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
1Chicago5 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 Lockwood Express café in Palmer House Hotel – the recipe was created in the hotel's kitchen 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 The Second City, where Bill Murray's career kicked off
  • Enjoy live blues and jazz music at numerous late night clubs
2New York City5 days
Central Park, New York, United States.

Take the two-hour United Airlines domestic flight to New York. We recommend you stay in Manhattan, because this city is almost entirely walkable. Our suggested five-day itinerary is action-packed. To avoid burn out, just pick the attractions and activities that appeal to you.

Options for arrival day

  • Explore Central Park - 843 acres of lawns, woodlands, parks, ponds and history. 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. Either pay to head up the Empire State Building or find a rooftop bar
  • Eat Italian. Try Marea or Café Altro Paradiso, if you want high style; Malatesta Trattoria or Bigoi Venezia, if you're on a budget

Ideas for Times Square day

  • 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
    Ideas for art and history 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

Ideas for Staten Island and 9/11 day

  • 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 you'll find 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 for extraordinary Japanese
  • A cheap dinner option is Rowdy Rooster for an Indian fried chicken sandwich
  • After dark, walk over Brooklyn Bridge to watch the city lights sparkle

Ideas for a shopping day

  • 5th Avenue, Bergdorf's, Barneys and Saks are iconic New York stores for high style
  • For big brands and little prices, check out Jacks in 32nd Street or Lot-Less in 40th Street
  • Dover Street Market is a seven-floor department store offering avant-garde labels and 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
  • NoLita (North of Little Italy) is a super-cool area for unique boutiques and socially-responsible shopping
3Washington DC3 days
Washington Capital Building, Washington DC, United States.

Catch a United Airlines domestic flight to Washington DC. We recommend you stay downtown, handy to the White House. Many Washingtonians walk, bike or scoot to get around, but there's also an efficient public transport system.

Ideas for arrival day

  • 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 Tavern, an authentic colonial fine dining restaurant with a long history
  • For a less-expensive meal, head into Chinatown

Ideas for White House and museum day

  • Walk past the White House and visit Capitol Hill. Washington is like a game of 'spot the destination I've seen on TV'
  • Take your pick from 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
  • Highly recommended is the Holocaust Memorial Museum, which remembers survivors and victims of WWII Nazi persecution
  • While you're musing around the museums, eat at some of the incredible food carts. They are everywhere and cover every cuisine
  • Later, try a chili-smothered half-smoke at Ben's Chili Bowl or wood-smoked barbecue at Federalist Pig

Ideas for a wider-Washington day

  • Head to the Washington National Cathedral, where Dr Martin Luther King gave his final Sunday service before his assassination
  • Just across the Potomac River from Washington DC is Arlington National Cemetery, where you can see JFK's gravesite and the Tomb of the Unknown Soldier
  • You could also visit George Washington's home in Mount Vernon, for a slice of his very famous life
  • Stroll around Annapolis to admire Palladian-inspired Georgian architecture. Famous historic residences to visit include Hammond-Harwood House, William Paca House and Chase-Lloyd House
  • Enjoy a crab dinner at Cantler's Riverside Inn in Annapolis. As well as soft-shell and hard-shell crab, they serve clams, shrimp, mussels and rockfish
4Boston4 days
Boston Quincy Market, Boston, United States.

Catch a United Airlines domestic flight to Boston - just one hour in the air. Staying in the downtown area gives you easy access to the 4km Freedom Trail, which connects 16 historic sites.

  • Stretch your legs after arrival by walking some of the Freedom Trail. Famous sites include Paul Revere House, Boston Massacre site, Bunker Hill, Bosto Common and Old State 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

Ideas for a Fenway Park day

  • Grab 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
  • Stroll around the Cottage Farm Historic District, an area of incredible heritage homes that's associated with Amos Adams Lawrence, a key player in the abolitionist movement.
  • Eat a famous brown butter lobster roll at Citizen Public House & Oyster Bar or Summer Shack

Ideas for a museums and libraries day

  • Donuts for breakfast from Union Square Donuts – choices include oatmeal cream pie, sea salt whiskey caramel, brown butter hazelnut crunch and maple bacon
  • 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

Ideas for a drink-appreciation day

  • Explore the menu at The Friendly Toast - chicken & waffles, Irish benny and churro bites are just a few of the delicious choices
  • Stroll around Arnold Arboretum, which has 265 acres of beautiful gardensTake a free tour at the Samuel Adams Brewery. Taste the grains that make the beers, and then try the beers themselves – they have about 15 on tap
  • 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
  • La Famiglia Giorgio's and Giacomo's are a couple of the most popular Italian eateries in a city filled with Italian food!

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    The Chicago Theatre image courtesy of Nigel Rliorm