Chicago’s historical tours offer practical ways to understand America’s great Midwestern metropolis. The well-organized Chicago in a Day Tour packs the most value – covering essential sights in 5 hours across 3-4 miles. Architecture buffs will appreciate the concise 2-hour Walkin with Colin Tour, which expertly explains the city’s famous buildings and public art.
We especially love the Field Museum’s docent tours for their behind-the-scenes access to over 40 million artifacts, while the African American Heritage Walking Tour provides crucial insights into the city’s cultural evolution.
Check out these top Chicago tours for an enriching historical experience:
Good To Know
Chicago offers a diverse range of historical walking and guided tours, including the Chicago in a Day Tour, Historic Treasures Tour, and Walkin with Colin Tour.
Field Museum, a renowned museum, provides admission options, early access tickets, and a 3D movie experience to enhance educational and family-friendly visits.
Architectural and cultural tours, such as the Architectural Icons Tour and Art Deco Focus tour, offer insights into Chicago’s rich architectural heritage and cultural significance.
Tour logistics and accessibility are well-considered, with small group sizes, flexible booking, and public transport accessibility to cater to diverse participants.
Unique experiences include a small boat river architecture tour, ghost and haunted tours, and cultural heritage tours that delve deeper into Chicago’s history and hidden gems.
Chicago in a Day: Food, History and Architecture Walking Tour
The “Chicago in a Day: Food, History and Architecture Walking Tour” offers a comprehensive introduction to the city’s top landmarks, historical significance, and culinary highlights.
Over approximately 5 hours, small groups of up to 12 travelers explore Chicago’s architectural icons, including the Chicago Riverwalk and Millennium Park, while sampling iconic local foods like deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs.
Knowledgeable local guides provide personalized attention and share insights into the city’s history and culture.
The tour covers 3-4 miles on foot and is suitable for all ages and fitness levels.
With exceptional reviews and a high recommendation rate, this Chicago tour is an excellent way to experience the city’s rich heritage and vibrant cuisine.
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Field Museum of Natural History Admission Tickets
Visitors to Chicago’s renowned Field Museum of Natural History can enjoy a captivating journey through 13,000 years of history, home to over 40 million artifacts.
The museum offers free daily docent-led tours, as well as ticketed exhibits and a 3D movie experience. With its impressive collection of Egyptian mummies, the world’s largest T. Rex, and a stunning Hall of Gems, the Field Museum is a must-visit destination.
Families will find the museum to be both educational and kid-friendly, with the option to upgrade for access to special exhibits.
While early closures and crowded conditions due to field trips can pose challenges, visitors are advised to arrive early, check for special events, and inquire about exit routes to make the most of their experience.
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Chicago Walking Tour: Historic Treasures of Chicago
A captivating Chicago walking tour, “Historic Treasures of Chicago,” immerses participants in the city’s rich architectural legacy. Rated 99% recommended with 326 reviews, this small-group tour focuses on the stunning art deco interiors and historic buildings along Michigan Avenue, State Street, and the Loop.
The knowledgeable guides, such as Russell, John, and Laurel, lead engaging narratives that bring the city’s history to life. Travelers can explore the impressive Chicago Architecture Center and enjoy the convenience of wheelchair accessibility, public transportation access, and flexible booking options.
Whether seeking an educational experience or a deeper appreciation for Chicago’s architectural wonders, this walking tour delivers an unforgettable journey through the city’s historic treasures.
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WALKIN WITH COLIN! Chicago : History-Mystery-Comedy-Tragedy
Oftentimes, travelers embark on Colin’s “Walkin with Colin: Chicago History-Mystery-Comedy-Tragedy” tour, a captivating 2-hour excursion that covers 2 miles in downtown Chicago.
Rated 5.0 out of 93 reviews, this tour is 100% recommended by visitors who praise Colin’s enthusiastic storytelling and ability to showcase the city’s hidden gems.
From Calder’s Flamingo to Picasso’s iconic sculpture, participants explore art, architecture, and the rich history that has shaped Chicago’s culture.
Tailored for groups of up to 10, the tour concludes at the stunning Chicago Cultural Center, providing a comprehensive introduction to the city’s past and present.
