18 days in New York City & Chicago Itinerary

18 days in New York City & Chicago Itinerary

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Route & dates

18 days in New York City & Chicago Itinerary

Petra - Wadi Musa
Fly:  28​h
New York City
— 10 nights
bus + Fly:  4​h 45​min
Chicago
— 5 nights
Fly:  32​h
Petra - Wadi Musa

10
days
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.
Satisfy your inner culture vulture at Times Square and The Metropolitan Museum of Art. Step out of the city life by going to Long Beach and Fire Island National Seashore. Change things up with these side-trips from New York City: Rockaway Beach (in Far Rockaway), Belmar Beach (in Belmar) and Gateway National Recreation (in Sandy Hook). Next up on the itinerary: make a trip to Fifth Avenue, appreciate the history behind 9/11 Memorial, head off the coast to Roosevelt Island, and enjoy breathtaking views from Empire State Building.

To find photos, reviews, traveler tips, and tourist information, read our New York City trip itinerary builder.

Petra - Wadi Musa, Jordan to New York City is an approximately 28-hour flight. The time zone difference when traveling from Petra - Wadi Musa to New York City is minus 8 hours. In December in New York City, expect temperatures between 11°C during the day and 3°C at night. Wrap up your sightseeing by early afternoon on the 24th (Sun) to allow enough time to travel to Chicago.

Things to do in New York City

Sightseeing Parks Beaches

Side Trips

Rockaway Beach, Fire Island National Seashore, Gateway National Recreation, Belmar Beach, Jones Beach State Park
Highlights from your plan
The Metropolitan Museum of Art
Times Square
9/11 Memorial

5
days
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Satisfy your inner culture vulture at The Art Institute of Chicago and Swedish American Museum. Take a break from the city and head to Grand Mere State Park and Chicago River. Get out of town with these interesting Chicago side-trips: Silver Beach County Park (in Saint Joseph) and Centennial Beach (in Naperville). The adventure continues: don't miss a visit to The Magnificent Mile, appreciate the extensive heritage of Millennium Park, explore the activities along Lake Michigan, and enjoy the sand and surf at Oak Street Beach.

To see maps, reviews, where to stay, and more tourist information, refer to the Chicago travel planner.

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Other options are to drive; or take a bus. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Traveling from New York City in December, things will get slightly colder in Chicago: highs are around 4°C and lows about -2°C. Finish your sightseeing early on the 29th (Fri) to allow enough time to travel back home.

Things to do in Chicago

Parks Beaches Outdoors

Side Trips

Silver Beach County Park, Lake Michigan, Centennial Beach, Grand Mere State Park
Highlights from your plan
Grand Mere State Park
The Art Institute of Chicago
The Magnificent Mile

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