Chicago, Illinois

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

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: Cody–yellowstone National Park–west Yellowstone

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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

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–visit To Graceland

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Great Lakes Treasures
Roundtrip from Milwaukee

from $8,195.00 (USD)

Per Person

May 08, 2026
through May 17, 2026

More offers from Viking Expeditions

Nights: 9

Ship: Viking Polaris

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

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: Albuquerque–gallup–winslow–williams

More Details Contact Us

Cruising the Great Lakes: Toronto to Chicago - Westbound
Small Ship Cruising

from $10,990.00 (USD)

Per Person

Aug 25, 2026
through Sep 05, 2026

More offers from Tauck

Nights: 11

Ship: Le Bellot

Price Per Night:$999.09 (USD)
(based on double occupancy, for comparison only)

Aug 25, 2026 through Sep 05, 2026

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!

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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, 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...

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

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: Chicago

More Details Contact Us

Rhythms Of The Road
Value Vacation

from $2,539.00 (USD)

Per Person

May 05, 2025
through Oct 06, 2025

More offers from Cosmos

Nights: 9

Price Per Night:$282.11 (USD)
(based on double occupancy, for comparison only)

May 05, 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: Nashville–brownsville–memphis

More Details Contact Us

Niagara & Great Lakes Treasures
Toronto to Milwaukee

from $14,490.00 (USD)

Per Person

May 01, 2026
through May 17, 2026

More offers from Viking Expeditions

Nights: 16

Ship: Viking Polaris

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

$14,490.00
Cat:N1
905.63 per night

Suite

$18,690.00
Cat:NP
1,168.13 per night

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

More offers from Viking Expeditions

Nights: 16

Ship: Viking Octantis

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
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, 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

Cruising the Great Lakes: Chicago to Toronto - Eastbound
Small Ship Cruising

from $11,390.00 (USD)

Per Person

Sep 01, 2026
through Sep 12, 2026

More offers from Tauck

Nights: 11

Ship: Le Bellot

Price Per Night:$1,035.45 (USD)
(based on double occupancy, for comparison only)

Sep 01, 2026 through Sep 12, 2026

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

Trans-American Adventure
Value Vacation

from $5,358.49 (USD)

Per Person

May 02, 2025
through May 25, 2025

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: Custer–cody

More Details Contact Us

Niagara & Great Lakes Treasures
Milwaukee to Toronto

from $14,890.00 (USD)

Per Person

May 22, 2027
through Jun 07, 2027

More offers from Viking Expeditions

Nights: 16

Ship: Viking Polaris

Price Per Night:$930.63 (USD)
(based on double occupancy, for comparison only)

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.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

$14,890.00
Cat:N2
930.63 per night

Suite

$19,890.00
Cat:NP
1,243.13 per night

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

More offers from Viking Expeditions

Nights: 16

Ship: Viking Polaris

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

Niagara & Great Lakes Treasures
Toronto to Milwaukee

from $13,890.00 (USD)

Per Person

May 06, 2027
through May 22, 2027

More offers from Viking Expeditions

Nights: 16

Ship: Viking Polaris

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

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: Detroit–frankenmuth

More Details Contact Us

Great Lakes Treasures
Roundtrip from Milwaukee

from $7,995.00 (USD)

Per Person

May 13, 2027
through May 22, 2027

More offers from Viking Expeditions

Nights: 9

Ship: Viking Polaris

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

Mackinac Island
Alternative

from $3,999.00 (USD)

Per Person

Apr 30, 2026
through May 08, 2026

More offers from Collette

Nights: 8

Price Per Night:$499.88 (USD)
(based on double occupancy, for comparison only)

Apr 30, 2026 through May 08, 2026

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...

More Details Contact Us

Mackinac Island
Standard

from $3,799.00 (USD)

Per Person

Oct 02, 2026
through Oct 10, 2026

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

Chicago, Illinois (20 offers included)