Chicago, Illinois (20 offers included)

USA Road Trip: New York to Nashville
18-to-Thirtysomethings
from $1,104.15 (USD)
Per Person
Nights: 6
Price Per Night:$184.03 (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
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. Take a week, an empty stomach, and a burning desire to see the East Coast and you've got one helluva road trip. On this speedy seven-day tour through the United States, you'll discover the best of the region's music, culture, cuisine, and history. Witness the resurgence of Detroit by visiting a community-based outdoor art project, dig into deep dish pizza in Chicago, sip your way t...
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 $2,464.15 (USD)
Per Person
Nights: 13
Price Per Night:$189.55 (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...
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. Why choose between the East Coast and West Coast when you can hit both in two weeks? This 14-day tour takes you from New York City to Los Angeles with some incredible stops in between. Explore the country music capital of Nashville (hello honky-tonks!), catch a glimpse of San Francisco's Golden Gate Bridge, and hike the trails of Joshua Tree National Park. It's the most epic way to...
from $5,895.00 (USD)
Per Person
Nights: 13
Price Per Night:$453.46 (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 $2,599.00 (USD)
Per Person
Nights: 7
Price Per Night:$371.29 (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 - Southfield, Southfield - 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 $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....
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, Breakfast|dinner, Dearborn – Frankenmuth, Frankenmuth – Mackinac Island, Breakfast, Breakfast|lunch, Mackinac Island, Breakfast, Mackinac Island – Mainland – Petoskey, Petoskey – Charlevoix – Traverse City – Grand Rapids...
8 Days, featuring: Breakfast|lunch
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 - Traverse City, Michigan, Traverse City - Charlevoix - Mackinac Island, Mackinac Island, Mackinac Island - Frankenmuth, Frankenmuth - Dearborn - Southfield, Southfield - 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....
Nights: 11
Ship: Le Champlain
Itinerary: Chicago, Illinois, USA, , Traverse City, Michigan, USA, , Detroit, Michigan, USA, , Toronto, Canada

The Great Lakes have played a vital role in the history and culture of North America for centuries... and this cruise invites you to explore the storied waters of Lakes Michigan, Huron, Erie and Ontario – and some of the unique cities and towns that have grown along their shores – with a 7-night voyage between Chicago and Toronto aboard Le Champlain, plus two-night stays at your choice of premium hotels in these great anchor cities!

from $2,999.00 (USD)
Per Person
Nights: 7
Price Per Night:$428.43 (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 - Southfield, Southfield - 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 $2,318.00 (USD)
Per Person
Nights: 11
Price Per Night:$210.73 (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)
Hit the road on a trip like no other through the eastern USA, where each city is a culture unto itself. One day you’re in Nashville munching Southern-style biscuits for breakfast, the next you’re wandering around the iconic buildings of Chicago. This 18-29s tour is full of flexibility, making it perfect for the independent traveller who wants to see as much of this part of the country as possible in a short amount of time. The Victorian-era homes of Louisville, the winding Shenandoah River, thundering Niagara Falls and a sunset over Lake Erie – this is a real east USA adventure.
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 – Nashville, Nashville, Nashville – Brownsville – Memphis, Memphis. Visit To Graceland, Memphis – Indianola – New Orleans, New Orleans
10 Days, featuring: Chicago–st. Louis
Nights: 11
Ship: Le Champlain
Itinerary: Toronto, Canada, , Detroit, Michigan, USA, , Traverse City, Michigan, USA, , Chicago, Illinois, USA

The Great Lakes have played a vital role in the history and culture of North America for centuries... and this cruise invites you to explore the storied waters of Lakes Michigan, Huron, Erie and Ontario – and some of the unique cities and towns that have grown along their shores – with a 7-night voyage between Chicago and Toronto aboard Le Champlain, plus two-night stays at your choice of premium hotels in these great anchor cities!

Nights: 11
Ship: Le Champlain
Itinerary: Toronto, Canada, , Detroit, Michigan, USA, , Traverse City, Michigan, USA, , Chicago, Illinois, USA

The Great Lakes have played a vital role in the history and culture of North America for centuries... and this cruise invites you to explore the storied waters of Lakes Michigan, Huron, Erie and Ontario – and some of the unique cities and towns that have grown along their shores – with a 7-night voyage between Chicago and Toronto aboard Le Champlain, plus two-night stays at your choice of premium hotels in these great anchor cities!

from $3,999.00 (USD)
Per Person
Nights: 23
Price Per Night:$173.87 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City – Philadelphia – Washington Dc Area, Washington Dc Area, Washington Dc – Niagara Falls, Canada, Niagara Falls, Canada – Dearborn, Dearborn – Chicago, Chicago, Chicago – Madison – Minneapolis, Minneapolis. Excursion To The Mall Of America, Minneapolis – Mitchell – Oacoma...
24 Days, featuring: Oacoma–badlands National Park–mount Rushmore–custer
from $1,171.00 (USD)
Per Person
Location(s): Chicago
This tour provides a great overview of this bustling city.
Private: Intro To Chicago
Private and Personal
from $428.00 (USD)
Per Person
Location(s): Chicago
You will enjoy Chicago even more if you learn where, when, and why.
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 – Tulsa – 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: Albuquerque–acoma Sky City–gallup–winslow–williams
from $4,040.00 (USD)
Per Person
Nights: 10
Price Per Night:$404.00 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Berlin, Niagara Falls/Toronto, Toronto, Ottawa, Montreal, Stowe, New York
Allow us to introduce Canada and America, you might have heard of them. Enjoy the sights of the Midwest and the North as you drive through scenic countryside and quaint towns. Feel the spray on your face at the thundering Niagara Falls, wander cobblestone alleyways in Old Montreal, enjoy a Chicago-style hotdog in the Windy City and have a meal with an Amish family in Berlin, Ohio. With this 11-day tour, you and North America will be best buds in no time.
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: Chicago