From the iconic landmarks of Millennium Park to the charming neighborhoods of Lincoln Park, every corner of Chicago has a story to tell. The best way to truly grasp the essence of this dynamic city is by embarking on a walking tour that will lead you off the beaten path and into the heart of Chicago’s hidden gems. If you’ve got three days in Chicago (or more) I highly suggest putting on walking shoes and heading out on a walking tour of Chicago.
I’ve personally done a few of these tours but didn’t have enough time to do them all, so I’ve done the research for you – here are the best walking tours in Chicago – whether you prefer ghost stories or food tastings! Please be sure to bring a tip for your guide 15 to 20% of the tour is fine.
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General Walking Tours of Chicago
These walking tours are perfect for first-time visits to Chicago. There’s a little bit of everything on these tours and many show you some icons, like the Art Institute of Chicago.
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
One of my favorite things to do in any city is find street art. I find the personality of the city comes alive with locally created art. With a knowledgeable guide leading the way, you’ll explore urban graffiti, murals, and art installations while learning about the street art community, the artists, and the stories behind their work. This walking tour offers a unique way to experience the city, showcasing areas that many tourists miss and providing engaging commentary on the creative expressions that color Chicago’s streets.
Key information:
5 stars with over 170 reviews
Not wheelchair accessible
You’ll walk about 2 miles in 2 hours
Operated by Offbeat Street Art Tour
Chicago in a Day: Food, History & Architecture Walking Tour
Ideal for first-time visitors, this three-in-one tour offers a comprehensive introduction to Chicago’s top landmarks, rich history, and culinary highlights. In a small group, you’ll explore the city’s architectural icons on foot, visiting spots like the Chicago Riverwalk and Millennium Park. Along the way, enjoy generous tastings of classic Chicago dishes, from deep-dish pizza to Italian beef sandwiches. Perfect for those short on time, this half-day tour combines the best of the city with enough bites to make up a hearty lunch, all while your guide brings Chicago’s vibrant history to life.
Key Information:
- 5 stars with over 800 reviews
- 4 food stops with four tastings including hot dogs, pizza, popcorn, and chocolate!
- Walk the Chicago Riverwalk, Millenium Park, and see the Chicago Theatre
Chicago: Prohibition Speakeasies Bus Tour or Walking Tour
On this walking tour, you’ll discover how alcohol flowed through the streets of Chicago during Prohibition. You’ll hear stories about gangster hangouts and the upscale venues for high society. Your guide will take you to three iconic speakeasies in the Loop and River North. You’ll learn about the notorious figures and gangsters who frequented these places and see how things have changed over the years.
Key Information:
4.9 stars with over 50 reviews
Not suitable for anyone under 21
Bring ID card or passport with you
Drinks are not included at the speakeasies, so bring cash/card if you want one.
Chicago Walking Tour: Historic Treasures of Chicago
You’ll get to immerse yourself in Chicago’s architectural wonders on this walking tour of Michigan Avenue, State Street, and the vibrant Loop area. You’ll explore celebrated buildings, revisiting the heyday of the skyscraper while marveling at stunning art deco interiors, including the Palmer House Hotel and the Chicago Cultural Center. With admission to the Chicago Architecture Center and an introduction by a knowledgeable docent, this small-group tour offers a personal and enriching way to see the city’s most iconic landmarks, uncovering architectural highlights often overlooked by other visitors.
Key information:
- 5 stars with almost 300 reviews
- Includes admission to the galleries of the Chicago Architecture Center
- Wheelchair and stroller accessible
- Hosted by the Chicago Architecture Foundation
Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour
Set off on an immersive downtown walking tour to uncover the fascinating stories and hidden secrets of the city in this must-do street-level adventure! As we loop through “Da Loop,” we’ll peel back the layers of this vibrant “Big Onion” town, stepping in and out of remarkable buildings and admiring stunning art and architecture. Along the way, you’ll discover how it all came to be in an engaging, entertaining, and eye-opening exploration of Colin’s beloved Chicago.
Key information:
- 5 stars with 75 reviews
- Wheelchair accessible
- Not recommended for travelers with back problems or heart problems
- The tour is 2 hours, 2 miles, upstairs & downstairs, inside & outside.
