Getting Around in Chi-Town

5 Can't Miss Activities on Your Trip to Chicago

Overlooking Chicago from the Skydeck

I've had the opportunity to visit Chicago a few times to see family, but you know how that goes- you mostly see living rooms and not really much of the city. My last trip I went as a tourist and a Green Bay Packers fan... more on that later.

Chicago is well known for its vibrant culture; stunning skyline, iconic architecture and one can't forget the deep-dish pizza. Musical genres of jazz and blues have a rich history here. There are also many famous sports teams such as the Chicago Bulls, Chicago Cubs, and the Chicago Bears. There are tons of attractions and activity options to choose from. Check out the guide below for more information on planning your next trip to Chicago.

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Activity Highlights from the Windy City

Confession time. My last trip to Chicago was planned to see the Green Bay Packers. They were playing against the Chicago Bears, and I wanted a chance to see Aaron Rogers play in person before he potentially retired. He would instead go on to play for the NY Jets, but this was back when every season concluded with retirement talks. So, in anticipation combined with a bit of anxiety... I decided to see him play in person as a Greenbay Packer. I'm so glad I booked that trip to Chicago. While I was there primarily for the football game, we did check out a few other popular activities as well.

Continue reading to get more highlights and recommendations for an awesome trip to Chicago.

The famous Bean sculpture

Millennium Park and Cloud Gate

Entrance to Millennium Park

Travelers tip for Millennium Park- Go early. It was absolutely worth the visit and hype, but the difference between 8 AM and 10 AM are shocking. The earlier you can swing by in the morning, the better chance you'll have at really enjoying the beautiful landscaping, art and architecture without an overwhelming crowd.

The 25-acre space located in the Loop area of Chicago, Illinois is one of the most iconic attractions in the park is the Cloud Gate sculpture, more popularly known as "The Bean" by locals. The Bean is one of the world's largest permanent outdoor art installations. If you get there early enough to capture your reflection in the Bean's stainless steel, it's pretty cool. The park hosts various concerts, festivals, and offers stunning views of Chicago's skyline. Get more information about Millennium Park and Cloud Gate, by visiting the official website of the Millennium Park Foundation.

One of the pieces from the museum

Art Institute Chicago

An art lover's MUST! The Art Institute of Chicago is one of the oldest and largest art museums in the United States. It is located in Chicago's Grant Park and was founded in 1879. The museum is home to an expansive collection of artifacts from across places, cultures, and times. It is known for its impressive collection of Impressionist and Post-Impressionist art, which is one of the largest outside the Louvre. The Art Institute of Chicago also hosts special exhibitions throughout the year. We were able to pay a visit after checking out the Bean. The Art Institute is less than a one-minute walk from the Bean which makes seeing both in one day super convenient. Be sure to plan for plenty of time for your visit. For more information about the Art Institute of Chicago, you can visit their official website https://www.artic.edu/visit here.

Skyline views from the top of Willis Tower

Willis Tower

No trip to Chicago is complete without a visit to the Willis Tower. Formerly known as the Sears Tower, this 108-story, 1,450-foot skyscraper is one of the tallest buildings in the United States. The tower offers breathtaking views of Chicago's skyline and visitors can step onto "The Ledge," an all-glass balcony located on the 103rd floor, for a thrilling and jaw-dropping experience. The Tower is home to more than 100 businesses, including law firms, insurance companies, and financial institutions. Time slots definitely fill up fast, so advanced reservations are highly encouraged. Get your tickets in advance here.

Scoreboard at a Bulls game I went to

Attend a Sporting Event

My personal favorite way to learn more about a place I'm visiting... A sporting event of course! Who reps their team and their town harder than a sports fan? You can get all the best information about which places to go or avoid. Not to mention all the insider scoops about the best hole-in-the-wall eateries. Chicago is home to several professional sports teams. Here are just a few of your options to check out:

Chicago Bulls: The Chicago Bulls are a National Basketball Association (NBA) team that plays at the United Center. The team has a storied past and was particularly successful during the 1990s, winning six NBA championships with legendary players like Michael Jordan.

Chicago Cubs: The Chicago Cubs are a Major League Baseball (MLB) team based in Chicago. They play their home games at Wrigley Field. The Cubs were winners of the World Series championship in 2016.

Chicago Blackhawks: The Chicago Blackhawks are a professional ice hockey team that competes in the National Hockey League (NHL). They have won multiple Stanley Cup championships and play their home games at the United Center.

Me at the Packers Vs Bears game

Chicago Bears: The Chicago Bears compete in the National Football League (NFL) as a member club of the league's National Football Conference (NFC) North Division. They play their home games at Soldier Field, an iconic stadium located on the shores of Lake Michigan.

These are just a few examples of the professional sports teams in Chicago. The city also has other teams like the Chicago White Sox (MLB), Chicago Sky (WNBA), and more.

Poem book title from Maya Angelou hung in the Writer's Museum

American Writer's Museum

I saved the best and my personal favorite experience of the entire trip (outside of Aaron Rogers) for last. The American Writers Museum was an absolute treat and a total hidden gem. This interactive museum celebrates the long-lasting influence of American writers on our history, identity, culture, and daily lives. The museum offers fun and interactive exhibits for readers and writers of all ages. I was unprepared for how truly inspirational this experience would be. In one afternoon, you can explore more than 400 years of American writing across various genres, vintage typewriters, a Word Waterfall, word games, and a Surprise Bookshelf that includes sounds, smells, videos, and dioramas. The American Writer's Museum is absolutely worth a visit the next time you're in Chicago.

Your Packing List

All the things you need to Pack on your Trip to Chicago

So you're heading to the Windy City. Here are some items you'll definitely want to throw in that carryon bag:

Lightweight Waterproof Raincoat - This little jacket is perfect for light rain and wind. It even comes in a cute travel pouch that easily fits in your purse.

Thermajane Long Johns- These thermals are the perfect foundational layer to stay warm even on the windiest of days. They are thin enough to fit under your clothes but still keep you nice and toasty.

Venture Travel Money Belt - I recommend a money belt for visits to any major city. Especially when you're going somewhere with a high tourist density. Better safe than sorry.

Inicat Small Sling Bag - This quickly became one of my favorite travel bags. It fits everything you need for a day out. I have it in multiple colors.

Adidas Cloudfoam Shoe- This is my official travel shoe. They are super lightweight and comfortable. I own them in four different colors.

Repel Umbrella - When there's wind, rain will hit you from all directions. That's why you need an umbrella that can handle both. This compact umbrella does the trick!

Nefeeko Collapsible Water Bottle- Walking is the best way to get around Chicago and this travel water bottle is super convenient and can clip onto any bag.

Me looking at Millennium Park from a bridge

Hope these summaries and tips have encouraged you to consider Chicago for your next destination. I was there only a weekend and feel like I was able to see and do a ton. Don't forget to subscribe to be the first to know when new blogs are posted.

Happy Exploring!