Chicago, Illinois (9 offers included)

Highlights Of Route 66
Value Vacation
from $3,259.00 (USD)
Per Person
Jul 05, 2025
through Jul 20, 2025
Nights: 15
Price Per Night:$217.27 (USD)
(based on double occupancy, for comparison only)
Jul 05, 2025 through Jul 20, 2025
Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Joplin, Joplin – Tulsa – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Williams. Excursion To Grand Canyon National Park
Rhythms Of The Road
Value Vacation
from $2,539.00 (USD)
Per Person
May 05, 2025
through Oct 06, 2025
Nights: 9
Price Per Night:$282.11 (USD)
(based on double occupancy, for comparison only)
May 05, 2025 through Oct 06, 2025
Location(s): Chicago, Chicago – St. Louis, St. Louis – Paducah - Nashville, Nashville, Nashville – Brownsville – Memphis, Memphis – Visit To Graceland, Memphis – Indianola – New Orleans, New Orleans
10 Days, featuring: Nashville–brownsville–memphis
Highlights Of Route 66
Value Vacation
from $3,719.00 (USD)
Per Person
Jul 11, 2026
through Jul 25, 2026
Nights: 15
Price Per Night:$247.93 (USD)
(based on double occupancy, for comparison only)
Jul 11, 2026 through Jul 25, 2026
Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Joplin, Joplin – Tulsa – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Albuquerque–gallup–winslow–williams
from $11,390.00 (USD)
Per Person
Sep 01, 2026
through Sep 12, 2026
Nights: 11
Ship: Le Bellot
Price Per Night:$1,035.45 (USD)
(based on double occupancy, for comparison only)
Sep 01, 2026 through Sep 12, 2026
Itinerary: Arrive Chicago, A Millennium Park and welcome to Chicago, Architectural cruise & embark ship, Dutch treats in Michigan, Timeless Mackinac Island, A day on Lake Huron, Detroit sights & The Henry Ford, A day in Cleveland, Ohio, Sailing on the Welland Canal, Discovering Toronto...
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 your Ponant Explorer-Class ship, plus two-night stays at your choice of premium hotels in these great anchor cities!
from $3,899.00 (USD)
Per Person
Aug 17, 2025
through Aug 24, 2025
Nights: 7
Price Per Night:$557.00 (USD)
(based on double occupancy, for comparison only)
Aug 17, 2025 through Aug 24, 2025
Location(s): Detroit, Michigan, Detroit – Frankenmuth, Frankenmuth – Mackinac Island, Mackinac Island, Mackinac Island – Mackinaw City – Charlevoix – Petoskey, Petoskey – Traverse City – Grand Rapids, Grand Rapids – Chicago, Illinois, Chicago
8 Days, featuring: Mackinac Island–mackinaw City–charlevoix–petoskey
from $4,199.00 (USD)
Per Person
Oct 03, 2025
through Oct 19, 2025
Nights: 16
Price Per Night:$262.44 (USD)
(based on double occupancy, for comparison only)
Oct 03, 2025 through Oct 19, 2025
Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Joplin, Joplin – Tulsa – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque - International Balloon Festival, Albuquerque. Excursion To Santa Fe, Albuquerque – Gallup – Winslow – Williams...
17 Days, featuring: Chicago
Sep 24, 2026
through Oct 09, 2026
Nights: 15
Price Per Night:$277.93 (USD)
(based on double occupancy, for comparison only)
Sep 24, 2026 through Oct 09, 2026
Location(s): Chicago, Chicago – Pontiac – Springfield - International Route 66 Mother Road Festival, Springfield – St. Louis, St. Louis – Joplin, Joplin – Tulsa – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Albuquerque–gallup–winslow–williams
Trans-American Adventure
Value Vacation
from $5,847.17 (USD)
Per Person
May 01, 2026
through May 24, 2026
Nights: 23
Price Per Night:$254.22 (USD)
(based on double occupancy, for comparison only)
May 01, 2026 through May 24, 2026
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: Cody–yellowstone National Park–west Yellowstone
Sep 25, 2025
through Oct 10, 2025
Nights: 15
Price Per Night:$254.60 (USD)
(based on double occupancy, for comparison only)
Sep 25, 2025 through Oct 10, 2025
Location(s): Chicago, Chicago – Pontiac – Springfield - International Route 66 Mother Road Festival, Springfield – St. Louis, St. Louis – Joplin, Joplin – Tulsa – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Las Vegas