Starting Point for 5:30pm Evening Tours only. Here you’ll meet your entertaining and energetic guide who will give you an introduction to Chicago’s epic history before indulging in a bubbling, cheesy, stuffed Chicago pizza pie

Stroll down elegant Michigan Avenue and pass renowned local attractions before walking down the start of Route 66 to Max's Take Out, a quintessential Chicago hot dog stand that has stood the test of time. Inside, taste what makes Chicago's unique hot dog so special!

See the first major skyscraper north of the Chicago River.

During colder months, your guide will make use of the Chicago Pedway system, a network of tunnels, ground-level concourses and bridges that connects sites throughout Chicago’s central business district, to keep you as cozy as possible. During warmer times of the year, walk along the large scenic promenades of the Loop. Expect to walk at a leisurely pace for 1.5 miles during the 2.5-hour tour, suitable for most fitness levels, with plenty of stops for tastings and photos. All tastings and beverages are included. Please give advance notice of any dietary restrictions.

AM tours only. Designed by world-famous architect, Frank Gehry, The Pritzker Pavilion is a stunning and unique band shell located in Grant Park. The lattice tower of speaker systems ensures full volume for all spectators at countless summer concerts and movie screenings.

The Loop is Chicago’s bustling business district, named for its location within the rectangular convergence of multiple “El” train tracks.

AM Tours Only. Chicago's iconic theatre Marquee on State Street.

AM Tours Only. Cloud Gate, located within Millennium Park, is known affectionately as “The Bean” and debuted in 2006. Designed by famed Indian artist, Anish Kapoor, this giant, stainless steel masterpiece has become one of the most famous symbols of Chicago arts and culture.

AM Tours Only. A modern town square with a collection of art, architecture, and gardens that provides a stunning backdrop for hundreds of cultural events. Full tour of the park.

AM Tours Only. Enjoy the original recipe brownie, which was first invented in Chicago for the 1893 World's Fair.

AM Tours Only. The Crown Fountain was designed by Spanish artist Jaume Plensa and features two fifty-foot tall statues of glass brick that showcase the LED faces of over 1000 Chicagoans laughing, smiling, and spitting.

FREE 2 HOUR BIKE or KAYAK RENTAL INFO: As an additional perk for booking this particular tour, you will get a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of your tour booking. Terms below: To be used within +/- 3 days of your tour booking. Bike rentals take place at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL60611. Bike shop is open year-round (excluding Thanksgiving & Christmas). Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611. Kayak shop open mid-May to mid-October, weather dependent. Offer excludes Saturday Bike/Kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September). Kayaking only available from June-September) No discounts for not using this activity or issues due to weather restrictions.

PM Tours Only. Chicago's Historic Water Tower sits at the north end of the Magnificent Mile as one of the only buildings to have survived the Great Chicago Fire.

PM Tours Only. One of the largest Cathedrals in North America, Holy Name Cathedral represents an achievement in Architecture and community building representative of Chicago.