301-346-4258

Chicago, Illinois (12 offers included)

Great Lakes Treasures
Roundtrip from Milwaukee
from $8,295.00 (USD)
Per Person
May 17, 2026
through May 26, 2026
Nights: 9
Price Per Night:$921.67 (USD)
(based on double occupancy, for comparison only)
May 17, 2026 through May 26, 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
N/A
Suite
$10,995.00
Cat:NP
1,221.67 per night
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: Albuquerque–gallup–winslow–williams
Niagara & Great Lakes Treasures
Toronto to Milwaukee
from $14,490.00 (USD)
Per Person
May 01, 2026
through May 17, 2026
Nights: 16
Price Per Night:$905.63 (USD)
(based on double occupancy, for comparison only)
May 01, 2026 through May 17, 2026
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
N/A
Suite
$18,690.00
Cat:NP
1,168.13 per night
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: Washington Dc–niagara Falls, Canada
Highlights Of Route 66
Value Vacation
from $3,259.00 (USD)
Per Person
Jul 05, 2025
through Jul 20, 2025
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: Los Angeles
Rhythms Of The Road
Value Vacation
from $2,539.00 (USD)
Per Person
May 26, 2025
through Oct 06, 2025
Nights: 9
Price Per Night:$282.11 (USD)
(based on double occupancy, for comparison only)
May 26, 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
Great Lakes Treasures
Roundtrip from Milwaukee
from $7,995.00 (USD)
Per Person
May 08, 2026
through May 17, 2026
Nights: 9
Price Per Night:$888.33 (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
N/A
Suite
$10,495.00
Cat:NP
1,166.11 per night
Great Lakes Treasures
Roundtrip from Milwaukee
from $7,995.00 (USD)
Per Person
May 13, 2027
through May 22, 2027
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
N/A
Suite
$10,995.00
Cat:NP
1,221.67 per night
Sep 25, 2025
through Oct 10, 2025
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
Niagara & Great Lakes Treasures
Milwaukee to Toronto
from $15,690.00 (USD)
Per Person
May 26, 2026
through Jun 11, 2026
Nights: 16
Price Per Night:$980.63 (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
N/A
Suite
$20,290.00
Cat:NP
1,268.13 per night
Niagara & Great Lakes Treasures
Toronto to Milwaukee
from $14,690.00 (USD)
Per Person
May 10, 2026
through May 26, 2026
Nights: 16
Price Per Night:$918.13 (USD)
(based on double occupancy, for comparison only)
May 10, 2026 through May 26, 2026
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
N/A
Suite
$19,390.00
Cat:NP
1,211.88 per night
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: Nashville–brownsville–memphis