Chicago’s best historical tours focus on three main themes: stunning architecture, cultural stories, and true crime. The city’s most worthwhile experience remains the river architecture cruise, which covers more than a century of spectacular buildings while floating past the best views in town. For cultural insights, the South Side walking tours bring the city’s African-American heritage to life through meaningful stories and local perspectives. History fans shouldn’t miss the gripping “Devil in the White City” tour, which traces the dark events of the 1893 World’s Fair.
These tours work especially well because they keep groups intimate and offer good accessibility, including wheelchair options and multiple languages. Smart guides share fascinating details while keeping things clear and engaging.
Let’s look at our favorite Chicago history tours and what makes each special.
Key Points
- Chicago River Tours offer 90-minute history and architecture tours showcasing over 130 years of architectural wonders along the Chicago River.
- Small Boat Tours provide a historic architecture tour exploring over 50 skyscrapers in a small group setting.
- The Chicago Walking Tour: Historic Skyscrapers highlights iconic skyscrapers in a small group with a 97% recommendation rate.
- The Chicago in a Day Tour covers 3-4 miles of the city, offering historical insights and local culinary specialties led by knowledgeable guides.
- The Devil in the White City Tour focuses on the 1893 World’s Fair and the notorious serial killer H.H. Holmes.
Chicago River 90-Minute History and Architecture Tour
The Chicago River 90-Minute History and Architecture Tour whisks travelers through the heart of the city, showcasing over 130 years of architectural wonders along the iconic waterway.
Aboard a climate-controlled boat, guests can admire skyscrapers like the Willis Tower, Chicago Water Tower, and Wrigley Building, while learning about the city’s rich history from expert local guides.
With 92% of travelers recommending the tour and an impressive 4.5-star average rating, it’s a must-do experience for both visitors and locals.
Though not wheelchair accessible, the tour offers indoor and outdoor seating options, as well as on-board amenities like restrooms and refreshments.
Read our full review: Chicago River 90-Minute History and Architecture Tour Review
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Chicago: Historic Architecture Chicago River Small Boat Tour
Exploring over 50 skyscrapers along the Chicago River, the Historic Architecture Chicago River Small Boat Tour offers a unique perspective on the city’s iconic skyline.
This 1.5-hour small boat experience accommodates around 30 guests, providing a more intimate setting to learn about Chicago’s architectural history from expert docents.
The tour showcases a mix of architectural styles, from Art Deco to modern skyscrapers, with detailed explanations of significant buildings.
Guests can enjoy complimentary Starbucks coffee, sodas, and lemonade, as well as snacks and alcoholic beverages for purchase.
With an overall rating of 5/5 based on 11 reviews, this tour is a popular choice for those seeking an informative and engaging exploration of Chicago’s architectural heritage.
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Chicago in a Day: Food, History and Architecture Walking Tour
This comprehensive Chicago walking tour offers visitors a delightful immersion into the city’s rich culinary, historical, and architectural heritage.
Over the course of 5 hours, travelers will cover 3-4 miles, exploring iconic landmarks and hidden gems while indulging in a full meal’s worth of local specialties like deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs.
Led by knowledgeable local guides, the tour provides valuable insights into the city’s history and architecture, as well as recommendations for further exploration.
With a maximum group size of 12, the experience is both informative and intimate, making it a must-do activity for anyone seeking to discover the heart and soul of Chicago.
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Black Heritage Tour
Offering a unique look into Chicago’s rich African-American history, the Black Heritage Tour takes visitors on a journey through the city’s Bronzeville neighborhood.
Priced at $125 per person, this 4-hour tour departs from the Chicago Theater, with free pickup from downtown hotels and standard rideshare fares for surrounding suburbs.
Led by a guide with personal experience in the black community, the tour explores the path of the Great Migration, visiting historic sites like the birthplace of modern gospel music.
Accommodating groups of 11 or less, the tour offers a more intimate experience, with customization options available.
