Itinerary

Starting Point for 11am & 11:30am Daytime 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
20 minutes
Admission Included
The Magnificent Mile
(Pass By)
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
20 minutes
The Magnificent Mile
(Pass By)
Then, 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!
20 minutes
Wrigley Building
(Pass By)
See the first major skyscraper north of the Chicago River.
5 minutes
Admission Included
The Chicago Theatre
(Pass By)
Chicago's iconic theatre Marquee on State Street.
5 minutes
Chicago Pedway
(Pass By)
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.
Jay Pritzker Pavilion
(Pass By)
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.
10 minutes
The Loop
(Pass By)
The Loop is Chicago’s bustling business district, named for its location within the rectangular convergence of multiple “El” train tracks.
Cloud Gate
(Pass By)
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.
15 minutes
Crown Fountain
(Pass By)
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.
15 minutes
Palmer House Hilton Historic Lobby
(Pass By)
Enjoy the original recipe brownie, which was first invented in Chicago for the 1893 World's Fair.
9 minutes
Admission Included
Millennium Park
(Pass By)
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.
30 minutes
Palmer House Hilton Historic Lobby
(Pass By)
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.