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Chicago, Illinois (18 offers included)

Coast to Coast Camping Westbound
18-to-Thirtysomethings
from $2,679.20 (USD)
Per Person
Nights: 21
Price Per Night:$127.58 (USD)
(based on double occupancy, for comparison only)
Location(s): New York, New York/Newburgh, Newburgh/Finger Lakes, Finger Lakes/Niagara Falls, Niagara Falls/Sandusky, Sandusky/Chicago, Chicago, Chicago/Frontenac, Frontenac/Sioux Falls, Sioux Falls/Badlands National Park...
Yellowstone, the Badlands, and Niagara Falls – once you’ve escaped the city limits, the US is a country defined by incredible wilderness. This affordable cross-country adventure keeps you on the ground between New York, Chicago, and San Francisco so you can experience what lies in between. Days feature magnificent sites like Yosemite and Old Faithful, while evenings offer experiences like cooking over a fire and camping in the great outdoors. Travel coast to coast and embrace the soul of this...
from $2,599.00 (USD)
Per Person
Nights: 7
Price Per Night:$371.29 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Illinois - Tour Begins, Chicago, Chicago - Holland, Michigan - Grand Rapids, Grand Rapids - Mackinac Island, Mackinac Island, Mackinac Island - Frankenmuth, Frankenmuth - Dearborn - Southfield, Southfield - Tour Ends
This classic Midwestern tour features Illinois and Michigan. Visit Holland Michigan’s yearly Tulip Festival. See the extraordinary flowers at the Veldheer Tulip Garden. Then visit the Windmill Island Gardens to experience a palette of color on the 36 acres of manicured gardens, dikes and canals and the only authentic Dutch windmill operating in the United States. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island....
Nights: 12
Price Per Night:$171.58 (USD)
(based on double occupancy, for comparison only)
Location(s): New York to Boston, Boston, Boston to Quebec City, Quebec City, Quebec City to Montreal, Montreal, Montreal to Toronto, Toronto, Toronto to Niagara Falls, Toronto to Cleveland...
Take in the fast paced life of New York and Boston, experience the charm, culture and sophistication of Quebec, Montreal and Toronto, get exhilarated by watching the Niagara Falls until you finally head back to the US where you'll see why 'Cleveland Rocks' is this cities unique motto and hold on to your hats as we enter the 'Windy City' of Chicago. While you're on this side of town, join us on the Eastern Discovery for a full ride along the east coast. Or if you want to see even more of the US, we'll see you on the Grand Southern.
Chicago to San Francisco Road Trip
18-to-Thirtysomethings
from $1,919.20 (USD)
Per Person
Nights: 15
Price Per Night:$127.95 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago/Frontenac, Frontenac/Sioux Falls, Sioux Falls/Badlands National Park, Badlands National Park/Custer State Park, Custer State Park/Devils Tower, Devils Tower/Bozeman, Bozeman/Yellowstone National Park, Yellowstone National Park, Yellowstone National Park/Jackson...
Remember the country they sing about in "America the Beautiful"? The one with the spacious skies, gleaming alabaster cities, and majestic purple mountains? It’s still out there. Come see it with us. Ideal for wildlife enthusiasts and outdoorsy folk who want to see the country by day and revel downtown by night, this tour takes you across the Great West, from the City of Big Shoulders through Yellowstone and Yosemite and past herds of grazing bison to the City by the Bay. In a word: Perfect.
from $4,874.25 (USD)
Per Person
Nights: 42
Price Per Night:$116.05 (USD)
(based on double occupancy, for comparison only)
Location(s): San Francisco, San Francisco/Yosemite National Park, Yosemite National Park, Yosemite National Park/Death Valley, Death Valley/Las Vegas, Las Vegas, Las Vegas/Grand Canyon National Park, Grand Canyon National Park, Grand Canyon National Park/Monument Valley, Monument Valley/Mesa Verde National Park...
