25 days in New York City, Boston & Chicago Itinerary

25 days in New York City, Boston & Chicago Itinerary

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Route & dates

25 days in New York City, Boston & Chicago Itinerary

Start: Auckland
Fly:  22​h 30​min
1
New York City
— 8 nights
bus + Fly:  3​h
2
Boston
— 7 nights
Fly:  4​h
3
Chicago
— 8 nights
Fly:  20​h 15​min
End: Auckland

8
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Head to Fifth Avenue and SoHofor plenty of shopping. Relax by the water at Cupsogue Beach County Park and Sasko Beach. Explore the numerous day-trip ideas around New York City: Great Neck Steppingstone Park (in Great Neck), Joel L. Lefkowitz Park at West Meadow Beach (in Stony Brook) and Lido Beach (in Lido Beach). Next up on the itinerary: make a trip to Central Park, explore the galleries of The Metropolitan Museum of Art, admire the striking features of Grand Central Terminal, and take in panoramic vistas at Empire State Building.

For photos, reviews, and other tourist information, use the New York City day trip planning site .

Auckland, New Zealand to New York City is an approximately 22.5-hour combination of flight and bus. You can also fly; or do a combination of flight and train. The time zone difference moving from New Zealand Standard Time to Eastern Standard Time is minus 17 hours. When traveling from Auckland in September, plan for much warmer days in New York City, with highs around 31°C, while nights are somewhat warmer with lows around 22°C. Wrap up your sightseeing on the 12th (Thu) to allow time to travel to Boston.

Things to do in New York City

Parks Beaches Outdoors

Side Trips

Lido Beach, Joel L. Lefkowitz Park at West Meadow Beach, Sasko Beach, Great Neck Steppingstone Park, Cupsogue Beach County Park
Highlights from your plan
Central Park ©
Central Park
Times Square ©
Times Square
Fifth Avenue ©
Fifth Avenue

7
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Visit Nauset Beach and Corporation Beach for some beach relaxation. Shop till you drop at Newbury Street and Addison Art Gallery. Get out of town with these interesting Boston side-trips: Mayflower Beach (in Dennis), Eastham (Nauset Light Beach & Coast Guard Beach) and Sydenstricker Glass Galleries (in Brewster). There's lots more to do: enjoy the sand and surf at Chatham Lighthouse Beach, tour the pleasant surroundings at Craigville Beach, and look for gifts at Brookline Booksmith.

To see photos, traveler tips, where to stay, and more tourist information, refer to the Boston vacation planner.

Traveling by combination of bus and flight from New York City to Boston takes 3 hours. Alternatively, you can fly; or drive. Expect slightly colder temperatures when traveling from New York City in September; daily highs in Boston reach 28°C and lows reach 17°C. Finish your sightseeing early on the 19th (Thu) to allow enough time to travel to Chicago.

Things to do in Boston

Beaches Outdoors Parks

Side Trips

Eastham, Dennis, Orleans, Chatham Lighthouse Beach, Brookline Booksmith
Highlights from your plan
Nauset Beach ©
Nauset Beach
Coast Guard Beach ©
Coast Guard Beach
Nauset Light Beach ©
Nauset Light Beach

8
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
For shopping fun, head to The Magnificent Mile or West Allis Farmers Market. We've included these beaches for you: Atwater Park & Beach and Rosewood Beach. Explore the numerous day-trip ideas around Chicago: Illinois Holocaust Museum & Education Center (in Skokie), Whiskey Acres Distilling Co. (in DeKalb) and Whihala Beach (in Whiting). The adventure continues: admire the masterpieces at The Art Institute of Chicago, tour the pleasant surroundings at Kathy Osterman Beach, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and stroll around Silver Beach County Park.

For maps, photos, reviews, and other tourist information, use the Chicago travel itinerary planner .

Traveling by flight from Boston to Chicago takes 4 hours. Alternatively, you can do a combination of bus and flight; or drive. The time zone difference when traveling from Boston to Chicago is minus 1 hour. In September, plan for daily highs up to 30°C, and evening lows to 19°C. Finish your sightseeing early on the 27th (Fri) so you can travel back home.

Things to do in Chicago

Parks Beaches Outdoors

Side Trips

Skokie, Silver Beach County Park, ZumBier, Atwater Park & Beach, Weko Park
Highlights from your plan
Whiskey Acres Distilling Co. ©
Whiskey Acres Distilling Co.
The Magnificent Mile ©
The Magnificent Mile
Whihala Beach ©
Whihala Beach

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