Chicago, Illinois

Great Lakes Explorer

from $5,399.00 (USD)

Per Person

Jun 13, 2023
through Jun 24, 2023

More offers from Alexander+Roberts

Nights: 11

Ship: Ocean Voyager

Price Per Night:$490.82 (USD)
(based on double occupancy, for comparison only)

Jun 13, 2023 through Jun 24, 2023

Itinerary: Welcome to Toronto, Enjoy Toronto + Embark the mv Ocean Voyager, Thrill to Niagara Falls, Fine Art + Rock & Roll, Surprising Detroit, Cruising Lake Huron, Ashore on Manitoulin Island, Ontario, The Soo Locks + Sault Ste. Marie, Mackinac Island with Lunch at the Grand Hotel, Cruising on Lake Michigan...

Step aboard the stylish, 202-guest mv Ocean Voyager for this all-inclusive Great Lakes cruise. Attentively hosted by A+R from start to finish, you'll enjoy a more rewarding and carefree voyage with extensive sightseeing and shore excursions, elegant shipboard dining, an Open Bar, and all shipboard and shore excursion gratuities.

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

from $9,990.00 (USD)

Per Person

Oct 04, 2024
through Oct 15, 2024

More offers from Tauck

Nights: 11

Ship: Le Bellot

Price Per Night:$908.18 (USD)
(based on double occupancy, for comparison only)

Oct 04, 2024 through Oct 15, 2024

Itinerary: Toronto, Canada, , Detroit, Michigan, USA, , Chicago, Illinois, USA

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 Le Dumont d'Urville, plus two-night stays at your choice of premium hotels in these great anchor cities!

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

from $9,490.00 (USD)

Per Person

Sep 23, 2023
through Oct 04, 2023

More offers from Tauck

Nights: 11

Ship: Le Dumont d'Urville

Price Per Night:$862.73 (USD)
(based on double occupancy, for comparison only)

Sep 23, 2023 through Oct 04, 2023

Itinerary: Toronto, Canada, , Detroit, Michigan, USA, , Traverse City, Michigan, USA, , Chicago, Illinois, USA

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 Le Dumont d'Urville, plus two-night stays at your choice of premium hotels in these great anchor cities!

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2023 NASCAR Chicago

from $1,995.00 (USD)

Per Person

Jun 30, 2023
through Jul 03, 2023

More offers from Sports Empire

Nights: 3

Price Per Night:$665.00 (USD)
(based on double occupancy, for comparison only)

Jun 30, 2023 through Jul 03, 2023

Location(s): Chicago

Just off Magnificent Mile, our suites are adjacent to the John Hancock Center. Within two blocks reach Water Tower Place and Navy Pier. Enjoy the top-floor pool and fitness center with views of Lake Michigan. The hotel is 2 miles from the course on the CTA, 15 miles from O'Hare International (ORD) and 10 miles from Chicago Midway (MDW).

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Highlights Of Route 66

from $2,819.00 (USD)

Per Person

Jul 08, 2023
through Aug 26, 2023

More offers from Cosmos

Nights: 15

Price Per Night:$187.93 (USD)
(based on double occupancy, for comparison only)

Jul 08, 2023 through Aug 26, 2023

Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Branson, Branson – Tulsa – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Acoma Sky City – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...

16 Days, featuring: Oklahoma City–elk City–amarillo

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

from $10,290.00 (USD)

Per Person

Aug 30, 2024
through Sep 10, 2024

More offers from Tauck

Nights: 11

Ship: Le Bellot

Price Per Night:$935.45 (USD)
(based on double occupancy, for comparison only)

Aug 30, 2024 through Sep 10, 2024

Itinerary: Chicago, Illinois, USA, , Detroit, Michigan, USA, , Toronto, Canada

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 Le Dumont d'Urville, plus two-night stays at your choice of premium hotels in these great anchor cities!