Is it possible to capture the complex, diverse flavour of a country and its 300-million-strong people in a single trip? Short answer: Yup. This epic sojourn across America from sea to shining sea (and back again) is, quite possibly, the most ambitious road trip you’ll ever take. Wide-open spaces, iconic monuments, sprawling national parks, quirky local slang, regional delicacies and the incredible cities you’ve always wanted to visit. It’s all here. Welcome to the US of A, where the "A" stand...
from $5,199.20 (USD)
Per Person
Nights: 42
Price Per Night:$123.79 (USD)
(based on double occupancy, for comparison only)
Location(s): New York, New York/Newburgh, Newburgh/Finger Lakes, Finger Lakes/Niagara Falls, Niagara Falls/Sandusky, Sandusky/Chicago, Chicago, Chicago/Frontenac, Frontenac/Sioux Falls, Sioux Falls/Badlands National Park...
From hip hop to country fiddles, Yankee accents to a western drawl, businessmen in power suits and ranchers in cowboy hats – the US is one heck of a country. And if you’ve got the time, this – our ultimate American tour – is the best way to explore the iconic cities, the legendary national parks, national monuments, and wide-open spaces. Centrally located hostels in the cities and campsites in the wilderness keep you in the heart of the action no matter where you are.
Nights: 25
Price Per Night:$159.40 (USD)
(based on double occupancy, for comparison only)
Location(s): New York to Boston, Boston, Boston to Quebec City, Quebec City, Quebec City to Montreal, Montreal, Montreal to Toronto, Toronto, Toronto to Niagara Falls, Toronto to Cleveland...
With 20 states & 2 Canadian provinces, get ready to go local. Start in the Big Apple before it’s all about Canada, America’s Great Lakes & Chicago en route to the American West. Chill at 4 National Parks before LAS Vegas.
from $2,459.00 (USD)
Per Person
Nights: 7
Price Per Night:$351.29 (USD)
(based on double occupancy, for comparison only)
Location(s): Detroit, Detroit – Frankenmuth, Frankenmuth – Mackinac Island, Mackinac Island, Mackinac Island – Tunnel Of Trees – Charlevoix – Petoskey, Petoskey – Sleeping Bear Dunes National Lakeshore – Grand Rapids, Grand Rapids – Chicago, Chicago
8 Days, featuring: Detroit
from $2,585.00 (USD)
Per Person
Nights: 13
Price Per Night:$198.85 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago to Madison, Madison to Sioux Falls, Sioux Falls to Mt. Rushmore, Mt. Rushmore, Mt. Rushmore to Cody, Yellowstone, Cody to Teton Valley via Yellowstone National Parl, Teton Valley to Salt Lake City, Salt Lake City to Kanab via Bryce Canyon National Park, Grand Canyon National Park...
True to its name, escape for 2 weeks to some of the USA’s hottest destinations & experience what this amazing country has to offer. Start in Chicago & roll through America’s Midwest on your way to Sioux Falls. Salute Presidents past at Mt Rushmore, buckle up for a rodeo in Cody, then get back to nature on a hike through a National Park. Take it up a notch at the end as you rub shoulders with Vegas' high rollers & spot an Elvis or two! This tour really is a unique mix of things to see & do in the good ol’ USofA.
from $2,749.00 (USD)
Per Person
Nights: 7
Price Per Night:$392.71 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Illinois - Tour Begins, Chicago, Chicago - Holland, Michigan - Grand Rapids, Grand Rapids - Mackinac Island, Mackinac Island, Mackinac Island - Frankenmuth, Frankenmuth - Dearborn - Southfield, Southfield - Tour Ends
This classic Midwestern tour features Illinois and Michigan. Visit Holland Michigan’s yearly Tulip Festival. See the extraordinary flowers at the Veldheer Tulip Garden. Then visit the Windmill Island Gardens to experience a palette of color on the 36 acres of manicured gardens, dikes and canals and the only authentic Dutch windmill operating in the United States. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island....
from $2,539.00 (USD)
Per Person
Nights: 15
Price Per Night:$169.27 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Branson, Branson – Claremore – Arcadia – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Santa Rosa – Albuquerque, Albuquerque, Albuquerque – Gallup – Winslow – Flagstaff, Flagstaff – Grand Canyon National Park...
