Chicago | Willis Tower Skydeck And The Ledge

As you drive from O’Hare International Airport into downtown Chicago, you get an incredible view of the city skyline. There’s no bigger presence on the horizon than the Willis Tower (Sears Tower for those of you who refuse to let go of its old name). The 108-story landmark towers over a city of massive buildings that seem to stretch for miles. Willis tower is like a magnet — it’s impossible not to stare.

Willis Tower Chicago Flag

Willis Tower in Chicago

Since my grandma lived right outside of Chicago, I visited the Windy City a lot as a kid. I remember going to the top of the Sears Tower with my family. Back then, the Sears Tower was the tallest building in the world (Willis Tower now ranks ninth on that list), so it was heaven for a little boy. It was impossible to not be in awe of the incredible views. It’s a moment I never forgot, and one I wanted to relive again — so I did.

I’ve been to Chicago a few times over the last year and a half, but I never took the time to visit the Willis Tower Skydeck until my most recent vacation there (check some of my other adventures/misadventures from the trip). My brother and I finally decided to take the 1,353 foot ascent to the summit of the city.

There was no line when we first arrived at Willis Tower, but little did I realize the wait didn’t start until you took a short elevator trip to a different floor. We were told by one of the workers the line would take an hour, and it looked like it would, because there was a horde of people snaking around to the ticket booth. The wait wasn’t very long at all though. It only took my brother and me 35 minutes from the time we stepped into the building to get onto the Willis Tower Skydeck. We were there on a Monday, but the place was still bustling with summer tourists.

Willis Tower Chicago Skydeck

A view of downtown Chicago and Lake Michigan from the Skydeck

NOTE: I have a quick tip for anyone who wants to save time at the Willis Tower Skydeck. Part of the waiting/line process includes a movie. The staff shuffles you into a little theater for a video about the building’s history, etc. If you’re like my brother and me; you want to see the views — not watch a movie. That’s why we walked into the theater and directly out the exit to get to the elevator to the Skydeck. I’m not sure how much time we saved, but I know we beat the crowd that sayed behind to watch the flick.

It costs $17.50 to visit the Willis Tower Skydeck, but it’s worth every penny. After a one minute+ elevator ride to the top (the Skydeck is on the 103rd floor), you’re introduced to unbeatable views of Chicago. I immediately felt like a kid again. I honestly think my jaw was hanging to my feet from the time I stepped onto the Willis Tower Skydeck to the time I stepped off. On a clear day, you can actually see four different states (Illinois, Wisconsin, Michigan and Indiana) from the Skydeck. Some of the highlights from my eyes were U.S. Cellular Field, Wrigley Field (a little tough to spot) and the United Center. The best view of all though is looking over downtown and Lake Michigan. It’s a view of the city you’ll never forget — and one that makes you realize how big Chicago really is (it almost looks fake).

Willis Tower Chicago Ledge

The Ledge

The biggest difference from my first trip to the Sears Tower Skydeck to my latest visit to the Willis Tower Skydeck is the Ledge. The Ledge is actually four glass boxes that extend more than four feet over the side of the building. Yes, the boxes — all glass from top to bottom — extend beyond the side of the building (meaning you can look STRAIGHT DOWN). The Ledge gives you a unique (and thrilling) view of the city — if you can stomach it. There was a short line to get onto the Ledge, but nothing that took more than two or three minutes to get through. It was a truly amazing experience, and something I would suggest to everyone (unless you’re deathly afraid of heights).

There are a million things to do and see in Chicago. I totally understand that. I’ve been there 10 to 15 times in my life, and there’s still more I want to accomplish every time I visit. The one thing you have to do — no matter what — is take the time to visit the Willis Tower Skydeck and the Ledge. You won’t regret it!

Have you been to the top of Willis Tower/Sears Tower? Have you braved the Ledge? I would love to hear about your experience. You can leave a comment right here, or you can connect with me on Twitter, Facebook and/or Google+. And, don’t forget, if you can’t travel the world; experience the world with me at!


  1. Judy Bougades says:

    Can you tell me how to purchase a copy of the Chicago flag photo?
    Thanks, Judy Bougades (

    • Tim Lewis says:


      I’m sorry for the delayed response. Please let me know what size you’re looking for and I can get you some pricing details.



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