Things to do in Chicago

12 Chicago Walking Tours Worth Exploring

Every nook and cranny in Chicago holds a niche world of activities to discover — with the right tour.

With so much to do, a typical itinerary won't cut it. For locals or those passing through, delving into Chicago's attractions through these guided walking tours promises a captivating exploration of the city's wonders.


1. Historic Chicago Walking Bar Tour 

In Chicago, drinks are best served with a side of local history. A walking bar tour blends delicious drinks with educational facts for an experience that stimulates your mind and taste buds.

Along with a guide well-versed in all things Windy City, you'll traverse the Chicago streets, stopping at notable bars for a drink and learning a few facts you can take home to wow friends and family.

What kind of knowledge can you absorb on a walking bar tour? The answer encapsulates everything from towering architectural wonders to organized crime. During the tour, you'll sip illicit cocktails in a real speakeasy while listening to stories from Chicago's Jazz Age.

Then, chug down a beer on Magnificent Mile while you're regaled with tales of historic buildings such as the iconic Tribune Tower.

The perfect blend of walking tour and mobile documentary, this excursion offers an inside look at the city from all angles. You'll also get some innovative beverages to sip along the way.

It’s recommended that travelers for this tour have a moderate level of physical fitness.

2. Chicago Food Planet Food Tours 

What's the only thing better than a walking tour with drinks? A walking tour with food, naturally, and Chicago Food Planet knows how to host one. From deep-dish pizza to brownies, these tours provide a thorough sampling of the Chicago fare you've been dreaming of, without the overwhelming hassle of reserving a spot at each restaurant. 

Chicago Food Planet offers a handful of themed tours, each with a unique Windy City menu. Opt for a neighborhood-specific one and uncover delectable culinary highlights in Chinatown or Pilsen, or succumb to your inner pop-culture fanatic with a tour that includes every restaurant featured in the hit series The Bear.

For a more classic route, reserve a spot on the Iconic Foods of Chicago Tour. Sample local favorites such as hefty Italian beef sandwiches and crunchy Chicago-style popcorn. Besides a fabulous meal, you'll skip the line and get an inside look at the chefs heating up the local food scene.

Tours with the Food Planet are wheelchair- and stroller-accessible.

3. Chicago Crime Tours 

True crime junkies know that Chicago was once a hotspot for illicit activity on a grand scale. From Al Capone to "Baby Face" Nelson, the city's rich history of organized crime has made it a prime location for walking tours.

Gangster-centric tours are plentiful here, with pit stops at notable locations such as the First National Bank robbed by John Dillinger and the courthouse which housed some of the city's most formidable characters.

But Chicago crime isn't limited to the mob. Travel back in time to the World's Columbian Exposition of 1893 for a deeper look at the vicious crimes of H. H. Holmes. Or, shake things up with a Prohibition tour, complete with historic bars and old-school drinks.

No matter what flavor you take your crime, there's a Chicago walking tour that will get to the heart of your darkest fascination.  

For those interested in delving deeper into the city’s past, a visit to one or many Chicago museums will offer a comprehensive look at its historical and cultural landscape.

A large part of this tour does take place on a bus, but there are stops, so a moderate level of physical fitness is recommended.

4. Chicago Hauntings Ghost Tour 

Some stories carry on into the afterlife, existing at the boundaries of our present reality. And the fine line between the normal and the paranormal is best blurred on a spooky Chicago Hauntings Ghost Tour.

Now in its second decade of guiding audiences through the city's darkest secrets, this long-standing tour is a popular destination for lovers of the unexplained and unhinged. Visitors will see for themselves the sites of Chicago's most famous apparitions.

Dashes of local history bring each tale to life, whether it's the remains of the Chicago Fire or a 1930s partygoer forever hailing a fatal cab ride. Pop culture fanatics will find some locations familiar. They inspired everything from Ghostbusters to Rosemary's Baby.

Just don't forget your camera and tape recorders — you may be one of the lucky visitors who go home with more than a souvenir. 

