Chicago Holidays
Chicago holiday ideas
A few suggestions to get the holiday planning process started
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The Musical Highway - From Chicago and Nashville to New Orleans and Austin
Pump up the volume on this tuneful two-week adventure along America’s musical highway, cruising through Chicago, Nashville, New Orleans and Austin
15 days, from £3100 to £5000
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Jazz, Rhythm and Blues - USA's Deep South by Train
Feel the rhythm of the Deep South on this 15-day train journey through its jazz, blues and country hotspots
15 days, from £3100 to £4550
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Discover The USA's Great Lakes - Shoreline Towns and Soulful Cities
Explore the USA’s Great Lakes over 14 days, including two of the most beautiful: Lake Michigan and Lake Superior
19 days, from £3450 to £5500
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Hops, Highways & Honky-tonks - A Craft Beer Road Trip Across the Midwest
Hit the road for 18 days of pints and pitstops in quirky towns from Chicago to Nashville
18 days, from £3600 to £5150
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Secrets of the Midwest - Chicago and the Great Lakes
Uncover the marvels of the Midwest on this 15-day exploration through one of America’s most humble regions
15 days, from £4600 to £6200
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Epic Route 66 Road Trip - From Chicago to Los Angeles
Trace a century of cross-country travel on this epic 23-day road trip along the iconic passage of Route 66
23 days, from £5150 to £7200
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24 Hours in Chicago
Why should you book a Chicago holiday with us?
The American Midwest has a staggering variety of sights to surprise and seduce. And the headline act is Chicago, the nerve centre of the region. Anyone looking to soak up culture won’t be disappointed. As the birthplace of the blues, it’s brimming with bars showcasing the latest talent and Chicago holidays are also renowned for their impressive architectural sights as designed by greats such as Frank Lloyd Wright and Frank Gehry. So why Original Travel? We have the knowledge and experience to plan every aspect of your stay so there’s nothing left to chance. Whether it’s the inside track on the best museums, tickets to the hottest sports games, or even directions to the tastiest hot dog stands, we have expert guides and a local concierge on the ground with the know-how to help you squeeze every last drop from your stay in the ‘Windy City’.
Need to know about Chicago
Chicago holidays are a chance to experience not only the city’s impressive music, architecture, art and food scenes, but to peel back the layers and see another, greener side that lies in wait. Many peaceful natural refuges can be found surrounding the urban centre; beaches fringed by dunes, expansive orchards and vineyards and the awe-inspiring landscapes of The Great Lakes. Be part of a crew on a Lake Michigan charter boat, ride the choppy waves and cast your line in an attempt to catch salmon and trout as the city skyline shimmers behind.
What is there to do in Chicago?
When it comes to planning your stay, Chicago holidays are anything but boring. Visit The Art Institute of Chicago and marvel at its extensive Impressionist collection; stroll along the Chicago Riverwalk and see murals and sculptures; get face to face with eagles, lions and crocodiles at Lincoln Park Zoo; taste the best noodles of your life in Chinatown or take a tour around the home of the Chicago Cubs at Wrigley Field. The city has 22 miles of shoreline that faces an expanse of blue so vast it looks like the sea, so watersports are also an excellent option during a holiday in Chicago. Whether you like to amp up the adrenaline on a kayak or jet ski, or you prefer things a little more low-key on a rowing boat or paddle board, there’s something to suit everyone.