Positive reviews highlight the knowledgeable guide and the tour’s ability to provide insightful cultural and historical context.
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Chicago Walking Tour: Historic Treasures of Chicago
Immersing visitors in the rich architectural heritage of Chicago, the “Chicago Walking Tour: Historic Treasures of Chicago” offers a captivating exploration of the city’s celebrated buildings.
With a near-perfect 99% recommendation from 325 travelers and a Badge of Excellence, this small-group walking tour delves into the iconic skyscrapers and art deco interiors that define Chicago’s skyline.
Highlights include the Palmer House Hotel and the Chicago Cultural Center, complemented by admission to the Chicago Architecture Center.
Led by knowledgeable, certified guides, the tour provides unique insights and educational value, earning praise for its engaging commentary and enjoyable pacing.
Accessible and convenient, this walking adventure is a must-experience for anyone seeking to uncover the historical treasures of Chicago.
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Chicago Historic Pullman Company Town Private Walking Tour
The “Chicago Historic Pullman Company Town Private Walking Tour” provides an immersive glimpse into the fascinating history of Pullman, a meticulously planned 19th-century community founded by The Pullman Palace Car Company.
During the 4-hour tour, visitors explore key sites like the Hotel Florence, Greenstone United Methodist Church, and Sonder Market Hall, all while learning about Pullman’s architectural and cultural legacy.
The tour includes a train ride, lunch, and an English-speaking guide who offers insights into the town’s historical significance, including its role in the labor strike that led to the hotel of Labor Day.
This private tour offers a unique opportunity to discover the well-preserved Pullman Historic District.
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Field Museum of Natural History Admission Tickets
The Field Museum of Natural History in Chicago is a renowned institution that offers visitors an immersive journey through 13,000 years of ancient history.
With a rating of 4.5 and a Badge of Excellence, the museum features over 26 million artifacts, including the world’s largest T. Rex, SUE.
Admission options range from general access to special exhibitions, with ticket prices starting at $29.00.
Visitors can explore the Dinosaur Hall, encounter 23 Egyptian mummies, and admire the Hall of Gems’ collection of Chinese jade.
The museum is wheelchair and stroller accessible, with docent-led tours and multilingual maps available.
While early arrival is recommended, the museum’s versatile exhibits cater to all ages, providing an educational and family-friendly experience.
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Chicago: Food, History and Architecture Tour
For those captivated by Chicago’s rich history and diverse culinary scene, the Chicago: Food, History and Architecture Tour offers a compelling opportunity to take in the city’s vibrant culture.
Priced at Kč 2,371 per person, this 5-hour guided tour explores the city’s architecture, Prohibition-era influences, and iconic food specialties like Chicago-style hot dogs and deep-dish pizza.
Suitable for all ages and fitness levels, the small-group tour (maximum 12 participants) provides personalized attention and rave reviews for its knowledgeable and entertaining guides.
With a 4.8/5 overall rating, the tour is an excellent choice for those seeking an insightful and delectable experience in the heart of Chicago.
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Field Museum of Natural History All-Access Pass
An all-access pass to the Field Museum of Natural History in Chicago provides visitors with an immersive journey through the museum’s vast collection of natural wonders.
With a Badge of Excellence and 92% traveler recommendation, the museum is one of Chicago’s most popular landmarks. Visitors can explore the Hall of Gems, marvel at the well-preserved T-Rex fossil Sue, and enjoy daily docent-led tours at no extra cost.
Tickets can be booked in advance, and the museum is fully accessible, with service animals allowed and public transportation nearby.
Positive reviews highlight the educational value and interactive exhibits, making the Field Museum a must-visit destination for both families and history enthusiasts.
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Chicago River Architecture and History by Private Boat Tour
Exploring Chicago’s architectural gems and rich history comes alive on the Chicago River Architecture and History by Private Boat Tour.
