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Chicago & New York Twin Centre Holiday

8 days from £1,125pp

Combine the relaxed city pace of a Chicago holiday with the vibrant and exciting hustle and bustle of a New York holiday. Explore the sights, museums, galleries, fascinating architecture and lakefront beaches that only Chicago can offer. Afterwards, fly on to the Big Apple and take in Manhattan. Shop along Fifth Avenue, see the panoramic views atop the Empire State Building, the list goes on…!

Holiday Highlights

  • There's no better way to see Chicago than by taking a ride 103 floors up the Willis Tower to the Skydeck for 360 degree view of the city.
  • Take a helicopter ride at sunset over New York City and watch Times Square come alive by night by air.
  • Plan a trip to Woodbury Common from New York where over 220 designer and retail shops and eateries await the avid shopper

Remember, we can tailor-make your twin centre holiday to suit your needs, contact our travel experts today, call us on 0208 290 9751.

Holiday Map

  • 41.878114
  • -87.629798
  • 4

Detailed Itinerary

Day 1: London – Chicago

First stop on this USA cities twin centre holiday is Chicago. As your flight arrives the same day, there’s ample time to drop your bags off at the hotel and to head out into the city. Why not enjoy sunset over Millennium Park or perhaps take in dinner at the Hard Rock Café where memorabilia by Eric Clapton and Ray Charles are on show? Stay 3 nights at the Doubletree by Hilton Chicago Magnificent Mile (or similar).

Day 2-3: Chicago

Sitting pretty along Lake Michigan, spend your days discovering the many attractions of the Windy City, from the aerial views from the John Hancock Observatory or the Skydeck in the Willis Tower, to the captivating art pieces dotted around Millennium Park, including the iconic Bean sculpture. Shop till you drop along Michigan Avenue with its Magnificent Mile of designer to boutique shops; enjoy classic Chicago cuisines, from the deep dish pizza to the original hot dog; explore the long stretch of shoreline where sandy beaches are waiting to be discovered; and no trip is complete without experiencing Chicago’s electric blues scene.

Day 4: Chicago – New York

Today, leave behind the relaxed pace of Chicago and be prepared to get immersed in the frenetic energy that New York City has to offer. Why not head down to the Meatpacking district and hang with the cool crowd, due to its selection of boutique shops and chic bars and restaurants. Stay 3 nights at the Holiday Inn New York City Midtown  - 57th Street (or similar).

Day 5-6: New York

You’ve seen the film, now it’s time to see the Big Apple for yourself! From the excitement of Times Square and the shows of Broadway to the tranquil expanse of Central Park, there’s something for everyone to see. Hop on a ferry to see the Statue of Liberty, head to the top of the The Empire State Building to take in the aerial views, shop along Fifth Avenue for its designer shops, then head down to Soho for the quirky boutique finds. Discover the arts of the Guggenheim and MoMa, and dine out NYC style, from the classic pizza joints to Michelin star restaurants – be sure to pack it all in!

Day 7: New York – London

Bid farewell to your discovery of the USA’s iconic cities today, as you head back to the airport to catch your overnight flight back to London.

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Included in your Twin Centre Holiday

  • Hotel accommodation
  • Economy flights
  • Airport taxes, fuel & duty
  • Car rental where stated
  • Any applicable offers

Not included: Airport transfers, meals, sightseeing & personal expenses

Flights from regional UK airports available

Remember, we can tailor-make your holiday to suit your needs, contact our travel experts today, call us on 0208 290 9751.



Deposits from £59pp 

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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:

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