Things to Do in Chicago

Embark on a history-based guided walking tour and discover the stories of Chicago’s gangsters and ghosts. Learn about the city’s darker side and creepy past as you explore the Chicago Loop district.

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment. What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Discover Chicago's iconic landmarks on a free walking tour, including a scenic park on Lake Michigan. Explore hidden gems in the Windy City!

Discover the hidden interiors of Chicago's most iconic buildings on a guided architecture tour. Explore the Rookery, Chicago Cultural Center, Marquette Building, and Chicago Board of Trade Building.

Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way). From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep dish pizza to sandwiches to a loaded hot dog! Your local guide will entertain with fascinating stories and 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 excellent city and the role food has played in the lives of all Chicagoans!

Learn about the stories of gangsters, politicians, and more in the spaces where it happened on a bus or walking tour. Visit the speakeasies that made the famous, infamous.

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the colorful, but often overlooked, Trustees System Service Building (now the Century Tower)—all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Take a comprehensive look at Chicago's architectural history

Explore downtown Chicago through its underground passageways, known as "The Pedway," accessing beautiful interiors from both above ground and below, with secrets along the way, on a walking tour.

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour! As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious gangster-ridden neighborhoods in Downtown Chicago.

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Let your curiosity be your guide with a Chinese-themed food tour of Chicago

Join the ultimate foodie adventure in Chicago with a food and tasting walking tour. Explore from deep-dish pizza to Chicago-style hot dogs and get the insider's take on the city’s culinary history.

Our tour takes place in Malt Row in the Ravenswood Neighborhood of Chicago, which has many breweries, a distillery, and a winery. Guests will be taken on a walking tour to three different breweries and will be given historical information and fun facts about the Chicago brewing scene. Reserved seating and exclusive tour discounts are included for most tour stops! Guests will be given plenty of time to get to know each brewery, and the guide will offer recommendations at each stop. Guests are encouraged to order drinks and purchase beers and merchandise at each stop. Located conveniently close to the Irving Park Brown Line and multiple bus lines, the tour is accessible via public transit or Taxi/Uber. Please note that guests must be of legal drinking age to order drinks. All ages are welcome to attend! Due to city law, drinks are not included in the price of admission.

This introductory tour to Chicago, features some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Chicago Theatre, and more

Insta Walk offers you a lot of stylish photos, shooting angles and ideas. This easy, relaxed and friendly walk will open Chicago for you from a new perspective! Throughout the tour, I'll use iPhone and Polaroid cameras to capture your perfect shot. You'll receive approximately 100 digital photos, 10 of which will be color-corrected to make them truly pop. And for a unique and timeless souvenir, I'll also give you 5 Polaroid prints that you can treasure forever.

Discover many of Chicago's architectural landmark buildings from the late 19th and early 20th century. This tour through Chicago's famous Loop includes the dazzling interiors of Marshall Field’s, the Palmer House Hotel and the Chicago Cultural Center.

Take a tour of Chicago Loop's Pedway system, a network of underground pedestrian tunnels. We'll also go above ground to view some special Chicago sights. Our tour begins in the lobby of the Swissotel with a brief overview of the Pedway system.  We then descend into the Pedway and head to the Cultural Center.  After a brief tour of the Cultural Center and its famous Tiffany Dome, we return to the Pedway to visit Macy's department store and its famous Tiffany ceiling, then stop by the store's iconic Walnut Room. Back to the Pedway, we head west to the Civic Center plaza to see the Picasso sculpture and view the Chicago Temple and its Sky Chapel, one of the world's tallest church buildings.  A brief walk to takes us to City Hall and Marriage Court then to a nearby L Stop. A quick train ride takes us to the origin/terminus of Route 66 where we'll enjoy the Art Institute’s lion statues then Millennium Park's to Cloud Gate sculpture (aka, The Bean), Lurie Gardens and Crown Fountain.

Discover the delicious, multiregional cuisine on this wonderful Chinatown Food & Culture Tour. Expand your culinary horizons with unique dishes while learning about the fascinating Chinese culture.

