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Chicago, Illinois (13 offers included)

from $5,249.25 (USD)
Per Person
Nights: 42
Price Per Night:$124.98 (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 $8,199.00 (USD)
Per Person
Nights: 52
Price Per Night:$157.67 (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.
Best of the US Express
18-to-Thirtysomethings
from $3,279.00 (USD)
Per Person
Nights: 17
Price Per Night:$192.88 (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...
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: Chicago
from $648.00 (USD)
Per Person
Nights: 3
Price Per Night:$216.00 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago
This chic hotel is ideally located in the heart of downtown Chicago, overlooking the Chicago River. All 1,209 guest rooms, including 40 suites, at the Sheraton Chicago Towers are newly decorated and feature a warm, contemporary look, with views of the Chicago River, Lake Michigan or the city skyline.
from $4,874.25 (USD)
Per Person
Nights: 42
Price Per Night:$116.05 (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: 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 – Claremore – Arcadia – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Santa Rosa – Albuquerque, Albuquerque, Albuquerque – Gallup – Winslow – Flagstaff, Flagstaff – Grand Canyon National Park – Williams...
16 Days, featuring: Chicago Area
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 $1,219.00 (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.
Coast to Coast Camping Westbound
18-to-Thirtysomethings
from $2,511.75 (USD)
Per Person
Nights: 21
Price Per Night:$119.61 (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...
New York to New Orleans Road Trip
18-to-Thirtysomethings
from $1,779.00 (USD)
Per Person
Nights: 10
Price Per Night:$177.90 (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 $8,199.00 (USD)
Per Person
Nights: 52
Price Per Night:$157.67 (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 $5,719.00 (USD)
Per Person
Nights: 31
Price Per Night:$184.48 (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...