16 Days, featuring: Flagstaff–grand Canyon National Park
from $1,348.00 (USD)
Per Person
Nights: 5
Price Per Night:$269.60 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago
Stay at Conrad Chicago and be in the center of it all. Enjoy globally inspired architecture and design with access to the city’s most exciting destinations. If you had 1/3/5 hours to explore Chicago, what would you do? Make the most of your journey at Conrad Chicago with a curated list of 1/3/5 experiences.
from $1,995.00 (USD)
Per Person
Nights: 10
Price Per Night:$199.50 (USD)
(based on double occupancy, for comparison only)
Location(s): Arrive Chicago (2 Nights), Chicago Sightseeing and Free Time, Chicago – Louisville, Louisville – Nashville (2 Nights), Nashville Sightseeing and Free Time, Nashville – Memphis (2 Nights), Graceland Visit and Free Time, Memphis – Clarksdale – Indianola, Indianola – New Orleans (2 Nights), New Orleans Sightseeing and Free Time...
Embark upon a journey of musical discovery, contrasting cultures, tastes, sights and sounds as you travel from Chicago through Bluegrass Country to the heart of the Deep South. From BBQ, Bourbon, Blues and Jazz to Country and Rock n Roll, add a touch of Cajun and this trip is a recipe for success.
from $2,799.00 (USD)
Per Person
Nights: 7
Price Per Night:$399.86 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Illinois - Tour Begins, Chicago, Chicago - Traverse City, Michigan, Traverse City - Charlevoix - Mackinac Island, Mackinac Island, Mackinac Island - Frankenmuth, Frankenmuth - Dearborn - Southfield, Southfield - Tour Ends
This classic Midwestern tour features Illinois and Michigan. Visit Holland Michigan’s yearly Tulip Festival. See the extraordinary flowers at the Veldheer Tulip Garden. Then visit the Windmill Island Gardens to experience a palette of color on the 36 acres of manicured gardens, dikes and canals and the only authentic Dutch windmill operating in the United States. Savor two incredible nights amid the luxury of the Grand Hotel on Mackinac Island. Enjoy a horse and buggy tour of Mackinac Island....
Nights: 13
Price Per Night:$448.08 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, the Jewel of the Midwest., Scaling Chicago., St Louis, Gateway to the West., St Louis Arch to Louisville., Spirited Residents and Resident Spirits of Louisville., A Corvette on the Honky-Tonk Highway to Nashville., Enjoy Nashville’s Musical History., Memphis and Graceland, Home of 'the King'., Sun Studios and National Civil Rights Museum., Mississippi Mystique in Natchez....
Two of life’s greatest pleasures - music and food - are at the forefront of this sensual journey through the American heartland. Start in Chicago, a great food city also known for its jazz and blues. Travel south to the musical meccas of Nashville and Memphis. Then head down through the Mississippi Delta and on to zesty New Orleans.
from $3,375.00 (USD)
Per Person
Nights: 7
Price Per Night:$482.14 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, the Jewel of the Midwest., Scaling Chicago., St Louis, the Gateway to the West., St Louis Arch to Louisville., Spirited Residents and Resident Spirits of Louisville., A Corvette on the Honky-Tonk Highway to Nashville., Enjoy Nashville’s Musical History., Depart Nashville.
From the famous architecture of Chicago to the warm hospitality of the Midwest, this quintessential USA itinerary reveals the very essence of the American dream. Start with Chicago - the birthplace of the modern skyscraper - then continue to Kentucky for bourbon, horses and fast cars. Finally, embrace the toe-tappin’ country music scene in Tennessee.
from $1,219.00 (USD)
Per Person
Nights: 5
Price Per Night:$243.80 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago
Our AAA Four Diamond hotel sits at the intersection of glam-packed city action and nautically inspired innovation. Socialize in the hotel's stylish bars, relax in the pool, or slip in a workout at FIT® or get ‘pedi' for an afternoon of pampering at Bliss® Spa.
from $8,849.00 (USD)
Per Person
Nights: 54
Price Per Night:$163.87 (USD)
(based on double occupancy, for comparison only)
Location(s): Los Angeles to Las Vegas, Las Vegas, Las Vegas to the Grand Canyon via Route 66, Grand Canyon National Park, Grand Canyon to Durango via Monument Valley, Durango to Albuquerque, Albuquerque to Amarillo, Amarillo to Dallas/Fort Worth, Dallas/Fort Worth, Dallas/Fort Worth to Memphis...
Epic = grand in scale, and that’s exactly what this trip is. From big cities & monuments to the great outdoors, historical sights, cool nightlife & endless experiences, this is 55 days of adventure guaranteed to feed the inner explorer & make every moment count. Let’s go!