12 days in New York City, Chicago & Kansas City Itinerary

12 days in New York City, Chicago & Kansas City Itinerary

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Route & dates

12 days in New York City, Chicago & Kansas City Itinerary

Start: New York City
1
New York City
— 2 nights
bus + Fly:  4​h 45​min
2
Chicago
— 6 nights
+2
Fly + foot + bus:  4​h 30​min
3
Kansas City
— 3 nights
Fly:  6​h 30​min
End: New York City

2
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.
Step off the beaten path and head to Food Tours and New York Public Library. There's much more to do: admire all the interesting features of Central Park, enjoy breathtaking views from Empire State Building, make a trip to Statue of Liberty National Monument, and browse the eclectic array of goods at Chelsea Market.

For other places to visit, maps, photos, and more tourist information, read New York City road trip planning website .

The Route module can give you travel options from your home to New York City. In May, daytime highs in New York City are 69°F, while nighttime lows are 55°F. Wrap up your sightseeing on the 20th (Mon) to allow time to travel to Chicago.

Things to do in New York City

Parks Museums Tours
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Statue of Liberty National Monument ©

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Discover out-of-the-way places like Starved Rock State Park and Cowles Bog. Venture out of the city with trips to Saint Joseph (Silver Beach County Park, Whirlpool Compass Fountain, & more), Garwood Orchards (in LaPorte) and Baker Lake Park (in Peru). There's much more to do: admire the majestic nature at Shabbona Lake State Park, explore and take pictures at Wrigley Field, pause for some photo ops at Cloud Gate, and don't miss a visit to Millennium Park.

For traveler tips, other places to visit, photos, and other tourist information, use the Chicago trip planner .

Do a combination of bus and flight from New York City to Chicago in 5 hours. Alternatively, you can fly; or drive. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. In May, daytime highs in Chicago are 71°F, while nighttime lows are 52°F. Finish your sightseeing early on the 26th (Sun) to allow enough time to travel to Kansas City.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Saint Joseph, Cowles Bog, Starved Rock State Park, Baker Lake Park, Shabbona Lake State Park
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Silver Beach Carousel ©
Silver Beach Carousel
Wrigley Field ©
Wrigley Field

3
nights
Kansas City

The largest municipality in Missouri, Kansas City has an impressive array of world-class museums, shopping areas, and great places to eat, all of which attract tourism to the area.
On the 27th (Mon), have fun and explore at Kaleidoscope, test your problem-solving skills at popular escape rooms, and then identify plant and animal life at Burr Oak Woods Conservation Area. On the 28th (Tue), you'll have a packed day of sightseeing: stop by Moon Marble Company, have some family-friendly fun at iFLY Indoor Skydiving - Kansas City, and then get your game on at Blade & Timber.

For other places to visit, where to stay, more things to do, and tourist information, go to the Kansas City itinerary planning tool .

Getting from Chicago to Kansas City by combination of flight and bus takes about 4.5 hours. Other options: do a combination of subway, bus, and flight; or drive. Expect a daytime high around 76°F in May, and nighttime lows around 57°F. Wrap up your sightseeing by early afternoon on the 29th (Wed) to allow enough time to travel back home.

Things to do in Kansas City

Fun & Games Museums Wildlife

Side Trips

Burr Oak Woods Conservation Area, Blade & Timber, Moon Marble Company, iFLY Indoor Skydiving - Kansas City
Highlights from your plan
Room Escape Games
Moon Marble Company ©
Moon Marble Company
Kaleidoscope ©
Kaleidoscope

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