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Chicago, Illinois (20 offers included)

Highlights Of Route 66
Value Vacation
from $3,259.00 (USD)
Per Person
Jul 05, 2025
through Jul 20, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$217.27 (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: St. Louis–joplin
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: Williams. Excursion To Grand Canyon National Park
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: Chicago
More Details Contact Us
Niagara & Great Lakes Treasures
Milwaukee to Toronto
from $14,790.00 (USD)
Per Person
May 08, 2026
through May 24, 2026
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 16
Price Per Night:$924.38 (USD)
(based on double occupancy, for comparison only)
May 08, 2026 through May 24, 2026
Itinerary: Milwaukee, Mackinac Island, Georgian Bay (Killarney), Georgian Bay (Frazer Bay), Fathom Five National Marine Park, The Benjamin Islands, Sault Sainte Marie, Door Peninsula (Algoma), Chicago, Milwaukee...
Experience the majesty of the largest freshwater system in the world, the Great Lakes. Discover the mighty waterfalls of Niagara and immerse yourself in nature amid the freshwater marshes of Point Pelee’s peninsula. Witness the creativity of Detroit’s urban development as you admire the city’s postmodern and art deco skyscrapers. Behold the stunning isles of Georgian Bay from the water and marvel at their verdant landscapes during this extended voyage.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$14,790.00
Cat:N1
924.38 per night
Suite
$18,990.00
Cat:NP
1,186.88 per night
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: Chicago
More Details Contact Us
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: Oacoma–badlands National Park–mount Rushmore–custer
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: Albuquerque–gallup–winslow–williams
More Details Contact Us
Niagara & Great Lakes Treasures
Toronto to Milwaukee
from $13,890.00 (USD)
Per Person
May 06, 2027
through May 22, 2027
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 16
Price Per Night:$868.13 (USD)
(based on double occupancy, for comparison only)
May 06, 2027 through May 22, 2027
Itinerary: Toronto, Niagara Falls (Port Colborne), Welland Canal, Point Pelee, Detroit, Alpena, Mackinac Island, Milwaukee, Mackinac Island, Georgian Bay (Killarney)...
Experience the majesty of the largest freshwater system in the world, the Great Lakes. Discover the mighty waterfalls of Niagara and immerse yourself in nature amid the freshwater marshes of Point Pelee’s peninsula. Witness the creativity of Detroit’s urban development as you admire the city’s postmodern and art deco skyscrapers. Behold the stunning isles of Georgian Bay from the water and marvel at their verdant landscapes during this extended voyage.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$13,890.00
Cat:N2
868.13 per night
Suite
$18,490.00
Cat:NP
1,155.63 per night
More Details Contact Us
Great Lakes Treasures
Roundtrip from Milwaukee
from $8,195.00 (USD)
Per Person
May 08, 2026
through May 17, 2026
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 9
Price Per Night:$910.56 (USD)
(based on double occupancy, for comparison only)
May 08, 2026 through May 17, 2026
Itinerary: Milwaukee, Mackinac Island, Georgian Bay (Killarney), Georgian Bay (Frazer Bay), Fathom Five National Marine Park, The Benjamin Islands, Sault Sainte Marie, Door Peninsula (Algoma), Chicago, Milwaukee
Sail the vast waterways of the Great Lakes, the largest freshwater system in the world. Explore the picturesque islands of the Georgian Bay Biosphere Reserve and admire their bucolic landscapes. Venture out to Flowerpot Island in the Fathom Five National Marine Park and marvel at the stunning pink granite isles of the Benjamin Islands. Participate in lab studies as you explore coastal wetlands and delve into the Native cultures of the Great Lakes.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$8,195.00
Cat:N1
910.56 per night
Suite
$10,495.00
Cat:NP
1,166.11 per night
More Details Contact Us
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, Illinois, Chicago, Chicago - Holland, Michigan - Grand Rapids, Grand Rapids - Mackinac Island, Mackinac Island, Mackinac Island - Bay City, Bay City - Frankenmuth - Southfield, Southfield - Dearborn - Southfield, Southfield - Tour Ends
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
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, Illinois, Chicago, Chicago - Grand Rapids, Michigan, Grand Rapids - Mackinac Island, Mackinac Island, Mackinac Island - Bay City, Bay City - Frankenmuth - Southfield, Southfield - Dearborn - Southfield, Southfield - Tour Ends
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
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, Illinois, Chicago, Chicago - Grand Rapids, Michigan, Grand Rapids - Mackinac Island, Mackinac Island, Mackinac Island - Bay City, Bay City - Frankenmuth - Southfield, Southfield - Dearborn - Southfield, Southfield - Tour Ends
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
Highlights Of Route 66 With Mother Road Festival & Albuquerque Balloon Fiesta
Value Vacation
from $3,819.00 (USD)
Per Person
Sep 25, 2025
through Oct 10, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 15
Price Per Night:$254.60 (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: Las Vegas–victorville–los Angeles
More Details Contact Us
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!
