Chicago, Illinois (12 offers included)

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: Chicago
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–mackinaw City–charlevoix-Petoskey
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: Minneapolis. Excursion To The Mall Of America
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 $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: Chicago–pontiac–springfield
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: Nashville
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: Chicago–pontiac–springfield-International Route 66 Mother Road Festival
from $4,945.00 (USD)
Per Person
Aug 09, 2024
through Sep 01, 2024
Nights: 23
Price Per Night:$215.00 (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: West Yellowstone. Day Excursion To Yellowstone National Park
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 $2,451.00 (USD)
Per Person
Apr 28, 2024
through May 31, 2024
Nights: 5
Price Per Night:$490.20 (USD)
(based on double occupancy, for comparison only)
Apr 28, 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.
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: Albuquerque–gallup–winslow–williams
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–gallup–winslow–williams