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Chicago, Illinois (20 offers included)

Rhythms Of The Road
Value Vacation
from $2,679.00 (USD)
Per Person
Nights: 9
Price Per Night:$297.67 (USD)
(based on double occupancy, for comparison only)
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
Nights: 15
Price Per Night:$287.27 (USD)
(based on double occupancy, for comparison only)
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, Williams – Seligman – Las Vegas, Las Vegas, Las Vegas – Victorville – Los Angeles, Los Angeles
16 Days, featuring: Las Vegas–victorville–los Angeles
Niagara & Great Lakes Treasures
Toronto to Milwaukee
from $17,690.00 (USD)
Per Person
Nights: 16
Price Per Night:$1,105.63 (USD)
(based on double occupancy, for comparison only)
Itinerary: Toronto, Niagara Falls (Port Colborne), Welland Canal, Point Pelee, Detroit, Alpena, Mackinac Island, 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
$17,690.00
Cat: N1
Suite
$20,990.00
Cat: NP
Niagara & Great Lakes Treasures
Milwaukee to Toronto
from $18,490.00 (USD)
Per Person
Nights: 16
Price Per Night:$1,155.63 (USD)
(based on double occupancy, for comparison only)
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, Mackinac Island, Alpena, Detroit, Point Pelee, Niagara Falls (Port Colborne), Welland Canal, Toronto
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
$18,490.00
Cat: N2
Suite
$22,490.00
Cat: NP
Mackinac Island & The Great Lakes
Classic, First-Class
from $4,049.00 (USD)
Per Person
Nights: 7
Price Per Night:$578.43 (USD)
(based on double occupancy, for comparison only)
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
Niagara & Great Lakes Treasures
Toronto to Milwaukee
from $15,990.00 (USD)
Per Person
Nights: 16
Price Per Night:$999.38 (USD)
(based on double occupancy, for comparison only)
Itinerary: Toronto, Niagara Falls (Port Colborne), Welland Canal, Point Pelee, Detroit, Alpena, Mackinac Island, 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
$15,990.00
Cat: N2
Suite
$19,590.00
Cat: NP
Highlights Of Route 66
Value Vacation
from $3,319.00 (USD)
Per Person
Nights: 15
Price Per Night:$221.27 (USD)
(based on double occupancy, for comparison only)
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, Williams – Seligman – Las Vegas, Las Vegas, Las Vegas – Victorville – Los Angeles, Los Angeles
16 Days, featuring: Chicago
Great Lakes Treasures
Roundtrip from Milwaukee
from $9,995.00 (USD)
Per Person
Nights: 9
Price Per Night:$1,110.56 (USD)
(based on double occupancy, for comparison only)
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
$9,995.00
Cat: N2
Suite
$11,995.00
Cat: NP
Great Lakes Treasures
Roundtrip from Milwaukee
from $10,995.00 (USD)
Per Person
Nights: 9
Price Per Night:$1,221.67 (USD)
(based on double occupancy, for comparison only)
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
$10,995.00
Cat: N2
Suite
N/A
Great Lakes Treasures
Roundtrip from Milwaukee
from $10,995.00 (USD)
Per Person
Nights: 9
Price Per Night:$1,221.67 (USD)
(based on double occupancy, for comparison only)
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
$10,995.00
Cat: DN1
Suite
$11,995.00
Cat: NP
Niagara & Great Lakes Treasures
Milwaukee to Toronto
from $20,890.00 (USD)
Per Person
Nights: 16
Price Per Night:$1,305.63 (USD)
(based on double occupancy, for comparison only)
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, Mackinac Island, Alpena, Detroit, Point Pelee, Niagara Falls (Port Colborne), Welland Canal, Toronto
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
$20,890.00
Cat: DN1
Suite
$22,990.00
Cat: NP
Rhythms Of The Road
Value Vacation
from $2,309.00 (USD)
Per Person
Nights: 9
Price Per Night:$256.56 (USD)
(based on double occupancy, for comparison only)
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–st. Louis
Nights: 15
Price Per Night:$267.93 (USD)
(based on double occupancy, for comparison only)
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, Williams – Seligman – Las Vegas, Las Vegas, Las Vegas – Victorville – Los Angeles, Los Angeles
