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Chicago, Illinois (13 offers included)

Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
from $3,619.00 (USD)
Per Person
Sep 26, 2024
through Oct 11, 2024
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$241.27 (USD)
(based on double occupancy, for comparison only)
Sep 26, 2024 through Oct 11, 2024
Location(s): Chicago, Chicago – Pontiac – Springfield - International Route 66 Mother Road Festival, Springfield – St. Louis, St. Louis – Branson, Branson – 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–seligman–las Vegas
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Highlights Of Route 66 And Albuquerque Balloon Fiesta
from $4,509.00 (USD)
Per Person
Oct 03, 2025
through Oct 19, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 16
Price Per Night:$281.81 (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–seligman–las Vegas
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Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
from $4,039.00 (USD)
Per Person
Sep 25, 2025
through Oct 10, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$269.27 (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: Chicago
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Cruising the Great Lakes: Toronto to Chicago - Westbound
Small Ship Cruising
from $10,790.00 (USD)
Per Person
Aug 18, 2025
through Aug 29, 2025
Offer Image
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 18, 2025 through Aug 29, 2025
Itinerary: Arrive Toronto , Toronto & Niagara Falls , Discover Toronto & Embark ship , Sailing on the Welland Canal , A day in Cleveland , Detroit sights & The Henry Ford , A day on Lake Huron , Timeless Mackinac Island , Dunes & Dutch treats in Michigan , Disembark ship & Discover Chicago ...
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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Palmer House Hilton
from $1,687.00 (USD)
Per Person
May 17, 2024
through May 31, 2024
Palmer House Hilton
Journese logo
More offers from Journese
Nights: 5
Price Per Night:$337.40 (USD)
(based on double occupancy, for comparison only)
May 17, 2024 through May 31, 2024
Location(s): Chicago
The Palmer House Hilton Hotel, an iconic, historic downtown Chicago hotel offers guests the opportunity to relish in the grandeur of tradition while experiencing an infusion of modern elegance.
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Highlights Of Route 66
from $3,049.00 (USD)
Per Person
Jun 08, 2024
through Sep 14, 2024
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$203.27 (USD)
(based on double occupancy, for comparison only)
Jun 08, 2024 through Sep 14, 2024
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 – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Oklahoma City–elk City–amarillo
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Cruising the Great Lakes: Toronto to Chicago - Westbound
Small Ship Cruising
from $9,990.00 (USD)
Per Person
Oct 04, 2024
through Oct 15, 2024
Offer Image
Tauck logo
More offers from Tauck
Nights: 11
Ship: Le Bellot
Price Per Night:$908.18 (USD)
(based on double occupancy, for comparison only)
Oct 04, 2024 through Oct 15, 2024
Itinerary: Arrive Toronto , Toronto & Niagara Falls , Discover Toronto & Embark ship , Sailing on the Welland Canal , A day in Cleveland , Detroit sights & The Henry Ford , A day on Lake Huron , Timeless Mackinac Island , Dunes & Dutch treats in Michigan , Disembark ship & Discover Chicago ...
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 Dumont d'Urville, plus two-night stays at your choice of premium hotels in these great anchor cities!
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Trans-American Adventure
from $5,419.00 (USD)
Per Person
May 02, 2025
through May 25, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 23
Price Per Night:$235.61 (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: Minneapolis–mitchell–oacoma
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Trans-American Adventure
from $4,970.00 (USD)
Per Person
Aug 09, 2024
through Sep 01, 2024
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 23
Price Per Night:$216.09 (USD)
(based on double occupancy, for comparison only)
Aug 09, 2024 through Sep 01, 2024
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: Las Vegas
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Rhythms Of The Road
from $2,639.00 (USD)
Per Person
Apr 07, 2025
through Apr 14, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 9
Price Per Night:$293.22 (USD)
(based on double occupancy, for comparison only)
Apr 07, 2025 through Apr 14, 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: Memphis–visit To Graceland
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Highlights Of Route 66
from $3,379.00 (USD)
Per Person
May 10, 2025
through May 24, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$225.27 (USD)
(based on double occupancy, for comparison only)
May 10, 2025 through May 24, 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
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Waldorf Astoria Chicago
from $2,451.00 (USD)
Per Person
May 17, 2024
through May 31, 2024
Waldorf Astoria Chicago main exterior
Journese logo
More offers from Journese
Nights: 5
Price Per Night:$490.20 (USD)
(based on double occupancy, for comparison only)
May 17, 2024 through May 31, 2024
Location(s): Chicago
Voted 2016 Reader's Choice ‘Best U.S. Hotel' by Condé Naste, Waldorf Astoria Chicago offers Parisian-inspired elegance in an urban sanctuary for an unforgettable stay.
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Mackinac Island & The Great Lakes
from $3,799.00 (USD)
Per Person
Jun 01, 2025
through Jun 08, 2025
Offer Image
Globus logo
More offers from Globus
Nights: 7
Price Per Night:$542.71 (USD)
(based on double occupancy, for comparison only)
Jun 01, 2025 through Jun 08, 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: Frankenmuth–mackinac Island
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