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.
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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

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

Secrets of the Midwest - Chicago and the Great Lakes

Discover architecture, culture and history in the vibrant lakeside cities of Chicago and Milwaukee

15 days, from £3,860 to £5,180

Epic Route 66 Road Trip - Chicago to Los Angeles

Self-drive through eight states between Chicago and LA: Illinois, Missouri, Oklahoma, Texas, New Mexico, Arizona, Nevada and California

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