32 days in New York City & Chicago Itinerary

32 days in New York City & Chicago Itinerary

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Route & dates

32 days in New York City & Chicago Itinerary

Start: Dammam
Fly + Drive:  28​h
1
New York City
— 16 nights
bus + Fly:  4​h 45​min
2
Chicago
— 13 nights
Fly:  29​h
End: Dammam

16
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.
You'll visit kid-friendly attractions like Central Park and Bronx Zoo. Change things up with a short trip to Yankee Stadium in Bronx (about 32 minutes away). There's still lots to do: admire the masterpieces at The Metropolitan Museum of Art, take in the pleasant sights at Times Square, take in panoramic vistas at Empire State Building, and pause for some photo ops at 9/11 Memorial.

For ratings, other places to visit, traveler tips, and tourist information, read our New York City trip itinerary planner .

Dammam, Saudi Arabia to New York City is an approximately 28-hour flight. The time zone changes from Arabia Standard Time to Eastern Standard Time, which is usually a -8 hour difference. Expect cooler weather when traveling from Dammam in June: highs in New York City hover around 31°C, while lows dip to 21°C. Wrap up your sightseeing on the 1st (Mon) to allow time to travel to Chicago.

Things to do in New York City

Museums Parks Tours

Side Trips

Bronx, Brooklyn
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Statue of Liberty National Monument ©

13
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Bring the kids along to Museum of Science and Industry and Wrigley Field. Get out of town with these interesting Chicago side-trips: Saint Joseph (Whirlpool Compass Fountain & Silver Beach Carousel), First Division Museum at Cantigny (in Wheaton) and Weko Park (in Bridgman). Next up on the itinerary: observe the fascinating underwater world at Shedd Aquarium, enjoy breathtaking views from Skydeck Chicago - Willis Tower, take in the waterfront at Navy Pier, and get your game on at Escape Artistry.

To see more things to do, reviews, photos, and more tourist information, read our Chicago itinerary builder .

Do a combination of bus and flight from New York City to Chicago in 5 hours. Alternatively, you can fly; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Traveling from New York City in July, Chicago is little chillier at night with lows of 22°C. On the 14th (Sun), you're off tohome.

Things to do in Chicago

Parks Museums Historic Sites

Side Trips

Oak Park, Saint Joseph, South Bend, Matt's Produce, Whiskey Acres Distilling Co.
Highlights from your plan
Escape Artistry ©
Escape Artistry
Museum of Science and Industry ©
Museum of Science and Industry
Lincoln Park Zoo ©
Lincoln Park Zoo

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