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Field Museum of Natural History Early Access Ticket
The Field Museum of Natural History Early Access Ticket offers travelers a unique opportunity to explore one of Chicago’s premier attractions with fewer crowds and enhanced access.
This private docent tour allows visitors to enter the museum before it opens to the public, providing an intimate experience of key exhibits, including the iconic dinosaur displays and the famous SUE the T. rex.
Knowledgeable guides share educational insights, and guests can also enjoy additional shows and 3D movie experiences.
With all-access admission, wheelchair and stroller accessibility, and high traveler recommendations, this early access ticket is worth the extra cost for a personalized museum visit.
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African American Heritage Tour of Chicago
Delving into Chicago’s rich African American heritage, the African American Heritage Tour offers travelers an immersive experience that showcases the city’s profound cultural and historical significance.
With 68 reviews and a 4.5-star rating, this 4.5-hour tour provides an in-depth look at the pivotal role of the Black community in shaping Chicago. Guided by local experts, the tour highlights notable landmarks and cultural insights, including sites tied to the Obama family.
While the tour receives praise for its informative content, some travelers note the need for a more balanced portrayal of the city’s Black history.
Priced at $125 per person, the tour is accessible to the public, though not wheelchair-friendly.
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Chicago: Architecture, History & Highlights Small Group Tour
Offering an immersive exploration of Chicago’s captivating architecture, history, and cultural highlights, the Chicago: Architecture, History & Highlights Small Group Tour provides an engaging and informative experience for visitors.
With a 92% traveler recommendation and a Badge of Excellence, the tour showcases the city’s iconic landmarks, from the Chicago Riverwalk to the Bean sculpture.
Led by friendly, English-speaking guides, the tour offers personalized attention, architectural insights, and opportunities to sample local treats.
Accessible and child-friendly, the tour covers approximately 3 miles, allowing participants to soak in the city’s stunning river views and beautiful parks.
Priced competitively with a lowest price guarantee, the tour’s flexible cancellation policy ensures a hassle-free booking experience.
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Chicago Walking Tour: Historic Skyscrapers
Enjoy the rich architectural heritage of Chicago on the Chicago Walking Tour: Historic Skyscrapers.
This highly-rated tour, with a 5-star review score, takes you on an engaging exploration of the city’s iconic skyscrapers.
Led by a professional and certified architecture expert, you’ll visit significant landmarks like the Fine Arts Building, Auditorium Building, and the Rookery Building, a National Historic Landmark.
The tour also includes access to the Chicago Architecture Center galleries.
With a maximum of 10 travelers, you’ll enjoy insightful commentary and have the opportunity to appreciate Chicago’s architectural masterpieces up close.
Wheelchair and stroller accessible, this tour offers an immersive experience for architecture enthusiasts and history buffs alike.
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Walking Tour of Historic Cottages and Buildings of Wicker Park
Travelers can explore the charming historic neighborhood of Wicker Park on the “Historic Homes and Cottages of Wicker Park Walking Tour.”
This guided tour showcases the area’s rich architectural heritage, from 19th-century workers’ cottages to grand mansions. Lasting 2 hours, the morning tour starts at 11:00 am and is limited to 8 travelers, priced at $45 per person.
Utilizing a free app with historical photos and information, the knowledgeable guide shares insider stories about Chicago’s architectural history. Positive reviews highlight the tour’s educational value and the guide’s passion.
While not wheelchair accessible, the tour requires a moderate fitness level and is located near public transportation.
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The Devil in the White City: A Haunting History Tour
The “Devil in the White City: A Haunting History Tour” explores the dark and captivating history of Chicago during the city’s iconic 1893 World’s Fair.
Operated by Chicago Hauntings, this 4.5-star rated tour takes participants on a bus journey through the city’s past, delving into the architecture, serial killers, and ghost stories associated with the event.
While the tour focuses more on historical aspects than paranormal experiences, the knowledgeable guides deliver an engaging narrative.
Participants should note the tour’s lengthy duration and potential mobility challenges.
Read our full review: The Devil in the White City: A Haunting History Tour Review
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Field Museum of Natural History Discovery Pass
The Field Museum of Natural History Discovery Pass offers visitors an immersive journey through the wonders of the natural world.
Located in Chicago, the museum is open year-round, with free daily docent-led tours and access to all general admission exhibits. Visitors can explore exhibits in over a dozen languages and enjoy one ticketed special exhibition.
