Top Chicago Art & Culture

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.

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.

Welcome to Chicago River Boat Architecture Tours! We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago. Tour departures from 465 N. McClurg Ct.

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).

Get off the beaten path to experience some of Chicago's best street art on this immersive tour. With a guide in the lead, you can leave the navigation to them and simply take in the scenery. Listen to in-depth commentary focused on the street-art community, the artists, and the history and meaning behind the art.

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.

Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.

Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.

Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.

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.

Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city’s most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.

Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.

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 and with the scenic L train or water taxi along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

Transport yourself back in time to Chicago’s roaring twenties at Tommy Gun’s Garage, a unique speakeasy dinner show in the Windy City. Say the password at the front door and then step into an era of mob guys and flappers, Broadway tunes by Cole Porter and George Gershwin and lively dances like the Charleston. This gut-busting show, full of song, dance and audience participation, is sure to please.

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.

A river runs through it: the Chicago River passes right through the heart of downtown and is a major part of city identity. You’ll begin this walking tour at Navy Pier and follow your local guide along the scenic river walk. You’ll learn the role of the river in Chicago’s history, and stop to admire iconic architecture and bridges celebrated as feats of engineering.

Explore the hidden side of Chicago on a 2-hour walking tour of The Loop, a bustling neighborhood that’s full of wild history, architectural landmarks and some of the city’s most fascinating characters. Follow your local guide along the sidewalk, and stop to notice the overlooked details and untold stories that even life-long locals sometimes miss. Experience the city one small piece at a time on a route that traces a path between Chicago’s littlest treasures, and get an inside look at life in the Second City.