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U.S. City Breaks: Chicago

  • Chicago - John Hancock Observatory night view ©John Hancock Observatory

    USA, US city break, Illinois, Chicago, Magnificent Mile
  • Chicago - John Hancock Observatory ©John Hancock Observatory

    USA, US city break, Illinois, Chicago, Hancock Tower
  • Skyline of Chicago ©City of Chicago, Choose Chicago

    Skyline of Chicago
5 day tour
Prices available on request

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.

For more tours to the USA, please click here.


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.


Greatdays Holidays Limited has an ATOL licence (4279) and many of the flights and flight-inclusive holidays on this website are financially protected by the ATOL scheme. But ATOL protection does not apply to all holiday and travel services listed on this website. Please ask us to confirm what protection may apply to your booking. If you do not receive an ATOL Certificate then the booking will not be ATOL protected. If you do receive an ATOL Certificate but all the parts of your trip are not listed on it, those parts will not be ATOL protected. Please see our booking conditions for information, or for more information about financial protection and the ATOL Certificate go to: www.atol.org.uk/ATOLCertificate Our website policy is to use only copyright free images or images which have been authorised to us for free use by the owner. If you consider an image to be unauthorised or to be your property, please contact us immediately and if valid we will have the image removed. If your image requires crediting or is missing a copyright statement then we will be pleased to add this to the webpage, contact us at info@greatdays.co.uk Tour will run with a minimum of 10 passengers. Picture is for illustrative purposes only. Greatdays Holidays Limited has an ATOL licence (4279) and all of our air package tours are protected under this licence. In the unlikely event of our insolvency, the Civil Aviation Authority will ensure that you are not stranded abroad and will arrange to refund any monies you have paid to us for an advance booking. All the flights and flight-inclusive holidays on this email are financially protected by the ATOL scheme. When you pay you will be supplied with an ATOL Certificate. Please ask for it and check to ensure that everything you booked (flights, hotels and other services)

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