PO Box 13349 Des Moines, IA 50310-0349
(515) 287 3170

Chicago, Illinois (14 offers included)

Mackinac Island
Reverse
from $3,899.00 (USD)
Per Person
May 30, 2025
through Jun 07, 2025
Nights: 8
Price Per Night:$487.38 (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.
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
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: Williams–seligman–las Vegas
Trans-American Adventure
Value Vacation
from $5,258.35 (USD)
Per Person
May 02, 2025
through May 25, 2025
Nights: 23
Price Per Night:$228.62 (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: Cody–yellowstone National Park–west Yellowstone
Mackinac Island
Alternative
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
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...
Highlights Of Route 66
Value Vacation
from $3,309.00 (USD)
Per Person
Jul 05, 2025
through Jul 20, 2025
Nights: 15
Price Per Night:$220.60 (USD)
(based on double occupancy, for comparison only)
Jul 05, 2025 through Jul 20, 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
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
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 $4,199.00 (USD)
Per Person
Oct 03, 2025
through Oct 19, 2025
Nights: 16
Price Per Night:$262.44 (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: Williams. Excursion To Grand Canyon National Park
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
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–indianola–new Orleans
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.
Mackinac Island
Standard
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
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 $3,499.00 (USD)
Per Person
Jun 08, 2025
through Jun 15, 2025
Nights: 7
Price Per Night:$499.86 (USD)
(based on double occupancy, for comparison only)
Jun 08, 2025 through Jun 15, 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
Mackinac Island
Alternative
from $3,799.00 (USD)
Per Person
May 01, 2025
through May 09, 2025
Nights: 8
Price Per Night:$474.88 (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...
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
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–mitchell–oacoma
Sep 25, 2025
through Oct 10, 2025
Nights: 15
Price Per Night:$247.93 (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: Los Angeles