More Details Contact Us
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, Southfield - Dearborn - Southfield, Southfield - Frankenmuth - Bay City, Bay City - Mackinac Island, Mackinac Island, Mackinac Island - Grand Rapids, Grand Rapids - Chicago, Illinois, Chicago, Chicago - Tour Ends
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.
More Details Contact Us
Trans-American Adventure
Value Vacation
from $5,358.49 (USD)
Per Person
May 02, 2025
through May 25, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 23
Price Per Night:$232.98 (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: Las Vegas
More Details Contact Us
Niagara & Great Lakes Treasures
Milwaukee to Toronto
from $15,390.00 (USD)
Per Person
May 26, 2026
through Jun 11, 2026
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 16
Price Per Night:$961.88 (USD)
(based on double occupancy, for comparison only)
May 26, 2026 through Jun 11, 2026
Itinerary: Milwaukee, Mackinac Island, Georgian Bay (Killarney), Georgian Bay (Frazer Bay), Fathom Five National Marine Park, The Benjamin Islands, Sault Sainte Marie, Door Peninsula (Algoma), Chicago, Milwaukee...
Experience the majesty of the largest freshwater system in the world, the Great Lakes. Discover the mighty waterfalls of Niagara and immerse yourself in nature amid the freshwater marshes of Point Pelee’s peninsula. Witness the creativity of Detroit’s urban development as you admire the city’s postmodern and art deco skyscrapers. Behold the stunning isles of Georgian Bay from the water and marvel at their verdant landscapes during this extended voyage.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$15,390.00
Cat:N2
961.88 per night
Suite
$20,290.00
Cat:NP
1,268.13 per night
More Details Contact Us
Mackinac Island & The Great Lakes
First-Class
from $3,899.00 (USD)
Per Person
Aug 17, 2025
through Aug 24, 2025
Offer Image
Globus logo
More offers from Globus
Nights: 7
Price Per Night:$557.00 (USD)
(based on double occupancy, for comparison only)
Aug 17, 2025 through Aug 24, 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: Detroit, Michigan
More Details Contact Us
Rhythms Of The Road
Value Vacation
from $2,539.00 (USD)
Per Person
Apr 14, 2025
through Oct 06, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 9
Price Per Night:$282.11 (USD)
(based on double occupancy, for comparison only)
Apr 14, 2025 through Oct 06, 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
More Details Contact Us
Great Lakes Treasures
Roundtrip from Milwaukee
from $7,995.00 (USD)
Per Person
May 13, 2027
through May 22, 2027
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 9
Price Per Night:$888.33 (USD)
(based on double occupancy, for comparison only)
May 13, 2027 through May 22, 2027
Itinerary: Milwaukee, Mackinac Island, Georgian Bay (Killarney), Georgian Bay (Frazer Bay), Fathom Five National Marine Park, The Benjamin Islands, Sault Sainte Marie, Door Peninsula (Algoma), Chicago, Milwaukee
Sail the vast waterways of the Great Lakes, the largest freshwater system in the world. Explore the picturesque islands of the Georgian Bay Biosphere Reserve and admire their bucolic landscapes. Venture out to Flowerpot Island in the Fathom Five National Marine Park and marvel at the stunning pink granite isles of the Benjamin Islands. Participate in lab studies as you explore coastal wetlands and delve into the Native cultures of the Great Lakes.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$7,995.00
Cat:N2
888.33 per night
Suite
$10,995.00
Cat:NP
1,221.67 per night
More Details Contact Us