especially when you visit for the very first time. Heck, there’s still so many of the best things to do in Chicago even if you’ve visited a few times. It’s the kinda city that’s always changing and there’s always something new popping up.

1.) Chill in Millennium Park

Located along Lake Michigan, Millennium Park is the most iconic and exciting green space in Chicago. Originally built for, you guessed it, the millennium; the park is host to lots of different events that take place throughout the year. If you’re visiting, make sure to check the schedule of upcoming performances and events as they’re usually pretty good. 

Dip into a little culture at one of the concerts that are held on the Great Lawn and Jay Pritzker Pavilion areas. If that’s not your thing, swing a ball or two at the famous Wrigley Stadium (or maybe just watch for us novices). 

Also, be sure to head to The Crown Fountain for a mix of technology and waterpark-style fun! Stroll down the Chase Promenade, making your way to the big bean (technically known as Cloud Gate). 

2.) Gorge on Art at the Art Institute of Chicago

Nestled in Grant Park, is the gorgeous Art Institute of Chicago. Founded in 1879, this magnificent institution is one of the oldest (and largest) art museums in the whole of the US!

They’re over 300,000 different artefacts to see, so make sure you set aside a few hours (or days) to see it all. It really is one of the best things to do in Chicago if you’re an art fiend. That being said, you might wanna give this spot a miss if you’re not interested in art. 

For a great breakfast spot in Chicago, head over to Lou Mitchell’s (on Jackson Boulevard). It’s so yummy and will totally set you right for a day of exploring. 

3.) Learn about conservation at Shedd 

An aquarium might not be the first thing that comes to mind when thinking of things to see in a major world city, but Chicago’s Shedd Aquarium is not to be missed! It is the largest indoor aquarium in the world, showcasing over 8000 aquatic animals.

Shedd also focuses their efforts to educate, promote and showcase the very best ways we can protect the marine environments and make the oceans a better place.

Interestingly, Shedd was the first inland aquarium to have permanent saltwater exhibits, with salt water taken directly from the seas of Key West and brought to Chicago via railroad tank cars.

Also, for some great pancakes in the city, head across to Wildberry Pancakes and Cafe. Honestly, they’re some of the best you’ll ever try. 

4.) Walk The Ledge at the Willis Tower

What used to be officially called (and is still frequently called) the Sears Tower, the Willis Tower is another iconic skyscraper in downtown Chicago. At 1,451 feet (442 m), this 108-story tall building is officially the tallest in Chicago and offers some incredible views from the top.

Known as the Skydeck, the observation deck in the Willis Tower includes The Ledge, a pretty scary glass ledge and box that you can stand in to see the city below.

Though, vertigo sufferers are warned! As the glass floors of The Ledge dangle off the side of the building, the sight might be worth giving a miss.

5.) Chow down, deep-dish style

No visit to Chicago would be complete without a hefty and chunky slice of deep-dish pizza. Honestly, it’s a must do and one of the best things to do in Chicago after a long day exploring. With so many places to try, it can be tricky finding the right place for you.

Make sure to try Lou Malnati’s Pizzeria on Wells Street, known for their signature crusts. Or maybe Pequod’s Pizza on North Clybourn Avenue, where food and drinks are served until late.

For more than just pizza, head to The Art of Pizza on North Ashland Avenue, where you can eat some carby fresh pasta too.

6.) Stroll across Navy Pier

Stretching out onto Lake Michigan, with its iconic Ferris wheel, is Chicago’s Navy Pier. Here, you’ll be able to enjoy plenty of little boutique shops, yummy restaurants, gardens, seasonal exhibitions, and age-old attractions as you make your way along the whole pier.

Just over 100 years old, it’s one of the best things to do in Chicago if you want some time to chill. Plus, over the summer months, the Navy Pier has some epic fireworks to watch and are totally amazing. Check out their schedule for their Fireworks nights, here. 

Also, for a yummy and totally iconic place to eat, reserve a table at 3 Arts Club Cafe. It’s stunning and the food is so delicious. 

7.) Spot The Bean

The Cloud Gate is easily one of the best things to do in Chicago if you love modern art. Fondly referred to as The Bean, Cloud Gate is a beautiful and impressive reflective sculpture by Indian-born British artist Anish Kapoor.

Located in Millennium Park, Cloud Gate is not only fabulous to see but has come to be a totally iconic part of Chicago. Now, if you want to avoid the crowds around here, you’ll need to visit early in the morning. That being said, a few other people doesn’t dampen the experience and it’s well worth going to see at any time. 

8.) Shop, eat and sleep around the Magnificent Mile

If you’re looking for a huge array of shops, international cuisine, live entertainment, and take in some of the most beautiful natural and architectural sites in the city, head for the Magnificent Mile. After all, it’s probably one of Chicago’s most-famous areas. 

The Mile is a total of 13 blocks along Michigan Avenue, stretching from the banks of the Chicago River up to Oak Street. With over 275 restaurants, 460 stores, 60 hotels, and all sorts of fantastic attractions, the Magnificent Mile is a must-see for anyone in Chicago.

For a great place to stay, check in to the Talbott Hotel that’s room are stunning. Plus, it’s a short walk from the John Hancock Building. 

9.) Enjoy the views at the John Hancock Center

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The John Hancock Center is a massive skyscraper located on North Michigan Avenue in downtown Chicago. For me, the 100-story tall building, which stands at 1,127 feet (344 m) tall, is one of the most iconic skyscrapers in the city.

Oh, and don’t forget, you can head to 360 CHICAGO, an incredible observation deck on the 94th floor of the building, for breathtaking views of the city, Lake Michigan, and the Magnificent Mile.

It’s really great at sunset or if there’s really low fog. Sometimes, the viewing deck will actually be above the clouds. It’s magical. 

10.) Learn about baseball at Wrigley Field

Whether you are a fan of baseball or not, you have certainly heard about Wrigley Field. Home of the Chicago Cubs, Wrigley Field was opened in 1914, originally as Weeghman Park. The Cubs played their first game there in 1916 when they beat the Cincinnati Reds.

Eventually, the owner of the popular Wrigley chewing gum bought out the Cubs, and the field was renamed after the company in 1927.

If baseball is your thing, you can enjoy daily and group tours of Wrigley Field, and even catch a game if ya go at the right time. Afterward, for a hearty meal, pop over to The Chicago Diner which will have you stuffed in no time.