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The third most populous city in the United States is situated along the scenic Lake Michigan in Northeastern Illinois with nicknames including "The Windy City" and "The Second City." Chicago, the world-class destination of unsurpassed beauty, was incorporated in 1837 and hosted the World's Colombian Exposition in 1893 in Jackson Park bringing more than 27 million people to the city. The city is known for many things such as deep dish pizza, Chicago-style hot dogs, theater, outdoor art and its sports teams. Attracting visitors from around the nation and the world, popular tourist Chicago attractions include the Willis Tower (formerly Sears Tower), Lincoln Park, Magnificent Mile, Grant Park, Millennium Park, Wrigley Field, Art Institute of Chicago, Field Museum of Natural History, Shedd Aquarium and Adler Planetarium & Astronomy Museum. Explore the world for joining New York Tours, Washington DC Tours, Hawaii Tours, and much, much more.

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29 Results - Find Great Deals On Chicago Vacation Packages

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4-Day Bus Tour from Chicago: Mammoth Cave National Park, Great Smoky Mountains, Gatlinburg and Chattanooga

4-Day Bus Tour from Chicago: Mammoth Cave National Park, Great Smoky Mountains, Gatlinburg and Chattanooga

(4 Reviews)
2% Group Discount Budget Friendly
Start /End City: Chicago / Chicago
Duration: 4 Days
Product Code: 16761
Highlights: • Explore Motorsports Hall of Fame • Be in the National Park with most visitors in US - Great Smoky Mountains • Southern dinner show Dixie Stampede featuring America's civil war • Tour in Lookout Mountain:  Rock City, Ruby Falls, Incline Railway
19-Day USA and Canada Panorama Tour from Los Angeles: New York, Boston, Montreal, Quebec, Ottawa, Toronto, Detroit, Chicago | Yosemite Natural Park | Mont Tremblant | Niagara Falls

19-Day USA and Canada Panorama Tour from Los Angeles: New York, Boston, Montreal, Quebec, Ottawa, Toronto, Detroit, Chicago | Yosemite Natural Park | Mont Tremblant | Niagara Falls

2% Group Discount
Free Airport Pick up
Start /End City: Los Angeles / Chicago
Duration: 19 Days
Product Code: 710112
Highlights: • Los Angeles Airport pick-up service • Evening transfer: Times Square in New York, Barrio The Loop
11-Day Unmissable Canada, Niagara and Chicago Tour from Montreal: Quebec, Ottawa, Toronto, Detroit, Chicago | Hotel Breakfast Included | Free Airport Pick-up

11-Day Unmissable Canada, Niagara and Chicago Tour from Montreal: Quebec, Ottawa, Toronto, Detroit, Chicago | Hotel Breakfast Included | Free Airport Pick-up

2% Group Discount
Free Airport Pick up
Start /End City: Montreal / Chicago
Duration: 11 Days
Product Code: 710106
Highlights: • Montreal Airport pick-up service • Evening transfer: Barrio The Loop
7-Day Toronto, Niagara and Chicago Tour | Hotel Breakfast Included | Free Airport Pick-up

7-Day Toronto, Niagara and Chicago Tour | Hotel Breakfast Included | Free Airport Pick-up

2% Group Discount
Free Airport Pick up
Start /End City: Toronto / Chicago
Duration: 7 Days
Product Code: 710094
Highlights: • Toronto Airport pick-up service • Evening transfer: Barrio The Loop
16-Day Cross-Country Tour from Los Angeles: Las Vegas, Flagstaff, Las Vegas, Chicago, New York, Philadelphia, Washington | Hotel Breakfast Included

16-Day Cross-Country Tour from Los Angeles: Las Vegas, Flagstaff, Las Vegas, Chicago, New York, Philadelphia, Washington | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: Los Angeles / Washington
Duration: 16 Days
Product Code: 710049
Highlights: • Los Angeles Airport pick-up service • Evening transfer: Downtown Disney, Long Beach , Georgetown
14-Day Cross-Country Tour  from Los Angeles: Las Vegas, Flagstaff, Chicago, Niagara Falls, New York | Hotel Breakfast Included

14-Day Cross-Country Tour from Los Angeles: Las Vegas, Flagstaff, Chicago, Niagara Falls, New York | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: Los Angeles / New York
Duration: 14 Days
Product Code: 710046
Highlights: • Los Angeles Airport pick-up service • Evening transfer: Downtown Disney, Long Beach
14-Day Essential East Coast, Niagara and Chicago Tour from New York: Boston, Montreal, Quebec, Ottawa, Toronto, Detroit, Chicago | Hotel Breakfast Included

