Chicago has the second-tallest skyline in the United States (after New York City), which includes 1,397 high rises, many of which are considered skyscrapers. The iconic Chicago skyline is a magnificent sight, but driving past or through Chicago isn't the only way to view those architectural wonders – a visit to Chicago can be a fun weekend adventure that's just a few hours drive from the Fox Cities.
On a recent 2-night trip to Chicago, I found 5 fun ways to explore and learn about these impressive, towering masterpieces, while also discovering the best of Chicago's attractions. Here are my favorite ways to see the Chicago skyline:
The author was hosted by Sheraton Grand Chicago Riverwalk, Blue Man Group, and Chicago CityPASS® to facilitate writing this article. All thoughts and opinions expressed are her own.
 Chicago as seen from Sheraton Grand Chicago Riverwalk |
Stay Downtown, Especially Along the River
For an overnight stay, the best views of downtown are found along the Chicago River where you can not only enjoy the cityscape, but also the beautifully developed riverfront. My top choice for riverfront hotels is the Sheraton Grand Chicago Riverwalk, which is not only in a great location for spectacular views of the architectural marvels, but also within walking distance of attractions like Shoreline Sightseeing Architecture River Tour, Navy Pier, Buckingham Fountain, and the Museum Campus, among many others.
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Enjoy a Boat Tour
Between Lake Michigan and the Chicago River, there are several boat companies waiting to show you around. We chose Shoreline Sightseeing Architecture River Tour and took a relaxing, but very interesting river tour while our guide shared information on the amazing buildings along the river. My favorite, The St. Regis Chicago (you may know it as the "wavy skyscraper," in the center of my photo above), caught my eye on a previous trip to Chicago, so I was eager to learn about it. Turns out it's the tallest structure in the world designed by a woman!
 Chicago as seen from 360 Chicago |  Chicago as seen from Skydeck |
Visit the Top of a Skyscraper
With a Chicago CityPASS™ you get the convenience of expedited entry to Skydeck Chicago where you can conquer your fears and step out onto The Ledge, a glass balcony that extends outside the 103rd floor of Willis Tower. Plus you also have the option of visiting 360 CHICAGO Observation Deck for another adventure above the rooftops, this time on the 94th floor of the John Hancock building. If you're feeling really adventurous, add on a ticket for TILT, one of the highest thrill rides in the world... or just relax in the CloudBar and take in the views from the comfort of a chair.
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Take a Walk
On a nice day, the walk through Grant Park or along Lakeshore Parkway is stunning, whether you're looking at the skyline, the lake, or the museum campus. Take in "the bean" at Millennium Park and time your walk past Buckingham Fountain on the hour when the center jet shoots 150 feet in the air, or after dusk when the display is accompanied by lights and music. Whatever time you choose to take a stroll, you won't be able to resist looking up and wondering what's at the very top of each of those impressively tall structures.
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Explore the Museum Campus
Besides Skydeck Chicago, your Chicago CityPASS also offers entry to the Shedd Aquarium and your choice between 3 more attractions, including Field Museum, Adler Planetarium, Museum of Science and Industry, and nearby Art Institute of Chicago. No matter what your interests, you'll find something you'll love to learn more about between these museums. Plus the museum campus is a great place to view the entirety of the Chicago skyline.
Ready to start planning your visit to Chicago? I recommend starting by choosing which attractions you'll visit with your Chicago CityPASS and booking your stay at the Sheraton Grand Chicago Riverwalk. Enjoy the view!