This extraordinary tour of the Prairie Ave District is one not to be missed. Get a sense for how Chicago's wealthiest residents lived around the turn of the century and what remains today. This unique Chicago tour begins with an exploration of one of the city's newly-revitalized spaces: The stunning Chicago Athletic Association Hotel. A short ride on the Green Line takes us to the Prairie Ave District, home to many historic sites such as Motor Row, the former Chess Records and the oldest house in the city. As we wander along Prairie Ave, we're treated to historic mansions and a beautiful park. The highlights of the tour, however, are TWO private, docent-led mini tours at the national landmark Second Presbyterian Church (with its many Tiffany windows) and the Glessner House. We'll also take a mid-tour break at a local employee-owned/woman-owned cafe. Then we board the train back to the Loop for our final stop (and a sweet treat) at the elegant Palmer House Hotel.

The Windy City is known for its food, architecture, and haunting history! Walk with us as the sun sets through downtown Chicago, hearing some of the most gruesome and creepy Chicago stories. The first stop is the Congress Hotel, the most haunted hotel in Chicago. Walk along the streets that H. H. Holmes, Chicago's first serial killer, wandered as he stalked his prey, get a glimpse of Chicago’s sordid past through stories of the Everleigh Club and the 1900s Red Light district, and learn about downtown prison breaks.

Learn the history that makes the Chicago River and its recently updated Riverwalk historically unique.   Chicago is home to one of the world’s most recognizable and celebrated skylines and the Riverwalk’s intimate vantage provides an ideal perspective from which to learn and appreciate its incredible buildings.Discover Chicago's Rich History and Iconic Architecture Experience the vibrant tapestry of Chicago’s past and present with our Chicago Riverwalk Tour. Perfect for history buffs, architecture enthusiasts, and curious visitors, this 2-hour guided tour uncovers fascinating stories and architectural marvels that define the Windy City.

Learn the history behind Chicago's famous elevated rail system and admire the city’s architecture on this guided walking tour. See the galleries at the Chicago Architecture Center and ride the “L.”

Our tour takes place in Chicago's Logan Square neighborhood. The vibrant and artistic neighborhood has many unique breweries, including Chicago's largest independent brewery. Guests will be taken on a walking tour to three different breweries and will be given historical information and fun facts about the Chicago brewing scene. Reserved seating and exclusive tour discounts are included for most tour stops! Guests will be given plenty of time to get to know each brewery, and the guide will offer recommendations at each stop. Guests are encouraged to order drinks and purchase beers and merchandise at each stop. Located conveniently close to the California and Logan Square Blue Line Stops and multiple bus lines, the tour is straightforward to reach via public transit or Taxi/Uber. Please note that guests must be of legal drinking age to order drinks. All ages are welcome to attend, but drinks are not included in the price of admission due to city laws.

Embark on a walking tour through Chicago's vibrant heart, from the bustling Navy Pier to the iconic Cloud Gate, topped off with the option to enjoy a classic Chicago savory treat.

Creative Tools: I’ll use both iPhone and Polaroid cameras to give you a variety of styles, from vibrant digital shots to timeless Polaroid prints. Stylish Keepsakes: Receive approximately 50 digital photos, 5 beautifully color-corrected, and 5 unique Polaroid prints to treasure forever. Relaxed Atmosphere: No posing stress—I’ll guide you through natural and flattering poses for Insta-worthy results.

Discover Chicago’s famous classic foods like pizza, hot dogs, and brownies on a guided food tour. Visit city highlights like Millennium Park and Chicago Riverwalk, and enjoy a bike or kayak rental.

Eat, drink and discover Chicago's Loop and River North neighborhoods on our Chicago historic pub tour via the Brown Line!  Join us on this "over age 21" adventure for a combination of great Chicago stories and adult beverages as we tour historic sites and legendary pubs in the city’s Near North Side. We'll kick off our Chicago tour at the beautiful Marquette Building then head to the Adams Street Brewery, part of The Berghoff, Chicago's oldest, continuously-operating restaurant for a drink and a snack. Next stop, we board the Brown Line for a brief train ride to River North. In River North, we'll visit Brehon Pub with a fascinating story involving bribery and the Chicago media. The Green Door Tavern is next on our list. It's the oldest pub in Chicago and sits above a well-hidden, authentic Prohibition-era speakeasy.  We'll then board the train again and make our way back to the Loop where we'll have "last call" at historic, antique-filled Monk's Pub.

