Where To See The Best Views Of Chicago


Big cities are thrilling when you’re on the ground, but getting a broader view is even more breathtaking, especially when it’s a real powerhouse like Chicago.

Here are 4 of the best views you’ll find in the Jewel of the Midwest:

1. From the Air

You might get a stellar view from the plane if you’re flying to Chicago from the Northeast. If possible, get a window seat on the left side, i.e. so you’re looking south out the window. After you cross the ocean-like expanse of Lake Michigan, you’ll see downtown Chicago right there on the shore. You might even be able to make out the Ferris wheel at Navy Pier. And then your plane will continue west, further and further, past all of Chicago, forcing you to take an hour’s worth of public transit to get back to the city proper. Hooray!

2. From the Observation Deck

The Hancock Center observation deck (now called 360 Chicago) has 94th– floor views in every direction, and it’s right in the downtown action on Magnificent Mile. Visit the observatory for $18 or get the views for free when you eat at the café, or have a drink at the bar. Is it touristy? Sure, and you should do it, it’s glorious. Starting this year, for those with steady stomachs, you can enjoy some horrifying downward views as part of the new “Tilt” attraction.

3. From the Harbor

The view of downtown from Montrose Harbor is understated, and ground-level, but well worth a trip north. It’s a nice quiet way to enjoy the skyline without wading through downtown crowds. Take a picnic and explore Montrose Beach while you’re up there.

4. From the Sea

Taking a cruise on Lake Michigan is the priciest option, but truly unparalleled, especially at sunset. You can join a gigantic party boat, but consider a smaller vessel with a company like Tall Ship Windy (most boats operate May through October, and trust me—you don’t want to be anywhere near the lake during the frigid off-season). Take a fireworks cruise for $35–40 and you’ll be treated to a fantastic display off Navy Pier on Wednesday and Saturday nights during the summer.

What’s your favorite view of Chicago? If it’s in your penthouse apartment, don’t tell us, we’ll just be jealous!


About Author

Sarah is the North America Editor for Go! Girl Guides and she wrote the New York City guidebook. Raised in rural Texas on mesquite barbecue and barrel racing, Sarah lived in Indiana for two years before moving to New York by herself. Some of her favorite experiences in North America include snowmachining outside of Anchorage, exploring Caladesi Island off the coast of Florida, touring a Cold War bunker in West Virginia, watching the sun set over Chicago from Lake Michigan, and taking an overnight train from Montreal to Halifax.


  1. Another beautiful place to visit where you can get a stunning view of the city is on the trail to the Shedd Aquarium. The Lakefront Trail goes along Lake Shore Drive and cuts through parts of grant park. Once you reach the Shedd Aquarium you can stop on the grassy hill, take out your picnic basket and enjoy a wonderful view of the city!

Leave A Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.