Chicago, Illinois (9 offers included)

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 $3,279.00 (USD)
Per Person
Aug 23, 2025
through Sep 07, 2025
Nights: 15
Price Per Night:$218.60 (USD)
(based on double occupancy, for comparison only)
Aug 23, 2025 through Sep 07, 2025
16 Days, featuring: Chicago
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: New Orleans
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: Albuquerque–gallup–winslow–williams
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.
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: Detroit, Michigan
Highlights Of Route 66
Value Vacation
from $3,719.00 (USD)
Per Person
Jul 11, 2026
through Jul 25, 2026
Nights: 15
Price Per Night:$247.93 (USD)
(based on double occupancy, for comparison only)
Jul 11, 2026 through Jul 25, 2026
16 Days, featuring: Albuquerque–gallup–winslow–williams
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.
Trans-American Adventure
Value Vacation
from $5,238.32 (USD)
Per Person
Aug 08, 2025
through Aug 31, 2025
Nights: 23
Price Per Night:$227.75 (USD)
(based on double occupancy, for comparison only)
Aug 08, 2025 through Aug 31, 2025
24 Days, featuring: West Yellowstone. Day Excursion To Yellowstone National Park