Top Chicago Walking Tours - page 7

Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walking tour. Go back in history while admiring one of the epicenters of the style’s birth. Immerse yourself into the life of the Windy City between World War I and World War II, the time when the design evolved and turned into neo archaic Mesoamerican grandeur, which can’t leave anyone indifferent. Be delighted with the variety of decorations and geometrical shapes which distinguish Art-Deco from Neoclassicism. Uncover the stories behind the famous Loop district of Chicago. Delve into the atmosphere of the 1920s as you listen to more insights and facts from your enthusiastic local guide. Overview the history and pay attention to the details you wouldn’t notice without a tour. Grab the chance to get inside famous buildings and revel in the Art Deco interiors.

Chicago Art Deco Architecture Tour - History of the Jazz Age

History of the Jazz Age at Chicago Art Deco Architecture Tour

Free Cancellation
1 hour 30 minutes

from $67

Chicago Architecture, Art and History Tour - Off The Beaten Path

This short but sweet and unique adventure will take you on a 2-hour walking tour by the interiors of the most iconic buildings of Chicago downtown. Dive into the extravaganza of splendid hidden gems of the city as you explore the details that no mainstream tours can offer. The itinerary is thoroughly designed by a professional local guide who knows every corner of the Chicago skyscrapers. • Get beyond the famous facades to experience the surprising interiors of the neighborhood • Follow your local guide to discover what’s hidden from most of the tourists • Be provided with fun and surprising facts about the destinations • The tour is interesting for the Chi guests as well as for the residents.

Chicago Architecture, Art and History Tour - Off The Beaten Path

Free Cancellation
2 hours

from $95

Chicago can sometimes feel inaccessible to visitors, but a private walking tour with a local guide takes the mystery out of the city. This personalized tour focuses on the exteriors of iconic monuments, including museums, while your guide shares insights into Chicago’s culture and history. If you wish to explore inside a museum, just let us know in advance and we can create a customized itinerary for you. Perfect for families, solo travelers, or couples, this tour highlights must-see landmarks and hidden gems alike. Connect with the city through local stories, insider knowledge, and expert guidance for an unforgettable experience.

Chicago Custom Private Walking Tour with A Guide ( Private Tour )

Free Cancellation
2 to 8 hours

from $129

Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local with your guide, dive into the bustling life of the business districts, be welcomed by the soothing green of the parks, and admire the lake scenery as you ride along the shore. The city boasts plenty of attractions and landmarks to discover, so the bike is a perfect way to save time to get there. Visit the most important landmarks of the city following your guide. Enjoy a safe bike trip around the city and get experience mainstream tours can’t offer. Be entertained with historical and cultural insights from your guide. The tour is great for families

Bike Tour in Chicago

Free Cancellation
3 hours

from $129

Get a taste of Chicago on this small-group walking food tour and explore the specialties of River North neighborhood. Dive deeper into the culinary history of the place while trying out the best dishes to illustrate different cuisines. Follow your guide’s advice not to get lost in a great diversity of options and enjoy the most peculiar delicacies including deep dish pizza, Italian beef, and hot-dogs. Feel your stomach with delight and your head with new information as you walk and learn something new with every step you make. - Eat your way through the River North neighborhood to get a real taste of the City by the Lake. - Combine walking tour with history insights and culinary tips from your guide. - Enjoy a small group for better personalized experience. - Benefit from your guides expertise and learn more about restaurants and cafés of Chicago.

Classic Chicago Food Lovers Tour in River North

Free Cancellation
2 hours

from $136

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes. Learn more about the art of styling your body features and take a figurative soft tour outside your comfort zone as your stylist pulls pieces for you to explore and try. Think of it as a mini style consultation followed by recommendations and a hands-on practice session during the shopping tour where you can ask any fashion and style-related questions. Throughout your shopping circuit and neighborhood's discovery, listen to fashion stories as told by your fashion savvy guide, and get a unique insight into the industry. Prior to your shopping tour, you will be sent a little shopping form to help personalize your experience. And following your fashion escapade, you will be sent a personal style summary of recommendations received by your stylist as well as some tour souvenir photos.