This 75-minute cruise takes visitors on a journey along the Chicago River, showcasing the city’s iconic skyscrapers and historic landmarks. Rated 4.8 out of 5 stars with over 4,000 reviews, the tour provides an in-depth look at the city’s architecture, from the early 20th-century buildings to modern marvels.
Priced at $53 per person, the Architecture River Cruise offers a unique and engaging way to discover Chicago’s storied past and present.
Whether you’re a first-time visitor or a local, this tour is a must-do activity for anyone interested in the city’s architectural and historical significance.
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The Devil in the White City: A Haunting History Tour
Delving into the captivating history of the 1893 Chicago World’s Fair and the dark legacy of serial killer H.H. Holmes, the “The Devil in the White City: A Haunting History Tour” offers an immersive experience.
This half-day tour explores key locations, including the Prairie Avenue Historic District, Jackson Park, and the infamous “Murder Castle.” Travelers journey by bus with guided commentary, complemented by walking segments.
Though reviews are mixed, with some noting a lack of emphasis on the haunted elements, the tour is praised for its knowledgeable guides, particularly Tony.
Visitors should be prepared for additional walking and limited restroom facilities on the buses.
Read our full review: The Devil in the White City: A Haunting History Tour Review
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Chicago Walking Tour: Historic Skyscrapers
Visitors seeking an in-depth exploration of Chicago’s architectural heritage will find the Chicago Walking Tour: Historic Skyscrapers an engaging and informative experience.
Capped at 10 participants, this small-group tour guides guests through the city’s most iconic skyscrapers from the late 19th and early 20th centuries.
Led by a certified architecture expert, the tour highlights key sites like the Rookery Building, Auditorium Building, and Monadnock Building, offering insights into influential architects and Chicago’s rich architectural culture.
With a 97% recommendation rate and an “Excellence” badge, this tour provides a comprehensive and immersive journey through the city’s architectural history, making it a must-do activity for history and architecture enthusiasts visiting Chicago.
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Saturday Chicago Pizza History and Tastings Bus Tour
Chicago’s Saturday Pizza History and Tastings Bus Tour offers an immersive exploration of the city’s iconic pizza culture.
The half-day tour takes guests on a delicious journey, tasting four distinct pizza styles: deep-dish, tavern-style, artisan, and Detroit.
Along the way, participants learn about Chicago’s rich pizza history and culture, all while indulging in a hearty meal.
The tour accommodates a maximum of 24 guests and includes live commentary, discounts at Goose Island taprooms, and a vegetarian option.
With 100% of travelers recommending the tour and a 5.0 rating, it’s an informative and enjoyable experience for pizza enthusiasts and history buffs alike.
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Chicago River Architecture Tour Aboard a Historic Yacht
Stepping away from the tantalizing pizza trail, the Chicago River Architecture Tour aboard a historic yacht offers a captivating exploration of the city’s renowned architectural landscape.
Rated an impressive 4.9 with a Badge of Excellence, this tour provides a unique perspective on the city’s iconic buildings. Guests can expect a small-group experience, with a maximum capacity of 60 travelers, and complimentary amenities like soda, water, and snacks.
The tour’s knowledgeable guides receive high praise for their engaging narration, though some guests suggest improvements for shade and seating.
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Field Museum of Natural History Discovery Pass
The Field Museum of Natural History’s Discovery Pass offers visitors a comprehensive exploration of the museum’s vast and captivating exhibits.
Located in Chicago, the museum is open daily from 9 AM to 5 PM, with last entry at 4 PM. The pass includes free docent-led tours and access to all general admission exhibits, plus one ticketed exhibition.
The museum is wheelchair and stroller accessible, and maps and highlights guides are available in multiple languages.
With an overall rating of 4.2/5 from 28 reviews, the museum is praised for its memorable exhibits, especially the dinosaurs and evolution displays, as well as its friendly staff.
