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Chicago, Illinois (20 offers included)

Nights: 12
Price Per Night:$173.25 (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 $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 $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.
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 City, New York City/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.
from $3,690.00 (USD)
Per Person
Nights: 23
Price Per Night:$160.43 (USD)
(based on double occupancy, for comparison only)
Location(s): Arrive Los Angeles, Los Angeles – Las Vegas (2 Nights), Las Vegas Free Time, Las Vegas – Grand Canyon – Williams, Williams – Zion National Park– Bryce Canyon National Park, Bryce Canyon – Salt Lake City, Salt Lake City – Jackson, Jackson – Yellowstone (2 Nights), Yellowstone Sightseeing, Yellowstone – Cody – Sheridan...
A cross-country exploration of America, we head from Los Angeles to New York City, with every stop on our most comprehensive U.S. journey revealing more about its history, culture and beauty.
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.
Nights: 54
Price Per Night:$171.02 (USD)
(based on double occupancy, for comparison only)
Location(s): Los Angeles to Las Vegas via Mojave Desert, Las Vegas, Las Vegas to Grand Canyon via Route 66, Grand Canyon National Park, Grand Canyon to Durango via Monument Valley, Durango to Albuquerque, Albuquerque to Amarillo via Santa Fe, Amarillo to Dallas, Dallas/Fort Worth, Dallas to Memphis via Little Rock...
How can we possibly begin to summarise the endless list of experiences that will be yours on this 55-day extravaganza of the Americas. Montreal, Memphis, Miami, you name it, we probably see it. This is a trip for those uninterested in leaving a single thing off the list.
from $3,440.00 (USD)
Per Person
Nights: 23
Price Per Night:$149.57 (USD)
(based on double occupancy, for comparison only)
Location(s): Arrive New York, New York – Philadelphia – Washington, D.C. (2 Nights), Washington, D.C. Sightseeing and Free Time, Washington, D.C. – Gettysburg – Pittsburgh, Pittsburgh – Niagara Falls, Canada (2 Nights), Niagara Falls Sightseeing, Niagara Falls, Canada – Cleveland, Cleveland – Chicago, Chicago Free Time, Chicago – Des Moines...
A cross-country exploration of America, we head from New York City to Los Angeles, with every stop on our most comprehensive U.S. journey revealing more about its history, culture, and beauty.
Nights: 12
Price Per Night:$182.42 (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.
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 City, New York City/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.
Nights: 13
Price Per Night:$187.31 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago to Madison via Milwaukee, Madison to Sioux Falls, Sioux Falls to Mt. Rushmore via Badlands National Park, Mt. Rushmore, Mt. Rushmore to Cody, Yellowstone, Cody to Teton Valley via Yellowstone National Park, Teton Valley to Salt Lake City, Salt Lake City to Kanab via Bryce Canyon National Park, Grand Canyon National Park...
Take in the big city lights and jaw-dropping natural sites of North America. This 2-week journey from Illinois to LA will see you journeying through Minnesota farmlands, Yellowstone National Park, and the casino crazed Las Vegas. The perfect balance of everything the USA has to offer.
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 U.S. 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 alongside sequoias, 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 $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....
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 City, New York City/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...
from $3,285.00 (USD)
Per Person
Nights: 7
Price Per Night:$469.29 (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.
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 $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 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 that connects each, cutting down on long drives so that you have more time to spend at the spots that matter most. Explore Chicago's riverside, be charmed by New Orleans' colonial architecture, and marvel at the rocky cliffs and rolling fog of California's famed Highway ...
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 $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.