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Chicago, Illinois (12 offers included)

Mackinac Island & The Great Lakes
First-Class
from $3,499.00 (USD)
Per Person
Jun 08, 2025
through Jun 15, 2025
Offer Image
Globus logo
More offers from Globus
Nights: 7
Price Per Night:$499.86 (USD)
(based on double occupancy, for comparison only)
Jun 08, 2025 through Jun 15, 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
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Cruising the Great Lakes: Chicago to Toronto - Eastbound
Small Ship Cruising
from $10,790.00 (USD)
Per Person
Aug 25, 2025
through Sep 05, 2025
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Tauck logo
More offers from Tauck
Nights: 11
Ship: Le Champlain
Price Per Night:$980.91 (USD)
(based on double occupancy, for comparison only)
Aug 25, 2025 through Sep 05, 2025
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!
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Trans-American Adventure
Value Vacation
from $5,847.17 (USD)
Per Person
May 01, 2026
through May 24, 2026
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Cosmos logo
More offers from Cosmos
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: Washington Dc Area
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Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
Value Vacation
from $4,169.00 (USD)
Per Person
Sep 24, 2026
through Oct 09, 2026
Offer Image
Cosmos logo
More offers from Cosmos
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: Los Angeles
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Rhythms Of The Road
Value Vacation
from $2,729.00 (USD)
Per Person
Nov 02, 2026
through Nov 11, 2026
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 9
Price Per Night:$303.22 (USD)
(based on double occupancy, for comparison only)
Nov 02, 2026 through Nov 11, 2026
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: Chicago
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Trans-American Adventure
Value Vacation
from $5,258.35 (USD)
Per Person
May 02, 2025
through May 25, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 23
Price Per Night:$228.62 (USD)
(based on double occupancy, for comparison only)
May 02, 2025 through May 25, 2025
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: Custer–cody
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Mackinac Island & The Great Lakes
First-Class
from $4,329.00 (USD)
Per Person
May 31, 2026
through Jun 07, 2026
Offer Image
Globus logo
More offers from Globus
Nights: 7
Price Per Night:$618.43 (USD)
(based on double occupancy, for comparison only)
May 31, 2026 through Jun 07, 2026
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: Detroit, Michigan
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Rhythms Of The Road
Value Vacation
from $2,389.00 (USD)
Per Person
Jun 16, 2025
through Jun 25, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 9
Price Per Night:$265.44 (USD)
(based on double occupancy, for comparison only)
Jun 16, 2025 through Jun 25, 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: Chicago
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Highlights Of Route 66 And Albuquerque Balloon Fiesta
Value Vacation
from $4,199.00 (USD)
Per Person
Oct 03, 2025
through Oct 19, 2025
Offer Image
Cosmos logo
More offers from Cosmos
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: Williams. Excursion To Grand Canyon National Park
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Highlights Of Route 66
Value Vacation
from $3,719.00 (USD)
Per Person
Jul 11, 2026
through Jul 25, 2026
Offer Image
Cosmos logo
More offers from Cosmos
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
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Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
Value Vacation
from $3,719.00 (USD)
Per Person
Sep 25, 2025
through Oct 10, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$247.93 (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: Los Angeles
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Highlights Of Route 66
Value Vacation
from $3,309.00 (USD)
Per Person
Jul 05, 2025
through Jul 20, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$220.60 (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: Chicago
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