Chicago is a city that invites exploration on foot—its neighborhoods are walkable and packed with architectural marvels, culinary delights, and tales of yesteryear. The city’s distinctive skyline, historic landmarks, and lively neighborhoods make it ideal for walking tours. Whether you’re marveling at the art deco skyscrapers, sampling classic Chicago foods, or uncovering secrets behind historic buildings, there’s a tour suited to every interest. We especially like the Chicago Walking Food Tour with Secret Food Tours for its combination of tasty bites and city sights, and the Gangsters and Ghosts tour for a spooky twist on Chicago’s dark past.
If you’re wondering how to choose the right experience, our list below offers a variety of options—from architecture and history to food and even haunted pubs—each with its own unique flavor. The key is to match your interests and schedule with the tour that feels like a perfect fit.
Quick Overview
On this list, you’ll find architecture-focused walks like Historic Treasures of Chicago and Art Deco Skyscrapers Loop, which explore Chicago’s iconic buildings. For food lovers, the Chinatown Food and Walking Tour and the Downtown Chicago Pizza Tour showcase Chicago’s culinary staples. History and crime buffs will enjoy the Gangsters and Ghosts and Prohibition Speakeasies. For something seasonal and festive, the Holiday Hike offers a wintertime taste of Chicago’s holiday traditions.
Now, let’s walk through each tour to see what makes it special.
1. Chicago Walking Food Tour With Secret Food Tours
This two-in-one tour combines Chicago’s culinary delights with a stroll around the Loop, taking in landmarks like the Willis Tower and the Rookery Building. For just about $89, you get enough bites to make a full meal, including deep-dish pizza and iconic Italian beef sandwiches. What makes this tour stand out is its focus on local bites paired with city landmarks, making it perfect for time-pressed travelers who want a taste of everything.
Led by a friendly guide, the small-group experience (or private upgrade) allows for personalized attention, and the walk itself is a great way to absorb Chicago’s lively atmosphere. Reviewers love the historic overview paired with delicious samples, with many noting the guide’s engaging storytelling. The itinerary includes stops at Chicago Public Library, the Financial District, and Calder’s Flamingo sculpture, adding cultural context to your food adventure.
Bottom Line: A fantastic choice for foodies who want to combine eating with sightseeing, especially if you’re short on time but want a hearty taste of Chicago.
2. Chicago: Gangsters and Ghosts Guided Walking Tour
At number 2, this tour digs into Chicago’s darker side. For $36, you’ll explore the Chicago Loop’s haunted corners and gangster history, learning how Al Capone ran his empire and hearing eerie tales of ghosts lurking near historic landmarks. This 2-hour tour is led by a historian guide who vividly describes Chicago’s Prohibition-era secrets and ghostly legends.
Highlights include Death Alley, the Chicago Riverwalk, and the Congress Hotel, where stories of creepy incidents still circulate. Reviewers frequently mention how the guide’s storytelling brings the city’s mysterious past to life. If you’re interested in crime history or ghost stories, this tour offers a perfect mix of entertainment and education.
Bottom Line: Ideal for those who enjoy mystery, history, and spooky tales, with a focus on Chicago’s notorious gangster era.
3. Chicago’s Chinatown Food and Walking Tour
Diving into Chicago’s Chinatown, this 3-hour experience for $79.99 takes you off the beaten path to enjoy authentic dim sum, Sichuan dishes, and other regional specialties. Your guide will reveal the history behind Chicago’s Chinese community and its culinary evolution, with tastings at Phoenix Restaurant, Yummy Yummy Noodles, and Pui Tak Center.
What makes this tour special is its generous tastings—enough for a hearty lunch—plus insights into Chinese culture within Chicago. Reviewers praise the knowledgeable guide and the authentic food. It’s perfect for food lovers and culture enthusiasts who want an up-close look at a neighborhood often overlooked by travelers.
Bottom Line: A tasty journey into Chinatown’s vibrant food scene and history, great for culinary curious travelers.
4. Chicago Walking Tour: Historic Treasures of Chicago
This 2-hour tour for just $35 offers a deep dive into Chicago’s architectural greatest hits, focusing on Michigan Avenue, State Street, and the Loop. During the walk, you’ll see buildings like the Palmer House Hotel, Chicago Federal Plaza, and Calder’s Flamingo, learning about architectural styles from Art Deco to Beaux-Arts.
