Chicago, Illinois

Palmer House Hilton

from $1,687.00 (USD)

Per Person

May 01, 2024
through May 31, 2024

More offers from Journese

May 01, 2024 through May 31, 2024

Nights: 5

Price Per Night:$337.40 (USD)
(based on double occupancy, for comparison only)

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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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

More offers from Tauck

Oct 04, 2024 through Oct 15, 2024

Nights: 11

Ship: Le Bellot

Price Per Night:$908.18 (USD)
(based on double occupancy, for comparison only)

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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Waldorf Astoria Chicago

from $2,451.00 (USD)

Per Person

May 01, 2024
through May 31, 2024

More offers from Journese

May 01, 2024 through May 31, 2024

Nights: 5

Price Per Night:$490.20 (USD)
(based on double occupancy, for comparison only)

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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Highlights Of Route 66

from $3,379.00 (USD)

Per Person

May 10, 2025
through May 24, 2025

More offers from Cosmos

May 10, 2025 through May 24, 2025

Nights: 15

Price Per Night:$225.27 (USD)
(based on double occupancy, for comparison only)

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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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

More offers from Tauck

Aug 18, 2025 through Aug 29, 2025

Nights: 11

Ship: Le Champlain

Price Per Night:$980.91 (USD)
(based on double occupancy, for comparison only)

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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Highlights Of Route 66 And Albuquerque Balloon Fiesta

from $4,509.00 (USD)

Per Person

Oct 03, 2025
through Oct 19, 2025

More offers from Cosmos

Oct 03, 2025 through Oct 19, 2025

Nights: 16

Price Per Night:$281.81 (USD)
(based on double occupancy, for comparison only)

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

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Mackinac Island & The Great Lakes

from $3,799.00 (USD)

Per Person

Jun 01, 2025
through Jun 08, 2025

More offers from Globus

Jun 01, 2025 through Jun 08, 2025

Nights: 7

Price Per Night:$542.71 (USD)
(based on double occupancy, for comparison only)

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

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Rhythms Of The Road

from $2,324.00 (USD)

Per Person

Sep 30, 2024
through Oct 09, 2024

More offers from Cosmos

Sep 30, 2024 through Oct 09, 2024

Nights: 9

Price Per Night:$258.22 (USD)
(based on double occupancy, for comparison only)

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

from $3,024.00 (USD)

Per Person

Aug 24, 2024
through Sep 08, 2024

More offers from Cosmos

Aug 24, 2024 through Sep 08, 2024

Nights: 15

Price Per Night:$201.60 (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 – 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: Chicago to Toronto - Eastbound
Small Ship Cruising

from $10,790.00 (USD)

Per Person

Aug 25, 2025
through Sep 05, 2025

More offers from Tauck

Aug 25, 2025 through Sep 05, 2025

Nights: 11

Ship: Le Champlain

Price Per Night:$980.91 (USD)
(based on double occupancy, for comparison only)

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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Rhythms Of The Road

from $2,639.00 (USD)

Per Person

Apr 07, 2025
through Apr 14, 2025

More offers from Cosmos

Apr 07, 2025 through Apr 14, 2025

Nights: 9

Price Per Night:$293.22 (USD)
(based on double occupancy, for comparison only)

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

More Details Contact Us

Chicago, Illinois (11 offers included)