Chicago’s Top 8 Places to Visit

I have been Chicago a handful of times and have loved every moment of this fantastic city. The people have New York hustle but with mid-western hospitality (also take a look at some true southern hospitality), the food scene is enormous from Michelin star restaurants to gourmet hot dogs, and don’t even get me started on the water (the Chicago River is gorgeous).

But we are really here to talk about the sites of Chicago. Now I will admit that most of my time in this city has been a couple of days at a time and I haven’t seen everything that Chicago has to offer. That just means I have to go back!

Whether you only have a day or a week these are the tops sites to see on your next visit to Chicago.

Skydeck (Willis Tower)

Now I know that it is called Willis Tower now but for me it will always be the Sears Tower. Once the tallest building in the world and standing at 1450 feet tall, it is an engineering marvel that provides panoramic views of the city. If you don’t suffer from vertigo or a fear of heights than check out the Ledge, a glass balcony that juts out 4.3 feet from the building which you can see Wrigley Field, Navy Pier, and Millennium Park. If you are lucky you can see over four states!

360 Observation Deck (John Hancock Center)

While the line for Skydeck was over two hours long, the John Hancock Center also provides great views of the city. The Observation deck is located on the 94^th floor has seating and a bar. I recommend going an hour before sunset to see the transition between day and night over the city. It is a sight to see. And for the daredevils out there try out Tilt, a ride that will tilt you 15 degrees, 25 degrees and 40 degrees outward over the Magnificent Mile.

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Millennium Park

Millennium Park is a popular area of Grant Park filled with bold architecture and open, green spaces. The Jay Pritzker Pavilion, designed by Frank Gehry, is a bandshell venue that has regular free performances. The Lurie Garden was designed and created to bring naturalistic plantings and ecology sensitivity into the urban city center. The Buckingham Fountain is one of the largest fountains in the world, the start of Route 66 and can spray water up to 15 stories high. And we can’t forget about Cloud Gate aka The Bean. Created by Anish Kapoor, The Bean consists of 168 highly reflective stainless steel plates molded into precise shapes while the inside arch stands at 12 feet high. It was designed to showcase and highlight the Chicago Skyline.

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Navy Pier

Navy Pier is a top attraction of the city consisting of an IMAX theatre, botanical gardens, a Ferris Wheel, the Miller Beer Garden and the Shakespeare Theatre. But the best part are the views of Lake Michigan.

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Magnificent Mile

Magnificent Mile is every shopaholics dream. You can find every shop in the US on this street and if shopping is not your thing don’t worry. There are so many great dining options and entertainment you can spend a whole day here.

The Chicago Pedway

Chicago’s best kept secret (and a winter escape) is the The Pedway, a maze of underground tunnels that connects over 50 buildings through bridges, hotels and retail shops. While it can be tricky to find, watch out for signs.

Chicago Riverwalk

The Chicago Riverwalk is 1.25 miles of public art, ceramic tile murals, graffiti, cafes, and bars. I would highly recommend finding a rooftop bar (there are bunch along the river) for views of city. My personal favorite is LondonHouse Rooftop.

Chicago River

The Chicago River is definitely a summer activity but is a must. You can either take a water taxi to other parts of the city like Chinatown or sign up for a river tour to learn more about the city’s history and classic architecture and style.