Chicago built some of the world’s first skyscrapers, with changing designs and technologies over time. Explore how these major developments came about, with examples from classic buildings to super-tall highrises from 1872 to the present.

Meet your tour guide at the beautiful Chagall Four Seasons mosaic as we begin our Creativity & Community neighborhood tour. After a short walk, we'll catch the Pink Line at the renovated Quincy L station (opened in 1897) and make our way to Pilsen — a vibrant neighborhood just southwest of the Loop originally settled by Czech immigrants. Pilsen ranks #10 on the Forbes magazine list of the "15 Coolest Neighborhoods in the World." Upon arrival in Pilsen, we'll take a break and grab a taste of authentic Mexican cuisine. Afterwards, we'll stroll the neighborhood where we'll view numerous public murals and learn about the architecture that is unique to Pilsen. We'll arrive at the renowned National Museum of Mexican Art and experience it's changing and permanent exhibitions. After that, we’ll hop back on the Pink line train to the Loop and wrap things up at the famous Picasso sculpture in Daley Plaza.

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting places, you'll encounter the final resting spots of architectural visionaries like William LeBaron Jenney, John Root, Louis Sullivan, Mies Van der Rohe, and Daniel Burnham. This unique walking tour not only unveils the grandeur of tombs and mausoleums but also shares the stories of Chicago's celebrated architects, whose creativity shaped the city's skyline. But our journey extends beyond the architects' realm, as we also discover the final resting places of other notable figures with deep pockets—pioneers of industry such as Marshall Field, Palmer Potter, George Pullman, Walter Newberry, and more. Their legacies, intertwined with the fabric of Chicago's history, add an extra layer of richness to this immersive tour.

Art Deco's lavish materials and geometric ornament epitomized the prosperity and optimism of the Roaring 20s. Learn the history and characteristics of this modern decorative style while touring some of the city's most beautiful skyscrapers.

Explore Chicago's rich history and vibrant culture on a walking tour starting at Millennium Park with the iconic Cloud Gate sculpture. Wander through lush gardens and public art, then delve into the Chicago Pedway's hidden gems. Enjoy breathtaking views on the Chicago Riverwalk, admire the Wrigley Building and Tribune Tower on the Magnificent Mile, and cross the historic Michigan Avenue Bridge. Learn about the Chicago Fire and have the opportunity to enjoy a classic Chicago savory treat (additional cost). Visit Starbucks Reserve Roastery, savoring the flavors that are as rich as the city’s heritage. Pass by several landmarks like the Tribune and Wrigley buildings. Gain a deeper appreciation of Chicago's spirit.

Join Chicago Movie Tours on the Midway, and discover the city's film history in an entirely new way! On this leisurely 75-minute walking tour led by a Ph.D. in film, you'll visit 5 spots on the historic Midway Plaisance, once the heart of the 1893 Chicago World's Fair. As you walk the now-grassy strip (0.5 mi.), you'll discover its many connections to early and modern cinema. Guests must digitally sign a general waiver of liability either before or when they arrive. Guardians must sign waivers for children under the age of 18. Note: This limited Chicago movie tour is available on Sunday mornings to give you the most accurate and unobstructed view of the Midway's monumental sculpture Fountain of Time.

Join us for an unforgettable 2-hour walking tour through the downtown Loop area and the iconic Millennium Park. This guided experience is perfect for visitors who want to uncover the vibrant history, breathtaking architecture, and artistic gems of Chicago. See the Chicago Theatre, where you'll marvel at its classic marquee and learn about its fascinating past as the "Wonder Theatre of the World." Stroll through the bustling streets of the Loop, exploring its architectural marvels and engaging in stories about the city’s dynamic history. We'll visit Millennium Park, a cultural and artistic centerpiece of Chicago. You'll have the chance to admire Cloud Gate—affectionately called "The Bean"—and take in its stunning reflection of the city skyline. Throughout the tour, your knowledgeable guide will provide engaging commentary, insider tips, and photo opportunities to ensure this is a Chicago experience you’ll never forget.

