Chicago · HISTORICAL TOURS
The 15 best historical tours you can book right now, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.
Taste Chicago classics and see major architecture fast on a small-group Loop walk with the Pedway and Millennium Park’s Bean.
“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.”
Chicago’s Field Museum options for dinosaurs and world cultures, from Sue and Maximo to jade, gems, and Tsavo lions.
“I took my 5 year old Grandson and he loved every exhibit from the Dinosaurs in the big hall to the rocks and crystals on 2, to the native exhibits and the birds. Lunch in the hall and then to the Trex and the life of Jane and probably the hit of the day - the Virtual Reality ride.”
Prebook tickets for Chicago’s Field Museum to see SUE the T. rex, Egyptian mummies, ancient Americas halls, and the Hall of Gems.
“Don’t go there unless you have a passion for ancient artifacts or different cultures or you have young children cause you’re gonna be bored and get field trip vibes. I’d rather go to a zoo instead of seeing lifeless taxidermy animals behind glass cases. Next time we’ll just go to the Science and Industry Museum cause that’s more our speed”
Chicago architecture walking tour from the Chicago Architecture Center to the Loop, with art deco interiors, small-group guides, and included galleries.
“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”
Ride a historic Chicago fireboat through locks from Lake Michigan to the Chicago River, with expert narration, sights, and snacks.
“I have lived in Chicago for many years, but it was a friend from out of town who found this tour online. The historic fireboat offers good views from all parts of the boat, and our guide provided a nice mix of architecture, city history, and funny stories. I have been on river tours many times, but the lake portion of the tour was something new for me. It was great to look back at the sweep of the city from a distance outside the breakwater.”
Walkin' with Colin: a 2-hour Chicago art-and-history walk ($44) from Chagall mosaics to Calder, Picasso, and the Cultural Center.
“This was a fantastic tour! Colin was very knowledgeable and upbeat! He kept us interested for the entire tour. It was a great variety of stops. I learned lots that I never knew about Chicago and have lived here 68 years! Take this tour!!!”
Skip stress with an All-Access Field Museum pass, timed entry, and free docent tours, plus major halls like SUE and Egypt.
“We went to see the “The First Kings of Europe “ exhibit and enjoyed it very much but there is so much more to see. We saw “Sue” the T-Rex, the lions of Tsavo and the Egyptian tomb exhibit. There was way too much to see in a day and we definitely want to go back. It was a great day.”
African American Heritage Tour of Chicago through Bronzeville, Hyde Park, and South Shore, ending with soul food and major figure stories.
“Mr. Steve was knowledgeable. Though I previously lived in Chicago, learned something new/interesting.”
Small-group Chicago food and architecture walk with Pedway tunnels, Prohibition-era stops, and three classic tastings plus popcorn.
“Excellent tour! The tour guide was very knowledgeable of history and architecture of the city. The food choices were great!”
A 90-minute small-group Loop walk past Chicago’s historic skyscrapers, led by a certified guide, with Chicago Architecture Center galleries included.
“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.”
A 1.5-hour Chicago River night cruise with spooky gangster tales, Eastland and Chicago Fire stories, plus skyline views from Tribune to Willis.
Get into the Field Museum early with a docent-led tour focused on SUE and Evolving Planet, then roam key galleries with fewer crowds.
“Fantastic early morning tour of the museum with everything quiet! The guide was so interested, knowledgeable and engaged and I was amazed by all the interesting exhibits. I met Sue!”
Historic Chicago River architecture cruise on a wooden yacht. Learn landmarks, sip soda and coffee, and take photos on a 90-min ride.
“The tour guide was amazing! He spoke without notes the entire time and knew pertinent facts about buildings, the architects and even dates. He later told one of the ladies in our group that he has a photographic memory - and it is easy to believe. He also knew about pending developments along the river which was an added bonus.”
See Wicker Park’s workers cottages and mansions on a small-group walk with an Atlas app and an architecture-focused guide. $45.
“I’ve taken several tours in Chicago and this is one of my favorites. The cottages themselves were very interesting to see, and our host provided us with great historical tidbits and the context of each house, which makes the whole experience full and rich. Thanks, Ronnie!”
A 90-minute small-boat Chicago River architecture tour with coffee, snacks, and live English commentary on 50+ iconic buildings.
“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. This wasn’t the guide’s fault, he was humorous and knowledgeable, but it did affect how much we learned while on the cruise. I also highly recommend arriving very early. Instructions said come 15 mins early and we got there 30 mins early to be safe, and almost every single seat was already taken. Overall, I…”
Every kind of day out in the city, and the best of each.