 

5. Free Tours by Foot 

Few things are better than a free walking tour of Chicago, and that's just what you can find at Free Tours by Foot. Home to a wide range of walking tours, each excursion is available to visitors for free or on a pay-what-you-like basis.

This lets you discover Chicago's most notable destinations without spending a small fortune. Don’t forget to bring comfortable shoes!  

Surrounded by a vibrant, local culture, these free tours aren't lacking in things to explore. Book a spot on the Architecture Tour for a history lesson in Windy City structures, from skyscrapers to the famed Buckingham Fountain.

Or, opt for the North Loop Tour for a guided stroll through the art-loving neighborhood that ends in Millennium Park. From ghosts to gangsters, Free Tours by Foot offers activities that impart memories and knowledge.

Free Tours by the Foot offers private tours for accessibility options, but not every public tour is accessible to all.

Photographer: VaultShots

6. Chicago Detours 

There's no one better to show you around Chicago than a local who's spent a lifetime gathering the secrets buried on every street. At Chicago Detours, this kind of intimate exploration is exactly what you're in for.

Hosted by a team of charismatic tour guides, each excursion is custom-made to cover the parts of the Windy City you're most excited to see. Blending history, architecture, cuisine, and modern culture, you'll get a glimpse of Chicago like you've never seen before. 

Work with a guide to plan your own memorable tour, or opt for one of the curated routes already beloved by visitors. The Downtown Bucket List Tour takes you through attractions both iconic and undiscovered in Chicago's bustling downtown area, while the Neighborhoods Tour offers an in-depth look at the city's historic districts and their rise to prominence.

Complete with jaw-dropping views, breathtaking art installations, gourmet lunches, and artisan gifts, these tours provide visitors and locals alike with a lively picture of Chicago. 

7. Chicago Elevated 

If wacky and wonderful is what you're looking for, Chicago Elevated could be the walking tour you've been waiting for. Founded by improv star Margaret Hicks, these tours are as funny as they are informational, letting attendees in on some of Chicago's lesser-known stories and attractions.

Get to know the Chicago Pedway and uncover the thrilling details of the underground city. School yourself in Chicago's disaster-filled history.

Chicago Elevated tours reflect their host's background in improvisation: No two are exactly alike. Limited to small groups, each excursion offers a chance to get involved in the journey through the city's weird side.

Hicks' theatrical approach to touring results in an experience you'll love in from the get-go. She highlights the fascinating aspects of mundane sights — even a pedestrian walkway system.

At Chicago Elevated, it's less about what you're looking at than how you're looking at it. And with Hicks at the helm, each tour is sure to feature an itinerary just kooky enough to leave you obsessed. 

There are stairs involved in this tour, so it’s unfortunately not accessible to all.

For those seeking even more off-the-beaten-path experiences, exploring unique things to do in Chicago can further enhance your adventure in the city.

8. The Chicago Tour Company 

Your unique interests and hobbies make you who you are, and now you can celebrate your fascinations with a Windy City walking tour. Since 2012, The Chicago Tour Company has specialized in completely custom walking tours catered to your tourist whims. Love chocolate? How about books or movies?

Your guide can design an excursion focused on any theme you like. Whether this means spending the day popping in and out of bookstores or traveling to every candy shop in Downtown Chicago, The Chicago Tour Company has turned itinerary design into an art form. 

The beauty of a full-service tour is that everything is arranged before you arrive, so you don't need to lift a finger. This means the hassle of researching, scheduling, and reserving is completely taken out of your hands. This lets you explore the Windy City as you choose, alongside a fun, knowledgeable tour guide. 

Photographer: Jaromir Chalabala

9. Chicago Foodways Tours 

If you're like most travelers, you've been caught up in the false glimmer of overhyped restaurants that fail to deliver on flavor. Popular with tourists but despised by locals, some restaurants aren't worthy of a spot on your vacation itinerary.

Luckily, there's a way to avoid the fakes and get a taste of the cuisine beloved by true Chicagoans. All it takes is a little help from Chicago Foodways Tours.