The pass, priced from $35 per person, provides flexibility with free cancellation and a reserve now, pay later option. Accessibility features, including wheelchair and stroller access, make the museum welcoming to all.
Visitor reviews praise the museum’s engaging exhibits, especially the popular dinosaur and evolution displays, and recommend dedicating a full day to fully experience the expansive collection.
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Saturday Chicago Pizza History and Tastings Bus Tour
This engaging Saturday Chicago Pizza History and Tastings Bus Tour takes visitors on a delectable journey through the rich culinary heritage of the Windy City.
Over approximately 3.5 hours, guests explore Chicago’s iconic pizza scene, visiting four diverse establishments and learning about the evolution of this beloved dish.
Led by knowledgeable guides, the tour provides fascinating insights into the city’s pizza history and culture.
Participants receive a lanyard/badge for social media and discounts at local restaurants, while soda and alcoholic drinks are available for purchase.
With a maximum of 24 guests per bus, the tour offers an intimate and personalized experience, and vegetarian options are accommodated upon request.
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Guided Historic Small Boat River Architecture Tour in Chicago
Navigating the serene waters of the Chicago River, the Guided Historic Small Boat River Architecture Tour offers an intimate exploration of the city’s iconic landmarks and captivating architecture.
With a 100% traveler recommendation and a Badge of Excellence, this 90-minute tour aboard a historic yacht provides an immersive experience for up to 60 guests.
Complemented by knowledgeable guides, the tour highlights the Wrigley Building, Chicago Riverwalk, and Michigan Avenue Bridge, among other architectural marvels.
Onboard amenities include complimentary refreshments, with alcoholic beverages available for purchase.
While the narration style may vary in pace, the tour is best suited for architecture enthusiasts and can be enjoyed throughout the summer season.
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Skip-the-Line The Field Museum of Natural History Exclusive Guided Tour
Visitors seeking an immersive exploration of the Field Museum of Natural History in Chicago can embark on a Skip-the-Line Private Guided Tour. This exclusive 2.5-hour excursion allows guests to bypass queues and explore the museum’s vast collections with a knowledgeable guide.
Accommodating a maximum of 8 people, the tour is wheelchair-accessible and situated near public transportation. While gratuities and transportation to/from the meeting point aren’t included, the experience provides unparalleled access to the museum’s treasures.
Reviewers consistently praise the guide’s exceptional expertise and engaging presentation, transforming each visit into a riveting history lesson. Regardless of the season, this Skip-the-Line tour promises a personalized and enriching journey through the Field Museum’s remarkable exhibits.
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Private Haunted History of Chicago Ghost Tour
For those seeking a thrilling exploration of Chicago’s haunted history, the Private Haunted History of Chicago Ghost Tour offers a spellbinding experience. Priced from $880.00 per person, this private tour promises a captivating journey through the city’s most notorious paranormal hotspots.
Led by professional guides, the tour includes hotel pickup, fuel surcharge, local taxes, and gratuities. Accessible to wheelchair users and stroller-bound guests, the tour has earned a perfect 5.0 rating based on 5 reviews across Viator and Tripadvisor.
Guests can enjoy the flexibility of free cancellation and unlimited rescheduling up to 24 hours before the tour. With the guide wearing a mask, this haunted adventure ensures a safe and unforgettable exploration of Chicago’s chilling past.
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Architectural and Historical Private Tour in Downtown Chicago
Embarking on an architectural and historical exploration of downtown Chicago, this private tour immerses visitors in the city’s iconic landmarks and captivating past.
With no fees during the tour, the focus remains solely on points of interest, operating daily from 9:20/2023 to 6/27/2025 between 10:00 AM and 3:00 PM.
The tour departs from the renowned Picasso sculpture, offering pickup at downtown hotels and Airbnbs, or guidance on using public transportation.
Participants can expect a breathtaking experience, as the private tour showcases the city’s architectural marvels and historical sites.
Though not wheelchair accessible, the tour is stroller-friendly and welcomes service animals.
Priced at €191.54 per group, the tour offers a lowest price guarantee and flexible cancellation and rescheduling policies.
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History of the Jazz Age at Chicago Art Deco Architecture Tour
The Jazz Age architecture tour in Chicago transports participants on a captivating journey through the city’s Art Deco masterpieces, unveiling the vibrant history and design elements that defined this iconic era.
