Top Chicago Cultural Tours

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue and State Street. Revisit the heyday of the skyscraper and visit stunning, Art Deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

Step on board a cruise boat bound for the waters of Lake Michigan, enjoying the sunset from the boat deck. Step up to the cash bar for drinks and snacks and find a place on board for a view of the epic fireworks display. A boat on the lake is the best place for catching the full fireworks spectacle and making great photos and videos.

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!

Short and highly selective information in the audio commentary for top 15 tourist attractions in around Chicago Highlights of this Self-Guided Audio Tour • It allows you to go as per your own convenience of time, pace and location. • Simply use our personally created itinerary which starts from main train station of the city then gradually moves one by one (if required). • Not necessary to download any location tracking apps. It can be listened online in any devices (smartphones, tablets, laptops, etc.) • Available in multiple languages, you can choose the one you’re most comfortable with (should be selected at the time of booking) • It is one of the best options with lowest price for travelers who prefer flexibility on their tour. • If you have any questions about any attractions, No worries, we will answer in your language instantly.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.

An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.

Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this full-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronzeville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Wrigley Building, Tribune Tower, and Cloud Gate on foot along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.

Get ready to discover the storied architecture of Chicago. You’ll take the first elevator ride of the morning up to Skydeck at Willis Tower to see the city from a birds-eye prime vantage spot. Journey back to street level for an immersive tour of the Loop guiding you from the iconic ‘L’ train circling downtown Chicago to the city’s impressive Art Deco architecture. This insider’s look will supply you with the history to truly appreciate these colossal structures. A 90-minute river cruise awaits at the end of the tour taking you from the Chicago River to Lake Michigan.

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

This small-group Best of Chicago tour highlights the best ways to experience the Windy City's most prominent sites and attractions including the breathtaking Chicago architecture illuminated at night. You'll visit the former tallest building in the world, visit Adler viewpoint and enjoy a relaxing boat tour on a Skyline cruise. You'll also experience a narrated drive through the Windy City passing by multiple points of interest including the remarkable Aqua Tower and stop at Buckingham Fountain to witness an outstanding night light show.

In the beloved 1980s teen comedy “Ferris Bueller’s Day Off,” the Art Institute of Chicago plays a starring role—and on this immersive, small-group tour, you’ll follow in the footsteps of Ferris and his friends all while visiting the museum’s best-known masterpieces. Meet your guide inside of the museum in the Modern Wing (tickets own expense). You can look forward to seeing masterworks by Chagall, Seurat, Cassatt, and more, all while hearing behind-the-scenes stories.

Explore the Loop's famous architecture during this 2-hour walking tour with an expert guide from the Chicago Architecture Foundation. Discover the beginnings of the Chicago School of Architecture through visits to some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. This sophisticated, informative tour is a must-do for history and architecture buffs.

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop whenver you want to take pictures and also explore by foot specific locations. Pick up is included from your hotel or place of choice inside the city and downtown Chicago. Please include this information as well as a contact number when booking. This private tour will give you a great experience to get to know Chicago. This is a 4 hour private tour with driver and separate tour guide. During this tour, you will explore great locations in Chicago like the Richard J. Daley Center. There will also be a photo stop at the Lakefront Trail and South Michigan Avenue. Don't miss the Grant Park, Cloud Gate and of course the Downtown / The Loop. This private tour will finish off at your hotel in Chicago.

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons. Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside.