The 15 Best Historical Tours in Chicago

1.Chicago in a Day: Food, History & Architecture Walking Tour

★★★★★★★★★★5.0 · 1,153 reviews · 4 hours 30 minutes (approx.) · from $100Our pick

Walk about 3 to 4 miles over roughly 4.5 hours with a local guide and no more than 11 other people. You’ll pass the Chicago Theatre, the Riverwalk, the Wrigley Building and Millennium Park, with tastings of Chicago favorites along the way. Guides have included Dave, Rich and Dash. Food is meant to add up to a meal, but the main tastings may come later in the tour.

“Informative; our guide Dave was passionate and knowledgeable. It was great to try Chicago’s iconic foods too!”

Check availability →Read our full review

2.Field Museum of Natural History Ticket or VIP Tour

★★★★★★★★★★4.7 · 717 reviews · 1 day · from $29Best value

Spend a day at Chicago’s Field Museum, home to Sue the T. rex, Maximo the Titanosaur, the Lions of Tsavo, and more than 35 exhibitions. Choose general admission, a pass with one special exhibition, an All-Access Pass, or an early VIP dinosaur tour with a museum docent. The VIP tour takes place before opening and includes all-access admission.

“Cool experience. Loved Egypt and the dinosaurs. The building is cool too!”

Check availability →Read our full review

3.Field Museum of Natural History Admission Tickets

★★★★★★★★★★4.5 · 489 reviews · 4 hours (approx.) · from $29

Visit Chicago’s Field Museum with general admission, see SUE the T. rex, 23 Egyptian mummies, and exhibits spanning natural history and ancient cultures. Free docent-led tours run daily, and you can stay at your own pace. Plan for plenty of walking; 3D films cost extra, and some special exhibits may require an upgrade.

“The Field Museum is great! You can easily spend all day there. I highly recommend one if the free tours done by volunteer docents.”

Check availability →Read our full review

4.Chicago Walking Tour: Historic Treasures of Chicago

★★★★★★★★★★5.0 · 362 reviews · from $35

Walk Michigan Avenue, State Street, and the Loop with a certified docent, stopping at the Wrigley Building, Palmer House, Carbide and Carbon Building, Reliance Building, and Chicago Cultural Center. The small-group tour includes Chicago Architecture Center gallery admission. Docents have included Bob, John, Jim, Maureen, and Laurel, though your guide may differ.

“Our tour guide John was extremely knowledgeable about the history and architecture of Chicago. We’re very glad we did the tour.”

Check availability →Read our full review

5.Historical and Architectural Chicago Fireboat River & Lake Cruise

★★★★★★★★★★5.0 · 246 reviews · 2 hours (approx.) · from $47

Spend about two hours aboard a historic Chicago fireboat, cruising the river and Lake Michigan with expert commentary on architecture, city history, and firefighting. You’ll pass through the locks between the lake and river, with open and enclosed seating, onboard restrooms, and snacks and drinks for sale. Guides such as Cliff have led entertaining tours.

“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.”

Check availability →Read our full review

6.Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

★★★★★★★★★★5.0 · 218 reviews · 2 hours (approx.) · from $44

Walk downtown Chicago with Colin on a small-group, two-mile tour that connects Chagall’s mosaic, the Rookery, Calder’s Flamingo, Picasso’s sculpture and more. Expect lively stories, architectural details, visual aids and a mix of indoor and outdoor stops. The tour lasts about two hours and costs $44 per person.

“Great tour. Fun facts & real history. Colin was just right, beautiful architecture & historical information….Daisy didn’t do it. 😂”

Check availability →Read our full review

7.Field Museum of Natural History All-Access Pass

★★★★★★★★★★4.5 · 135 reviews · 1 to 8 hours (approx.) · from $41

Spend 1 to 8 hours at Chicago’s Field Museum with an All-Access Pass for $41. See SUE the T. rex, Egyptian mummies, gems, and more than 35 exhibitions. Free daily docent-led tours are available, though you should ask about joining one early. The 3D movie costs extra.

“We were visiting family in Michigan and flew out of Chicago. We needed something dun to do before our flight. I can't recommend the museum more.”

Check availability →Read our full review

8.African American Heritage Tour of Chicago

★★★★★★★★★★4.5 · 127 reviews · 4 hours (approx.)

