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

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,...

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...

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...

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...

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...

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace....

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the...

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your...

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the...

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a...

This self-guided Adventure is perfect for last-minute travelers who love animals and games, and for families traveling with kids! Travelers will use the eATLAS app...

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and...

Embark on an engaging scavenger hunt through the historic streets of Chicago! Explore the beautiful Magnificent Mile. Stroll the happening riverwalk See the historic sights...

Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots...

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on...

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers...

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important...

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent...

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer...