CHICAGO · ILLINOIS
The best of Chicago.
The 15 best historical tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Deep-dish, hot dog, Italian beef and Chicago skyline stories on a small-group 4.5-hour walk with the Pedway and The Bean.
Most Popular“Excellent Tour guide. David was so knowledgeable, patient and helpful. I was on a rolator David knew exactly where the elevators were located. By preparing for the locations, it made everyone comfortable.”
Skip the line at Chicago’s Field Museum. See Sue and Maximo with optional VIP early access and special exhibits, from gems to lions.
“Unfortunately our timing was short, so we will have to come back! But…, we enjoyed your special of “The First Kings of Europe” in which we spent nearly two hours. For us was quite a surprise to know everything started in the Balcalns Peninsula! Congrats!”
Field Museum tickets in Chicago for $29 per person. See SUE the T. rex, Egyptian mummies, Chinese jade, and more with docent tours.
“The museum is easily accessible and has many exhibits. Very interesting and informative. We certainly enjoyed ourselves.”
Historic treasures of Chicago on a small-group 2-hour walk: CAC galleries, Wrigley Building views, Palmer House lobby, Cultural Center.
“John, our docent, was great - the tour was super interesting and he really took the time to answer questions and being the buildings to life. Thank you for a great tour”
Cruise Chicago from a historic fireboat, mixing lake views, river architecture, and fire-service stories for about 2 hours.
“Be prepared for a very entertaining 1 hour tour on the river and 1 hour on the lake. Tour boat cozy and historic with a very knowledgeable guide.”
A small-group Chicago walk mixing big-name art, iconic skyscrapers, and humor, ending at the Chicago Cultural Center.
“Colin was extremely knowledgeable about the history and architecture of Chicago. The tour was interesting, entertaining, and highly enjoyable. He puts a tremendous amount of effort into preparation with added electronic images to supplement the discussion. Lots of hidden gems that are well worth seeing and photographing. The walking pace was not strenuous and time…”
Get easy, flexible entry to the Field Museum in Chicago with access to ticketed exhibits, plus free docent tours for a smart day out.
“Amazingly beautiful space! A must see if visiting Chicago for the first time or a return visit. Thank you!”
A 4-hour African American Heritage tour of Chicago’s Bronzeville, Hyde Park, and South Shore with stops tied to music, politics, and soul food.
“Steven was a phenomenal tour guide with lots of experience and knowledge! The tour was also interactive and Steven is hilarious! Pleased to be able to experience parts of Black Chicago by a person from Chicago. Great tour!”
A 5-hour small-group Chicago tour mixing Prohibition-era architecture and classic food tastings, ending at Millennium Park and the Bean.
“Our guide was great! Extremely knowledgeable and helpful. Highly recommend the tour.”
Chicago’s Loop skyscrapers on a 90-minute small-group walk, with a certified guide and included Chicago Architecture Center gallery admission.
“Excellent! Our tour guide, Angela Platt, was wonderful. She had a lot of knowledge about all of the buildings. We learned things about the different styles of architecture and she took us in the buildings and pointed out the inside and the styles inside. I would highly recommend this tour.”
Chicago Field Museum early access with a one-hour docent tour before crowds, featuring Sue the T. rex and time to explore.
“Fantastic. If you are a museum person doing the early admission is worth every penny. Our tour guide was great and we didn’t have to fight the crowds. This is an amazing museum and would recommend it.”
A 90-minute Chicago River night cruise with skyline views and spooky stories about disasters, the Chicago Fire, and H. H. Holmes.
“So much fun and so much history fed onto us in forms of tales and stories. Loved it all!”
Ride a historic yacht on the Chicago River for a 90-minute architecture tour past Wrigley Building, the Riverwalk, and bridges. $49.
“The information was awe inspiring. My husband and I had no idea of the great history and architecture of Chicago. We are still so impressed with the knowledge of our tour guide and how proud and exciting her tone as she presented. Great tour and we recommend anyone who visits Chicago to take this tour!…”
A small-group Wicker Park walk through workers’ cottages and landmark homes, led by an architecture-obsessed guide with an easy mobile guide.
“Great tour! Ronnie taught us a lot of history through Wicker Park’s houses and streets, changing the way in which we look at the city forever. Highly recommend!”
A small Chicago River architecture cruise with 50+ skyline buildings, a live English guide, plus coffee and snacks. 90 minutes from $67.
“We enjoyed the smaller feel of this tour vs others that have hundreds of people, but we had a hard time hearing the guide. We were at the front of the boat and between the people around us talking nonstop and the low volume of the speaker, we only heard about half of the tour.…”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