14-Day Essential East Coast, Niagara and Chicago Tour from New York: Boston, Montreal, Quebec, Ottawa, Toronto, Detroit, Chicago | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: New York / Chicago
Duration: 14 Days
Product Code: 710031
Highlights: • New york Airport pick-up service • Highlights attractions: Sainte Agathe Des Monts, Mont Tremblant, Thousand Islands, Niagara Falls • Evening transfer: Times Square in New York, Barrio The Loop
16-Day Eastern Round Tour from Washington: New York, Boston, Montreal, Quebec, Ottawa, Toronto, Detroit, Chicago | Mont Tremblant | Thousand Islands | Niagara Falls

16-Day Eastern Round Tour from Washington: New York, Boston, Montreal, Quebec, Ottawa, Toronto, Detroit, Chicago | Mont Tremblant | Thousand Islands | Niagara Falls

2% Group Discount
Free Airport Pick up
Start /End City: Washington / Chicago
Duration: 16 Days
Product Code: 710022
Highlights: • Washington Airport pick-up service • Hotel breakfasts included • Evening transfer: Georgetown, Barrio The Loop
10-Day Chicago, New York and Washington Tour: Cleveland, Niagara Falls, Corning, Philadelphia | Hotel Breakfast Included

10-Day Chicago, New York and Washington Tour: Cleveland, Niagara Falls, Corning, Philadelphia | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: Chicago / Washington
Duration: 10 Days
Product Code: 709968
Highlights: • Chicago Airport pick-up service • Evening transfer: Barrio The Loop, Georgetown • Take a boat trip on the River Potomac • Take a tiny boat - Maid of the Mist to the foot of the famous Niagara Falls
8-Day Chicago and New York Tour: Niagara Falls, Corning, Maid of the Mist | Hotel Breakfast Included

8-Day Chicago and New York Tour: Niagara Falls, Corning, Maid of the Mist | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: Chicago / New York
Duration: 8 Days
Product Code: 709965
Highlights: • Chicago Airport pick-up service • Evening transfer: Barrio The Loop • Take a tiny boat - Maid of the Mist to the foot of the famous Niagara Falls
8-Day Chicago Cultural In-depth Tour and Niagara Falls Scenery Tour | Hotel Breakfast Included

8-Day Chicago Cultural In-depth Tour and Niagara Falls Scenery Tour | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: Chicago / Chicago
Duration: 8 Days
Product Code: 709962
Highlights: • Chicago Airport pick-up service • Evening transfer: Barrio The Loop, Barrio The Loop
16-Day Canadian Capitals West Coast Tour from Montreal: Quebec, Mt Tremblant, Toronto, Niagara Falls, Detroit, Chicago, Los Ángeles, Las Vegas | Hotel Breakfast Included

16-Day Canadian Capitals West Coast Tour from Montreal: Quebec, Mt Tremblant, Toronto, Niagara Falls, Detroit, Chicago, Los Ángeles, Las Vegas | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: Montreal / Las Vegas
Duration: 16 Days
Product Code: 709953
Highlights: • Montreal Airport pick-up service • Evening transfer: Barrio The Loop, Long Beach
20-Day Canadian Capitals and West Coast Tour from Montreal: Quebec, Mt Tremblant, Thousand Islands Cruise, Toronto, Niagara Falls, Los Angeles, Las Vegas | Hotel Breakfast Included

20-Day Canadian Capitals and West Coast Tour from Montreal: Quebec, Mt Tremblant, Thousand Islands Cruise, Toronto, Niagara Falls, Los Angeles, Las Vegas | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: Montreal / San Francisco
Duration: 20 Days
Product Code: 709950
Highlights: • Montreal Airport pick-up service• City tour in: CHICAGO, LOS ANGELES, MONTREAL, OTTAWA, QUEBEC, SAN FRANCISCO, TORONTO, TORONTO• Evening transfer: Barrio The Loop, Long Beach
16-Day Cross-Country Tour from San Francisco: Monterey, Los Angeles, Chicago, Cleveland, Niagara Falls, New York, Philadelphia, Washington | Hotel Breakfast Included

16-Day Cross-Country Tour from San Francisco: Monterey, Los Angeles, Chicago, Cleveland, Niagara Falls, New York, Philadelphia, Washington | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: San Francisco / Washington
Duration: 16 Days
Product Code: 709944
Highlights: • San francisco Airport pick-up service• City tour in: SAN FRANCISCO, CHICAGO, CLEVELAND, NEW YORK, WASHINGTON• Evening transfer: Georgetown
14-Day Cross-Country Tour from San Francisco: Los Angeles, Chicago, Cleveland, Niagara Falls, Corning, New York | Hotel Breakfast Included

14-Day Cross-Country Tour from San Francisco: Los Angeles, Chicago, Cleveland, Niagara Falls, Corning, New York | Hotel Breakfast Included

2% Group Discount
Free Airport Pick up
Start /End City: San Francisco / New York
Duration: 14 Days
Product Code: 709941
Highlights: • San francisco Airport pick-up service• City tour in: CHICAGO, CLEVELAND, NEW YORK, SAN FRANCISCO

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