Ghosts & Gangs Walking Tours of Chicago
These walking tours feature the stories of some infamous Chicago-ians. You could learn about Al Capone and other gangsters and how they ran the city. You may learn about the SS Eastland tragedy in the Chicago River and Death Alley.
Chicago: Discover the Gangsters & Ghosts of the City’s Past
Spencer and I took this tour during our three days in Chicago and were impressed. Our guide was knowledgeable and passionate about the topic and made the tour.
The tour primarily takes place in Chicago’s South Loop, but we also explored Death Alley, the Riverwalk, Palmer House, and the Chicago Theater. We learned about Al Capone and the history of Chicago’s gangster past. You’ll also listen to heartbreaking stories of the ghosts that are said to lurk around historic landmarks.
We took this tour at night to add to the ambiance of the tour.
Key information:
- 4.7 star rating, over 1,000 reviews!
- 1.5 miles of walking, with a 20-minute break at a famous gangster hangout
- Children 6 and under join for free, but it is not recommended for people with infants
Windy City Ghosts: Hauntings of Chicago Walking Tour
Delve into Chicago’s spookiest ghost stories and step back in time to the era of gangsters, bootleggers, and jazz on this small-group walking tour. Starting in Lincoln Park after dark, you’ll explore haunted former burial grounds, pubs, theaters, and more, all while hearing eerie legends and tales of unexplained happenings. This tour offers a unique way to experience the city’s haunted history, with an option to upgrade for even more frights and ghostly encounters at Lincoln Park’s most notorious sites.
Key information:
- 4.5 starts with 80 reviews
- This tour starts at 8:00 pm
- Wheelchair and stroller accessible
- Travelers should have a moderate physical fitness level
Haunted Chicago Booze and Boos Ghost Walking Tour
Experience a unique side of Chicago on this haunted pub tour, where a costumed guide—dressed as a Flapper or 1920s Gangster—will lead you on a mile-long journey filled with spooky tales of forgotten cemeteries and lingering spirits. As you explore the city’s hidden corners, you’ll stop at three different bars for drinks (at your own expense) while uncovering the eerie secrets behind Chicago’s haunted past. This tour offers a memorable way to dive into the city’s history and enjoy a night out with a ghostly twist.
Key information:
- 4.5 stars with 49 reviews
- Tour is about 1 mile long with 3-4 stops in pubs
- Travelers should have a moderate physical fitness level, it is not wheelchair accessible
- Tour operates in all weather conditions, dress appropriately
- Minimum age of 21, bring ID with you
Chicago Gangsters & Food Tour
This unique tour pairs Chicago’s Prohibition-era history with its most famous foods, offering a rare combination of flavors and stories. Explore the trendy River North neighborhood as you visit historic “gangster” hideouts, such as a steakhouse with a secret tunnel and a mansion serving deep-dish pizza. With a small group, you’ll enjoy personalized attention from your guide while learning about the city’s notorious past, making stops at iconic spots that bring Chicago’s gangster history to life.
Key information:
- 5 stars with almost 400 reviews!
- You’ll enjoy Prime Cut Steak, a Chicago Hot Dog, and Deep Dish Pizza
- Walk the River North neighborhood and learn about one of Al Capone’s hideouts
- Try an iconic hot dog at one of the oldest serving establishments in the city
Food Walking Tours of Chicago
For my fellow foodie travelers, here are the best walking tours that feature Chicago’s distinct culinary scene. See the city and tantalize your taste buds with these tours.
Chicago: Ultimate Food Walking Tour with Tastings
Get ready for a delicious Chicago food tour in the River North neighborhood. This area is known as the original foodie destination in the city. You’ll get to sample some iconic dishes, local favorites, and even some sweet treats! From the famous Chicago-style hot dog, to deep dish pizza – this is the ultimate foodie Chicago walking tour.
Key Information:
- 4.5 stars, about 50 reviews
- The company is a Carbon-Neutral Company!
- It’s a kid-friendly tour, children under 6 can join for free
- Suitable for all ages and fitness, but it does cover about 1.5 miles (2.4 kilometers) of walking.
