59 days in Chicago, New Orleans & New York City Itinerary

59 days in Chicago, New Orleans & New York City Itinerary

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Route & dates

59 days in Chicago, New Orleans & New York City Itinerary

Start: London
Fly:  12​h
1
Chicago
— 22 nights
Fly:  4​h 45​min
2
New Orleans
— 19 nights
Fly + bus:  6​h
3
New York City
— 15 nights
Fly:  11​h 15​min
End: London

22
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Visiting Lincoln Park Zoo and Swallow Cliff Stairs will get you outdoors. Deepen your sense of the past at sights like Ernest Hemingway Birthplace and Pleasant Home. Explore Chicago's surroundings by going to Little Red Schoolhouse (in Willow Springs), Veteran Acres Park (in Crystal Lake) and Springbrook Prairie Forest Preserve (in Naperville). On the 14th (Sat), spend an exhilarating day on the slopes at Raging Buffalo Snowboard Ski Park. There's still lots to do: admire the masterpieces at The Art Institute of Chicago, look for all kinds of wild species at Volo Bog State Natural Area, take a peaceful walk through Hawthorn Hollow - Nature Sanctuary and Arboretum, and stroll through Cowles Bog.

To see ratings, reviews, traveler tips, and tourist information, use the Chicago road trip site .

London, UK to Chicago is an approximately 12-hour flight. You can also do a combination of flight and bus; or do a combination of flight and train. You'll gain 6 hours traveling from London to Chicago due to the time zone difference. Expect a bit cooler temperatures when traveling from London in March; daily highs in Chicago reach 8°C and lows reach -1°C. Wrap up your sightseeing on the 30th (Mon) early enough to travel to New Orleans.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Chesterton, Oak Park, Veteran Acres Park, Prairie Wolf Slough, Springbrook Prairie Forest Preserve
Highlights from your plan
Lincoln Park Zoo ©
Lincoln Park Zoo
The Art Institute of Chicago ©
The Art Institute of Chicago
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace

19
nights
New Orleans

New Orleans ©
Known for its Creole cuisine, rich musical tradition, and nearby swamps and plantations, New Orleans is one of the nation's oldest cities.
Your cultural itinerary includes sights like Chalmette National Historical Park and Garden District. Get in touch with nature at Audubon Zoo and Global Wildlife Center. Get out of town with these interesting New Orleans side-trips: Covington (Tammany Trace & Insta-Gator Ranch & Hatchery), Slidell (Bogue Chitto National Wildlife Refuge, Therapy Charters, & more) and Crosby Arboretum (in Picayune). Spend the 1st (Wed) exploring nature at Jean Lafitte National Historical Park and Preserve. And it doesn't end there: brush up on your military savvy at The National WWII Museum, see the interesting displays at New Orleans Museum of Art, hike along Mandeville Trailhead Cultural Interpretive Center, and get to know the fascinating history of Jackson Square.

To see other places to visit, traveler tips, reviews, and tourist information, refer to the New Orleans sightseeing planner .

You can fly from Chicago to New Orleans in 5 hours. Alternatively, you can drive; or take a train. Traveling from Chicago in March, expect nights in New Orleans to be much warmer, around 19°C, while days are somewhat warmer, around 19°C. Finish your sightseeing early on the 18th (Sat) so you can travel to New York City.

Things to do in New Orleans

Parks Outdoors Wildlife

Side Trips

Slidell, Covington, Mandeville, Brownell Memorial Park, Mike the Tiger Habitat
Highlights from your plan
Chalmette National Historical Park ©
Chalmette National Historical Park
The National WWII Museum ©
The National WWII Museum
Garden District ©
Garden District

15
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.
Your inner history buff will appreciate 9/11 Memorial and Cathedral Church of Saint John the Divine. Visiting East River Waterfront Esplanade and West Side Community Garden will get you outdoors. You'll find plenty of places to visit near New York City: Alley Pond Environmental Center (in Douglaston), Valley Cottage (Rockland Lake State Park & Hook Mountain State Park) and Bayard Cutting Arboretum (in Great River). There's much more to do: admire the masterpieces at The Metropolitan Museum of Art, learn more about the world around you at American Museum of Natural History, tour the pleasant surroundings at Bronx Zoo, and explore the landscape on two wheels at Hudson River Greenway.

To plan New York City vacation without wasting time, ask Inspirock to design an itinerary.

You can fly from New Orleans to New York City in 6 hours. Other options are to do a combination of flight and train; or drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Traveling from New Orleans in April, expect nights in New York City to be much colder, around 8°C, while days are a bit cooler, around 19°C. Finish your sightseeing early on the 4th (Mon) to allow enough time to travel back home.

Things to do in New York City

Parks Museums Outdoors

Side Trips

Valley Cottage, Alley Pond Environmental Center, Teatown Lake Reservation, Bronx Zoo, Bayard Cutting Arboretum
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©

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