The tour includes admission to the Chicago Architecture Center, making it a great value at under $40. Reviewers note the personalized experience and the insightful commentary from the guide, which brings Chicago’s architectural gems to life. It’s perfect for history buffs or those simply eager to understand Chicago’s skyline.
Bottom Line: An excellent, budget-friendly way to uncover Chicago’s architectural highlights and learn about its design evolution.
5. Chicago: Secret Interiors Architecture Walking Tour
For those fascinated by hidden details and design secrets, this 2-hour tour at $36 explores Chicago’s most iconic interiors, including the Rookery Building and the Chicago Cultural Center. You’ll discover design elements, engineering feats, and the stories behind these architectural masterpieces.
Guests mention the stories of innovation and hidden features that make Chicago buildings unique. The tour is ideal for architecture aficionados who want to understand the engineering ingenuity behind the city’s skyline. It’s a good choice if you’re keen on seeing the secrets that many pass right by.
Bottom Line: Perfect for architecture lovers eager to see Chicago’s interior design secrets and hidden details.
6. Chicago Walking Tour: A Walk Through Time
This speedy 1.5-hour tour for $35 offers a chronological overview of Chicago’s architectural history, from the earliest buildings to the modern era. Starting at the Chicago Architecture Center, the tour covers famous buildings like the Aqua Tower and Virgin Hotels, emphasizing evolution over time.
Reviewers appreciate the deep dive into history packed into a short session, making it ideal for first-time visitors or those with limited time. The guide’s insights help you appreciate the city’s architectural growth and plan future visits.
Bottom Line: A quick but comprehensive overview—great for first-timers and time-conscious travelers wanting a snapshot of Chicago’s architectural timeline.
7. Haunted Chicago Booze and Boos Ghost Walking Tour
This 2.5-hour ghost-themed pub crawl at $35.87 combines spooky stories with drinks in period-authentic bars. Costumed guides, dressed as flappers or gangsters, lead you through Chicago’s Prohibition-era bars, telling tales of ghostly residents, gangsters, and secret speakeasies.
Stops include Glascott’s Saloon and Hook and Ladder, each with its own haunted history. Reviewers enjoy the interactive storytelling and the unique atmosphere of the bars, making it a lively way to explore Chicago’s haunted past.
Bottom Line: Ideal for nightlife lovers and history buffs who want a spirited evening with stories and drinks.
8. Chicago Walking Tour: Art Deco Skyscrapers Loop
Rated 5 stars with many reviews, this 1.5-hour tour at $35 is perfect for lovers of architecture and design. It focuses on Chicago’s iconic Art Deco buildings, including the Chicago Board of Trade and Reliance Building.
Guided by an architecture expert, you’ll see ornamental facades and interior details many visitors miss. The tour is praised for its personalized approach and insightful commentary. It’s excellent for those who want to understand Chicago’s decorative style in a short time.
Bottom Line: A compact, high-quality tour for architecture enthusiasts eager to explore the ornamental details of Chicago’s Art Deco era.
9. Chicago: Treasures of the Golden Age Walking Tour
This 2-hour tour for $30 covers Chicago’s architectural landmarks from the late 1800s to the early 1900s. You’ll see Marshall Field’s, the Palmer House, and the Chicago Cultural Center, learning about notable architects and historic designs.
Reviews highlight the engaging guides and the rich stories behind each building. Perfect for those interested in Chicago’s cultural rise after 1893 and how the architecture reflected that ambition.
Bottom Line: A cost-effective way to explore Chicago’s Golden Age architecture with educational storytelling.
10. Chicago: Underground Pedway & Downtown Secrets Walking Tour
Explore Chicago’s underground passages on this 2-hour tour priced at $35. You’ll access beautiful interiors, see public art, and learn hidden stories behind the Pedway system.
It’s a unique way to experience the city beneath the streets and uncover secrets many visitors never see. Reviewers appreciate the insider knowledge and the cool interiors explored along the way.
Bottom Line: A fun, offbeat tour perfect for adventurous travelers curious about Chicago’s underground.
11. Chicago: Prohibition Speakeasies Bus Tour or Walking Tour
At around $48, this 3-4 hour tour takes you through Chicago’s Prohibition-era bars and secret speakeasies. You’ll visit 3 or 4 venues while learning about gangsters, politicians, and underground activities.
