Michigan Avenue Walking tours

Our most recommended Michigan Avenue Walking tours

Chicago: Underground Pedway & Downtown Secrets Walking Tour

1. Chicago: Underground Pedway & Downtown Secrets Walking Tour

Come experience Chicago's famous "Pedway" – the mysterious underground tunnels downtown that keeps us all warm & dry in bad weather. Wandering the Pedway, through hidden corridors of stained glass and even underground swimming pools, you'll access interiors that seem to come up out of nowhere. In the first part of our 2-hour walk, on weekdays, you'll see beautiful and historic government building interiors, learning not only about the design and history of the buildings, but also about the movies filmed there. On weekends, as government buildings are closed, we instead explore a couple stunning interiors with stained glass mosaics that will leave you awe-struck. You'll walk under full blocks of buildings, up and down staircases, accessing these buildings through the Pedway's secret passages. In the second part of our walk, you'll discover some of the other "secrets of the Loop" hidden in plain sight. What is the meaning behind "The Bean"? What is the significance of Chicago and Route 66? How can someone walk right by a garden and not even SEE it -- or walk by a building and not see it, for that matter? You'll find so many secrets, packed into a leisurely 2-hour walk with your expert Chicago guide. Ending with a fabulous “secret” interior near the Art Institute, you’ll be in the perfect central spot for continuing your exploration of downtown Chicago on your own after the tour!

Chicago: Treasures of the Golden Age Walking Tour

2. Chicago: Treasures of the Golden Age Walking Tour

This Historic Treasures of Chicago tour covers the most significant historic architectural landmarks in Chicago’s Loop. Your expert guide, trained by the Chicago Architecture Center, will focus on great cultural buildings from the late 19th and early 20th centuries, which harkened back to earlier time periods and were designed in revival styles such as Beaux Arts, neo-Georgian and neo-Gothic. Marvel at exteriors and interiors of dazzling beauty and startling originality, and get a glimpse inside some of the city's most beloved buildings.    The highlights of this walking tour will include the Chicago Cultural Center, home to the world's largest Tiffany dome; the iconic Marshall Field's department store, now Macy's on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

Chicago: Food, History and Architecture Tour with Tastings

3. Chicago: Food, History and Architecture Tour with Tastings

Discover the architecture and food scene of Chicago on a guided day tour. Learn more about the city's history and vibrant food scene as you discover various bustling neighborhoods and historic areas. Start the tour under the dazzling marquee of the Chicago Theater. Explore the bustling city where the first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then, head towards the Chicago Pedway. This unique feature of Chicago is used by locals and commuters daily to move about the city in a network of underground tunnels. Make your way above ground at City Hall, and admire its classic interior design and architecture. Next, visit a spot for a tasty sweet treat, and a local tradition, Chicago-style popcorn. Take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Sears Tower (now known as the Willis Tower). From there, visit another delicious destination for locally made chocolates from a Chicago staple. Meander through the beautiful lakefront parks along Michigan Avenue, finishing at picturesque Millennium Park, home to the iconic Bean sculpture. Travel by ‘L” train or ride share with your guide from Millennium Park up to the River North neighborhood, the original Chicago foodie destination. Your food tour starts with a very well-known Chicago fare, the Chicago-style hot dog. Every Chicagoan has his or her own preference as to how the dog should be made, and you’ll get a chance to try your guide’s favorite version. Next up is the world-famous Chicago deep-dish pizza. An entire meal unto itself, this staple of the Chicago food scene originated in River North in the 1940s when workers and families needed filling dishes at low prices. Your guide will take you to a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, continue your tasting journey with a classic Chicago sandwich, the Italian beef. Sample this sandwich in a real Chicago institution with no-frills decor. Our tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to see in the city.

