36 days in Chicago & New York City Itinerary

36 days in Chicago & New York City Itinerary

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Route & dates

36 days in Chicago & New York City Itinerary

Start: New York City
bus + Fly:  4​h 45​min
1
Chicago
— 16 nights
Fly + bus:  4​h 45​min
2
New York City
— 18 nights
End: New York City

16
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: Whihala Beach Co Park (in Whiting), Anderson Japanese Gardens (in Rockford) and Elawa Farm (in Lake Forest). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, meet the residents at Shedd Aquarium, admire the landmark architecture of Skydeck Chicago - Willis Tower, and appreciate the extensive heritage of Millennium Park.

To see other places to visit, maps, traveler tips, and more tourist information, use the Chicago route tool .

New York City to Chicago is an approximately 5-hour combination of bus and flight. You can also fly; or drive. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. In August, plan for daily highs up to 83°F, and evening lows to 67°F. Wrap up your sightseeing on the 31st (Fri) early enough to travel to New York City.

Things to do in Chicago

#Parks, #Outdoors, #Museums

Side Trips

Oak Park, Saint Joseph, Elawa Farm, Anderson Japanese Gardens, Kernel's Gourmet Popcorn & More
Highlights from your plan
Bengtson's Pumpkin Farm ©
Bengtson's Pumpkin Farm
The Art Institute of Chicago ©
The Art Institute of Chicago
Wrigley Field ©
Wrigley Field

18
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.
Explore the numerous day-trip ideas around New York City: Bronx (Bronx Zoo & Yankee Stadium). And it doesn't end there: take in the pleasant sights at Central Park, pause for some photo ops at Statue of Liberty National Monument, take in panoramic vistas at Empire State Building, and admire the landmark architecture of Grand Central Terminal.

To find photos, ratings, other places to visit, and tourist information, you can read our New York City visit planner.

Getting from Chicago to New York City by combination of flight and bus takes about 5 hours. Other options: fly; or drive. The time zone difference when traveling from Chicago to New York City is 1 hour. In September in New York City, expect temperatures between 80°F during the day and 66°F at night. Finish your sightseeing early on the 19th (Wed) so you can travel back home.

Things to do in New York City

#Museums, #Parks, #Tours

Side Trips

Bronx, Brooklyn Botanic Garden
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Empire State Building ©
Empire State Building

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