Chi-Town is the 3rd most populated city in the United States and offers a multitude of sights and unique activities. I have only visited Chicago a few times, and each trip only allowed for about 1-day of sightseeing. Whether you are visiting Chicago for a business trip, a wedding, or as a day trip, it can be difficult to decide what to include on a short itinerary. If you are working with a limited time-budget, I would recommend picking one major item (such as a trip to Wriggly Field or The Willis Tower Skydeck) and filling in the rest of tour time with smaller sights (The Bean or Tribune Tower). Below is my itinerary from a 1-day trip I took to Chicago a few years ago. I hope this inspires you as your plan your time in the Windy City. Even though I didn't get to spend a long time in Chicago, I managed to squeezed a lot into my itinerary which allowed me to have a full experience in this city.
The Willis Tower
I tend to be a sucker for gorgeous city views (I mean who isn'?!). I have visited many observation decks in my travels, including the top of the Eiffel Tower, the Empire State Building, and the Space Needle just to name a few. While these could be considered overpriced tourist traps, there is something fun about reaching the top of these icons. I knew I wanted to visit the Skydeck at the top of the Willis Tower, so I made this my first stop during my day in Chicago. I was prepared for a long wait, so I wanted to make sure I was not rushed during this experience. Adult admission is $24, and tickets can be purchased online or on-site.
I am working on my fear of heights, but when I visited The Willis Tower I was still very nervous to step onto The Ledge. The Ledges are glass boxes that extend about 4 feet from the side of the Skydeck. This offers a very unique view of the city, and is a feature that separates this observation deck from others I have visited. I am proud to say I walked into one of these glass boxes but 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.
If this is your first visit to Chicago you should strongly consider visiting the Skydeck. The Willis Tower is such an iconic and prominent part of the Chicago skyline and I think every visitor to Chicago should experience this view at least once.
The Bean
Speaking of iconic Chicago landmarks, The Bean in Millennium Park is a must-see on anyone's first trip to Chicago. This public art piece entitled "Cloud Gate" was erected between 2004-2006. I highly recommend stopping by Millennium Park to observe 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, so 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 Lillies 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, but this historic tower is still worth checking out. Since I only had one-day in Chicago, I only briefly walked around this building. This gorgeous tower was made with almost 150 pieces of other historic and important buildings. This allows for a unique 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. This is truly a unique building and it is worth your time to visit. 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 do wonder 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. The trail passes the shores of Lake Michigan and 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.
The trail connects many of the city's major attractions, including Navy Pier, Lincoln Park, and the Museum of Science and Industry. Since I couldn't squeeze everything into my short trip to Chicago, I decided to make a short visit the Lincoln Park zoo. This high-quality zoo located in Lincoln Park is free everyday (yes you read that right). This zoo blended very well with the park, and the wide paths and landscaping helped you feel that you were still just walking through the park instead of the streets in a zoo.
If the weather is nice, I strongly 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. Truthfully I am more of a fan of thin-crust New York style pizza, but I knew I wanted to try this version while I was in the city. Chicago-style pizza is a unique experience. These pizza's take roughly 45-minutes to cook, so be prepared to wait for your meal. I don't particularly enjoy the sauce on top and toppings in the middle, but this is something you should at least once during your time in Chicago.
I had tickets to see The Jungle Book at The Goodman Theater that night, which was a fantastic show. Chicago is a great place to see live theater, and there are many opportunities to see Broadway-style and comedy shows 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 on some of the city's top shows. If this is something you are interested in, a show is a great way to cap off a full day in Chicago.
There are so many sights to see in Chicago and it can be overwhelming to visit such a major city on a time-limit. I hope my post helped you decide what to include on your Chicagoland itinerary. Is there anything I left out that you think belongs on a 1-day trip to Chicago? Let me know in the comments below!
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