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Chicago, Illinois (15 offers included)

Rhythms Of The Road
Value Vacation
from $2,539.00 (USD)
Per Person
Jun 16, 2025
through Jun 25, 2025
Nights: 9
Price Per Night:$282.11 (USD)
(based on double occupancy, for comparison only)
Jun 16, 2025 through Jun 25, 2025
10 Days, featuring: Chicago
from $3,999.00 (USD)
Per Person
Apr 30, 2026
through May 08, 2026
Nights: 8
Price Per Night:$499.88 (USD)
(based on double occupancy, for comparison only)
Apr 30, 2026 through May 08, 2026
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...
Highlights Of Route 66
Value Vacation
from $3,409.00 (USD)
Per Person
Jul 05, 2025
through Jul 20, 2025
Nights: 15
Price Per Night:$227.27 (USD)
(based on double occupancy, for comparison only)
Jul 05, 2025 through Jul 20, 2025
16 Days, featuring: Williams–seligman–las Vegas
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
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 $4,049.00 (USD)
Per Person
Aug 17, 2025
through Aug 24, 2025
Nights: 7
Price Per Night:$578.43 (USD)
(based on double occupancy, for comparison only)
Aug 17, 2025 through Aug 24, 2025
8 Days, featuring: Detroit, Michigan
Sep 24, 2026
through Oct 09, 2026
Nights: 15
Price Per Night:$277.93 (USD)
(based on double occupancy, for comparison only)
Sep 24, 2026 through Oct 09, 2026
16 Days, featuring: Williams–seligman–las Vegas
from $11,390.00 (USD)
Per Person
Sep 01, 2026
through Sep 12, 2026
Nights: 11
Ship: Le Bellot
Price Per Night:$1,035.45 (USD)
(based on double occupancy, for comparison only)
Sep 01, 2026 through Sep 12, 2026
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!
Mackinac Island
Classic
from $3,799.00 (USD)
Per Person
Oct 02, 2026
through Oct 10, 2026
Nights: 8
Price Per Night:$474.88 (USD)
(based on double occupancy, for comparison only)
Oct 02, 2026 through Oct 10, 2026
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 $10,990.00 (USD)
Per Person
Aug 25, 2026
through Sep 05, 2026
Nights: 11
Ship: Le Bellot
Price Per Night:$999.09 (USD)
(based on double occupancy, for comparison only)
Aug 25, 2026 through Sep 05, 2026
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!
Rhythms Of The Road
Value Vacation
from $2,729.00 (USD)
Per Person
Nov 02, 2026
through Nov 11, 2026
Nights: 9
Price Per Night:$303.22 (USD)
(based on double occupancy, for comparison only)
Nov 02, 2026 through Nov 11, 2026
10 Days, featuring: St. Louis–paducah-Nashville
Mackinac Island
Classic
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
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.
Trans-American Adventure
Value Vacation
from $5,847.17 (USD)
Per Person
May 01, 2026
through May 24, 2026
Nights: 23
Price Per Night:$254.22 (USD)
(based on double occupancy, for comparison only)
May 01, 2026 through May 24, 2026
24 Days, featuring: Grand Canyon National Park–las Vegas
Sep 25, 2025
through Oct 10, 2025
Nights: 15
Price Per Night:$254.60 (USD)
(based on double occupancy, for comparison only)
Sep 25, 2025 through Oct 10, 2025
16 Days, featuring: Los Angeles
from $4,329.00 (USD)
Per Person
May 31, 2026
through Jun 07, 2026
Nights: 7
Price Per Night:$618.43 (USD)
(based on double occupancy, for comparison only)
May 31, 2026 through Jun 07, 2026
8 Days, featuring: Chicago
Trans-American Adventure
Value Vacation
from $5,488.67 (USD)
Per Person
Aug 08, 2025
through Aug 31, 2025
Nights: 23
Price Per Night:$238.64 (USD)
(based on double occupancy, for comparison only)
Aug 08, 2025 through Aug 31, 2025
24 Days, featuring: Minneapolis. Excursion To The Mall Of America