USA · WALKING TOURS IN CHICAGO
Good walking tours in Chicago fill up weeks ahead and the great ones go first. Below: the 8 to book early, what each includes and how they differ.
Explore Chicago’s Loop through Al Capone stories, haunted hotels, Death Alley, Millennium Park, and the Riverwalk on a lively 2-hour walk.
“We had been walking the same area but knowing the history definitely made our trip more interesting. Sophia was great! Congrats on getting engaged Sophia!”
Taste deep dish, hot dogs, Italian beef, brownies, and popcorn while walking Chicago landmarks, with a free bike or kayak rental included.
“Very fun tour full of delicious food. Great portions and a nice variety. Walking was just right in between stops to digest! Had two young teens with us and they enjoyed the tour as well. Would recommend!”
Explore Chicago’s gangster past and ghost lore on a 2-hour South Loop walk covering Death Alley, Palmer House, and the Congress Hotel.
“It was excellent!! Max was very informative and really made it so much fun!!”
Taste deep-dish pizza, Italian beef, and Chicago hot dogs while exploring the Loop, Riverwalk, Millennium Park, and landmark architecture.
“Dash was fantastic! He loves the City and showed us hidden treasures I’d never seen after traveling to Chicago for nearly 25 years. He pointed us to a list of his favorite off the beaten track finds, so I’d say START your stay in Chicago with this tour. You will NOT be disappointed. He took into account food needs for all. Also, I was having some medical issues I didn’t know about. It resulted in me struggling with the stairs and uphills more than usual. Appreciated that he keyed in and could see I was having some challenges and worked around them, without making a deal of it. Great guide!!!!…”
Explore Chicago’s grandest interiors, from the Rookery to Tiffany glass, with a lively two-hour Loop architecture walk for $35.
“Ethan was great! I was surprised how many people showed up on a rainy Chicago day. Ethan kept our group engaged and safe as we moved around the city going in and out of some very beautiful buildings. He has extensive knowledge of the city and its architecture and history. I highly recommend!”
Taste dumplings, noodles, Sichuan chicken, Xi’an lamb, and egg tarts while exploring Chicago Chinatown with a local guide.
“Great sampling. Good variety. Some spicy so beware! Absolutely delicious and worth it! Mickey was super!!!”
Explore Chicago’s secret interiors, grand domes, mosaics, and engineering feats on a two-hour Loop architecture walk.
“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!”
Explore Chicago gangster history while tasting steak, deep dish pizza, and a classic hot dog on a small-group River North food walk.
“Taka was great! Knowledgeable and kept us moving with lots of super info! Delicious food too— definitely could make it a lunch or early dinner!”
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