16 Days, featuring: Chicago–pontiac–springfield-International Route 66 Mother Road Festival
Trans-American Adventure
Value Vacation
from $5,368.18 (USD)
Per Person
Nights: 23
Price Per Night:$233.40 (USD)
(based on double occupancy, for comparison only)
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, Oacoma – Badlands National Park – Mount Rushmore – Custer, Custer – Cody, Cody – Yellowstone National Park – West Yellowstone, West Yellowstone. Day Excursion To Yellowstone National Park, West Yellowstone – Jackson, Jackson – Salt Lake City, Salt Lake City – Bryce Canyon National Park, Bryce Canyon National Park – Zion National Park – Grand Canyon National Park, Grand Canyon National Park – Las Vegas, Las Vegas, Las Vegas – Los Angeles, Los Angeles
24 Days, featuring: Bryce Canyon National Park–zion National Park–grand Canyon National Park
from $3,596.00 (USD)
Per Person
Nights: 8
Price Per Night:$449.50 (USD)
(based on double occupancy, for comparison only)
Location(s): Welcome to Chicago, Discover Chicago’s Icons, Swapping Illinois for Michigan, To Mackinac Island via Charlevoix, Welcome to Mackinac Island, Mackinac Island to Frankenmuth, Head into the City in Detroit, Innovation and History in Motor City, Farewell Detroit
This tour takes you through charming small towns, scenic waterfronts and storied landmarks of the Midwest. Starting in Chicago, you’ll journey north to Mackinac Island, where horse-drawn carriages and historic hotels capture a bygone era. Along the way, roll up your sleeves for pretzel rolling in Frankenmuth, cruise across Lake Huron, and explore the legacy of Henry Ford in Detroit.
Last Minute Deal: Must book by 2026-06-05
Highlights Of Route 66
Value Vacation
from $3,779.00 (USD)
Per Person
Nights: 15
Price Per Night:$251.93 (USD)
(based on double occupancy, for comparison only)
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, Williams – Seligman – Las Vegas, Las Vegas, Las Vegas – Victorville – Los Angeles, Los Angeles
16 Days, featuring: Las Vegas
Niagara & Great Lakes Treasures
Milwaukee to Toronto
from $17,990.00 (USD)
Per Person
Nights: 16
Price Per Night:$1,124.38 (USD)
(based on double occupancy, for comparison only)
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, Mackinac Island, Alpena, Detroit, Point Pelee, Niagara Falls (Port Colborne), Welland Canal, Toronto
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
$17,990.00
Cat: N2
Suite
$21,490.00
Cat: NP
from $3,596.00 (USD)
Per Person
Nights: 8
Price Per Night:$449.50 (USD)
(based on double occupancy, for comparison only)
Location(s): Welcome to Chicago, Discover Chicago’s Icons, Swapping Illinois for Michigan, To Mackinac Island via Charlevoix, Welcome to Mackinac Island, Mackinac Island to Frankenmuth, Head into the City in Detroit, Innovation and History in Motor City, Farewell Detroit
This tour takes you through charming small towns, scenic waterfronts and storied landmarks of the Midwest. Starting in Chicago, you’ll journey north to Mackinac Island, where horse-drawn carriages and historic hotels capture a bygone era. Along the way, roll up your sleeves for pretzel rolling in Frankenmuth, cruise across Lake Huron, and explore the legacy of Henry Ford in Detroit.
Last Minute Deal: Must book by 2026-06-05
Niagara & Great Lakes Treasures
Toronto to Milwaukee
from $18,590.00 (USD)
Per Person
Nights: 16
Price Per Night:$1,161.88 (USD)
(based on double occupancy, for comparison only)
Itinerary: Toronto, Niagara Falls (Port Colborne), Welland Canal, Point Pelee, Detroit, Alpena, Mackinac Island, 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
$18,590.00
Cat: DN1
Suite
$20,990.00
Cat: NP
Great Lakes Treasures
Roundtrip from Milwaukee
from $8,995.00 (USD)
Per Person
Nights: 9
Price Per Night:$999.44 (USD)
(based on double occupancy, for comparison only)
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
$8,995.00
Cat: N2
Suite
$10,995.00
Cat: NP

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