1. Travel

Sightseeing, Tours, and Day Trips

There is so much to see and do in Chicago, planning your day can sometimes be a challenge. To help ease the burden, use this directory I've put together of guided tours, day trips, and sightseeing adventures. Your visit to Chicago can be a whirlwind of activity and fun!
  1. Al Capone / Gangster Tours (72)

Seadog Wine Flight River Cruise
The Seadog River Cruise takes place on the third Thursday of every month through Labor Day.

Happy Birthday, Chicago!
Happy 176th Birthday, Chicago!

Quirky Chicago Shops To Fit All Tastes
Where can you score specialty goodies in Chicago? We've gathered some of the most notable shops showcasing almost everything imaginable.

Chicago Architecture Walking Tour - Downtown
Taking a Chicago Architectural Walking Tour is a fantastic way to experience the city and discover the little details that make Chicago great.

Rooftop Dance Series Waltzes Across Chicago
Month Long Performance Series Set to Wake Up Morning Commuters

A Guide to Tipping in Chicago
A Guide to Tipping in Chicago, from maid service to cab drivers to bartenders

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Noble Horse Chicago Carriage Rides
The Noble Horse Carriage Rides are a fun way to tour the North Michigan Avenue shopping district.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Weird Chicago Tour
Weird Chicago Tours is a great way to explore "Chicago's ghosts, gangsters & ghouls" and would be perfect for someone that wants to take in Chicago along an offbeat path.

Untouchable Tours
Untouchable Tours bills itself as "Chicago's Original Gangster Tour" -- a 2 hour driving tour in a jet black school bus to be shown many of the city's notorious gangster landmarks and hangouts. The tour guides wear period costumes and get into the gangster role -- expect to hear a lot of "dees, dems, and does," as in "dees guys, dem dolls, and does times."

Chicago Chocolate Tours
What can make any walking tour of Chicago even better? Just add chocolate! And that's exactly what Chicago Chocolate Tours does.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Chicago Gangster Tours
The fascination with Chicago gangsters continues today despite the height of the gangster culture having taken place even before World War II. Here are some ways you can take a Chicago gangster tour and immerse yourself into the world of the likes of Al Capone and John Dilinger.

Chicago Must-Sees
A general overview of the main Chicago attractions to see when traveling to Chicago on a romantic getaway.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

Michael Jordan's Steak House
Michael Jordan's Steak House, with its main dining room overlooking the bustling Magnificent Mile shopping strip, gets it right from the chops right down to an insanely decadent 23-layer chocolate cake.

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