Quick Enquiry

Chicago, Illinois

the windy City

Chicago is a city proud of it’s history and artistic values, so much that the natives refuse to accept its name as the Second City. The home of some of America’s most spectacular skyscrapers, sporting teams, and gangsters can be explored by trolley, bus, boat or bike, every corner presenting the visitor with a delightful experience. The city truly comes alive in the summer months, beaches and festivals accessible for your pleasure.

PRICES FROM JUST £1599 pp - includes flights, hotels, car hire & a fab road trip pack

Visit Chicago, Illinois

Visit Chicago, Illinois, and discover the birthplace of electric blues and house music. Not to mention the constant hum of jazz that travels on the wind. Enjoy one of Americas most iconic skylines as you take in glistening glass skyline from the rooftop bars as you relax with a cold craft brew, or along one of the legendary riverboat cruises.

What’s in Chicago, Illinois?

Relax in the green space of Millennium Park, supercharged shopping along Magnificent Mile and uncover the historic Navy Pier.  The windy city is great for getting around on foot. There is 26 miles of uninterrupted lakefront and a trail to walk along, as well as 15 miles of sandy beaches.

What to do when Visiting Chicago?

Take one of the many cruises that run along the river. Visit Cloud Gate, in Millennium Park. Also known as ‘The Bean’ it’s a mirrored sculpture and is a popular shot for your Instagram feed! Take a tour around Wrigley Field, one of the oldest ballparks in the nation, you may be lucky enough to catch a game! Discover the dynamic dining scene when you visit Chicago, and you mustn’t leave without trying a Chicago style hotdog, of course! As you tour the city you can’t miss the iconic sounds of Jazz music playing around every corner.

When is the best time to visit Chicago, Illinois?

Whether you’re visiting in the hot summer or the chillier months through the winter, there’s a different adventure to be had, giving you a new experience of Chicago with each visit. Winter brings picturesque snow and summers undeniably hot, you can always find a cool spot by the lake. 

explore the road trips that visit Chicago, Illinois below...

End of the Trail Route 66 Sign, Santa Monica

Route 66 Explorer

Visit Chicago, Pontiac, Springfield, St Louis, Oklahoma City, Amarillo, Albuquerque, Winslow, The Grand Canyon, Las Vegas, Joshua Tree NP, Palm Springs & Los Angeles

Pontiac Mural on Route 66, Illinois

Original Route 66

Chicago, Springfield IL, St. Louis, Springfield MO, Tulsa, Oklahoma City, Amarillo, Santa Fe, Petrified Forest National Park, Winslow, Meteor Crater, Oatman, Barstow, Los Angeles & more

Country Music in Nashville American Roadtrip Music Tour

American Music Tour

Visit Chicago, Louisville, Nashville, Natchez Trace Parkway, Muscle Shoals, Tupelo (Birthplace of Elvis), Memphis, Clarksdale, Historic Natchez & New Orleans

Chicago Skyline at night reflections on the water, Route 66 Holidays

Ultimate Route 66

Chicago, Springfield, St. Louis, Tulsa, Oklahoma City, Amarillo, Santa Fe, Monument Valley, Lake Powell, Antelope Canyon, Grand Canyon NP, Las Vegas, Palm Springs, Los Angeles & more

Route 66 road signs in the Route 66 and Highway 1

The Big Two

Chicago, St Louis, Oklahoma City, Amarillo, Albuquerque, Grand Canyon NP, Las Vegas, Los Angeles, Santa Barbara,Big Sur, Monterey, San Francisco & more

Mount Rushmore Monument, South Dakota, Northern Crossover USA

Northern Crossover

Boston, Niagara Falls, Chicago, Mount Rushmore, Devil's Tower, Yellowstone NP, Grand Teton NP, Lake Tahoe, Yosemite NP, Napa, San Francisco & more

get all the latest news and offers by signing up to our newsletter