A few suggestions to get the holiday planning process started
Soak up the creative energy of two musical cities
9 days, from £2,430 to £3,300
Experience two sides of Chicago: its iconic sites followed by its burgeoning music and food scene
9 days, from £2,505 to £3,475
Enjoy dinner alongside a jazz show at Andy’s Jazz Club in Chicago
15 days, from £2,600 to £3,800
Enjoy evenings in blues and jazz speakeasies in Chicago.
14 days, from £2,610 to £4,200
Escape the crowds and discover the lesser-known landscapes of the Golden State
13 days, from £2,740 to £4,170
Visit two of the most beautiful Great Lakes: Lake Michigan and Lake Superior
19 days, from £2,880 to £4,600
Sip on sour ales, co-fermented with sauvignon grapes, in Chicago
17 days, from £3,000 to £4,300
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
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
Practical advice and inspiration to help you prepare for your holiday
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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’.
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.
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.
Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
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