Chicago: Art Institute of Chicago Exclusive Guided Tour

4. Chicago: Art Institute of Chicago Exclusive Guided Tour

Getting to see famous artworks by true contemporary masters is a rare experience, but on a busy day at the art museum you might not even be able to enjoy what you’re seeing! On this exclusive, small group tour of the Art Institute of Chicago, your guide will show you the most famous pieces in a collection of 300,000, and you’ll actually get to enjoy them before the crowds. Meet your expert guide by the Lions on Michigan Avenue, then slip into the doors of the Art Institute for an exclusive guided tour. First, visit the gallery and take in George Seurat’s can’t-miss masterpiece A Sunday on La Grande Jatte. Then, wander over to enjoy alone time with three of Van Gogh’s pieces: The Bedroom, Self Portrait, and The Drinkers. Next, continue your journey into Impressionism with the Claude Monet’s mesmerizing artworks such as Stacks of Wheat, Water Lilies, and Water Lily Pond. Watch these pieces come to life as your guide shares the stories behind these iconic paintings. Visit galleries featuring works by American artists such as Georgia O'Keefe, Edward Hopper, and Jacob Lawrence. Here, you will even get to see the iconic American Gothic by Grant Wood! Finally, enjoy the intriguing works of Spanish artists Pablo Picasso and Salvador Dalí. Learn the story behind Picasso's The Old Guitarist before seeing Dalí’s Inventions of the Monsters and the head-scratching Venus de Milo With Drawers statue.

Chicago: History, Culture and Architecture Walking Tour

5. Chicago: History, Culture and Architecture Walking Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.

Chicago: Architecture and Food Walking Tour with Tastings

6. Chicago: Architecture and Food Walking Tour with Tastings

Experience the best of Chicago on a guided walking tour that explores the city's architecture and food culture. Your 2-part walking tour begins by exploring the heart of Downtown Chicago. Join your guide as you discover the city's architectural highlights, both old and new. Admire views of the Chicago River, see Chicago's City Hall, the Wrigley Building, the Water Tower, Cloud Gate, and much more. Then, hit the Central Loop, where locals go to grab their favorite foods. Sample some of Chicago's famous fare and learn about the history behind street food staples in the Windy City. Let your local guide show you the how-tos (and how-not-tos) of legendary dishes, from deep dish pizza to sandwiches, to a loaded hot dog. Listen as they entertain you with fascinating stories of the everyday immigrant chefs and vendors responsible for Chicago's eclectic food scene. By the end of the tour, you'll have a deep appreciation for both the evolution of this city and the role food has played in the lives of its residents.

Chicago: Downtown Highlights Walking Tour

7. Chicago: Downtown Highlights Walking Tour

Explore the vibrant downtown district of Chicago in the company of a local guide. Take a walking tour through the modern architecture and colorful street art, learn the history behind the city's renowned buildings, and gaze at the biggest must-sees including Cloud Gate, better known as "The Bean". Step into the city center with your local guide and become surrounded by the soaring architecture of iconic buildings, such as the Wrigley Building. Get an up-close look at the famous Chicago Bean for the chance to snap some Instagram-worthy photos. Take in views of the Chicago River and even stroll along the River Walk if the weather allows. Allow your guide to show you some local-favorite hidden gems and enjoy a delicious surprise treat.

Other Sightseeing Options in Michigan Avenue

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What people are saying about Michigan Avenue

Overall rating

4.6 / 5

based on 38 reviews

With so many buildings and architecture to see, which ones are the most significant and relevant? This is where the tour comes in. The tour guide did not disappoint; you enter into some of the buildings where if you go by yourself, you wouldn’t dare. The tour is awesome and it leaves you with a nice feeling of appreciating the architecture of the city. Buildings we entered: Chicago Cultural Center Palmer House Marshall Field and Company Building - this is the Macy's store, its public, but the surprise is something that you wouldn't see if you are wandering by yourself (Ceiling with Tiffany Mosaics). Impressive and highly recommended.

I was impressed with receiving a communication from "Chicago Dave" the morning of the tour. The meeting location was clear and he made it easy to find him. He is personable and it was like spending the day with an old friend. He was energized from start to finish while demonstrating his knowledge of Chicago and its rich history. He was also willing to tweak the tour route based on my interest, as time allowed. I can attest that you'll see the BEST of downtown attractions. I even learned a few things about Chicago (and I live nearby). Take the tour!

Dash was a really friendly and has so much knowledge about the city as a tourguide! Highly recommend this guided walking tour through the beautiful city of Chicago!

Highly recommend! Dash has an extensive knowledge about the city, making the the tour worth the value!

Guide (Frankie) was very knowledgeable and friendly. She made the tour very enjoyable.