7 Unique Ways To See Chicago

Disclosure: This is a sponsored post but all thoughts are my own.

Whether you are visiting Chicago for the first time, rediscovering “the windy city” you fell in love with years ago, or call Chicago home, you’ll discover new and exciting things every time you explore it. Since I live in the suburbs I’ve been to Chicago dozens of times and each time I visit I have a different experience. There are some ways to get unique views of the city that will help you see it in a new way that both Chicago tourists and locals would enjoy.

Take a trolley ride.

While you could drive around the city on your own, taking a trolley is such a better way to explore the city because the tour guide shares interesting facts along the way. Chicago Trolley & Double Decker Co. offers four distinct tours this summer that highlight the best sites Chicago has to offer: Chicago Trolley’s iconic Downtown Tour, the Wrigley Field/Lincoln Park Zoo Route, the Museum of Science & Industry/Chinatown Route and the Night Tour. For those wanting to experience Chicago by water, Chicago Trolley also offers the Land, Lake and River Package combining the best of the Downtown Tour together with Mercury Skyline Cruises boat tour. 

The Downtown Tour stops at 13 distinct locations around the city. Beginning at the Sheraton Hotel, tours will venture south over the Michigan Avenue Bridge to Skydeck at the Willis Tower, then over to Millennium Park, stopping by the Art Institute, Hilton Chicago, Adler Planetarium, Field Museum, Shedd Aquarium and Maggie Daley Park. Looping north, the tour continues to Navy Pier, Magnificent Mile, Water Tower Place, the Hancock Tower featuring 360 Chicago and ending at the Hard Rock Café. The full Downtown Tour departs from downtown Chicago Trolley kiosks with all day access to hop-on and hop-off. Tours operate daily from 9 a.m. – 5 p.m., and are approximately two hours in duration.

The Wrigley Field/Lincoln Park Zoo Route (approx. 90 minutes) departs from the Sheraton Hotel and heads to the Chicago History Museum, Chicago’s oldest cultural institution. Passengers then visit Lincoln Park Zoo before the tour ends with a trip to Wrigley Field.

The Museum of Science & Industry/Chinatown Route (approx. 90 minutes) departs from Sheraton Hotel and travels south directly to the Museum of Science & Industry. The tour then explores one of the richest cultural communities in the Midwest, Chicago’s Chinatown.

The Night Tour showcases Chicago’s dazzling skyline and illuminated landmarks after the sun goes down. Beginning at Sheraton Hotel the Night Tour makes stops at the Skydeck, Hilton Chicago, Navy Pier and the Hancock Tower featuring 360 Chicago, allowing passengers to hop-on or hop-off throughout the evening. The Night Tour operates daily from 6:30 p.m. to 10 p.m., and is approximately 90 minutes in duration.

Take a tour by boat. 

There are a number of companies that offer architecture river cruises because Chicago’s rich history can be told through the beautiful buildings in our city. The breeze as you travel down the river feels nice on a hot, sticky day, too!

Get a birds eye view of the city from Skydeck Chicago’s Ledge. 

The Ledge is located at the top of the Sears Tower (yes, I called it the Sears tower because Chicagoans don’t call it by it’s new name of “Willis Tower”….) Skydeck Chicago’s Ledge offers spectacular views of up to 50 miles and four states from the 103rd floor. Their glass boxes with glass floors extend out the side of the building and let you stand 1,353 feet up in the air looking down.

Go on a carriage ride.

There’s no more relaxing way to explore the city than from the comforts of a horse-drawn carriage. The carriage ride is a memorable way to explore the city at a slower pace.

Get a beautiful view of the skyline from the lake.

Whether you go out on a friend’s boat or a chartered ride, there’s nothing like seeing Chicago’s skyline from the lake. I’d recommend going later in the day on a Wednesday or Saturday so you can watch the sunset and then stay for the firework show over Navy Pier.

Go out in a kayak on the river.

Want to explore Chicago at your own pace on the water? Rent a kayak and travel down the river for a unique view of the city while you get some exercise.

Take a ride on the new ferris wheel at Navy Pier. 

Navy Pier’s Centennial Wheel is an iconic part of the Chicago skyline. At nearly 200 feet tall, the wheel offers visitors unparalleled, 360-degree views of Chicago and Lake Michigan. The Centennial Wheel’s enclosed gondolas provide a comfortable experience year-round.

BONUS IDEA! Ride around the city in style in your very own limo or party bus! As a kid I always dreamed of riding around in a limo but now that I’m an adult I think a party bus full of my friends sounds fun. Use Limo Find to locate a limo or party bus nearby and book it to explore Chicago.

Have you ever been to Chicago? If so, I’d love to hear about your visit, and if not, what are you waiting for!?