More Details Contact Us

Rhythms Of The Road

from $2,189.00 (USD)

Per Person

Apr 08, 2024
through Apr 17, 2024

More offers from Cosmos

Nights: 9

Price Per Night:$243.22 (USD)
(based on double occupancy, for comparison only)

Apr 08, 2024 through Apr 17, 2024

Location(s): Chicago, Chicago – St. Louis, St. Louis – Nashville, Nashville, Nashville – Brownsville – Memphis, Memphis – Visit To Graceland, Memphis – Indianola – New Orleans, New Orleans

10 Days, featuring: Chicago

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Highlights Of Route 66 - Mother Road Festival

from $2,869.00 (USD)

Per Person

Sep 21, 2023
through Oct 06, 2023

More offers from Cosmos

Nights: 15

Price Per Night:$191.27 (USD)
(based on double occupancy, for comparison only)

Sep 21, 2023 through Oct 06, 2023

Location(s): Chicago, Chicago – Pontiac – Springfield – International Route 66 Mother Road Festival, Springfield – St. Louis, St. Louis – Branson, Branson – 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

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Mackinac Island
Reverse

from $3,599.00 (USD)

Per Person

Oct 06, 2023
through Oct 14, 2023

More offers from Collette

Nights: 8

Price Per Night:$449.88 (USD)
(based on double occupancy, for comparison only)

Oct 06, 2023 through Oct 14, 2023

Location(s): Southfield, MI, Bay City, MI, Mackinac Island, MI, Grand Rapids, MI, Chicago, IL

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.

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Highlights Of Route 66

from $3,099.00 (USD)

Per Person

May 11, 2024
through Sep 14, 2024

More offers from Cosmos

Nights: 15

Price Per Night:$206.60 (USD)
(based on double occupancy, for comparison only)

May 11, 2024 through Sep 14, 2024

Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Branson, Branson – Tulsa – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Acoma Sky City – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...

16 Days, featuring: Las Vegas

More Details Contact Us

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

from $9,490.00 (USD)

Per Person

Sep 02, 2023
through Sep 13, 2023

More offers from Tauck

Nights: 11

Ship: Le Dumont d'Urville

Price Per Night:$862.73 (USD)
(based on double occupancy, for comparison only)

Sep 02, 2023 through Sep 13, 2023

Itinerary: Chicago, Illinois, USA, , Traverse City, Michigan, USA, , Detroit, Michigan, USA, , Toronto, Canada

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 Le Dumont d'Urville, plus two-night stays at your choice of premium hotels in these great anchor cities!

More Details Contact Us

Trans-American Adventure

from $4,522.00 (USD)

Per Person

Aug 18, 2023
through Sep 10, 2023

More offers from Cosmos

Nights: 23

Price Per Night:$196.61 (USD)
(based on double occupancy, for comparison only)

Aug 18, 2023 through Sep 10, 2023

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–los Angeles

More Details Contact Us

Lakeside Treasures
Hotel Stay in Chicago, IL to Chicago, IL

from $6,299.00 (USD)

Per Person

Jun 02, 2023
through Jun 17, 2023

More offers from American Queen Voyages

Nights: 15

Ship: Ocean Navigator

Price Per Night:$419.93 (USD)
(based on double occupancy, for comparison only)

Jun 02, 2023 through Jun 17, 2023

Itinerary: Hotel Stay in Chicago, IL, Embark in Chicago, IL, Mackinac Island, MI, Marquette, MI, Houghton, MI, Duluth, MN, Thunder Bay, ON, Sault Ste. Marie, MI, Green Bay, WI, Muskegon, MI...

Other Categories Starting At:

Inside

N/A

Outside

$6,299.00
Cat: E

Balcony

N/A

Suite

$12,499.00
Cat: OS

More Details Contact Us

Splendor of the Great Lakes
Hotel Stay in Toronto, ON to Chicago, IL

from $4,699.00 (USD)

Per Person

May 17, 2023
through May 27, 2023

More offers from American Queen Voyages

Nights: 10

Ship: Ocean Voyager

Price Per Night:$469.90 (USD)
(based on double occupancy, for comparison only)

May 17, 2023 through May 27, 2023

Itinerary: Hotel Stay in Toronto, ON, Embark in Toronto, ON, Port Colborne (Niagara Falls), ON, Cleveland, OH, Detroit, MI, Scenic Sailing on Lake Huron, Little Current/Manitoulin Island, ON, Sault Ste. Marie, MI, Mackinac Island, MI, Scenic Sailing on Lake Michigan...

