Chicago and the East Coast in 17 days

Get to know Chicago and the East Coast with this 17-day itinerary

Chicago and the East Coast

Air New Zealand's alliance with United Airlines makes it easy to connect to New York and other East Coast cities. You can use the multistop booking feature to book every flight you need for your entire USA trip

17 days
1Chicago at leisure5 days
Boat cruise, Chicago, United States.

Here are some of the best things to do and see in Chicago. For more information, check out our Chicago your way itinerary.

  • Hop-on Hop-off Big Bus sightseeing day to orient yourself
  • Ascend the Skydeck for amazing 'glass box' views right under your feet
  • Eat a brownie at Palmer House, where it was originally created way back in 1893
  • Ride the Centennial Wheel at Navy Pier
  • Discover huge public art installations sprinkled though the CBD, an area known as The Loop
  • Cruise the Chicago River to admire the architecture
  • Visit the Art Institute of Chicago in Millennium Park
  • Catch a Broadway show at CIBC Theatre - all the big shows play here
  • See the dinosaurs and mummies at the Field Museum
  • Eat deep-dish pizza, which was invented in Chicago
  • Watch a live baseball game at Wrigley Field or NFL game at Soldier Field
  • Explore the ethnic neighbourhoods of Chicago, including Greek Town, Chinatown and Little Italy
  • Catch some comedy at Second City, where Bill Murray's career kicked off
  • Enjoy live blues and jazz music at numerous late night clubs
2New York, New York1 day
Central Park, New York, United States.
  • Take the two-hour United Airlines domestic flight to New York
  • Stay in Manhattan, because this city is almost entirely walkable
  • Explore Central Park on your first day. For kids, there's a zoo and playgrounds; for adults, lots of green space and a great walk around the lake
  • Find a place to watch the sunset. You can pay to head up the Empire State Building and admire the views or find a rooftop bar
  • There are more restaurants per capita in NYC than almost anywhere else in the world. Italian restaurants are a big part of the culture here - try Marea or Café Altro Paradiso
2The lights of Times Square1 day
New York at night, New York, United States.
  • There is so much to do in this area! Madame Tussauds NY, the Chrysler Building, Grand Central Terminal Building and the NYC Public Library are all worthy of Instagram space
  • Visit the High Line and walk along it. It's a park located on an old railway line; the river and city views are fantastic
  • In the evening, watch the lights come on and the characters come out of the woodwork. There's a riot of activity here
    2Art and history abound1 day
    • The Met! This museum alone could fill in an entire day, but there are others to discover as well - such as the Museum of the City of New York, the Guggenheim and MOMA. Pick a couple and devote the day to art appreciation
    • Broadway is filled with bright lights and blockbuster shows. Make sure you pre-book your ticket and head off to a night of live entertainment
      2Out and about on the water1 day
      Statue of Liberty, New York, United States.
      • The Staten Island Ferry departs every 15 minutes and it's free. It brings you close to the Statue of Liberty, and then drops you off at Staten Island
      • At Staten Island, take in the peaceful 9/11 memorial
      • Visit the 9/11 site for a sobering reminder of the lives lost, then head up the new World Trade Centre for a magnificent view
      • For dinner, try the iconic Nobu or Racines
      • After dark, walk over Brooklyn Bridge to watch the city lights sparkle
        2Shopping in the home of style1 day
        Shopping in New York, United States.
        • 5th Avenue, Bergdorf's, Barneys and Saks are all NY institutions and must be visited, even if only to admire the beautiful range of luxe clothing and shoes
        • Dover Street Market is a seven-floor department store offering avant-garde labels and excruciatingly hip clothing
        • If you're a book lover, Strand bookstore will keep you entertained for hours
        • Brooklyn Flea on Saturdays and Sundays sells crafts, clothing, collectibles and vintage pieces
          3Washington DC1 day
          Washington Capital Building, Washington DC, United States.
          • Catch a United Airlines domestic flight to Washington. The roads are easy to navigate and there's plenty of parking in DC
          • The Washington Memorial, the Lincoln Memorial, the National World War II Memorial, and the striking Vietnam War Memorial are all in the same area
          • In Alexandria, walk the streets and admire the beautiful traditional buildings. Have dinner at Gadsby's, an authentic colonial restaurant with a long history
          3Museums in the National Mall1 day
          Washington DC, United States.
          • You will need to book some of these in advance online. All the museums are centred around the National Mall. Highly recommended is the Holocaust Memorial, for insight into the staggering suffering and injustice of WWII
          • Walk past the White House (although it has high fences around it now) and visit Capitol Hill. Washington is like a game of 'spot the destination I've seen on TV'
          • Eat at some of the incredible food carts. They are everywhere and cover every cuisine
          • Visit the Newseum, the Smithsonian National Air & Space Museum, The Smithsonian Institute (which looks like Hogwarts), the National Museum of African American Art or the Smithsonian National Museum of American History
          • The Smithsonian National Museum of Natural History offers a live butterfly encounter, which is a beautiful break from the seriousness of Washington
            3Wider Washington DC1 day
            • Head to the Washington National Cathedral. It's where Dr Martin Luther King gave his final Sunday service before his assassination
            • You could also visit George Washington's home in Mount Vernon, for a slice of his very famous life
            • Visit Annapolis for a crab dinner. Cantler's is the local haunt, with tables covered in paper, steamed crabs served by the bucket and hush puppies (maize cakes) on the side
              4Boston1 day
              Boston Quincy Market, Boston, United States.
              • Catch a United Airlines domestic flight to Boston - just one hour in the air
              • One of the oldest cities in the USA and the site of many significant events, there is plenty of history to discover here
              • Walk the 4km Freedom Trail to visit 16 significant sites, including Paul Revere's house
              • Along the walk, you'll come across Faneuil Hall Marketplace. Grab a bite to eat at any of the Quincy Market stalls and investigate the pushcart wares
              • Try Boston cream pies at Omni Parker House and clam chowder at Legal Sea Foods
              4Watch a baseball game at Fenway Park1 day
              Public gardens, Boston, United States.
              • Eat a hotdog and join the locals at a Red Sox game, or just have a beer at The Bleacher Bar
              • Head to Beacon Street and visit 'Cheers' Bar, the original bar where the TV series was filmed
              • Wander around Boston Public Gardens, opposite Cheers. There's plenty to see in this green peaceful area
              • Eat a famous brown butter lobster roll at Eventide Fenway. A simple but utterly delicious meal
                4Boston museums and libraries1 day
                • The Boston Public Library has free guided tours. Discover exhibitions in the Map Room, great architecture and art
                • The Museum of Fine Arts has one of the most comprehensive art collections in the world, with Asian, Egyptian and early American art
                • At the Boston Tea Party Ship and Museum, actors play their way through the events of 230 years ago. Live history!
                • The John F. Kennedy Presidential Museum explores the Kennedy-Nixon debate, the space programme and the Cuban Missile Crisis
                • Attend an evening performance by the Boston Pops Choir and Boston Symphony
                  4Sip it and see1 day
                  • Stroll around Arnold Arboretum, which has 265 acres of beautiful gardens
                  • Take a free tour at the Samuel Adams Brewery. Taste the grains that make the beers, and then try the beers themselves
                  • Boston's first craft distillery, Bully Boy Distillers, produces vodka, gin, white rum, and more. The tour includes free tastings as well as a lesson on their history
                  • Salumeria Italiana is one of the most popular Italian restaurants in a city filled with Italian food! 

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