Chicago, Illinois

Chicago, Illinois (12 offers included)

Mackinac Island
Reverse

from $3,899.00 (USD)

Per Person

May 30, 2025
through Jun 07, 2025

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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Mackinac Island
Standard

from $3,399.00 (USD)

Per Person

Oct 02, 2025
through Oct 10, 2025

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.

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Mackinac Island
Alternative

from $3,799.00 (USD)

Per Person

May 01, 2025
through May 09, 2025

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...

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Mackinac Island & The Great Lakes
First-Class

from $4,329.00 (USD)

Per Person

May 31, 2026
through Jun 07, 2026

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: Grand Rapids–chicago, Illinois

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Rhythms Of The Road
Value Vacation

from $2,339.00 (USD)

Per Person

Jun 16, 2025
through Jun 25, 2025

More offers from Cosmos

Nights: 9

Price Per Night:$259.89 (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: Memphis–indianola–new Orleans

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Trans-American Adventure
Value Vacation

from $5,258.35 (USD)

Per Person

May 02, 2025
through May 25, 2025

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. Excursion To The Mall Of America

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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

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: Las Vegas–victorville–los Angeles

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Mackinac Island & The Great Lakes
First-Class

from $3,469.00 (USD)

Per Person

Jun 01, 2025
through Jun 08, 2025

More offers from Globus

Nights: 7

Price Per Night:$495.57 (USD)
(based on double occupancy, for comparison only)

Jun 01, 2025 through Jun 08, 2025

8 Days, featuring: Mackinac Island

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Highlights Of Route 66 And Albuquerque Balloon Fiesta
Value Vacation

from $4,099.00 (USD)

Per Person

Oct 03, 2025
through Oct 19, 2025

More offers from Cosmos

Nights: 16

Price Per Night:$256.19 (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

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Rhythms Of The Road
Value Vacation

from $2,729.00 (USD)

Per Person

Nov 02, 2026
through Nov 11, 2026

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

10 Days, featuring: Chicago–st. Louis

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Trans-American Adventure
Value Vacation

from $5,847.17 (USD)

Per Person

May 01, 2026
through May 24, 2026

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

24 Days, featuring: Minneapolis. Excursion To The Mall Of America

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Highlights Of Route 66
Value Vacation

from $3,719.00 (USD)

Per Person

Jul 11, 2026
through Jul 25, 2026

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: Chicago–pontiac–springfield

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