USA · WALKING TOURS IN CHICAGO
Every trip has one free day too few. These 5 walking tours in Chicago justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
Chicago Loop gangsters and ghosts tour with a historian guide, haunted hotel stops, Cloud Gate, and an optional minibus upgrade. About 2 hours.
“Taka, with her passionate love of history, gave us a fascinating introduction to the history of Chicago. She switched easily from Al Capone and gang warfare of the prohibition era and then told of tragic loss life on the SS Eastland. So many great stories, we loved it!”
Eat Chicago classics on a guided 1.5-mile walk through the Loop, with big tastings, landmark stops, and a free 2-hour bike or kayak.
“Great exposure to the iconic Chicago food items. Fran also did a great job explaining the architectural high points on our tour route.”
2-hour South Loop walk through gangster and ghost stories, from Al Capone sites to Death Alley, Palmer House, and the Congress Plaza.
“It was a fun and interesting tour. Baylor was a great and entertaining guide.”
Chicago in a Day walking tour: deep-dish and hot dog bites, pedway and river views, Millennium Park and Tribune Tower, small-group guide.
“I was only in Chicago for a couple of days and this tour covered a lot in a few hours. I’m definitely glad I did it. There was even a guy in your with us who lived in Chicago for a couple of years and he loved it too.”
Chicago Loop walking tour of secret interiors, domes, mosaics, and engineering stories. 2 hours, $35, start at Union Station.
“Grant was an absolutely phenomenal guide! Even after living in the suburbs most of my life, I saw parts of the city that I’d never experienced before. Grant’s depth of knowledge and engaging storytelling made the tour fascinating and fun! Our tour was a comfortable pace and it was a great way to enjoy our walk from the train station to the river walk. This tour is a CAN'T MISS for tourists, and I highly recommend it for locals as well. You'll find something to appreciate everywhere you look in Chicago, and I'll certainly be coming back for another tour with more friends!”
Every kind of day out, and the best of each.
