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Chicago, Illinois (15 offers included)

from $10,790.00 (USD)
Per Person
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)
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!
from $5,179.00 (USD)
Per Person
May 10, 2024
through Jun 02, 2024
Nights: 23
Price Per Night:$225.17 (USD)
(based on double occupancy, for comparison only)
May 10, 2024 through Jun 02, 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: Jackson–salt Lake City
from $2,451.00 (USD)
Per Person
May 02, 2024
through May 31, 2024
Nights: 5
Price Per Night:$490.20 (USD)
(based on double occupancy, for comparison only)
May 02, 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 $1,687.00 (USD)
Per Person
May 02, 2024
through May 31, 2024
Nights: 5
Price Per Night:$337.40 (USD)
(based on double occupancy, for comparison only)
May 02, 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.
Oct 04, 2024
through Oct 20, 2024
Nights: 16
Price Per Night:$256.19 (USD)
(based on double occupancy, for comparison only)
Oct 04, 2024 through Oct 20, 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 – International Balloon Festival, Albuquerque. Excursion To Santa Fe, Albuquerque – Gallup – Winslow – Williams...
17 Days, featuring: Albuquerque. Excursion To Santa Fe
Oct 03, 2025
through Oct 19, 2025
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: Chicago
Mackinac Island
Standard
from $3,299.00 (USD)
Per Person
Oct 04, 2024
through Oct 12, 2024
Nights: 8
Price Per Night:$412.38 (USD)
(based on double occupancy, for comparison only)
Oct 04, 2024 through Oct 12, 2024
Location(s): Chicago, IL, Grand Rapids, MI, Mackinac Island, MI, Bay City, MI, Southfield, MI
This classic Midwestern tour features Illinois and Michigan. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide. Visit the Bavarian-influenced town of Frankenmuth. In Dearborn, experience the inspirational Henry Ford Museum and view historic homes at Greenfield Village including the famous American workshops of Thomas Edison, Henry Ford and Robert Frost.
Mackinac Island
Standard
from $3,399.00 (USD)
Per Person
Oct 02, 2025
through Oct 10, 2025
Nights: 8
Price Per Night:$424.88 (USD)
(based on double occupancy, for comparison only)
Oct 02, 2025 through Oct 10, 2025
Location(s): Chicago, IL, Grand Rapids, MI, Mackinac Island, MI, Bay City, MI, Southfield, MI
This classic Midwestern tour features Illinois and Michigan. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide. Visit the Bavarian-influenced town of Frankenmuth. In Dearborn, experience the inspirational Henry Ford Museum and view historic homes at Greenfield Village including the famous American workshops of Thomas Edison, Henry Ford and Robert Frost.
from $3,799.00 (USD)
Per Person
Jun 01, 2025
through Jun 08, 2025
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: Mackinac Island–mackinaw City–charlevoix-Petoskey
from $10,790.00 (USD)
Per Person
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)
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!
from $3,379.00 (USD)
Per Person
May 10, 2025
through May 24, 2025
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: Las Vegas
Mackinac Island
Reverse
from $3,799.00 (USD)
Per Person
May 30, 2025
through Jun 07, 2025
Nights: 8
Price Per Night:$474.88 (USD)
(based on double occupancy, for comparison only)
May 30, 2025 through Jun 07, 2025
Location(s): Southfield, MI, Bay City, MI, Mackinac Island, MI, Grand Rapids, MI, Chicago, IL
This classic Midwestern tour features Illinois and Michigan. In Dearborn, experience the inspirational Henry Ford Museum and view historic homes at Greenfield Village including the famous American workshops of Thomas Edison, Henry Ford and Robert Frost. Visit the Bavarian-influenced town of Frankenmuth. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide.
from $2,639.00 (USD)
Per Person
Apr 07, 2025
through Apr 14, 2025
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
Mackinac Island
Alternative
from $3,599.00 (USD)
Per Person
May 01, 2025
through May 09, 2025
Nights: 8
Price Per Night:$449.88 (USD)
(based on double occupancy, for comparison only)
May 01, 2025 through May 09, 2025
Location(s): Chicago, IL, Grand Rapids, MI, Mackinac Island, MI, Bay City, MI, Southfield, MI
This classic Midwestern tour features Illinois and Michigan. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide. View extraordinary flowers in bloom at Holland’s Tulip Time Festival. Visit the Bavarian-influenced town of Frankenmuth. In Dearborn, experience the inspirational Henry Ford Museum and view historic homes at Greenfield Village including the famou...
Mackinac Island
Alternative
from $3,599.00 (USD)
Per Person
May 07, 2024
through May 15, 2024
Nights: 8
Price Per Night:$449.88 (USD)
(based on double occupancy, for comparison only)
May 07, 2024 through May 15, 2024
Location(s): Chicago, IL, Grand Rapids, MI, Mackinac Island, MI, Bay City, MI, Southfield, MI
This classic Midwestern tour features Illinois and Michigan. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island. Explore the wonderful city of Chicago with a local guide. View extraordinary flowers in bloom at Holland’s Tulip Time Festival. Visit the Bavarian-influenced town of Frankenmuth. In Dearborn, experience the inspirational Henry Ford Museum and view historic homes at Greenfield Village including the famou...