Other Categories Starting At:

Inside

N/A

Outside

$4,699.00
Cat: E

Balcony

N/A

Suite

$9,399.00
Cat: OS

More Details Contact Us

Mackinac Island
Standard

from $3,499.00 (USD)

Per Person

May 19, 2023
through May 27, 2023

More offers from Collette

Nights: 8

Price Per Night:$437.38 (USD)
(based on double occupancy, for comparison only)

May 19, 2023 through May 27, 2023

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.

More Details Contact Us

Chicago (Ottawa) to St. Louis (Alton)
Hotel Stay in St. Louis, MO to Chicago, IL (Ottawa)

from $2,799.00 (USD)

Per Person

Jul 20, 2024
through Jul 28, 2024

More offers from American Queen Voyages

Nights: 8

Ship: American Countess

Price Per Night:$349.88 (USD)
(based on double occupancy, for comparison only)

Jul 20, 2024 through Jul 28, 2024

Itinerary: Hotel Stay in St. Louis, MO, Alton, IL, River Cruising, Hannibal, MO, Grafton, IL, Havana, IL, Peoria, IL, Ottawa, IL, Chicago, IL (Ottawa)

Other Categories Starting At:

Inside

$2,799.00
Cat: E

Outside

N/A

Balcony

$3,299.00
Cat: SO

Suite

$4,299.00
Cat: A

More Details Contact Us

Mackinac Island & The Great Lakes

from $3,339.00 (USD)

Per Person

Jun 02, 2024
through Jun 09, 2024

More offers from Globus

Nights: 7

Price Per Night:$477.00 (USD)
(based on double occupancy, for comparison only)

Jun 02, 2024 through Jun 09, 2024

Location(s): Detroit/Dearborn, Michigan, Dearborn – 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: Frankenmuth–mackinac Island

More Details Contact Us

Rhythms Of The Road

from $2,059.00 (USD)

Per Person

Jun 26, 2023
through Sep 04, 2023

More offers from Cosmos

Nights: 9

Price Per Night:$228.78 (USD)
(based on double occupancy, for comparison only)

Jun 26, 2023 through Sep 04, 2023

Location(s): Chicago, Chicago – St. Louis, St. Louis – Nashville, Nashville, Nashville – Brownsville – Memphis, Memphis – Visit To Graceland, Memphis – Indianola – New Orleans, New Orleans

10 Days, featuring: Memphis–visit To Graceland

More Details Contact Us

Trans-American Adventure

from $4,811.00 (USD)

Per Person

May 03, 2024
through May 26, 2024

More offers from Cosmos

Nights: 23

Price Per Night:$209.17 (USD)
(based on double occupancy, for comparison only)

May 03, 2024 through May 26, 2024

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

More Details Contact Us

Splendor of the Great Lakes
Hotel Stay in Toronto, ON to Chicago, IL

from $3,999.00 (USD)

Per Person

Jun 29, 2024
through Jul 09, 2024

More offers from American Queen Voyages

Nights: 10

Ship: Ocean Navigator

Price Per Night:$399.90 (USD)
(based on double occupancy, for comparison only)

Jun 29, 2024 through Jul 09, 2024

Itinerary: Hotel Stay in Toronto, ON, Embark in Toronto, ON, Port Colborne (Niagara Falls), ON, Cleveland, OH, Detroit, MI, Scenic Sailing on Lake Huron, Little Current/Manitoulin Island, ON, Sault Ste. Marie, MI, Mackinac Island, MI, Scenic Sailing on Lake Michigan...

Other Categories Starting At:

Inside

N/A

Outside

$3,999.00
Cat: E

Balcony

N/A

Suite

$10,425.00
Cat: OS

More Details Contact Us

Chicago, Illinois (20 offers included)