Best sightseeing tours in Chicago 

In a city as big and varied as Chicago, it can be difficult to figure out the best things to do while visiting. Joining an organized tour does much more than just filling a free morning or afternoon. It’s also a great way to learn about the local culture and history, as well as get a feel for what the city offers and what you might want to do next. From food tours to river cruises, there is no shortage of options to choose from in this bustling metropolis, whether you’re spending the day with family or looking for fun date ideas. Before you pack your bags, book yourself a spot on one of the best sightseeing tours in Chicago.

14 top tours in Chicago

Cruise tours in Chicago

With the Chicago River cutting through the city and Lake Michigan beyond the shoreline, joining a boat tour is a wonderful way to enjoy the city’s famed architecture without bumping into other pedestrians as your gaze is fixed upward.

1. Chicago skyline cruise

It’s thrilling to be in downtown Chicago surrounded by towering skyscrapers, but it’s impossible to see beyond the next block. If you want to zoom out a bit, take a seat on a Lake Michigan cruise and kick up your feet as you see the city’s skyline — and coastline — from a unique perspective. 

2. Chicago architecture tour

Architecture lovers will appreciate this guided boat tour that focuses on the history of the buildings that flank the Chicago River. This tour typically lasts around 90 minutes, and you’ll learn all the juicy details on the design and construction of some of the city’s most noteworthy buildings. 

3. Chicago sunset cruise

A romantic way to experience the city by twilight is to take a sunset cruise. Not only do you get to see the same sights you would in the daytime, you can also enjoy a delicious meal while you relax in the evening glow. A 90-minute tour is the perfect prelude to a night out downtown.

4. Chicago 3D fireworks cruise

If the Chicago skyline at night isn’t bright enough for you, check out a fireworks cruise during the summer months. In addition to watching a gorgeous display from the Chicago River and Lake Michigan, you’ll also enjoy music while aboard and have the chance to purchase snacks and drinks.

Bus tours in Chicago

Chicago is a large city, spanning around 228 miles geographically. With so much to see, joining a bus tour can be a great way to cover some serious ground in a limited time. And luckily, there are many options to choose from, depending on your interests.

5. Hop-on hop-off tour

The extensive route that this bus tour takes makes it a great option if you want to cover a lot of ground in a short period of time. You’ll be able to get off the bus at stops that interest you while seeing some of the city’s most famous landmarks from the comfort of a seat. When you’re ready to move on, just wait at the designated stop for the next bus to pick you up. Pre-recorded audio commentary is included, too. 

6. Chicago night bus tour

Chicago is dreamy by night with its dazzling skyscrapers and Navy Pier’s Centennial Wheel all lit up. After a long day of exploring, this tour is the perfect way to unwind and relax while soaking in the best of Chicago.

7. Gangsters and crime bus tour

Chicago certainly has a dark history of organized crime, and it’s most notably known as the adopted hometown of Al Capone after he left New York. Take this Chicago driving tour specifically devoted to the stories and locations of the city’s historical underworld.

8. Chicago night crimes bus tour

Amp up your crimes tour by experiencing the nighttime version. This chilling tour includes stories about Al Capone and Frank Nitti, and you’ll even get to disembark to explore some of the sights in person. 

9. Haunted ghost bus tour

Ready to explore the paranormal side of the Windy City? Take a group Chicago driving tour that gives you the inside scoop on spooky stories at locations like the site of the St. Valentine’s Day Massacre, Chicago City Cemetery and The Alley of Death (Couch Place).

10. Craft brewery bus tour

Chicago is practically overflowing with amazing craft beer. Hang up your car keys for the day and join a bus tour that takes beer lovers around to some of Chicago’s finest breweries. You can even experience this tour on a bus made to look like a giant barrel. You’ll get tastings at several breweries, plus a guided tour of a production facility to learn more about the brewing process.

Other sightseeing tours in Chicago

Hit the streets or the sky for a unique Chicago experience. If you’re looking for a fun day, these sightseeing tours allow you to see the city in a completely different way. 

11. Signature Dish bike tour

Chicago has a thriving food scene and it’s also known for classics like deep dish pizza, Italian beef sandwiches and hot dogs (served with mustard, relish and no ketchup). Experience the best local spots for these signature dishes while joining a group bike tour to work off some of the calories in-between destinations. 

12. Lakefront Segway tour

The Lakefront Trail stretches more than 18 miles along the Lake Michigan shoreline. Take in these views with a relaxing Segway tour that lets you enjoy the great outdoors for 2.5 hours while also seeing some nearby sights like Michigan Avenue and the Field Museum campus. 

13. Chicago skyline helicopter tour

Get a bird’s-eye view of the city with a private helicopter tour that can be arranged for anywhere between 10 and 45 minutes depending on your schedule and budget. You can get an aerial view of attractions like Wrigley Field and the Lincoln Park Zoo. 

14. Chicago self-guided driving tour

Consider making your own self-guided driving tour of Chicago based on your personal interests. Whether you want to explore the city’s architecture, urban parks or food destinations, you can simply map out your own path and use a rental car to navigate the area.

Best sights to see in Chicago

If you’re creating your own itinerary, here are a few must-visit spots you can’t miss on your trip to Chicago.

Navy Pier

This lakefront destination has rides, games, restaurants and shops to enjoy all year round. And in the summer, you can watch a free fireworks show from the pier on Wednesday and Saturday evenings.

Cloud Gate

Also known as the Chicago Bean, Cloud Gate is a public sculpture at Millennium Park. Its reflective surface provides the perfect backdrop for an iconic Chicago selfie. 

Art Institute of Chicago

Two bronze lions stand at the entrance of this world-class museum. It features the works of great artists like Pablo Picasso, Edward Hopper and Mary Cassatt.

Tour Chicago your way

Driving a rental car to the best sights in Chicago — and short road trips beyond — gives you the freedom and flexibility to do as you please and on your schedule. You can make the rental process the easiest part of your trip by booking with Avail. We have dozens of locations throughout neighborhoods in Chicago, and each one is equipped for self-service, so you can just grab the keys (or return them) and head on your way. Every trip is protected by Allstate insurance and offers 24/7 roadside assistance. Your booking also includes a second driver at no added cost, so you can share the wheel (and your experiences) at an affordable price.