Chicago Tours

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for their tours.99/person...

Take a tour of Chicago’s underground Pedway system and enjoy seasonal holiday decorations and sights along the way. Our tour begins in the lobby of the Swissotel (323 W. Wacker) where we descend into the Pedway and journey to the Cultural Center to see its famous Tiffany Dome. ...

On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s, but also to little-known stops that contain some of the best holiday decorations downtown...

Come get spooked on Bobby’s Fright Hike! Bobby’s Bike Hike is America’s longest running city bicycle company, and this is Chicago’s premiere Halloween ghost tour. Hop on two wheels and follow Bobby’s expert tour guides through some of the most paranormal and frightening spots in the Windy City...

There’s nothing more magical than downtown Chicago during the holiday season. 2-hour guided walking tour through the Chicago Loop, Millennium Park and the Magnificent Mile. This tour is brought to you, internationally recognized tour company headquartered right here in Chicago....

“Chicago’s Festive Lights: A Magical Christmas Journey” takes you through the heart of the Windy City during the most wonderful time of the year. Stroll down N State St, a vibrant area bustling with holiday shoppers and seasonal displays. *For reference only. Itineraries subject to change. ...