U.S. City Breaks: Chicago
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Chicago - John Hancock Observatory night view ©John Hancock Observatory
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Chicago - John Hancock Observatory ©John Hancock Observatory
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Skyline of Chicago ©City of Chicago, Choose Chicago
Join us on this US city break where you’ll be blown away by Chicago, the Windy City. Whether it is the stunning skyscrapers or Picasso-inspired street art, you’re sure to be gawping at this city. Begin your adventure by taking in all the sights from the highest point in Chicago. It’s hard to beat the dramatic experience of the observation deck and with a recommended evening trip, watch the sunset whilst indulging in the views and perhaps, with a glass of Prosecco.
A trip to Chicago isn’t complete without seeing Lake Michigan. This gigantic Lake is a key resource as well as a perfect viewing point of the city. Perhaps cruise along the waterfront while enjoying panoramic views of the iconic skyline. It’ll blow you away. Chicago isn’t just about the views, there’s deeper connection to the history to this relatively young country. During the infamous prohibition era of 1920s, Chicago had a booming underground scene of bootleg liquor and speakeasies.
As well as this, we can take you to the heart of Downtown, Chicago; the home of the Magnificent Mile: a scenic stretch considered one the great retail boulevards in the world. Perhaps take a guided tour to gauge the historical context of this boulevard. Head downtown in this food-fuelled city and try six of the Windy City’s quintessential staples. Visit local restaurants and speciality food shops including the oldest family run-establishment in Chicago.
Lastly, why not go Dutch? Take this opportunity to experience a day like no other with a day trip from Chicago to Holland, MI. Here, you may wish to visit the Veldheer Tulip Gardens, where 5 million of the flowers explode into bloom each spring. As well as this, try the homely restaurants and visit the picturesque parks, which will be sure to give you a relaxing end to your trip.
There’s a whole host of additional delights of Chicago to discover – perhaps head to Wrigley Field, home of the Chicago Cubs, for some baseball or for a floral fantasy, visit the Botanical gardens. This city has so much to offer, and with a tour tailored to your interests, you’re sure to fall in love with it.
Dates
Dates on request
Day 1
Arrive in Chicago
Arrive in Chicago and what better way to get your bearings of the Windy City than to head to the skies. When it comes to the best views in Chicago, it’s hard to beat the city’s dramatic observation decks. Experience this magnificence with a beautiful sunset – a perfect beginning to your Chicago adventure. Upgrade your experience with a glass of Prosecco on arrival.
Day 2
Lake Michigan and Prohibition Tour
Start today with more incredible views, this time from Lake Michigan. Cruise along the waterfront enjoying a panorama of this iconic skyline. Along the way, enjoy informative narration and perhaps take advantage of the onboard bar.
Attention all Gatsby Boys and Flapper Fashion girls, if you are looking for an in-depth and informative yet fun tour of Chicago’s prohibition era, this is the tour for you. Chicago has long been known as the speakeasy capital, known for its booming underground movement. With visits to Chicago’s historic bars that have been in operation since the infamous era, you will get the chance to hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. As well as this, you can try the recommended craft cocktails and signature drinks of the 1920s.
Day 3
Chicago Downtown: Shopping, Food and History
Located in the heart of Downtown Chicago, the Magnificent Mile is a scenic stretch loved by tourists and locals alike, and considered one of the great retail boulevards in the world. A guided tour takes you to all the best shops for some retail therapy as well as providing you with local historic knowledge. Unveil the history of the street’s significant locations, standing here for over 344 years.
When you think of Chicago, deep dish pizzas spring to mind! However, this city’s food culture is much vaster. Try six of the Windy City’s quintessential staples from local restaurants and speciality food shops including the oldest family run-establishment in Chicago. Taste local favourites including deep-dish pizza, of course, but also Chicago Italian Beef Sandwich and chocolate. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
Later, perhaps head to the award-winning Millennium Park, known as the front lawn of Downtown Chicago. This beautiful space is free to enter and features art as well as free concerts and yoga classes.
Day 4
Holland, MI
Fancy going Dutch? Take this opportunity to experience a day like no other with a day trip from Chicago to Holland, MI. Calvinist separatists arrived from the Netherlands in the mid-19th century, to the town of Holland, and this town continues to celebrate its Dutch heritage. Here, you may wish to visit the Veldheer Tulip Gardens, where 5 million of these beautiful flowers explode into bloom each spring. When hunger hits, make your way downtown for lunch and a beer at New Holland Brewing, one of the Midwest’s best-loved brewpubs. Not sure what to sip on? Look for limited-release variations on brewery favourite Dragon’s Milk, a bourbon barrel-aged stout, featuring quirky ingredients like maple coffee and peanut butter. To finish of the excursion, why not take a leisurely stroll around Windmill Island Gardens, a picturesque park centred around a 250-year-old Dutch windmill purchased by Holland residents in the 1960s.
Day 5
Departure
Leave Chicago behind and transfer to the airport for your return flight to the UK.
