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Chicago, Illinois (17 offers included)

Mackinac Island
Alternative
from $3,999.00 (USD)
Per Person
May 03, 2026
through May 11, 2026
Offer Image
Collette logo
More offers from Collette
Nights: 8
Price Per Night:$499.88 (USD)
(based on double occupancy, for comparison only)
May 03, 2026 through May 11, 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...
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Highlights Of Route 66
Value Vacation
from $3,309.00 (USD)
Per Person
Jul 05, 2025
through Jul 20, 2025
Offer Image
Cosmos logo
More offers from Cosmos
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: Amarillo–tucumcAri–albuquerque
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Mackinac Island
Reverse
from $3,899.00 (USD)
Per Person
May 30, 2025
through Jun 07, 2025
Offer Image
Collette logo
More offers from Collette
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.
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Trans-American Adventure
Value Vacation
from $5,847.17 (USD)
Per Person
May 01, 2026
through May 24, 2026
Offer Image
Cosmos logo
More offers from Cosmos
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. Excursion To The Mall Of America
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Mackinac Island
Standard
from $3,399.00 (USD)
Per Person
Oct 02, 2025
through Oct 10, 2025
Offer Image
Collette logo
More offers from Collette
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.
More Details Contact Us
Mackinac Island & The Great Lakes
First-Class
from $4,329.00 (USD)
Per Person
May 31, 2026
through Jun 07, 2026
Offer Image
Globus logo
More offers from Globus
Nights: 7
Price Per Night:$618.43 (USD)
(based on double occupancy, for comparison only)
May 31, 2026 through Jun 07, 2026
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: Detroit, Michigan
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Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
Value Vacation
from $3,719.00 (USD)
Per Person
Sep 25, 2025
through Oct 10, 2025
Offer Image
Cosmos logo
More offers from Cosmos
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: Amarillo–tucumcAri–albuquerque
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Rhythms Of The Road
Value Vacation
from $2,389.00 (USD)
Per Person
Jun 16, 2025
through Jun 25, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 9
Price Per Night:$265.44 (USD)
(based on double occupancy, for comparison only)
Jun 16, 2025 through Jun 25, 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: Chicago
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Cruising the Great Lakes: Chicago to Toronto - Eastbound
Small Ship Cruising
from $10,790.00 (USD)
Per Person
Aug 25, 2025
through Sep 05, 2025
Offer Image
Tauck logo
More offers from Tauck
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!
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Mackinac Island
Standard
from $3,799.00 (USD)
Per Person
Oct 02, 2026
through Oct 10, 2026
Offer Image
Collette logo
More offers from Collette
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.
More Details Contact Us
Mackinac Island & The Great Lakes
First-Class
from $3,499.00 (USD)
Per Person
Jun 08, 2025
through Jun 15, 2025
Offer Image
Globus logo
More offers from Globus
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: Petoskey–traverse City–grand Rapids
More Details Contact Us
Trans-American Adventure
Value Vacation
from $5,258.35 (USD)
Per Person
May 02, 2025
through May 25, 2025
Offer Image
Cosmos logo
More offers from Cosmos
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: Minneapolis–mitchell–oacoma
More Details Contact Us
Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
Value Vacation
from $4,169.00 (USD)
Per Person
Sep 24, 2026
through Oct 09, 2026
Offer Image
Cosmos logo
More offers from Cosmos
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: Amarillo–tucumcAri–albuquerque
More Details Contact Us
Highlights Of Route 66
Value Vacation
from $3,719.00 (USD)
Per Person
Jul 11, 2026
through Jul 25, 2026
Offer Image
Cosmos logo
More offers from Cosmos
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
More Details Contact Us
Rhythms Of The Road
Value Vacation
from $2,729.00 (USD)
Per Person
Nov 02, 2026
through Nov 11, 2026
Offer Image
Cosmos logo
More offers from Cosmos
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: New Orleans
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Mackinac Island
Alternative
from $3,799.00 (USD)
Per Person
May 01, 2025
through May 09, 2025
Offer Image
Collette logo
More offers from Collette
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...
More Details Contact Us
Highlights Of Route 66 And Albuquerque Balloon Fiesta
Value Vacation
from $4,199.00 (USD)
Per Person
Oct 03, 2025
through Oct 19, 2025
Offer Image
Cosmos logo
More offers from Cosmos
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: Las Vegas
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