- It happens in rain, shine, or snow. Dress appropriately.
Chicago: Classic Food Walking Tour with Bike or Kayak Rental
Take a delightful 3-hour guided walk around downtown Chicago. You’ll get to see some of the city’s most famous sites while tasting its best foods. Enjoy the iconic deep-dish pizza and the original recipe brownie. Don’t miss the classic Chicago-style hot dog and a tasty Italian beef sandwich. If you’re interested, you can opt for a VIP craft beer sample for an extra $19.99 per person. This includes three craft beer pairings offered when you arrive.
As you stroll, you’ll pass by notable spots like the Magnificent Mile, the Wrigley Building, and the Chicago Theatre. Make sure to check out Millennium Park, the Chicago Riverwalk, the Art Institute, and the world-famous Bean.
After your walking tour, you can enjoy a free 2-hour bike or kayak rental. Bike rentals are at Bobby’s Bike Hike, 540 N Lake Shore Drive, and Kayak rentals are at Bobby’s Kayak on Ohio Street Beach. This has to be used within 3 days of your tour booking.
Key Information:
- 4.8 starts with over 100 reviews
- Kayak or bike rental has to be used within 3 days of tour booking
- There is a mid-day and evening tour available
- Tours run in rain, shine, or snow. Dress accordingly.
- Drinks are available for purchase.
Chicago: Taste of Chinatown Food Walking Tour
Chinese culture is rich and has greatly influenced both Chicago and the world. One of the best ways to experience this culture is through food. This Chicago walking tour will help you navigate any confusion and overcome language barriers.
Your tour starts at Phoenix Restaurant. Here, you can enjoy yummy dim sum dumplings and participate in a traditional Chinese tea tasting. Afterward, it’s time for a sweet treat: buttery custard tarts from Chinatown’s oldest bakery.
Next, you’ll try a unique spicy meat sandwich from the Xi’an region. Following that, take a stroll through the charming Chinatown Square, where you can explore ethnic grocery stores and souvenir shops.
To wrap up your tour, you’ll sample succulent dry chili chicken and the famous spicy Szechuan hot pot. On this delicious journey, you’ll experience a taste of different regions in China while only walking a few blocks in one of Chicago’s most interesting (and often overlooked) neighborhoods.
Key Information:
- 4.8 starts with 60 reviews
- You can upgrade for $19.99 per person, payable on site, which includes 3 adult drink pairings.
- Bring your passport or ID card
- Vegetarian options are available, please let your guide know in advance.
- 3 people are required to for this tour to take place, if less, then it’ll be canceled with a full refund or rescheduled.
Chicago Favorites Ultimate Food & Walking Tour
Enjoy all the icons of the city with this Chicago walking tour. Enjoy deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. You’ll also get a nice tour of the city – strolling down the Magnificent Mile, seeing the Wrigley Building and Chicago Theatre, and of course Millenium Park with the Chicago Bean (or its more formal name, the Cloud Gate).
This tour also comes with a free 2-hour bike or kayak rental to be used within 3 days of the walking tour booking. You can rent a bike at Bobby’s Bike Hike World on Lake Shore Drive or the kayak at Bobby’s Kayak at Ohio Street Beach.
Key Information:
- 5 stars with over 1,000 reviews!
- Suitable for all ages & fitness levels, but it does cover 1.5 miles (2.4 kilometers)
- Kayak or bike rental has to be used within 3 days of tour booking
- Vegetarians can be accommodated, just let the tour guide know in advance. Also allows for those that don’t eat beef or pork. It cannot accommodate gluten-free or vegan.
- You can upgrade for $19.99 per person, payable on-site, which includes 3 adult drink pairings.
- TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
Chicago’s Delicious Donut Adventure with Underground Donut Tour
Dessert lovers rejoice! Indulge in the Windy City’s sweetest treats on the Underground Donut Tour, where you’ll sample some of Chicago’s best donuts. This unique excursion takes donut lovers on a journey through the city’s top donut shops in the Chicago Loop, offering a chance to savor a variety of delicious styles, from glazed to cream-filled. With all tastings included and options for vegan, gluten-free, and nut-free diets, this tour is perfect for anyone looking to celebrate the magic of donuts.
