Chicago, Illinois (20 offers included)

from $1,889.00 (USD)
Per Person
Nights: 9
Price Per Night:$209.89 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – St. Louis, St. Louis – Paducah – Nashville, Nashville, Nashville – Memphis, Memphis. Visit To Graceland, Memphis – Indianola – New Orleans, New Orleans
10 Days, featuring: Nashville
USA Road Trip: New York to Orlando
18-to-Thirtysomethings
from $2,549.00 (USD)
Per Person
Nights: 8
Price Per Night:$318.63 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
From beach to barbecue and blues, this 14-day road trip through the east coast of the United States ticks all the boxes. Experience Detroit's cultural resurgence by visiting a community art project, dig into delicious farm-to-table eats in Louisville, and follow the footsteps of music legends like Elvis Presley and Johnny Cash in Memphis. Leave with full stomachs and fuller playlists.
from $2,899.00 (USD)
Per Person
Nights: 8
Price Per Night:$362.38 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville/San Francisco, San Francisco/Yosemite National Park, Yosemite National Park/Sierra Nevadas...
Got two weeks and a burning desire to see the best highlights of the United States? Then we've got the trip for you. This 14-day tour takes you from Vegas to Los Angeles with some incredible stops in between. Explore the country music capital of Nashville, catch a glimpse of San Francisco's Golden Gate Bridge, and hike the trails of Joshua Tree National Park. Cross-country explorations should always be this fun.
from $3,620.00 (USD)
Per Person
Nights: 11
Price Per Night:$329.09 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Berlin, Niagara Falls/Toronto, Toronto, Ottawa, Montreal, Stowe, Boston, New York
from $2,599.00 (USD)
Per Person
Nights: 15
Price Per Night:$173.27 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Branson, Branson – Arcadia – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – – Albuquerque, Albuquerque, Albuquerque – Acoma Sky City – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Williams–seligman–las Vegas
USA Road Trip: New York to LA
18-to-Thirtysomethings
from $8,749.00 (USD)
Per Person
Nights: 8
Price Per Night:$1,093.63 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
See a side of the States that few Americans experience in their lifetime on a truly epic 56-day road trip through the country. You'll embark on two comprehensive circuits along the East and West coasts with a flight in between to minimize long drives and maximize your time at the best highlights. What makes this journey even better is the company you'll keep-a fine crew of worldly wanderers like yourself and a CEO taking care of all the little details.
from $2,196.00 (USD)
Per Person
Nights: 11
Price Per Night:$199.64 (USD)
(based on double occupancy, for comparison only)
Location(s): New York (Newark), Philadelphia/Washington DC, Washington DC, Appalachian Mountains, Nashville, Louisville, Chicago, Sundusky, Niagara Falls, New York (Newark)
Chicago - Make It A Memory
Make it a Memory
from $505.00 (USD)
Per Person
Location(s): Chicago
Lower the selfie stick and raise your photographic expectations!
from $1,125.00 (USD)
Per Person
Location(s): Chicago
This tour provides a great overview of this bustling city.
Nights: 15
Price Per Night:$196.60 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – Pontiac – Springfield – International Route 66 Mother Road Festival, Springfield – St. Louis, St. Louis – Branson, Branson – Arcadia – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Albuquerque Balloon Fiesta – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Las Vegas
USA Road Trip: Highlights of America
18-to-Thirtysomethings
from $5,249.00 (USD)
Per Person
Nights: 8
Price Per Night:$656.13 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
Got a month, a camera, and a sense of adventure? Then book yourself this 29-day road trip through the United States that leaves no stone unturned. You'll hit the big cities, like New York and Los Angeles, and spend time in stunning natural settings like the Grand Canyon and Yosemite. In between, there are countless opportunities to get up-close and personal with the culture around you, whether it's joining a line dancing party at a cowboy bar in Jackson or visiting a community arts project in...
