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Chicago, Illinois (19 offers included)

Tour The Art Institute Of Chicago
Our Classic Sightseeing
from $99.00 (USD)
Per Person
Location(s): Chicago
Are you aware of the Art Institute of Chicago and its influence on the world stage?
from $6,111.75 (USD)
Per Person
Nights: 52
Price Per Night:$117.53 (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.
Full Day Private Tour Of Chicago
Private and Personal
from $1,400.00 (USD)
Per Person
Location(s): Chicago
This full day tour will show you just about every inch of Chicago!
New York to New Orleans Road Trip
18-to-Thirtysomethings
from $1,299.35 (USD)
Per Person
Nights: 10
Price Per Night:$129.94 (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...
An epic East Coast experience awaits on this nine-day tour through bustling cities and stunning landscapes. Feel the mist of Niagara Falls on your face as you get up close to this natural wonder, 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 $1,820.00 (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 $6,375.00 (USD)
Per Person
Nights: 13
Price Per Night:$490.38 (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., Spirit of Louisville., The Honky-Tonk Highway., Enjoy Nashville's Musical History., Memphis and Graceland., Sun Studios and National Civil Rights Museum., Mississippi mystique in Natchez....
Join us for a toe-tapping trip of rock, jazz and country music, as you delve into the sumptuous soul of America. You'll start in Chicago, a great food city also known for its jazz and blues, before heading south to the musical meccas of Nashville and Memphis. End your trip with a little jazz as you head to the Mississippi Delta and on to zesty New Orleans. From visiting the Country Music Hall of Fame in Nashville to the iconic Graceland mansion, this trip not only comes with behind-the-scenes experiences, but with its own memorable soundtrack. On select Chairman’s Collection departure dates you’ll meet iconic multi-instrumentalist Charlie McCoy. From playing the saxophone on Roy Orbison’s...
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: Williams. Excursion To Grand Canyon National Park
from $3,280.00 (USD)
Per Person
Nights: 7
Price Per Night:$468.57 (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. On select Chairman’s Collection departure dates you’ll meet iconic multi-instrumentalist Charlie McCoy. From playing the saxophone on Roy Orbison’s "Oh Pretty Woman", to the harmonica on Elvis and Simon & Garfunkel tracks, he has played a huge role in making music history. Join him at Studio B in Nashville where you’ll record your own group s...
Last Minute Deal: Must book by 2019-04-24
Private: Intro To Chicago
Private and Personal
from $404.00 (USD)
Per Person
Location(s): Chicago
You will enjoy Chicago even more if you learn where, when, and why.
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: Detroit
2020 NBA All-Star Game
February 15-17, 2020
from $2,595.00 (USD)
Per Person
Nights: 2
Price Per Night:$1,297.50 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago
The package includes a stay at the Embassy Suites Chicago Downtown Magnificent Mile, made-to-order breakfast, a complimentary evening reception, roundtrip airport shuttle transfers, and tickets to the NBA All-Star Game (300 level baseline).
Best of the US Express
18-to-Thirtysomethings
from $2,371.85 (USD)
Per Person
Nights: 17
Price Per Night:$139.52 (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...
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: Chicago
USA East Coast Road Trip Encompassed
18-to-Thirtysomethings
from $2,129.40 (USD)
Per Person
Nights: 19
Price Per Night:$112.07 (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.
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 $2,799.00 (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 $5,704.30 (USD)
Per Person
Nights: 52
Price Per Night:$109.70 (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 $1,106.00 (USD)
Per Person
Location(s): Chicago
This tour provides a great overview of this bustling city.
from $1,839.00 (USD)
Per Person
Nights: 9
Price Per Night:$204.33 (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: St. Louis–nashville