18 days in Woodbridge, New York City & Chicago Itinerary

18 days in Woodbridge, New York City & Chicago Itinerary

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Route & dates

18 days in Woodbridge, New York City & Chicago Itinerary

Start: Des Moines
Fly + Drive:  6​h 30​min
1
Woodbridge
— 4 nights
Drive:  2​h
2
New York City
— 7 nights
Bus + Fly:  4​h 45​min
3
Chicago
— 6 nights
Fly:  3​h 15​min
End: Des Moines

4
nights
Woodbridge

Woodbridge ©
Woodbridge is a town in New Haven County, Connecticut, United States. Step out of Woodbridge to go to Newtown and see Rowanwood Farm, which is approximately 30 minutes away. And it doesn't end there: examine the collection at Osborne Homestead Museum, indulge your thirst for a good beer at New England Brewing Company, learn about winemaking at Savino Vineyards, and look for all kinds of wild species at Ansonia Nature & Recreation Center.

To find reviews, maps, ratings, and more tourist information, you can read our Woodbridge trip itinerary planner.

Des Moines to Woodbridge is an approximately 6.5-hour combination of flight and car. You can also drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Des Moines in January, expect a bit warmer with lows of 23°F in Woodbridge. You will leave for New York City on the 5th (Sun).

Things to do in Woodbridge

Museums Breweries & Distilleries Childrens Museums

Side Trips

Newtown, Ansonia Nature & Recreation Center, Osborne Homestead Museum, Barker Character Comic and Cartoon Museum
Highlights from your plan
New England Brewing Company ©
New England Brewing Company
Ansonia Nature & Recreation Center ©

7
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.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: go for a walk through Central Park, make a trip to 9/11 Memorial, admire the landmark architecture of Grand Central Terminal, and take some stellar pictures from Top of the Rock.

To see more things to do, traveler tips, and other tourist information, use the New York City holiday maker tool .

You can drive from Woodbridge to New York City in 2 hours. In January, plan for daily highs up to 40°F, and evening lows to 24°F. Finish your sightseeing early on the 12th (Sun) to allow enough time to travel to Chicago.

Things to do in New York City

Museums Parks Shopping
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Empire State Building ©
Empire State Building

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, engage your brain at Field Museum, observe the fascinating underwater world at Shedd Aquarium, and wander the streets of The Magnificent Mile.

To find more things to do, photos, and other tourist information, read our Chicago trip planner.

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Other options are to fly; or drive. Due to the time zone difference, you'll gain 1 hour traveling from New York City to Chicago. Plan for little chillier temperatures traveling from New York City in January, with highs in Chicago at 32°F and lows at 18°F. Finish your sightseeing early on the 18th (Sat) to allow enough time to travel back home.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Frank Lloyd Wright's Unity Temple
Highlights from your plan
BATL-The Backyard Axe Throwing League ©
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

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