Key Information:
- 5 stars with over 1,000 reviews
- Stop at 4 donut shops and try a few donuts at each place
- Donuts are included in the cost of the tour. You can purchase additional donuts if you want
- Vegan, Gluten-free, and nut-free options are available
Downtown Chicago Walking Pizza Tour
Dive into Chicago’s pizza culture on this small-group walking tour, where you’ll savor a variety of styles, from deep-dish and Neapolitan to Roman and artisanal. As you indulge in these delicious slices, you’ll also learn about the city’s rich culinary history and spot key landmarks along the way. With enough samples to make a generous meal, this tour offers a personalized experience as you explore vibrant neighborhoods like the Loop and River North, all while discovering the dish that Chicago is famous for.
Key information:
- 5 stars with 82 reviews
- Tour happens in all weather conditions, dress appropriately
- Children under 6 are free, but let the tour operator know. Infants must sit on laps.
- Wheelchair & stroller accessible
Architecture Walking Tours of Chicago
Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
Discover the hidden gems of Chicago’s Loop district on a walking tour that showcases the neighborhood’s most impressive interior spaces. Step beyond the façades to explore beautifully designed interiors along a carefully curated route, led by an expert guide. As you delve into the city’s architecture, art, and history, you’ll uncover a side of Chicago that’s often missed by tourists, gaining a fresh, local perspective on the Windy City.
This tour takes you through various spots of The Loop
Key Information:
- 5 stars with over 900 reviews!
- Not wheelchair accessible
- Max of 15 travelers
- Operated by Inside Chicago Walking Tours
Chicago Architecture Tour: Underground Pedway and the Loop
Discover the hidden side of Downtown Chicago on a small-group walking tour that takes you through the Pedway, an underground network of tunnels connecting the city’s buildings, and the vibrant Loop. If you’ve ever wondered how Chicago-ians handle the winter, this is the walking tour for you! Perfect for architecture enthusiasts, this tour reveals insider stories and landmarks often missed by locals, offering a chance to see iconic sights like the Picasso Statue and Millennium Park. With a small group, you’ll enjoy a personal sightseeing experience, uncovering Chicago gems that are frequently overlooked on other tours.
Key information:
- 5 stars with almost 200 reviews
- Not wheelchair accessible
- Travelers should have a moderate physical fitness level
- Tour operates in all weather conditions, dress appropriately
Final Thoughts
Chicago’s walking tours offer an incredible way to experience the city’s rich history, diverse neighborhoods, and iconic architecture up close. Whether you’re a foodie eager to taste local specialties, a history buff intrigued by the tales of Prohibition-era gangsters, or an architecture enthusiast fascinated by the evolution of skyscrapers, there’s a tour tailored to your interests. Each step through Chicago’s streets reveals a new story, making these walking tours an unforgettable way to connect with the Windy City’s vibrant culture and charm. So, lace up your walking shoes and get ready to explore the best of Chicago, one step at a time.
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Save “Best Walking Tours in Chicago” for Later
Love all the great tours that you recommended espescially the food tours! Next time we are in Chicago will check out some of your recommendations! Thanks!
The architectural tour looks like it would be our choice. Thanks for highlighting these top tours, as there are so many to choose from.
Chicago is a great city to take a walking tour in. The architecture is exciting and plentiful.
Blooming ‘eck, that is a lot of tour options! I do love exploring cities on food – but I think it’s the food tours (and the ghost tour) that are the most appealing. 🙂
I’d go for the underground pedway in the wintertime!
Perfect timing – my son is going to Chicago next weekend – I have shared this article with him!!!
I love Chicago, but I’ve never really thought of it as being a “foodie” city, but the amount of food tour options is telling me I’m wrong about that!
Maybe I should check one out next time I’m visiting (:
Oh boy, those deep dish pizza pictures made me hungry! I’ll definitely be booking one of those tours when i visit Chicago!
Hadn’t wanted to visit Chicago until recently but this really affirms I need to go, so much to do!
I didn’t think there would be so many tours. How fun! I would love to do the walking pizza tour. Thank you for sharing!