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Chicago, Illinois (20 offers included)

Best of the US Express
18-to-Thirtysomethings
from $3,649.00 (USD)
Per Person
Nights: 17
Price Per Night:$214.65 (USD)
(based on double occupancy, for comparison only)
Location(s): New York, New York/Finger Lakes, Finger Lakes/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis...
This whirlwind 18-day camping trip throughout the United States covers nearly every major cultural touchstone of this massive (and hugely exciting) destination. Experience the lights of NYC's Times Square, discover the Elvis fan in you at Graceland, mosey down noisy Bourbon Street in New Orleans, peer across the majesty of the Grand Canyon, and then walk down the crookedest street in the world in San Francisco, all the while camping out beneath a night sky that has had countless songs written...
USA East Coast Road Trip Encompassed
18-to-Thirtysomethings
from $3,549.00 (USD)
Per Person
Nights: 19
Price Per Night:$186.79 (USD)
(based on double occupancy, for comparison only)
Location(s): New York, New York/Finger Lakes, Finger Lakes/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis...
Big city hearts and spirits swell on this 20-day road trip through America's East Coast. You'll hit bustling metropolises and experience cultural traditions you might have only seen in the movies. Witness the resurgence of Detroit's arts scene, follow Kentucky's Bourbon Trail, and explore the home of Mardi Gras—New Orleans. With free time and flexibility along the way, you can customize this tour so it's right up your alley.
from $2,135.00 (USD)
Per Person
Nights: 12
Price Per Night:$177.92 (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 via Rockport, Toronto and Niagara Falls, Toronto, Toronto to Cleveland...
Take in the fast paced life of Boston, experience the charm, culture and sophistication of Quebec, Montreal and Toronto, get exhilarated by watching Niagara Falls until you finally head back to the US where you'll see why 'Cleveland Rocks'. Hold on to your hats as we enter the 'Windy City' of Chicago.
Coast to Coast Camping Westbound
18-to-Thirtysomethings
from $3,349.00 (USD)
Per Person
Nights: 21
Price Per Night:$159.48 (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 $2,799.00 (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....
from $5,499.00 (USD)
Per Person
Nights: 31
Price Per Night:$177.39 (USD)
(based on double occupancy, for comparison only)
Location(s): Seattle, Seattle/Portland, Portland/Bend, Bend/Redwood National Park, Redwood National Park/Napa Valley, Napa Valley/Lake Tahoe, Lake Tahoe/Yosemite National Park, Yosemite National Park, Yosemite National Park/San Francisco, San Francisco...
Road tripping is an iconic American pastime, but don't let your lack of a driver's license or vehicle stop you from exploring the country's best sites. On this 32-day tour, you'll visit the best of the east and west coasts with a flight connect each leg of the tour, cutting down on long drives so that you have more time to spend at the spots that matter most. Explore Chicago's riverside and vibrant music scene, be charmed by New Orleans' colonial architecture, and marvel in the rocky cliffs a...
from $2,529.00 (USD)
Per Person
Nights: 15
Price Per Night:$168.60 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Branson, Branson – Arcadia – 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: Branson–arcadia–oklahoma City
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 $2,499.00 (USD)
Per Person
Nights: 7
Price Per Night:$357.00 (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 – Grand Rapids, Grand Rapids – Chicago, Chicago
8 Days, featuring: Grand Rapids–chicago
from $2,135.00 (USD)
Per Person
Nights: 12
Price Per Night:$177.92 (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 via Rockport, Toronto and Niagara Falls, Toronto, Toronto to Cleveland...
Take in the fast paced life of Boston, experience the charm, culture and sophistication of Quebec, Montreal and Toronto, get exhilarated by watching Niagara Falls until you finally head back to the US where you'll see why 'Cleveland Rocks'. Hold on to your hats as we enter the 'Windy City' of Chicago.
from $3,799.00 (USD)
Per Person
Nights: 25
Price Per Night:$151.96 (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 via Rockport, Toronto and Niagara Falls, Toronto, Toronto to Cleveland...
Just think, there are some poor unfortunate souls that have to fly from New York to LA, trapped above the clouds while we're down here seeing every damn thing this country has on offer. Niagara Falls, the Rock & Roll Hall of Fame, deep dish pizza in Chicago, farmlands of the Midwest. You guys, the grass is very green down here.
from $1,809.00 (USD)
Per Person
Nights: 9
Price Per Night:$201.00 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – St. Louis, St. Louis – Nashville, Nashville, Nashville – Memphis, Memphis. Visit To Graceland, Memphis – Amtrak City Of New Orleans Train – New Orleans, New Orleans
10 Days, featuring: Chicago
from $8,149.00 (USD)
Per Person
Nights: 52
Price Per Night:$156.71 (USD)
(based on double occupancy, for comparison only)
Location(s): Los Angeles, Los Angeles/San Diego, San Diego/Lake Havasu City, Lake Havasu City/Grand Canyon, Grand Canyon, Grand Canyon/Monument Valley, Monument Valley/Las Vegas, Las Vegas, Las Vegas/Zion National Park, Bryce Canyon NP/Moab...
There's no better way to do the US justice than a great American road trip. This 53-day tour hits all the marks, going coast-to-coast from bustling cities to incredible natural wonders, and charming small towns in between. Hike along geysers, waterfalls, and wildlife in Yosemite National Park, get weird among Portland's artsy shops, indie breweries, and up-and-coming eateries, and join party revellers on New Orleans' famed Bourbon Street. Epic road trips are made of this.
from $8,149.00 (USD)
Per Person
Nights: 52
Price Per Night:$156.71 (USD)
(based on double occupancy, for comparison only)
Location(s): New York, New York/Finger Lakes, Finger Lakes/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis...
See a side of the States that few Americans experience in their lifetime on a truly epic 53-day road trip through the country. You'll embark on two comprehensive circuits along the East and West coasts with a flight in between to minimize long drives and maximize your time at the best highlights. What makes this journey even better is the company you'll keep—a fine crew of worldly wanderers like yourself and a CEO taking care of all the little details.
Chicago to San Francisco Road Trip
18-to-Thirtysomethings
from $2,399.00 (USD)
Per Person
Nights: 15
Price Per Night:$159.93 (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 $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: 15
Price Per Night:$177.27 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – Pontiac – Springfield, Springfield – St. Louis, St. Louis – Branson, Branson – Arcadia – 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 $1,820.00 (USD)
Per Person
Nights: 10
Price Per Night:$182.00 (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.
New York to New Orleans Road Trip
18-to-Thirtysomethings
from $1,999.00 (USD)
Per Person
Nights: 10
Price Per Night:$199.90 (USD)
(based on double occupancy, for comparison only)
Location(s): New York, New York/Finger Lakes, Finger Lakes/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis...
An epic East Coast experience awaits on this nine-day tour through bustling cities and stunning landscapes made by Mother Nature. Feel the mist of Niagara Falls on your face as you get up close to this natural wonder by boat, indulge in barbecue eats in Kentucky, and join the party on New Orleans' Bourbon Street. It's a flexible itinerary that you can customize with unique experiences at every stop, turning this road trip into one that you can make all your own.
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.