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.

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

unique ways to see Chicago


  1. Jenna Wood says

    I never considered a tour by boat- we visited Chicago a few years back for a concert and there was truly so much to do in such a short time. It’s a wonderful city!

  2. I’ve been to Chicago several times, and I love it there. I had no idea they had a trolley ride. That’s really cool!

  3. Chicago looks like such a fabulous place to visit. Believe it or not, I have never been in a trolley – in any city!

  4. How did I not know that there are trolleys in Chicago!? That would be so much fun to do with my family. If I ever get back over to Chicago I am definitely going to do the trolley.

  5. Chicago has been on my bucket list for a long time. I use to go all the time before we had kids!

  6. I haven’t had a chance to visit Chicago yet. It sounds like a wonderful place to visit. I would love to do a boat tour.

  7. It is fun to have so many fun options for seeing Chicago. I am a huge fan of trolley rides!

  8. I was in Chicago for 24 hours last month. I tried to cram everything in and got so overwhelmed!

  9. Meagan Ivie says

    My friend just got back from Chicago! I’ve always wanted to visit! Looks like such a breathtaking city.

  10. Claudia Krusch says

    Chicago is one of my favorite places to go. We always enjoy a trolley ride and see the sights.

  11. Love these ideas! I’ve never been to Chicago but I would love to go. It could be a super fun family vacation.

  12. I’ve always wanted to go to Chicago for a family vacation. I think the trolley ride would be an awesome choice since it offers so many places to visit along the routes. Plus the hop off/on option is nice too.

  13. These are really great tips! We’ve been to Chicago but never did some of these. Will have to add these to our list next time.

  14. Jennifer G says

    WOW! I have never been to Chicago. This has totally inspired me to book a trip asap and try some of these ideas!

  15. Its been years since Ive been there. We keep saying we want to take a drive there some weekend.

  16. We’re in Chicago frequently to see family and these look like a great excuse to rediscover some fun parts of the city that we often over look. My boys are all about any unique transportation so they’d get a kick out of these!

  17. ah, you did that! That is so cool. I want to wait for the little one to get a bit older to take Chicago tour. As of right now it is so challenging – he doesn’t want to sit still at all

  18. Great roundup of Chicago. We were just there last weekend and took the Chicago Architecture Foundation River Cruise and it was amazing. Such a different perspective of the city and its buildings.

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