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The 16 Best Historical Tours in Chicago
Chicago is a city that wears its history on every building, street corner, and river bend. It’s a place where skyscrapers tell stories of innovation, fireboats remind us of dramatic resilience, and neighborhoods whisper secrets of a diverse past. If you’re passionate about uncovering the stories behind a city’s architecture, its pivotal moments, or its colorful characters, Chicago offers a treasure trove of options. We love tours that combine breathtaking architecture with fascinating tales—like the Chicago in a Day: Explore Food, History, and Iconic Architecture which delivers a comprehensive half-day adventure, or the Chicago Architecture and True Crime History Tour for those intrigued by both design and the city’s darker side.
Chicago’s appeal as a history destination lies in its mix of old and new, the grandeur of its early skyscrapers, and stories of survival and crime that echo through its streets. Whether you’re exploring the Chicago Riverwalk, marveling at the Field Museum, or wandering through historic districts, each tour offers a chance to see the city through a different lens.
Quick Overview
This list features 16 top-rated Chicago tours that focus on history, architecture, crime, and more. You’ll find options perfect for short visits, like the Chicago Walking Tour: Historic Treasures that covers key landmarks in just 2 hours, and more immersive experiences like the Private Chicago History Museum Tour that offers a personalized deep dive. There are walking, boat, and even themed tours that explore everything from Chicago’s iconic skyscrapers to its haunted past. Whatever your interests, this list has something for every history enthusiast.
1. Chicago in a Day: Explore Food, History, and Iconic Architecture
This 5-hour tour is a fantastic overview, especially if you’re visiting Chicago for the first time. It combines architecture, food tasting, and history into a small-group experience, with a maximum of 12 people. You’ll start at the Chicago Theatre and walk through the Pedway, exploring underground tunnels used by locals in winter. Along the way, you’ll see major landmarks such as the Wrigley Building, Tribune Tower, Millennium Park, and the Chicago Riverwalk. The tour also offers generous tastings of deep-dish pizza, Italian beef, and other Chicago staples.
Guests praise the informative narration and the well-paced itinerary. One reviewer notes, “Despite the weather, I learned a lot about Chicago and enjoyed every bite.” The tour strikes a great balance between sightseeing, storytelling, and food, making it ideal for first-timers wanting a comprehensive introduction.
Bottom Line: Perfect for those with limited time who want a taste of Chicago’s architecture, cuisine, and history in one go.
2. Chicago Walking Tour: Historic Treasures of Chicago
For around $35, this 2-hour walking tour takes you through Michigan Avenue, State Street, and the Loop, focusing on Chicago’s architectural gems. The tour includes admission to the Chicago Architecture Center and visits to landmarks like the Palmer House Hilton, Carbide and Carbon Building, and the Chicago Cultural Center. The guide shares insights on Chicago’s skyscraper evolution and art deco interiors—like the stunning lobby of the Palmer House.
Reviews highlight how informative and engaging the tour is, with many praising guides like Bob P., who make architecture come alive. One comment states, “I learned fascinating details about Chicago’s buildings I never noticed.” The tour is great for travelers wanting a short, focused introduction to Chicago’s architecture, especially if you’re interested in interior details and lesser-known facts.
Bottom Line: A compact, insightful tour ideal for architecture lovers who prefer walking and want to see the city’s icons from a new perspective.
3. Chicago: Field Museum of Natural History Ticket or VIP Tour
This 1-day ticket grants access to over 35 exhibits, including the world-famous Sue the T. Rex and the Ancient Egypt collection. The museum’s extensive collection spans dinosaurs, minerals, ancient cultures, and more, making it an excellent stop for history and science fans alike. You can choose to explore on your own or upgrade to a VIP tour for extra insights.
The museum’s highlight is the full-sized mastaba tomb and the Hall of Gems, which dazzle visitors. People praise the large, well-curated exhibits and the opportunity to spend as much time as they like exploring. It’s perfect for families or those wanting a flexible, in-depth experience.
Bottom Line: A must-visit for natural history fans, with the flexibility to tailor your visit and see some of the top dinosaur, Egypt, and gem collections.
4. Chicago Architecture and True Crime History Tour
This 1 hour 30-minute walking tour blends architecture and crime stories, inspired by Devil in the White City. You’ll visit iconic buildings like the Marshall Field’s Building and Chase Tower, learning about Chicago’s architectural innovations and its darker history of serial killers and mysterious crimes.
