Top things to do in Chicago in Summer (Updated October 2026)

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience...

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture,...

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront...

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and...

Experience the best Chicago kayak rentals and Chicago SUP & paddleboard rentals from our unbeatable location at Ohio Street Beach, just steps from Navy Pier...

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary...

S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely...

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of...

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only...

Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks,...

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago...

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views...

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional...

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline....

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the...

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with...

Uncover the best of Chicago on an unforgettable highlights tour designed for travelers, sightseers, and history lovers alike! Step off the bus to admire Frank...