Incredible Walking Tours of Chicago

Mar 28, 2025

After a long, cold winter, we’re all hankering to get out there in the sunshine and enjoy some fresh air. What better way to do so than experiencing the beautiful cityscape with a walking tour! Whether you’re in the city regularly for work, or perhaps there frequently to catch a game, concert, or show, we can still bet you’ll find something new and intriguing to experience. Browse the cities tantalizing local eateries and food trucks, take a tour down memory lane by visiting classic family friendly destinations, travel back in time to days gone by as you learn about local art and culture, the city’s beautiful architecture, and local history!

Let’s start off with some food for fuel!

Here are some fantastic walking tours around Chicago highlighting some of the most incredible eateries and restaurateurs in the metropolitan area. We bet you’re going to find your new favorite go-to restaurant when you’re in the city!

History on Tap shares the secrets, history, and legends behind Chicago’s drinking history. Step back in time and learn about the speakeasies of the Prohibition era, find top tier bars that are a locally kept secret, visit bars frequented by celebrities and legends of bygone eras. You’ll get a walking tour of the city’s best and most beloved taverns and bars with a side of local lore.

Spice of Life Tours offers a unique experience with insight into the rich tapestry of cultures that make Chicago so unique. You’ll take a trek through global regions in each of Chicago’s many neighborhoods: Little India, Little Arabia, and Little Chinatown. You’ll experience the savory and sweet from different cultures, shop for unique goods from around the world, discover a world of architectural delights in each ethnic neighbourhood, and experience art and entertainment from each region.

Chicago Food & City Tours are a fantastic way to get bite sized snippets of the city’s best kept secrets: dine at authentic cultural restaurants, relish the wares from the most exquisite specialty bakeries, sample the finest and most delectable street food options, and so much more. You can select 3 hour tours, full-day tours, and even book multi-day itineraries!

Let’s uncover secrets and explore unique destinations of the windy city!

Now that you’re all fueled up and have some energy to burn, we’ll be taking some more serious walking tours around the city. Explore your home base like you’ve never seen it before as you learn about its secrets, mysteries, and oddities along with historic sites.

Bizarre Bucktown is where it’s at if you’re looking for interesting, quirky, and memorable experiences of Chicago. It doesn’t matter how many times you’ve been to the city, you’ve never seen it like this! On your 90 minute walk with a small, intimate group of folks, you’ll learn about the history and hauntings of Bucktown and Wicker Park. Tickets are just $15 per person, but the memories are priceless!

Weird Chicago Tours is an excellent option for adults, finicky teens and older tweens to experience history with a bit of mystery. With options for Walking tours and Bus tours, you’ll enjoy a wide range of entertainment and education. It’s a dark, mysterious, and dramatic Chicago tour touching on true crime, gangsters and mobsters, and haunted happenings in the city.

The Offbeat Street Tours are the best way to explore the city and its unique characteristics. Celebrate the street scene and indie arts culture that has helped turn the metro area into a living, breathing gallery of murals and drawings. Explore the vibrant arts scene of Wicker Park, Bucktown, and Logan Square and get a background about each artist, their painting styles, and their inspiration.

Descubre Chicago offers customized sightseeing tours exclusively for Spanish speaking visitors. You’ll be able to comfortably explore the city and never miss a word. Experience the city’s best attractions and learn about its architectural history with these convenient, comfortable tours.

Urban Adventure Quest morphs the city into a gigantic board game for you to explore as you collect clues and complete challenges along the way. This play at your own pace game is perfect for families and groups, and can be used with any smart phone through a self-guided quest. You’ll walk through amazing parks, explore outdoor art installations, visit historic streets, marvel at the architecture of hotels and restaurants and businesses, and get a great overview of the city.

Let’s see the best and brightest that Chicago has to offer!

Free Chicago Walking Tours are led by local guides who know the neighborhoods inside and out for free public tours or reasonably priced paid private tours for groups of more than 6 and up to 20! (Tipping your guide is recommended, especially on the free options.) This group’s tours are perfect for those who do not want to do endurance training via sightseeing, because they’re just 1 to 3 miles in distance! It’s the perfect option for those with kids and teens, because it’s just the right amount of time. It’s a great way to make new friends and socialize with locals and tourists alike.

Chicago Greeter is a free, year-round option for small groups to tour the city with a local volunteer. You can book a tour and select the region of your choice, and the guide will curate a customized walk through the city just for you! You can select from 10 languages, 25 neighborhoods, and 40 niche interests. It’s the perfect way for your family and friends to experience all that Chicago has to offer with nothing boring for your taste, because it’s tailored specifically to you!

The Loop Mural Walk is a free downtown adventure tour and self-guided journey to view the ever-changing landscape of street art in Chicago. It features more than 20 murals by internationally recognized artists and creatives around the globe. You can use your phones to navigate the turn-by-turn directions to view the works in the recommended order, or check out “The Murals” option to take your own path. It’s a colorful, creative, and unforgettable experience for the whole family, and makes a fun day out with pals as well! Be sure to bring your camera or leave extra room on your smartphone, because the murals make excellent backdrops for selfies and portraits.

Chicago Architecture Center offers an impressive 70 different walking tours to select from. Volunteer docents are certified and trained by the CAC to provide you with knowledgeable guided tours through the city’s most vibrant neighborhoods as well as downtown. You can’t go wrong with booking a CAC tour. Your guide will show you a wide array of architectural styles and explain the detailed history and design behind each one.