Chicago Local Fashion Designers Shopping Tour with a Stylist

3 hours

from $151

To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cultural context. What was important in that era, and what was the architecture of that era thus trying express? I do know a lot about this. Thus, you will gain this information about each point of interest. I have taken other tours here, and I just do not hear a word from that point of view. This tour will be like an open history book to an America that no longer exists: Roman and Greek architectural styles, as well as French and British-influenced styles. Of course, you will see the latest in office building architectural styles from around the world, for those of you who just love the modern era as well.

Architectural and Historical Private Tour in Downtown Chicago

Free Cancellation
2 hours 20 minutes to 2 hours 30 minutes

from $199

Per group

Capture your Chicago adventure with a professional photoshoot at the city’s most famous landmarks. Perfect for solo travelers, couples, or friends — no posing experience needed! We’ll visit: The Bean, Chicago Theatre, Riverwalk, Millennium Park & colorful street art spots. You will receive: • 100 high-resolution edited photos • Natural posing guidance • Optional outfit changes • Insider local tips for dining & exploring Come as you are — I’ll take care of the angles, lighting & magic!

Iconic Photoshoot in Chicago

Free Cancellation
1 hour

from $250

Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary landscape, tracing the influence of immigrants on the city's gastronomy. Indulge in the iconic Chicago deep-dish pizza, renowned for its thick crust and flavorful fillings, followed by a visit to a historic eatery for the famed dipped Italian beef sandwich, a local favorite. Amidst culinary delights, marvel at architectural marvels like Cloud Gate and the Chicago Cultural Center, adding depth to your exploration. As the tour unfolds, anticipate a tantalizing surprise: a secret dish, revealed only on the day of your adventure, promising an unexpected culinary delight. This immersive experience offers not only a feast for the palate but also insights into Chicago's rich culinary heritage and architectural splendor.

Private Chicago Street Food Walking Tour With A Local Guide

Free Cancellation
3 hours

from $303

2 hours Private Evening Walking Tour with the Ghosts of Chicago

Free Cancellation
2 hours

from $350

Per group

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, historical grandeur, and cultural allure. From the soaring heights of 1150 Lake Shore Drive to the opulent corridors of the Original Playboy Mansion, this tour invites you to delve into the heart of the city’s rich heritage. Discover hidden stories behind iconic facades, walk the paths of the influential, and immerse yourself in the elegance that has shaped Chicago. This isn’t just a tour; it’s your gateway to experiencing the soul of a city that prides itself on architectural marvels and legendary tales. Make history your playground and become the hero of your own Chicago adventure with us.

Echoes of Elegance Private Tour Chicago’s Architectural Splendors

Free Cancellation
2 hours

from $649

Skip the crowds this is a private tour for your group only! “Lincoln Park Spirits: A Ghostly Walk Through Chicago’s Past” takes you on an eerie exploration of the Lincoln Park neighborhood. Begin at Julia Porter Park, a serene spot with a hidden history. Then, venture past the Alphawood Foundation, a place surrounded by Chicago’s architectural charm and possibly, its spectral tales. Stop by The Red Lion Pub, known for its ghost stories and historical allure. Visit the Victory Gardens Theater, a cultural landmark with its own ghostly rumors. Conclude at Oz Park, a whimsical space that might hold more than just memories of the famous story. This tour is perfect for those who love to explore the mysterious and paranormal side of Chicago.

Lincoln Park Spirits Ghost Private Walking Tour

Free Cancellation
2 hours

from $649

Looking for something truly local, active, & unforgettable for your kids while you explore Chicago? Bobby’s Chicago Kids Camp is a one-of-a-kind day camp Chicago experience designed with both visiting families and locals in mind. While you enjoy adult time—deep dish at Lou Malnati’s, a stroll through the Art Institute, or an adult-oriented bike tour up to Wrigley—your child is biking the lakefront, kayaking calm waters, & making new friends at the best summer camp in Chicago. Our camp blends active outdoor fun with real Chicago stories. Campers visit landmarks like Millennium Park, the Lincoln Park Zoo, & Buckingham Fountain—learning fun facts & building confidence along the way. We offer flexible booking by the day or week, with half-day & full-day options—perfect for travelers building an itinerary. It’s not just a Chicago kids camp—it’s a chance for your child to experience the city like a local, while you enjoy some grown-up adventure of your own. Book your kids adventure today

At our Chicago kids camp, adventure & friendship go hand in hand. Kids team up for biking, hiking, & kayaking—all while building confidence & lifelong bonds at one of the best summer camps in Chicago.

