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Chicago, Illinois (16 offers included)

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: Las Vegas–barstow–los Angeles
Highlights of the US
18-to-Thirtysomethings
from $5,249.00 (USD)
Per Person
Nights: 28
Price Per Night:$187.46 (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...
from $8,749.00 (USD)
Per Person
Nights: 55
Price Per Night:$159.07 (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 $2,619.00 (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: Detroit/Dearborn
Epic East Coast Road Trip
18-to-Thirtysomethings
from $3,599.00 (USD)
Per Person
Nights: 20
Price Per Night:$179.95 (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.
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 $2,899.00 (USD)
Per Person
Nights: 13
Price Per Night:$223.00 (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 $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: Chicago–pontiac–springfield–international Route 66 Mother Road Festival
New York to Orlando Road Trip
18-to-Thirtysomethings
from $2,549.00 (USD)
Per Person
Nights: 13
Price Per Night:$196.08 (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.
Private: Intro To Chicago
Private and Personal
from $411.00 (USD)
Per Person
Location(s): Chicago
You will enjoy Chicago even more if you learn where, when, and why.
from $1,839.00 (USD)
Per Person
Nights: 9
Price Per Night:$204.33 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – St. Louis, St. Louis – Nashville, Nashville, Nashville – Memphis, Memphis. Visit To Graceland, Memphis – Amtrak City Of New Orleans Train – New Orleans, New Orleans
10 Days, featuring: Chicago
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–memphis
from $8,749.00 (USD)
Per Person
Nights: 55
Price Per Night:$159.07 (USD)
(based on double occupancy, for comparison only)
Location(s): Los Angeles, Los Angeles/San Diego, San Diego/Lake Havasu City, Lake Havasu City/Grand Canyon, Grand Canyon, Grand Canyon/Monument Valley, Monument Valley/Las Vegas, Las Vegas, Las Vegas/Zion National Park, Bryce Canyon NP/Moab...
You've admired the sights, sounds, celebrities, and culture of the United States. Now's your chance to experience it first-hand on an epic 56-day American road trip, heading to stunning national parks, seeing game-changing cultural hotspots, and digging into the tastiest eats along the way. It's an unforgettable trip that few Americans themselves can say they've accomplished in their lifetime.
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 $99.00 (USD)
Per Person
Location(s): Chicago
Are you aware of the Art Institute of Chicago and its influence on the world stage?