Learn how the Magnificent Mile developed from a warehouse district into the Champs Elysee of Chicago. Admire a wide range of architectural styles including Parisian, Gothic, Neoclassical, Art Deco, Mid-20th Century Modern, and 21st-Century Contemporary.

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment. What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Discover the best food in Chicago with this 3-hour walking tour of the historic River North neighborhood. Explore the history and culture of the city with an expert local guide while tasting regional specialties at some of the best restaurants around.

Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way). From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep dish pizza to sandwiches to a loaded hot dog! Your local guide will entertain with fascinating stories and 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 excellent city and the role food has played in the lives of all Chicagoans!

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the colorful, but often overlooked, Trustees System Service Building (now the Century Tower)—all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Take a walking tour and learn about the life of Louis Comfort Tiffany. View some of his most well-known glass works as you stroll around Chicago.

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour! As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Our tour takes place in Malt Row in the Ravenswood Neighborhood of Chicago, which has many breweries, a distillery, and a winery. Guests will be taken on a walking tour to three different breweries and will be given historical information and fun facts about the Chicago brewing scene. Reserved seating and exclusive tour discounts are included for most tour stops! Guests will be given plenty of time to get to know each brewery, and the guide will offer recommendations at each stop. Guests are encouraged to order drinks and purchase beers and merchandise at each stop. Located conveniently close to the Irving Park Brown Line and multiple bus lines, the tour is accessible via public transit or Taxi/Uber. Please note that guests must be of legal drinking age to order drinks. All ages are welcome to attend! Due to city law, drinks are not included in the price of admission.

Taste the finest examples of Artisan, Neapolitan, Detroit Style, and Chicago deep-dish pizza on this professionally guided walking tour that takes you to highly-rated and historic Chicago pizzerias.

Insta Walk offers you a lot of stylish photos, shooting angles and ideas. This easy, relaxed and friendly walk will open Chicago for you from a new perspective! Throughout the tour, I'll use iPhone and Polaroid cameras to capture your perfect shot. You'll receive approximately 100 digital photos, 10 of which will be color-corrected to make them truly pop. And for a unique and timeless souvenir, I'll also give you 5 Polaroid prints that you can treasure forever.

With captivating stories and delectable treats, discover the rich tapestry of Chicago's history and flavors, ensuring an unforgettable journey through the Windy City!

Take a tour of Chicago Loop's Pedway system, a network of underground pedestrian tunnels. We'll also go above ground to view some special Chicago sights. Our tour begins in the lobby of the Swissotel with a brief overview of the Pedway system.  We then descend into the Pedway and head to the Cultural Center.  After a brief tour of the Cultural Center and its famous Tiffany Dome, we return to the Pedway to visit Macy's department store and its famous Tiffany ceiling, then stop by the store's iconic Walnut Room. Back to the Pedway, we head west to the Civic Center plaza to see the Picasso sculpture and view the Chicago Temple and its Sky Chapel, one of the world's tallest church buildings.  A brief walk to takes us to City Hall and Marriage Court then to a nearby L Stop. A quick train ride takes us to the origin/terminus of Route 66 where we'll enjoy the Art Institute’s lion statues then Millennium Park's to Cloud Gate sculpture (aka, The Bean), Lurie Gardens and Crown Fountain.

This extraordinary tour of the Prairie Ave District is one not to be missed. Get a sense for how Chicago's wealthiest residents lived around the turn of the century and what remains today. This unique Chicago tour begins with an exploration of one of the city's newly-revitalized spaces: The stunning Chicago Athletic Association Hotel. A short ride on the Green Line takes us to the Prairie Ave District, home to many historic sites such as Motor Row, the former Chess Records and the oldest house in the city. As we wander along Prairie Ave, we're treated to historic mansions and a beautiful park. The highlights of the tour, however, are TWO private, docent-led mini tours at the national landmark Second Presbyterian Church (with its many Tiffany windows) and the Glessner House. We'll also take a mid-tour break at a local employee-owned/woman-owned cafe. Then we board the train back to the Loop for our final stop (and a sweet treat) at the elegant Palmer House Hotel.