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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 (61)

Chicago Architecture Tours
Chicago has a rich, architectural history, and has a wide mix of styles from Beaux Arts to Art Deco to Modernist. You would really do yourself a service by taking a Chicago architecture tour. Here are a few favorites.

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

Chicago Architecture Foundation River Tour
The Chicago Architecture Foundation River Tour

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

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

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.

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

Chicago's Best Views
Chicago, with its home on Lake Michigan and wonderful skyline, provides visitors with some great scenery. The flat prairie land on which Chicago was built makes it possible to sometimes see for up to 80 miles on a crystal clear day from certain vantage points. Here is my list of some of my favorite views in Chicago.

A Day Trip to Lincoln Park
Lincoln Park is not just grass and trees, you can spend a whole day here and visit the zoo, beach, conservatory, and nature museum.

Odyssey Dinner Cruise
An Odyssey Cruise offers a great night of dinner and dancing while cruising along Lake Michigan enjoying the spectacular skyline views.

Shoreline Sightseeing Architecture River Cruise
The Chicago Shoreline Sightseeing Architecture River Cruise provides a tour of some of Chicago's iconic buildings with a different point of view -- from the side of the Chicago River.

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 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.

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

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.

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."

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.

Neighborhood Watch: Chinatown
Where to dine, shop and play in the close-knit community of Chinatown.

Neighborhood Watch: River North
Where to dine, shop and play in River North, Chicago’s trendiest area.

Neighborhood Watch: West Loop
Where to dine, shop & play in the West Loop, an area considered to be celeb chef central.

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