Chicago Kids Camp - Daily or Weekly Summer Adventures

5.0

(1)

Free Cancellation
1 day

from $149

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago Architecture and True Crime Tour

Leslie_W, Mar 2026

A Little Something for Everyone

This tour is as the perfect mix of architecture, history, true crime, and pop culture for us—a little something for everyone. We loved that most of the stops were indoors so we could hear our guide well and dip out of the blustery cold for a bit each time.

Chicago Architecture Tour: Underground Pedway and the Loop

Julienne_T, Mar 2026

Pedway Tour

Heath was our tour guide and he was terrific! His face seemed very familiar and probably have met him as one of the various other tours that we have done. He was very knowledgeable about the history of the pedway and he did it with great enthusiasm, very funny and sarcastic (in a good way). What a way to learn about Chicago than traveling the city through the pedway! Awesome tour, bring a water bottle and have comfy sneakers for the tour! Thanks!

Chicago Mobs and Haunts Walking Tour

Sven_Z, Mar 2026

Great experience - not only for visitors.

Bryson is a great guide who enthusiastically engaged in riveting stories about Chicago. Living in Chicagoland for 20+ years, this experience is not only for tourists and visitors - you learn about the hidden sides of Chicago. I am somewhat glad that I didn't live in the 1920's Chicago.

Chicago City Minibus Tour

Katy_C, Feb 2026

Avery was the GOAT!

I’ve been on a few tours of Chicago and this was the absolute best one yet! So much of that was due to our guide, Avery. He brought a new twist to the tour, shared facts that I had never heard, and was so funny and charismatic. We will definitely do this again!

Haunted Chicago Booze and Boos Ghost Walking Tour

Marissa_B, Dec 2025

SO worth it!

Our tour guide was amazing! She felt like a friend just hanging out telling stories with us. She was an amazing storyteller and had a wonderful personality. Highly recommend! I felt like I learned so much. It was one of those hidden gem things to do that didnt feel touristy. The tour made me feel connected in a way to chicago. Very cool experience.

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Amy_F, Nov 2025

Even Stevie Wonder Would Give 5 Stars

We have done several tours in Chicago over the years, including one that was architectural-specific. Collin was by far the most knowledgeable. He took us to several hidden gems that other tours didn't even hint at. On top of his witticism, we are still discussing some of the historical stories he shared. Best time investment of our visit! Now we just need Collin to do a Chicago foodie tour.

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Sabrina_C, Oct 2025

Excellent

Michael was our tour guide and he was excellent. He even helped us find parking on the street .The tour starts with a short visit inside the library which was the meeting spot. He had lots of stories to tell, and he was very entertaining. He was also very knowledgeable about Chicago. I expected sample servings of all the food, but we actually had an entire slice of pizza, a half of a beef sandwich, an entire hotdog, an entire churro, an entire brownie, and a small sample bag of popcorn. The tour took exactly 3 hours as advertised. I recommend this tour and hopefully you have Michael as your tour guide.

Delicious Donuts & City Sights: Chicago's Original Donut Tour

DJ_O, Oct 2025

Great tour every time

This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.

Chicago Sightseeing River and Lake Cruise

Erica_S, Sep 2025

Great experience but hard to find

The tour was great with a very knowledgeable narrator. I enjoyed it. However, we missed out scheduled tour because. Of the difficulty in finding the location. We had to call and a wonderful agent stayed on the phone with us gave us directions and told us where to park. Patrons should be given more information on the location.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Alison_P, Sep 2025

Bike tour around Chicago

I had an afternoon to myself and live the outdoors so I booked the 4 hr bike, bites, and brews tour. I had a great time and was completely comfortable doing this tour by self as the guide was great and others in the group very friendly. Not overly strenuous at all, just a decent ride with plenty of stops to learn about Chicago.