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Chicago, USA: Tours, Trips, Adventures and Packages

flag USA Chicago, on Lake Michigan, with nick name The Windy City, is one of the largest US cities. The Sears Tower is one of the tallest buildings in the USA.

Top Destinations

Below are our most visited cities, destinations and national parks in The United States of America.


Chicago (9)

Chicago, on Lake Michigan, with nick name The Windy City, is one of the largest US cities. The Sears Tower is one of the tallest buildings in the USA.

Grand Canyon

Grand Canyon (4)

The Grand Canyon is really grand. When standing on the ridge of the canyon and looking 1 mile (1600m) down to the river Colorado that created all this, you do owe the river a lot of respect. It is possible to walk all the way down and back up in a day, what can be recommended.

Las Vegas

Las Vegas (4)

Las Vegas is the show and gambling capital of the USA. World famous and featured in many, many movies. A wide variety of hotels from budget places to top-class resorts.

Los Angeles

Los Angeles (4)

Los Angeles (aka. City of Angels) is the 2nd largest city in the USA and has a lot to offer, including great shopping (a la Pretty Woman), Hollywood, Venice Beach and sports (L.A. Lakers).

New York City

New York City (3)

New York City has a few nick names, for example "The Big Apple", "The City That Never Sleeps" and "The Financial Capital of the World". We cannot list everything that there is to do in NYC, because it is too much. The basics however are the Statue of Liberty, Times Square, Broadway, Little Italy / China Town and the Empire State Building.

Search and compare tours

We have 4 tour operators that conduct 9 group tours, individual tours and cruises in Chicago with duration 7 - 24 days and rates starting at USD 1,760.00.


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Categories / Activities

  • Horse Back Riding
  • Bicycling
  • Nature, Landscape
  • Boat Tours & Short Cruises
  • Safari, wildlife

Age Group

  • 18-39
  • 40+
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  • 60+


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  • USA Outbound Operators (6)
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Sample Tours (Operators with widest selection)

Highlights of Route 66 (Cosmos)
Google Map

1/3 Highlights of Route 66

Tour Type Follow legendary Route 66 and see how Americans traveled from the 1920s through the 1960s. This historic route begins in Chicago, travels through eight states, and ends in Los Angeles. On this trip down memory lane, you’ll get the opportunity to travel to...
Going From/To
Chicago - Los Angeles
Visited Countries

Tour Variations:

Highlights of Route 66 - Mother Road Festival

Starting at

USD 2,869.00

16 Days

Next Departure
Chicago To Toronto (American Queen Voyages)
Google Map

1/1 Chicago To Toronto

Tour Type Dive into North America’s maritime legacy on board the Ocean Voyager or Ocean Navigator. Set sail on a Great Lakes adventure filled with intrigue, charm and marvels of nature. Explore the dual American-Canadian culture of Sault Ste. Marie, the throwback l...
Visited Countries
Canada, USA
Ports of call
Chicago, Detroit, Toronto
Travel Quality
Luxury Tour
Ocean Voyager

Starting at

± USD 5,658.00

11 Days

Mackinac Island (Collette)
Google Map

1/1 Mackinac Island

Tour Type This classic Midwestern tour features Illinois and Michigan. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide. Visi...
Going From/To
Chicago - Southfield
Visited Countries
tour category

Starting at

USD 3,599.00

9 Days

Next Departure
16-Jun-20231 Spots
23-Jun-20234+ Spots
New York to Hollywood (Indus)
Google Map

1/1 New York to Hollywood

Tour Type Discover futuristic cities, sleeping Midwest towns, breathtaking beauty of America's famed National Park, landmark monuments and rich History, the best America has to offer!
Going From/To
New York City - Los Angeles
Visited Countries

Starting at

USD 3,464.00

17 Days

Next Departure