Activities

Cruises, Sailing & Water Tours

Chicago Architecture 75-Minute River Cruise Guided Tour

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.
$44
1.25 hours
Cultural & Theme Tours

Chicago Criminals, Mobsters and Gangsters Bus History Tour

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more. From a luxury coach, see the sites of storied crime scenes including Biograph Theatre, Holy Name Cathedral, Clark Street Bridge and the St Valentine's Day Massacre, one of Chicago's most notorious murders. Snap photos of the historic criminal courthouse, and hop off the coach to walk the path that Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths.
$40
1.5 hours
Shows, Concerts & Sports

Tommy Gun's Garage Dinner and Show

Welcome to the only speakeasy dinner show in Chicago Tommy Gun's Garage! Just say the password and you'll be transported back to the roaring twenties. You'll be entertained by gangsters and flappers, dancing the Charleston to the music of Cole Porter and George Gershwin. It's a night out in Chicago you'll never forget!
$67
3 hours
Cruises, Sailing & Water Tours

Chicago Architectural River Cruise

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city that defied all expectations … even the laws of gravity.
$48
1.5 hours
Food, Wine & Nightlife

Small-Group Chicago Food Tour: Gold Coast and Old Town

Discover Chicago's culinary side on this three-hour walking tour to taste the delicious flavors of the Gold Coast and Old Town. Along the way, your guide will show you the history and architecture in these culture-rich neighborhoods, just north of the downtown area. After stops at seven quintessential Chicago restaurants in these two neighborhoods, you'll feel like a real Chicagoan! The tour operates with a maximum of 18 people, ensuring you’ll receive personal attention from your expert guide. Tastings at 7 different locations is included.
$60
3 hours
Cultural & Theme Tours

Chicago Loop and Pedway Architecture Tour

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors of the Marshall Fields Building, Chase Tower, Chicago Cultural Center and more, plus see public art by Chagall and Picasso. Stroll through elegant lobbies, under glittering domes and into the sprawling network of Chicago Pedway tunnels. Your expert guide shares insights about the city’s diverse architectural styles and history, bringing the details of the Windy City into vivid focus.
$26
2 hours
Shows, Concerts & Sports

Blue Man Group at the Briar Street Theater in Chicago

See the Blue Man Group, one of Chicago's longest running shows, at the Briar Street Theater in downtown Chicago. The phenomenon that has visited cities around the globe is integrating new technology into their shows with their 'GiPad,' a giant tablet. This family friendly show combines the traditional 'Blue Man' antics with 21st-century technology for an amazing visual experience.
$55
1.75 hours
Food, Wine & Nightlife

Chicago Neighborhoods Guided Pizza Bus Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
$60
3.5 hours
Food, Wine & Nightlife

Chicago Historic Bar and Speakeasy Tour for Adults-Only

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the sale of alcohol was banned for more than a decade in the United States, and the subsequent popularity of illicit establishments where liquor, jazz, and mobsters ruled. An air-conditioned coach shuffles you from bar to bar, so feel free to buy a drink or two. This small-group tour, limited to 20 people, ensures a more customized experience with your guide.
$45
3.5 hours
Cruises, Sailing & Water Tours

Chicago Small-Group Tour With Optional Architecture Cruise

Don’t miss Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like the Willis (Sears) Tower, The Rookery in downtown Chicago (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view), The Magnificent Mile, Lincoln Park, Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. The small-group atmosphere with maximum of 12 people ensures a more personal experience. You also have the option to upgrade to include a 75-minute Architecture Cruise down the Chicago River! This popular open-top boat tour offers the perfect vantage point to admire the city’s renowned buildings.
$35
2 hours