Chicago Tours

Chicago is a sprawling city, comprised of dozens of neighborhoods with unique characteristics and singular attractions. It can be hard to approach exploring the city without an insider’s knowledge of the best way to get to Wicker Park, or the top pizza place in River North. Fortunately, there’s a wide variety of tours available in Chicago to help visitors make the most of their time in the city while easily navigating the best attractions, areas, and cuisines.

For first-time visitors, bus tours are a smart option. They can help you see more of the city than you would be able to via mass transit (without some very complex planning, that is). Bus tours also allow you to see the highlights of the city via a pre-planned route that maximizes sightseeing potential and minimizes driving time. Hop-on hop-off options are key here, too, as they facilitate exploring the city at your own pace, and visiting attractions that pique your interest from the bus. There are even themed bus tours that cover topics like food, drink, and Chicago culture.

Chicago boasts many types of tours beyond the typical bus tour, however. If you’d like to experience Lake Michigan or the Chicago River – two essential components to the city’s identity – then a boat tour is a smart option. You can choose a tour that simply showcases the lake, or one that highlights city architecture. Visitors can also opt to explore the via bike: take a guided tour or explore on your own. Given that Chicago is a very walkable city, it’s unsurprising that another popular type of tour is a walking tour. These are usually themed around a concept like food, drink, pop culture, local legends, and more. The Chicago Architecture Center also runs many architecture-specific tours, and many companies offer guided tours (on foot or via bus) related to culinary concepts.

Whatever kind of tour you’re interested in, you’ll find a number of excellent options in Chicago. Here’s an overview of the most popular tour types in Chicago.

Bus Tours

The classic option for exploring Chicago, bus tours come in a variety of styles ranging from guided tours of the North and South Sides to fully-narrated hop-on hop-off tours.

Boat Tours

With Lake Michigan and the Chicago River being so important to the city, it’s no surprise that you can tour the city via boat. Choose a theme, or just enjoy the sail.

Bike Tours

Explore the city in an eco-friendly way by making your way through the parks and trails of Chicago on two wheels. Take a self-guided tour, or opt for the full experience.

Walking Tours

In spite of its massive size, Chicago is the ideal city for a walking tour. Explore a neighborhood, a theme, a concept, or a story on these guided excursions.

Food Tours

If you’re interested in Chicago’s culinary scene, then a food tour is a must. They’re organized around neighborhoods or cuisines and are perfect for foodies.

Architecture Tours

Chicago’s architectural legacy is among the best in the country. Enjoy the amazing, inspiring buildings that populate the city skyline on an architecture tour.

Tour Companies

Gray Line Chicago

Gray Line Tours offers 5 different tour options in Chicago. Popular Gray Line Chicago tours include the Chicago Grand City tour, the Chicago North Side tour, and the Historic Chicago South Shore tour.

Chicago Crime Tours

Takes visitors on guided outings to a number of famous crime scenes. Along the way, guests will learn about Chicago’s history as a hotbed for criminals like John Dillinger, Al Capone, and more.

Bike and Roll Chicago

Offers a variety of guided bike and Segway tours that take visitors to a number of Chicago’s most iconic attractions. They also offer bike rentals by the hour or day.

Tall Ship Windy

Based out of Navy Pier, Tall Ship Windy operates a variety of scenic cruises on its approximately 150-foot schooner. Popular tours include the Lakeside Architecture Sail and the Skyline Sail, with several other options available.

Big Bus Chicago

With their distinctive fleet of open-top, double-decker buses, Big Bus Chicago offers hop-on, hop-off tours that let you choose where and when you stop at a given attraction.

Shoreline Sightseeing

Has been running scenic tours of Chicago along Lake Michigan and the Chicago River for 80 years. Their most popular tours include a river excursion highlighting Chicago’s acclaimed architecture and a lake cruise departing from Navy Pier.