Priced from $67 per person, the small-group walking tour is led by professional local experts, offering access to the Galleries of the Chicago Architecture Center.
With a maximum group size of 10 travelers, the experience is ideal for Instagram enthusiasts seeking iconic photo opportunities.
The tour is wheelchair accessible and conveniently located near public transportation, making it accessible for visitors of all abilities.
Travelers can reserve now and pay later, with free cancellation up to 24 hours before the tour.
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Chicago : African American Heritage Walking Tour
Enjoy the rich tapestry of Chicago’s African American heritage on this captivating 3-hour walking tour.
Explore the city’s significant landmarks and uncover the stories that shaped the community’s vibrant history. Led by a knowledgeable local guide, you’ll visit the Black History Museum and discover the cultural and social impact of African Americans in Chicago.
The tour’s meeting point is conveniently located near the Indiana Green Line station, and the end point is the DuSable Black History Museum and Education Center.
While transportation, food, and tips aren’t included, the tour is wheelchair and stroller accessible, making it suitable for travelers with varying mobility needs.
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Skip-the-Line Field Museum Natural History Semi-Private Guided Tour (8ppl Max)
Discover the captivating treasures of the Field Museum of Natural History on this Skip-the-Line Semi-Private Guided Tour.
This 2.5-hour excursion takes you through the museum’s highlights with a maximum of 8 guests, ensuring a personalized experience. You’ll explore the museum’s impressive collections, guided by a knowledgeable professional.
The tour includes all entrance fees, though gratuities and transportation aren’t covered. While the tour isn’t wheelchair accessible, strollers are welcome.
Guests should maintain a moderate fitness level and adhere to the museum’s dress code. Though occasional closures may occur, alternatives will be provided if delays exceed an hour, ensuring you make the most of your visit.
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Chicago Architecture, Art and History Tour – Off The Beaten Path
Though Chicago is renowned for its iconic skyscrapers, this guided tour takes visitors off the beaten path to uncover the city’s lesser-known architectural marvels, captivating art, and rich historical tapestry.
Priced at €91.44 per person, the 3-hour tour is led by local experts and covers a range of topics, from history and architecture to art. Capped at 15 participants, the tour provides an intimate experience for architecture enthusiasts.
Conveniently starting at 11 AM and ending at the Chicago Cultural Center, the tour is accessible via public transportation and operates in all weather conditions.
With free cancellation up to 24 hours in advance and a lowest price guarantee, this tour is a must-do for those seeking a deeper dive into Chicago’s hidden gems.
Read our full review: Chicago Architecture, Art and History Tour – Off The Beaten Path Review
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Frequently Asked Questions
Can I Bring My Own Food on the Tours?
Participants can generally bring their own food on historical tours in Chicago, but it’s best to check with the tour operator beforehand. Some may have restrictions or recommendations to enhance the experience.
Are the Tours Wheelchair/Disability Accessible?
Most historical tours in Chicago are wheelchair and disability accessible, accommodating visitors with various mobility needs. Tour operators strive to ensure an inclusive experience, providing necessary assistance and accessible routes to key landmarks and sites.
Do the Tours Accommodate Large Groups/Families?
Many historical tour companies in Chicago accommodate large groups and families by offering private tours, group discounts, and customizable itineraries. They’ll work with you to ensure your entire party can participate and enjoy the experience.
Can I Take Photos During the Tours?
Most historical tours in Chicago allow participants to take photos during the tour. Tour guides often encourage capturing the sights and scenery, though they may request that visitors refrain from using flash photography in certain areas.
Do the Tours Include Transportation to and From the Sites?
Most historical tours in Chicago do provide transportation to and from the sites, allowing visitors to easily explore the city’s rich history without the hassle of driving or navigating public transit. This convenient service is often included in the tour package.
The Sum Up
Chicago offers a diverse range of historical tours that explore the city’s rich cultural heritage. From walking tours exploring iconic architecture and art deco landmarks to museum visits uncovering natural history and African American heritage, there’s something for every traveler interested in Chicago’s captivating past. These tours provide an immersive and informative experience, allowing visitors to discover the city’s multifaceted history and appreciate its enduring legacy.