Top Chicago Public Transportation Tours in 2026

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot and by L train, and see the city’s most iconic landmarks like The Rookery Building, Chicago Cultural Center, First Arts Building, and more 19th and early 20th-century masterpieces. Be ready to see the City by the Lake from a new perspective and get to know it even closer as you stroll down its streets and travel by train. Enjoy the small-group experience and don’t miss a thing as you travel Discover the downtown and historical building together with your local knowledgeable guide Marvel at architectural landmarks of the City by the Lake and get to know the stories behind them Combine a walking tour with a train to see more landmarks and iconic sights on one tour.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.