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Chicago, Illinois

(12 offers included)
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Cruising the Great Lakes: Chicago to Toronto - Eastbound Small Ship Cruising
Departing on Aug 25, 2025 on the Le Champlain
Nights: 11
Dates: Aug 25, 2025 through Sep 05, 2025
Ship: Le Champlain
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
$10,790.00
(USD)
Per Person
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Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
Nights: 15
Dates: 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
from
$4,039.00
(USD)
Per Person
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Highlights Of Route 66 And Albuquerque Balloon Fiesta
Nights: 16
Dates: 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: Oklahoma City–elk City–amarillo
from
$4,509.00
(USD)
Per Person
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Rhythms Of The Road
Nights: 9
Dates: 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: Chicago
from
$2,639.00
(USD)
Per Person
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Palmer House Hilton
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Palmer House Hilton
Nights: 5
Dates: May 15, 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.
from
$1,687.00
(USD)
Per Person
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Trans-American Adventure
Nights: 23
Dates: 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: West Yellowstone–jackson
from
$5,419.00
(USD)
Per Person
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Mackinac Island & The Great Lakes
Nights: 7
Dates: 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: Detroit Michigan
from
$3,799.00
(USD)
Per Person
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Highlights Of Route 66
Nights: 15
Dates: 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: Chicago
from
$3,379.00
(USD)
Per Person
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Waldorf Astoria Chicago main exterior
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Waldorf Astoria Chicago
Nights: 5
Dates: May 15, 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.
from
$2,451.00
(USD)
Per Person
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Cruising the Great Lakes: Toronto to Chicago - Westbound Small Ship Cruising
Departing on Oct 04, 2024 on the Le Bellot
Nights: 11
Dates: Oct 04, 2024 through Oct 15, 2024
Ship: Le Bellot
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!
from
$9,990.00
(USD)
Per Person
More Details Contact Us
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Cruising the Great Lakes: Toronto to Chicago - Westbound Small Ship Cruising
Departing on Aug 18, 2025 on the Le Champlain
Nights: 11
Dates: Aug 18, 2025 through Aug 29, 2025
Ship: Le Champlain
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!
from
$10,790.00
(USD)
Per Person
More Details Contact Us
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Cosmos Logo
Highlights Of Route 66
Nights: 15
Dates: 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: Las Vegas
from
$3,099.00
(USD)
Per Person
More Details Contact Us