Guests love the immersive experience and the drink recommendations at each stop. Whether by bus or on foot, you’ll get a taste of Chicago’s rebellious past.
Bottom Line: Perfect for history and cocktail lovers wanting to experience Chicago’s Prohibition nightlife.
12. Chicago: Gangsters and Food Tasting Walking Tour
Combining history and food, this 2-hour tour at $81 takes you through a gangster-ridden neighborhood, sampling Chicago staples like hot dogs, pizza, and steak. You’ll learn about Mob figures while visiting historic hideouts and tunnels.
Tourists note the fascinating stories and the generous tastings. It’s tailored for those interested in Chicago’s criminal past and culinary traditions.
Bottom Line: An engaging mix of crime history and classic Chicago foods, ideal for food and history buffs.
13. Chicago Walking Tour: Must-See Chicago
Starting at just $35 for 1.5 hours, this overview walk covers Chicago’s top landmarks like the Tribune Tower, the Art Institute, and Willis Tower. It’s designed for first-timers wanting a quick orientation.
Reviewers rave about the friendly guide and interesting stories. It’s perfect if you want a bite-sized introduction to Chicago’s architecture and culture.
Bottom Line: A great starter tour for newcomers wanting to get their bearings.
14. Downtown Chicago Walking Pizza Tour
For $69, this 2-3 hour pizza tour explores River North, the Loop, and the Magnificent Mile, sampling various styles including deep-dish and Neapolitan. You’ll walk past attractions like Holy Name Cathedral while tasting some of Chicago’s most famous dish.
Reviewers praise the delicious pizza and the well-paced walking. It’s perfect for pizza lovers who want to combine eating and sightseeing.
Bottom Line: An appetizing way to explore downtown Chicago, especially if pizza is your thing.
15. Chicago: Classic Food and Walking Tour with Free Bike/Kayak
This 3-hour tour at $80 combines food tasting with iconic sights like Millennium Park and Chicago Riverwalk. You’ll sample deep-dish pizza, hot dogs, and Italian beef, plus enjoy free bike or kayak rental within three days.
Reviews mention the informative guide and the generous samples. It’s especially suited for active travelers who want a mix of tasting and outdoor activity.
Bottom Line: Great for those who want variety—eating, sightseeing, and outdoor fun—in one experience.
16. Chicago-Style Holiday Hike: Festive Food and Walking Tour
This 3-hour holiday-themed walk for $84.99 takes you through Chicago’s winter streets, including Christkindlmarket and Millennium Park’s ice rink. Along the way, you’ll indulge in seasonal treats and learn about local holiday traditions.
Guests love the intimate size (just 15 travelers) and the festive atmosphere. Optional VIP craft beer upgrades are available. It’s ideal if you want a seasonal experience.
Bottom Line: A cozy, festive tour perfect for winter visitors wanting a holiday-themed outing.
How to Choose Your Perfect Chicago Walk
When selecting the right walking tour, consider your interests, budget, and schedule. If architecture excites you, the Historic Treasures or Art Deco Skyscrapers are excellent options. For food lovers, the Chinatown Food Tour or the Pizza Tour deliver hearty bites and local flavor.
History buffs craving tales of gangsters and ghosts should consider the Gangsters and Ghosts or Prohibition Speakeasies. For those who want a seasonal experience, the Holiday Hike offers a festive walk through Chicago’s winter traditions.
Booking early is advisable, especially for popular tours during peak seasons. Match your interests with the tour details to ensure you get the most out of your walk through Chicago.
Final Thoughts
Chicago offers an incredible variety of walking experiences that highlight its architecture, history, food, and spooky stories. Whether you’re interested in stunning skyscrapers, craving authentic street food, or intrigued by gangster legends, there’s something here for every traveler. For a comprehensive introduction, the Must-See Chicago Tour and the Historic Treasures walk are excellent starting points. If you’re a foodie, the Chinatown Food Tour or Pizza Tour will satisfy your appetite.
To truly appreciate the city’s architecture and character, consider booking the tours that match your interests early in your trip—many are popular and fill up quickly. No matter your choice, exploring Chicago on foot promises a more intimate and memorable experience.