Chicago Picasso (The Picasso) Tours

Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.

This Chicago grand tour covers four hours of sightseeing with admission to 360 Chicago (John Hancock Observatory). Get oriented to the Windy City on a coach tour that takes you along a scenic route on Lake Shore Drive, and past North Side and South Side highlights including Museum Campus, Lincoln Park, Washington Park, Grant Park and Wrigley Field. Finish on the 94th floor of the Hancock Center, one of Chicago's tallest landmarks, for panoramic views of the Magnificent Mile from the open-air observation deck.

Explore the North Side of Chicago on this guided sightseeing tour by coach. During this 2-hour tour, experience the bustle of the Loop, the central business district and one of the financial centers of the country. Visit State Street, an important thoroughfare in Chicago's history and the Magnificent Mile along Michigan Avenue. Learn about the history and culture of the city from your local guide; upgrade your tour to include a Chicago River cruise.

Take a walk back in time through the history of Chicago's Loop on this app-enabled tour. After downloading the app and tour to you smartphone, you and your party will listen to author Amy Bizzarri, an author and expert in Chicago history, as she leads you through walking tour of the city. The GPS-enabled tour will trigger commentary at just the right times, and you can stop and start whenever you like for a flexible experience that lets you move at your own pace. Highlights include Daley Plaza, the Chicago Theater, Berghoff Restaurant, and the Art Institute of Chicago.

Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch. Focus can be on public or street art, architecture, food, and much more!

Not only will you receive a safe and scenic guided tour through the city, your guide is an excellent resource to answer those questions you may have about biking the streets of Chicago or the history of a neighborhood we've cycling through! Finally, an environment where you can explore biking at your own pace, without mad cyclists scorching past.

Explore the hidden side of Chicago on a 2-hour walking tour of The Loop, a bustling neighborhood that’s full of wild history, architectural landmarks and some of the city’s most fascinating characters. Follow your local guide along the sidewalk, and stop to notice the overlooked details and untold stories that even life-long locals sometimes miss. Experience the city one small piece at a time on a route that traces a path between Chicago’s littlest treasures, and get an inside look at life in the Second City.

Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.

Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.

Soak up the Windy City’s festive holiday feel and explore local landmarks with ease on this Segway tour in Chicago. Hop onto your Segway and spin through Chicago’s Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive department store displays. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city’s Christmas tree. Get the personalized feel of a small-group experience.

Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this walking tour. Your expert guide will share insights about interior architectural features of this design-rich city—from mosaic domes to the sprawling Chicago Pedway System—bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.