Committed to uncovering the gems of the city's cuisine, these tours highlight tasty treats in every neighborhood. Munch on flavor-packed arepas and crunchy birria tacos on the Global Street Foods Tour, or eat your way through Sweden, Vietnam, and the Middle East on the Saigon to Stockholm Tour.

Each tour dishes up the history behind the cuisines and the Chicago communities in which they flourish.

The Chicago Foodways Tour is completely ADA accessible.

10. Inside Chicago Walking Tours 

Chicago from the street is magnificent in its own right. Step inside any of these historic skyscrapers and you're met with a world of intrigue and architectural intricacies. This is the idea behind Inside Chicago, a company with walking tours that show the spaces within.

Since 2014, the guides at Inside Chicago have introduced visitors and locals alike to the beauty hidden right under their noses. Find wonder in the lobbies, staircases, and sky decks of the city's concrete giants.

Choose from four guided tours, each journeying through a handful of iconic Chicago spaces. Your group will see art deco masterpieces and wonders like stained glass corridors, hidden tunnels, and gilded lobbies.

Take in Jazz-Age glamor and sleek modern marvels, all accompanied by a history lesson supplied by your tour guide.

Whether you're moved by the story behind dazzling arches and delicate windows, or you're looking for a magnificent view from the top of a skyscraper, Inside Chicago will alert you to the wonders lurking within the city's structures. 

Inside Chicago Walking Tours recommends contacting them for questions about accessibility.

Photographer: MSTPhotography

11. Loop Interior Architectural Tour 

For another Chicago architectural masterpiece walking tour, there's no better place to start than the Loop. Bursting with stunning high-rises and gleaming lobbies, a Loop interior architectural tour covers the area in meticulous detail, leaving no structure overlooked.

A helpful guide will lead you into some of the most interesting spaces in the city, from art deco stair wells to massive mosaic domes. On this tour, you'll see Chicago from new perspectives as you uncover the stunning world of careful design all around you.

The city's wonders sing as you venture into iconic structures, from the Chicago Cultural Center to the Willis Tower. Then, head underground for a visit to the Pedway to experience a walking tour beneath the skyline of the Windy City.

Traversing in, out, and below these iconic structures will leave you entranced in the feats of engineering it took to build this magnificent city from the ground up. 

The center makes an effort to make its facility accessible to all.

Photographer: Rudy Balasko

12. Chicago Architecture Foundation Center River Cruise (Bonus Sightseeing Tour)

One of Chicago's best tours takes place on the water — but you won't have to grow fins to enjoy it. Put together by the Chicago Architecture Center, this river cruise gives passengers a view of the city skyline.  

Climb aboard Chicago's First Lady, and embark on a journey of architectural exploration. Each voyage is led by a charming, educational volunteer determined to impart knowledge before you return to port.

You'll hear the epic tale of how Chicago came to be, rising from a tiny settlement to one of the world's largest cities in less than a century. Standing tall throughout this saga are the 50-plus historic buildings throughout the tour, from the Aon Center to the Willis Tower.

A cruise down the Chicago River creates the perfect atmosphere to learn about decades of architectural wonders. To keep the fun going, opt for a combo ticket that includes admission to the Chicago Architecture Center. Here, you'll dive deeper into Chicago's foundation and look at the engineering that put the city on the global stage.

Photographer: Sergii Figurnyi

Discover the Windy City on Foot With Chicago Walking Tours 

There's no better way to get to know Chicago than by perusing the streets on a spectacular walking tour. With larger-than-life architecture, culinary delights, and spooky apparitions to feast your eyes upon, you'll get a taste of the city in all its flavors.

And when you're ready to kick up your feet and relax, an entertainment experience is minutes away at one of our Chicago featured performances. Beloved around the world for its breathtaking storylines and powerful feats of human nature, our performances turn any ordinary day into a treasured lifelong memory.

Ready to be swept off your feet by a performance that pushes the bounds of imagination and creativity? Check out our shows in Chicago, and end your wondrous walking tour with a bang.  Discover the Windy City on Foot With Chicago Walking Tours .

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