Guide Joseph’s storytelling brings the city’s shadowy side to life, making it especially appealing to those who enjoy dark history alongside design. One reviewer notes, “Great stories behind buildings and some gruesome facts,” underscoring its unique appeal. The tour offers a different perspective on the city’s skyline, revealing secrets most visitors never hear.
Bottom Line: Ideal for curious travelers wanting a quick yet compelling mix of architecture and true crime tales.
5. Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour
This 2-hour walk combines art, architecture, and storytelling through downtown Chicago. Colin leads you past Calder’s Flamingo, the Chicago Theatre, and the James R. Thompson Center, sharing stories of Chicago’s entertainers, tragedies, and architectural feats.
Guests rave about Colin’s engaging storytelling and insider knowledge. One review mentions, “Left wanting to come back for more,” highlighting its appeal. The tour includes interior visits and outdoor sights, making it a flexible, engaging experience for those interested in Chicago’s cultural fabric.
Bottom Line: Perfect for those who want a lively, story-driven walk that connects Chicago’s art and architecture with its vibrant history.
6. Field Museum of Natural History Admission Tickets
This 4-hour visit provides general access to the Field Museum’s extensive exhibits, including Sue the T. Rex, the Hall of Gems, and Ancient Americas. It’s designed for visitors who prefer to explore at their own pace and includes free daily tours led by docents.
People love the vast, detailed displays and the opportunity to spend hours among fossils, artifacts, and minerals. It’s suitable for families or anyone wanting a comprehensive and flexible experience. The museum’s size means you’ll want to prioritize your favorites or plan for multiple visits.
Bottom Line: The best choice for self-guided exploration of a world-class natural history collection.
7. Chicago Walking Tour: Historic Skyscrapers
This 1 hour 30-minute tour explores Chicago’s oldest skyscrapers, including the Rookery Building and Marquette Building. Led by a Chicago Architecture Center–certified guide, the walk dives into the city’s architectural evolution from the late 19th century.
Reviews praise the passion and knowledge of guides like Deborah, who make even the most familiar buildings fascinating. One enthusiast writes, “Learning about the history of the skyscraper was a highlight.” The tour is well-suited for visitors who want an intimate look at Chicago’s iconic skyline.
Bottom Line: A quick, informative walk perfect for architecture aficionados with limited time.
8. Chicago: Food, History and Architecture Tour
This 4.5-hour tour combines food tasting with architectural highlights. You’ll explore the Chicago Pedway, sample hot dogs and deep-dish pizza, and learn about the Prohibition era and its influence on the city.
Reviewers mention the personalized attention and the chance to see the city’s hidden culinary and architectural gems. It’s ideal for travelers wanting a comprehensive introduction blending taste and tales.
Bottom Line: A delightful way to see, taste, and learn about Chicago’s past and present.
9. Historical and Architectural Chicago Fireboat River/Lake Cruise
Board a historic fireboat—the Fred A. Busse—for a 2-hour cruise on Lake Michigan and the Chicago River. You’ll view notable buildings like the Wrigley Building and explore the firefighting history of Chicago through artifacts on board.
Guests love that it’s not just a boat ride but a “floating museum,” with firefighting stories and architecture combined. It’s an excellent choice for families or those interested in Chicago’s rescue efforts and historic vessels.
Bottom Line: Unique and educational, this cruise offers a different vantage point on the city’s skyline and firefighting past.
10. Historic Homes and Cottages of Wicker Park Walking Tour
Wicker Park’s architectural diversity shines on this 2-hour walk past over 25 historic homes, cottages, and mansions. Led by a passionate guide, you’ll discover late 1800s workers’ cottages and scenic landmarks that define the neighborhood’s charm.
Reviewers appreciate the insider stories and the chance to see Chicago vernacular architecture. It’s well-suited for travelers interested in local architectural styles and neighborhood history without the crowds.
Bottom Line: An intimate look at one of Chicago’s most picturesque neighborhoods, ideal for architecture and history enthusiasts.
11. Field Museum of Natural History All-Access Pass
This flexible pass gives you 1 to 8 hours to explore the Field Museum. It’s perfect for visitors who want to prioritize exhibits like Sue, Ancient Egypt, or Dinosaurs at their own pace.