Visitors should plan to spend a full day to fully experience the museum’s diverse offerings.
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Historic Homes and Cottages of Wicker Park Walking Tour
This remarkable Historic Homes and Cottages of Wicker Park Walking Tour offers visitors a captivating glimpse into Chicago’s architectural heritage.
Led by knowledgeable guides, the tour takes participants on a journey through the picturesque Wicker Park neighborhood, showcasing 19th-century workers’ cottages, stately mansions, and historic landmarks.
Utilizing a free app, guests can explore the area’s rich history and insider stories.
The tour, which is rated 5.0 out of 34 reviews and has a 100% traveler recommendation, is priced at $45 per person with a maximum group size of 8.
While not wheelchair accessible, the tour is near public transportation and requires a moderate level of physical fitness.
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Field Museum of Natural History Early Access Ticket
Visitors seeking a captivating and educational experience in Chicago can explore the renowned Field Museum of Natural History through the Early Access Ticket.
This private docent tour provides early entry before the museum opens, allowing for a unique, crowd-free encounter. Priced at $73.00 per person, the tour includes all-access admission, a meeting and pickup, and a guided exploration of the museum’s highlights, from history and science to cultures and the iconic SUE the T. rex exhibit.
With 91% of travelers recommending the experience and an impressive 4.6-star rating, the Early Access Ticket offers an intimate, personalized museum visit that educates and delights.
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African American Heritage Tour of Chicago
Explore Chicago’s rich African American heritage on a captivating half-day tour. This immersive experience takes visitors through significant sites, including the birthplace of gospel music and the childhood homes of notable figures like Jennifer Hudson.
The tour includes an interior visit to an African American museum, offering a deeper understanding of the community’s history and contributions. Travelers appreciate the knowledgeable guide, Steve, who provides personal insights and thoughtful perspectives.
While the pace and focus on some negative aspects have received mixed reviews, the overall experience is praised for its cultural relevance and depth of information.
Convenient transportation and optional airport pickup make this tour an accessible and enriching way to explore Chicago’s African American legacy.
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Chicago River Architecture and History-Private Boat Tour
For those who’ve uncovered the rich African American heritage of Chicago, the city offers another fascinating historical perspective – the Chicago River Architecture and History-Private Boat Tour.
This private boat tour provides an intimate exploration of the Chicago River, allowing visitors to learn about the waterway’s impact on the city’s identity and witness its remarkable architectural marvels.
Led by a knowledgeable local guide, the tour covers the city’s growth from pre-settlement to present day, offering a comprehensive historical narrative.
With 100% traveler recommendation and a 5-star rating, this tour is a must-do for anyone seeking to dive deeper into Chicago’s captivating past.
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Walkin With Colin: Chicago History-Mystery-Comedy-Tragedy Tour
The Walkin with Colin: Chicago History-Mystery-Comedy-Tragedy Tour immerses participants in the captivating narratives that have shaped the Windy City.
Over the course of two hours, this highly-rated walking tour covers 2 miles, showcasing the city’s art, architecture, and influential history.
Led by Colin, an engaging guide known for his humor and deep knowledge, the tour explores notable sites like Calder’s Flamingo and Picasso’s 50-foot sculpture.
Featuring stunning interiors and exteriors, the experience concludes at the renowned Chicago Cultural Center.
With a maximum group size of 10, this personalized tour offers an opportunity to discover Chicago’s hidden gems and deepen one’s understanding of the city’s vibrant past.
Read our full review: Walkin With Colin: Chicago History-Mystery-Comedy-Tragedy Tour Review
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The Sum Up
Chicago’s rich history and diverse architecture come alive through these engaging historical tours. From guided boat tours along the Chicago River to walking tours exploring the city’s cultural heritage, visitors can enjoy the stories that have shaped this vibrant metropolis. Whether you’re interested in architecture, history, or cultural diversity, Chicago’s historical tours offer something for all.