Chicago, Illinois (14 offers included)

from $3,299.00 (USD)
Per Person
Sep 15, 2024
through Sep 22, 2024
Nights: 7
Price Per Night:$471.29 (USD)
(based on double occupancy, for comparison only)
Sep 15, 2024 through Sep 22, 2024
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
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
from $1,687.00 (USD)
Per Person
May 03, 2024
through May 31, 2024
Nights: 5
Price Per Night:$337.40 (USD)
(based on double occupancy, for comparison only)
May 03, 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 $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!
Sep 25, 2025
through Oct 10, 2025
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–pontiac–springfield-International Route 66 Mother Road Festival
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
from $9,990.00 (USD)
Per Person
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)
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!
from $2,249.00 (USD)
Per Person
Aug 26, 2024
through Sep 04, 2024
Nights: 9
Price Per Night:$249.89 (USD)
(based on double occupancy, for comparison only)
Aug 26, 2024 through Sep 04, 2024
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: Nashville
from $5,419.00 (USD)
Per Person
May 02, 2025
through May 25, 2025
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: Chicago
from $3,069.00 (USD)
Per Person
May 11, 2024
through May 26, 2024
Nights: 15
Price Per Night:$204.60 (USD)
(based on double occupancy, for comparison only)
May 11, 2024 through May 26, 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
from $10,290.00 (USD)
Per Person
Aug 30, 2024
through Sep 10, 2024
Nights: 11
Ship: Le Bellot
Price Per Night:$935.45 (USD)
(based on double occupancy, for comparison only)
Aug 30, 2024 through Sep 10, 2024
Itinerary: Arrive Chicago , Art Institute or Millennium Park , 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 , Disembark in Toronto & Niagara Falls ...
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!
Sep 26, 2024
through Oct 11, 2024
Nights: 15
Price Per Night:$244.60 (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
from $5,020.00 (USD)
Per Person
Aug 09, 2024
through Sep 01, 2024
Nights: 23
Price Per Night:$218.26 (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: Jackson–salt Lake City