Chicago Holidays

Inspiration for your own tailor-made trip

America’s ‘Windy City’ has plenty to impress. With its mighty skyline, vast lakes and swinging blues music scene, a holiday in Chicago is guaranteed to blow you away. Chicago holidays are all about culture and art; home to Hemingway, its very own blend of soulful blues and a generous spattering of high-flying architecture from Frank Gehry's futuristic Pritzker Pavilion to Frank Lloyd Wright's stained-glass Robie House, Chicago is nothing short of a cultural treasure trove. Wander along the streets and stop to admire whimsical public art or duck into one of the many art museums housing everything from impressionist masterpieces to psychedelic paintings. As well as culture, the city boasts an eclectic array of nature from long stretches of coastline studded with beaches and recreational areas to hills blanketed in orchards and vineyards. And don’t miss a visit to The Great Lakes - so vast they could be mistaken for inland seas; explore quaint resort towns, climb substantial sand dunes and stop off to snap a shot of a picturesque lighthouse.
Sort

Art, Architecture and Music in the Midwest - Discovering Detroit and Cleveland

Soak up the creative energy of two musical cities

9 days, from £2,430 to £3,300

On the Shores of Lake Michigan - Chicago and Saugatuck

Experience two sides of Chicago: its iconic sites followed by its burgeoning music and food scene

9 days, from £2,505 to £3,475

Jazz, Rhythm and Blues - USA’s Deep South by Train

Enjoy dinner alongside a jazz show at Andy’s Jazz Club in Chicago

15 days, from £2,600 to £3,800

The Musical Highway - From Chicago and Nashville to New Orleans and Austin

Enjoy evenings in blues and jazz speakeasies in Chicago.

14 days, from £2,610 to £4,200

An Alternative Californian Road Trip from San Francisco to Napa Valley

Escape the crowds and discover the lesser-known landscapes of the Golden State

13 days, from £2,740 to £4,170

Discover The USA's Great Lakes

Visit two of the most beautiful Great Lakes: Lake Michigan and Lake Superior

19 days, from £2,880 to £4,600

Craft Beer Crawl of the Midwest USA

Sip on sour ales, co-fermented with sauvignon grapes, in Chicago

17 days, from £3,000 to £4,300

A Musical Journey through the Deep South - from Chicago to New Orleans

A wonderful road trip from Illinois to the Deep South, set to a blues, country and rock soundtrack

15 days, from £3,860 to £5,270

Secrets of the Mid West - Chicago and the Great Lakes

A large loop around Lake Michigan travelling through Chicago, Wisconsin and Michigan, Lake Superior and Lake Huron

15 days, from £3,860 to £5,180

Chicago to San Francisco - the Great US Train Journey

Glide through the Midwest Plains, Rockies and Colorado Rapids all the way to the American West on board the iconic California Zephyr

10 days, from £4,185 to £5,270

Epic Route 66 Road Trip from Chicago to Los Angeles

Choose which vehicle you’ll be travelling over 2,000 miles in, be it a sleek convertible or an iconic Harley Davidson

23 days, from £4,305 to £6,000

100% tailor-made holidays

Understanding Your Needs

Our team of destination experts will get to know you and your unique requirements for your holiday

Personalisation

We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities

Our Services

All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges