1 Day in Chicago- The Adventuring Millennial

Chi-Town is the 3rd most populated city in the United States and is FULL of things to see and do. I’ve only visited Chicago a few times. And each trip only included 1-day of sightseeing.

If you are visiting Chicago for business, a wedding, or as a day trip, it can be difficult to decide what to include on a short itinerary.

My suggestion? Pick one major item (such as a trip to Wrigley Field or The Willis Tower Skydeck). Fill the rest of your time with smaller sights (The Bean or Tribune Tower).

Ok, if you are ready, let’s talk Chicago! Below is my ultimate itinerary for 1 day in Chicago. Let’s go!

The Willis Tower

I tend to be a sucker for gorgeous city views (I mean who isn’t?). Some of my favorite observation decks are the top of the Eiffel Tower, the Empire State Building, and the Space Needle. While these could be considered overpriced tourist traps, there is something fun about reaching the top of these icons.

So start your day at the Skydeck in Willis Tower. To avoid some of the crowds, plan to go first thing in morning. Adult admission is $24, and tickets can be purchased online or on-site.

So, I am still working on my fear of heights and when I visited The Willis Tower I was very nervous to step onto “The Ledge”. These are glass boxes that extend about 4 feet from the side of the Skydeck. But, I’m proud to say I did venture onto The Ledge!

I’m not going to lie though, looking down at the clear floor to the city below really freaked me out. Luckily there are plenty of other viewing areas on the Skydeck to observe the view, so I spent most of my time looking out of these windows.

First timers, you don’t want to miss the Skydeck. The Willis Tower is such an iconic part of the Chicago skyline. And you really should experience the view from the top at least once.

The Bean

Speaking of iconic Chicago landmarks, The Bean in Millennium Park should be a must-see on anyone’s first trip to Chicago. This public art piece entitled “Cloud Gate” was erected between 2004-2006.

Stop by Millennium Park to see the buildings reflected on The Bean. Walk under the 12-ft arch and grab a picture of yourself reflected on the structure.

Millennium Park hosts many events, including concerts in the summer and a skating rink in the winter. Be sure to check their website before planning your trip. The park is also near the Art Institute of Chicago, which houses many famous works including Water Lilies by Monet, American Gothic by Wood, and The Bedroom by Van Gogh.

Tribune Tower

The former home of the Chicago Tribune, this gorgeous neo-Gothic skyscraper is a sight to behold. Work has begun to convert the building into condos (rumor has it that Chance the Rapper wants to move in), but even during construction, this historic tower is still worth checking out.

With only 24-hours, you really only have time to briefly walk around this building. This gorgeous tower was made with almost 150 pieces of other historic and important buildings. This allows for a museum-quality exhibit that is free for any person to observe as they walk past the structure.

The building includes fragments from the Great Pyramids of Giza, Notre Dame in Paris, the Berlin Wall, and many more.

The designers of the building wanted to make the Tribune Tower a monument of the world. The intriguing exterior is worthy of its spot on this one-day itinerary.

I could have spent an hour walking around the building and looking at all the fragments, but even if you only have a few minutes to spare, it is still enjoyable to see pieces of stone from all over the world.

I am curious about how these pieces were acquired. Since they come from so many historic sites, were they taken legally? Were they gifts or were they taken before it was considered wrong to take “souvenirs” from historic sites. If you know the history of this building I would love to hear from you! Let me know in the comments below.

Lakefront Trail

The Lakefront Trail was an unexpected highlight of my time in Chicago. This 18-mile paved trail is the perfect place for a welcomed break without venturing out of the city. The path is ideal for bikers, runners, or walkers wanting a leisurely stroll. Walk past the shores of Lake Michigan (in the summer this is a great place to picnic, play volleyball, or wade into the water). The trail passes 4 parks and 13 neighborhoods, so this is a great way to travel between different parts of the city.

It also connects many of the city’s major attractions, including Navy Pier, Lincoln Park, and the Museum of Science and Industry.

Next, make a short visit to the Lincoln Park Zoo. This high-quality zoo located in Lincoln Park is free every day (yes, you read that right). This zoo blends very well with the park. The wide paths and landscaping make you feel that you are just walking through the park instead of a zoo.

If the weather is nice, I recommend spending some time along the Lakefront Trail. Weather you opt for the entire 18-mile path, or just a few select parts, this trail is a unique treasure in the Windy City that should not be missed.

Dinner and a Show

It wouldn’t be a trip to Chicago without trying some famous Chicago-style pizza. While there are countless places serving deep-dish pizza in the city, I decided to visit the iconic Giordano’s. To be honest, I’m more of a thin-crust New York style pizza-kind of gal. But I knew I HAD to try this version while I was in the city. Chicago-style pizza is a unique experience.

And head’s up, these pizzas take roughly 45-minutes to cook. And even if you don’t enjoy the sauce on top and toppings in the middle of your pizza, this is still something you should at least once during your time in Chicago.

Chicago is a great place to see live theater. Plan to see a Broadway-style or comedy show to end your day in the city. Second City, a popular comedy theater in Chicago, was the starting point for many comedians including Amy Poehler, Tina Fey, and Steve Carell. I recommend checking out TodayTix to see what deals you can find for some of the city’s top shows.