16 days in Chicago & New York City Itinerary

16 days in Chicago & New York City Itinerary

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Route & dates

16 days in Chicago & New York City Itinerary

Start: Peoria
Drive:  2​h 45​min
1
Chicago
— 5 nights
Drive:  13​h 15​min
2
New York City
— 8 nights
Drive:  15​h 30​min
End: Peoria

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get a sense of the local culture at The Magnificent Mile and Gaylord Building Historic Site. You'll explore the less-touristy side of things at Starved Rock State Park and Dollinger Family Farm. Venture out of the city with trips to Baker Lake Park (in Peru), Tom's Farm Market and Greenhouse (in Huntley) and Hawks View Golf Club (in Lake Geneva). There's lots more to do: look for all kinds of wild species at Kishwauketoe Conservancy, admire the landmark architecture of 360 Chicago Observation Deck, learn about winemaking at Carpenter Creek Cellars, and play a few rounds at Oak Grove Golf Course.

For maps, where to stay, photos, and more tourist information, read Chicago trip itinerary maker website .

Peoria to Chicago is an approximately 3-hour car ride. April in Chicago sees daily highs of 59°F and lows of 40°F at night. Wrap up your sightseeing on the 3rd (Fri) to allow time to travel to New York City.

Things to do in Chicago

Outdoors Parks Golf

Side Trips

Hawks View Golf Club, Starved Rock State Park, Baker Lake Park, Gaylord Building Historic Site, Oak Grove Golf Course
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Carpenter Creek Cellars ©
Carpenter Creek Cellars
The Magnificent Mile ©
The Magnificent Mile

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.
Get a sense of the local culture at Stone Church and St. Patrick's Cathedral. Eschew the tourist crowds and head to Upper Delaware River and Wertheim National Wildlife Refuge. Change things up with these side-trips from New York City: Peconic River Herb Farm (in Calverton), Golden Fish Gallery (in Milford) and Faraway Farm Alpacas (in Yorktown Heights). There's still lots to do: look for all kinds of wild species at Quogue Wildlife Refuge, explore the activities along Delaware Water Gap, step off the mainland to explore Fire Island National Seashore, and relax in the rural setting at Marshall's Farm Market.

To see maps, traveler tips, more things to do, and more tourist information, read our New York City holiday planner.

You can do a combination of flight and bus from Chicago to New York City in 5 hours. Alternatively, you can fly; or drive. The time zone difference when traveling from Chicago to New York City is 1 hour. May in New York City sees daily highs of 69°F and lows of 55°F at night. Wrap up your sightseeing on the 12th (Sun) to allow time to travel back home.

Things to do in New York City

Parks Outdoors Nature

Side Trips

Columbia, New Milford, Goodale Farms, Golden Fish Gallery, Stone Church
Highlights from your plan
Wertheim National Wildlife Refuge ©
9/11 Memorial ©
9/11 Memorial
Times Square ©
Times Square

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