This four-hour Chicago tour travels through Bronzeville, Hyde Park, and South Shore in an air-conditioned vehicle, with commentary from local guide Steve. Expect stories about gospel, jazz, migration, and Black public figures, plus views of landmark homes and a planned soul food restaurant stop. Pickup options are available, including conditional airport pickup.

“The tour guide was excellent! He was passionate about the city of Chicago and wanted to share his excitement with us.”

Check availability →Read our full review

9.Food, History and Architecture Tour

★★★★★★★★★★4.8 · 104 reviews · from $99

Walk 3 to 4 miles through downtown Chicago, from the Pedway and landmark buildings to the Riverwalk and Millennium Park. Along the way, hear about Prohibition and city history, sample popcorn, a Chicago hot dog, deep-dish pizza and Italian beef, and get tips for exploring next. Groups are capped at 12; guides include Chicago native Dave and Dash.

“Chicago Dave was awesome! He gave us lots of Chicago native information and he was really into his job. Loved it!”

Check availability →Read our full review

10.Chicago Walking Tour: Historic Skyscrapers

★★★★★★★★★★5.0 · 67 reviews · from $35

Walk from the Fine Arts Building to the Monadnock Building with a Chicago Architecture Center-certified guide. In about 90 minutes, you’ll see the exteriors of the Auditorium, Rookery, Board of Trade and Marquette buildings, hear about Chicago’s early skyscrapers and architectural styles, and get admission to the Center’s galleries. Groups are capped at 10.

“WOW!! What a wonderful tour.. The Guide was outstanding and kept us all so interested!! So worth the money...”

Check availability →Read our full review

11.Historic Gangsters & Twilight Tales Night Cruise

★★★★★★★★★★4.1 · 63 reviews · from $45

Spend 90 minutes on a guided evening cruise along the Chicago River, pairing views of the Tribune Tower, Wrigley Building, Merchandise Mart, and Willis Tower with tales of the Eastland disaster, the Great Chicago Fire, H. H. Holmes, and more. The guide speaks English, and drinks are available to buy onboard.

Check availability →Read our full review

12.Field Museum of Natural History Early Access Ticket

★★★★★★★★★★4.5 · 52 reviews · 2 to 4 hours (approx.) · from $73

Start at 8 a.m. for a one-hour guided visit before the Field Museum opens, focused on Evolving Planet and SUE the T. rex. Then explore the galleries on your own. Guides have included Katie, Jacob, Eleanor, Dimitri, and Demetric. The ticket costs $73, and the full visit usually takes two to four hours.

“Super awesome being alone in amazing museum for an hour in the morning. Beyond amazing, thx so much for organizing. Docent knowledgeable and kind.”

Check availability →Read our full review

13.Chicago River Architecture Tour Aboard a Historic Yacht

★★★★★★★★★★5.0 · 45 reviews · from $49

Settle aboard a historic wooden yacht for a roughly 90-minute Chicago River cruise with a docent explaining landmarks such as the Wrigley Building, Riverwalk, and Michigan Avenue Bridge. Soda, coffee, and snacks are included, with alcohol available to buy. The group is capped at 60, and the cruise returns to its starting point.

“Lots of info shared, small boat experience was awesome plus free soda! Felt very professional and safe.”

Check availability →Read our full review

14.Historic Homes and Cottages of Wicker Park Walking Tour

★★★★★★★★★★5.0 · 44 reviews · 1 hour 30 minutes (approx.) · from $45

Explore Wicker Park on foot with a small group of up to eight. Guide Ronnie has been praised for connecting the neighborhood’s workers’ cottages, mansions, and historic buildings to Chicago’s past. The route is described as about three miles, with an Atlas app offering photographs and information about properties along the way.

“Ronnie was awesome he's extremely passionate and knowledgeable about architecture and it showed by his passion and his information he was able to share on the tour. The tour uses an application called Atlas which is really nice because it has all the stops on it with photographs and other information about the properties that you're viewing on the trip.”

Check availability →Read our full review

15.Historic Architecture Chicago River Small Boat Tour

★★★★★★★★★★4.6 · 26 reviews · 1h 30m · from $67

See more than 50 Chicago buildings from the river on a 90-minute cruise aboard a smaller historic yacht. An English-speaking guide explains the designs, construction, people, and ideas behind the skyline, from Art Deco and Gothic towers to modern skyscrapers. Coffee, soft drinks, lemonade, and snacks are included; alcoholic drinks cost extra.

“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…”

Check availability →Read our full review