USA Road Trip: Epic East Coast
18-to-Thirtysomethings
from $3,599.00 (USD)
Per Person
Nights: 8
Price Per Night:$449.88 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
Ready to cross a whackload of items off your must-see list? This 21-day circuit through the east coast of the United States leaves no stone unturned. Feel the thunderous roar of Niagara Falls on a Maid of the Mist boat tour, dig into deep dish pizza in Chicago, and explore the Home of Blues, Soul & Rock 'N' Roll with a free day in Memphis. And since this tour starts and ends in New York City, it's easy to plan for additional time to explore the city that never sleeps.
USA Road Trip: New York to Nashville
18-to-Thirtysomethings
from $1,299.00 (USD)
Per Person
Nights: 6
Price Per Night:$216.50 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville
This speedy seven-day road trip through the U.S. east coast combines the best of music, culture, and history. Witness the cultural resurgence of Detroit by visiting a community-based outdoor art project, dig into deep dish pizza in Chicago, indulge in Louisville's barbecue and bourbon, and soak in the country music culture of Nashville. Your heart, and stomach, won't know what hit it.
from $3,905.00 (USD)
Per Person
Nights: 11
Price Per Night:$355.00 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Berlin, Niagara Falls, Toronto, Montreal, Stowe, Boston, Cape Cod, New York
from $2,799.00 (USD)
Per Person
Nights: 7
Price Per Night:$399.86 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Illinois - Tour Begins, Chicago, Chicago - Holland, Michigan - Grand Rapids, Grand Rapids - Mackinac Island, Mackinac Island, Mackinac Island - Frankenmuth, Frankenmuth - Dearborn , Dearborn - Tour Ends
This classic Midwestern tour features Illinois and Michigan. Visit Holland Michigan’s yearly Tulip Festival. See the extraordinary flowers at the Veldheer Tulip Garden. Then visit the Windmill Island Gardens to experience a palette of color on the 36 acres of manicured gardens, dikes and canals and the only authentic Dutch windmill operating in the United States. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island....
from $5,647.50 (USD)
Per Person
Nights: 13
Price Per Night:$434.42 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, the Jewel of the Midwest., Scaling Chicago., St. Louis, Gateway to the West., St. Louis Arch to Louisvulle., Spirit of Kentucky., Highway to Nashville., Nashville's Musical History., Memphis and Graceland., The Best of Memphis., Mississippi mystique in Natchez....
Join us for a toe-tapping trip of rock, jazz and country music, as you delve into the sumptuous soul of America. You'll start in Chicago, a great food city also known for its jazz and blues, before heading south to the musical meccas of Nashville and Memphis. End your trip with a little jazz as you head to the Mississippi Delta and on to zesty New Orleans. From visiting the Country Music Hall of Fame in Nashville to the iconic Graceland mansion, this trip not only comes with behind-the-scenes experiences, but with its own memorable soundtrack.
from $99.00 (USD)
Per Person
Location(s): Chicago
Are you aware of the Art Institute of Chicago and its influence on the world stage?
from $2,619.00 (USD)
Per Person
Nights: 7
Price Per Night:$374.14 (USD)
(based on double occupancy, for comparison only)
Location(s): Detroit/Dearborn, Detroit – Frankenmuth, Frankenmuth – Mackinac Island, Mackinac Island, Mackinac Island – Tunnel Of Trees – Charlevoix – Petoskey, Petoskey – Grand Rapids, Grand Rapids – Chicago, Chicago
8 Days, featuring: Mackinac Island–tunnel Of Trees–charlevoix–petoskey
Full Day Private Tour Of Chicago
Private and Personal
from $1,423.00 (USD)
Per Person
Location(s): Chicago
This full day tour will show you just about every inch of Chicago!
from $2,699.00 (USD)
Per Person
Nights: 7
Price Per Night:$385.57 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Illinois - Tour Begins, Chicago, Chicago - Traverse City, Michigan, Traverse City - Charlevoix - Mackinac Island, Mackinac Island, Mackinac Island - Frankenmuth, Frankenmuth - Dearborn , Dearborn - Tour Ends
This classic Midwestern tour features Illinois and Michigan. Visit Holland Michigan’s yearly Tulip Festival. See the extraordinary flowers at the Veldheer Tulip Garden. Then visit the Windmill Island Gardens to experience a palette of color on the 36 acres of manicured gardens, dikes and canals and the only authentic Dutch windmill operating in the United States. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island....