Many visitors appreciate the ability to customize their visit and the availability of free docent-led tours. The size of the museum makes it a full-day destination for the most adventurous.
Bottom Line: Versatile and comprehensive, suitable for those wanting an unhurried, in-depth museum experience.
12. African American Heritage Tour of Chicago
This 4-hour tour explores Bronzeville, the home of gospel music, and visits significant sites like Obama’s Hyde Park neighborhood. It offers insights into Chicago’s Black culture, notable figures, and landmarks.
Guests praise guide Steve’s knowledge and storytelling, which make the tour both educational and engaging. It’s best suited for travelers eager to learn about Chicago’s African American community’s contributions through direct neighborhood visits and cultural stops.
Bottom Line: A meaningful way to connect with Chicago’s Black history and culture, suitable for those wanting more than just architecture.
13. Private Chicago History Museum Tour
This private 2-hour tour offers an intimate and tailored experience at the Chicago History Museum. Led by experts, it covers the Great Fire, civil rights, Chicago blues, and more.
It’s an excellent choice for travelers seeking personalized insights and a deep dive into Chicago’s story. The tour’s flexibility allows you to focus on your specific interests, making it ideal for history lovers or groups with particular focuses.
Bottom Line: Personalized, informative, and flexible—perfect for private groups wanting a custom Chicago history experience.
14. Chicago: Architecture & True Crime History
This 1.5-hour tour combines Chicago’s architecture with stories about serial killers like Gacy and Holmes. It’s a short, themed walk that shares intriguing stories and lesser-known facts about the city’s darker side.
Guide local true crime buffs make it fun and engaging, especially for those interested in urban legends and criminal history. It’s best suited for adults or older teens with curiosity about Chicago’s haunted past.
Bottom Line: A fast-paced, macabre twist on Chicago’s history, making it a memorable experience for crime history fans.
15. Chicago Ghosts & Haunted History Walking Tour
Walking through downtown as night falls, you’ll hear ghost stories connected to landmarks like the Congress Hotel and Everleigh Club. This 2-hour tour emphasizes haunted tales, legends, and ghostly legends.
Reviewers report an entertaining, spooky experience with guides like Kelly who “made it fun and very spooky.” It’s excellent for adults and teenagers who enjoy ghost stories and supernatural lore.
Bottom Line: Perfect for a spooky evening exploring Chicago’s haunted past—fun and a little eerie.
16. Chicago’s Riverwalk & History 2 Hour Small Group Walking Tour
This 2-hour tour explores Chicago’s Riverwalk, including Battle of Fort Dearborn sites and architectural landmarks like Marina City. You’ll learn how the Chicago River shaped the city’s development.
Guests enjoy the personalized small-group size and the insightful commentary, which makes it a great way to understand Chicago’s maritime and urban history from a local guide.
Bottom Line: A balanced mix of history and architecture with an intimate tour setting.
How to Choose the Best Chicago Historical Tour for You
When selecting a tour, consider your interests, schedule, and budget. Want a rundown? The Chicago in a Day offers a bit of everything. Interested in architecture? The Chicago Walking Tour: Historic Treasures or the Chicago: Architecture & True Crime are excellent choices. For those intrigued by Chicago’s darker stories, the True Crime Tour and the Ghosts & Haunted History provide thrilling narratives.
Budget-wise, shorter walking tours like the Historic Skyscrapers or Treasure of Chicago’s architecture are affordable, while private or VIP options demand more. Think about your fitness level, too—some tours involve significant walking, while others are boat or vehicle-based. Booking in advance is recommended, especially during peak season, to secure your preferred times.
Final Thoughts
Chicago offers a fascinating mix of architectural marvels, historical milestones, and spooky stories. For a deep dive into its skyscrapers, choose the Chicago Architecture Tour. If you’re interested in the city’s darker side, the True Crime Tour or the Ghost Tour are sure to entertain. Families or curious travelers might prefer the Field Museum, which makes history tangible through artifacts and dinosaurs.
No matter your interest, early booking is wise. Many tours fill quickly during the busy season, and securing your spot ensures a smooth, enriching experience. After all, Chicago’s stories are best enjoyed with a knowledgeable guide, a curious mind, and plenty of camera batteries ready to capture those moments that make history come alive.