Chicago, Illinois

(20 offers included)
Niagara & Great Lakes Treasures Milwaukee to Toronto
Departing on May 22, 2027 on the Viking Polaris
Nights: 16
Dates: May 22, 2027 through Jun 07, 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...
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.
from
$14,890.00
(USD)
Per Person
Nights: 7
Dates: 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–frankenmuth
from
$4,329.00
(USD)
Per Person
Great Lakes Treasures Roundtrip from Milwaukee
Departing on May 13, 2027 on the Viking Polaris
Nights: 9
Dates: 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.
from
$7,995.00
(USD)
Per Person
Nights: 7
Dates: Sep 07, 2025 through Sep 14, 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: Grand Rapids–chicago, Illinois
from
$3,899.00
(USD)
Per Person
Departing on Aug 18, 2025 on the Le Champlain
Nights: 11
Dates: Aug 18, 2025 through Aug 29, 2025
Ship: Le Champlain
Itinerary:
Arrive Toronto, Toronto & Niagara Falls, Discover Toronto & Embark ship, Sailing on the Welland Canal, A day in Cleveland, Detroit sights & The Henry Ford, A day on Lake Huron, Timeless Mackinac Island, Dunes & Dutch treats in Michigan, Disembark ship & Discover Chicago...
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!
from
$10,790.00
(USD)
Per Person
Nights: 23
Dates: 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: Custer–cody
from
$5,358.49
(USD)
Per Person
Nights: 23
Dates: 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: Dearborn–chicago
from
$5,847.17
(USD)
Per Person
Mackinac Island Alternative
Nights: 8
Dates: May 04, 2025 through May 12, 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...
from
$3,799.00
(USD)
Per Person
Nights: 16
Dates: 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
from
$3,999.00
(USD)
Per Person
Nights: 8
Dates: 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.
from
$3,399.00
(USD)
Per Person
Nights: 15
Dates: 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
from
$3,744.00
(USD)
Per Person
Niagara & Great Lakes Treasures Toronto to Milwaukee
Departing on May 01, 2026 on the Viking Polaris
Nights: 16
Dates: 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.
from
$14,190.00
(USD)
Per Person
Highlights Of Route 66 Value Vacation
Nights: 15
Dates: 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: Los Angeles
from
$3,719.00
(USD)
Per Person
Highlights Of Route 66 Value Vacation
Nights: 15
Dates: May 24, 2025 through Jun 07, 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
from
$3,329.00
(USD)
Per Person
Niagara & Great Lakes Treasures Toronto to Milwaukee
Departing on May 06, 2027 on the Viking Polaris
Nights: 16
Dates: 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.
from
$13,890.00
(USD)
Per Person
Niagara & Great Lakes Treasures Milwaukee to Toronto
Departing on May 26, 2026 on the Viking Octantis
Nights: 16
Dates: 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.
from
$15,390.00
(USD)
Per Person
Nights: 15
Dates: 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
from
$4,169.00
(USD)
Per Person
Departing on Aug 25, 2025 on the Le Champlain
Nights: 11
Dates: Aug 25, 2025 through Sep 05, 2025
Ship: Le Champlain
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!
from
$10,790.00
(USD)
Per Person
Rhythms Of The Road Value Vacation
Nights: 9
Dates: 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
from
$2,729.00
(USD)
Per Person
Niagara & Great Lakes Treasures Milwaukee to Toronto
Departing on May 08, 2026 on the Viking Polaris
Nights: 16
Dates: 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.
from
$14,490.00
(USD)
Per Person