Things to Do in Chicago

Explore the vibrant city of Chicago on a private walking tour led by a knowledgeable local guide

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!

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!

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!

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!

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!

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!

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!

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!

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!

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

Explore the highlights of Chicago on a guided tour that includes a stroll around town as well as a boat cruise on the Chicago River.

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.

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.

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.

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.

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.

Take photos of The Bean and ride the Shoreline Architecture cruise

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.

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.

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.

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.

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.

Explore Chicago's architectural wonders on a walking tour, discovering iconic buildings and Art Deco treasures with insightful commentary.

Embark on a walking tour through Chicago's vibrant heart, from the iconic Cloud Gate to bustling Navy Pier. Enjoy the Shoreline Architecture Boat Cruise along the Chicago River.

Make the most of your day in Chicago by sampling Chicago's iconic style foods, seeing top attractions with a local, expert guide. Includes a FREE 2 hr bike or kayak rental to explore even more.

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.

Book this Chinatown food and walking tour in Chicago today! Enjoy dim sum, Chinese tea, Sichuan chicken and more!

Book a Chicago favorites food walking tour today and feast on Chi-Town's most delicious dishes while learning about their history!

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.

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.

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.

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.

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.

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.

Experience the magic and tradition that brings Chicago to life during the holidays on this walking tour through the Loop’s iconic holiday destinations. Join in the fun with some holiday food, sweets & beverages that make winter in Chicago so delicious!

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

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.

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.

Book a festive food and walking tour in Chicago and experience a winter wonderland in the Windy City with pizza, brownies and craft beer!

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.

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.

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.

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.

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.

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.

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.

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.

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.