19 days in Chicago, Pittsburgh & New York City Itinerary

19 days in Chicago, Pittsburgh & New York City Itinerary

Created using Inspirock United States holiday planner

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Route & dates

19 days in Chicago, Pittsburgh & New York City Itinerary

Start: Auckland
Fly:  20​h 15​min
1
Chicago
— 6 nights
Fly:  3​h 45​min
2
Pittsburgh
— 3 nights
Fly:  4​h 15​min
3
New York City
— 8 nights
Fly:  22​h
End: Auckland

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Venture out of the city with trips to South Bend (Basilica of the Sacred Heart & Grotto of Our Lady Lourdes). And it doesn't end there: explore the world behind art at The Art Institute of Chicago, get to know the resident critters at Lincoln Park Zoo, have some family-friendly fun at Ragnarok Axe Throwing, and stroll around Millennium Park.

Inspirock's itinerary builder makes planning a Chicago trip simple and quick.

Auckland, New Zealand to Chicago is an approximately 20.5-hour flight. You can also do a combination of bus and flight. The time zone difference moving from New Zealand Standard Time to Central Standard Time is minus 18 hours. Traveling from Auckland in April, you will find days in Chicago are a bit cooler (17°C), and nights are much colder (5°C). Finish your sightseeing early on the 10th (Fri) to allow enough time to travel to Pittsburgh.

Things to do in Chicago

Museums Historic Sites Parks

Side Trips

Oak Park, South Bend
Find places to stay Apr 4 — 10:
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

3
nights
Pittsburgh

Pittsburgh ©
Known primarily for its steel-related heritage and 446 bridges, Pittsburgh sits at the confluence of the Monongahela and Allegheny Rivers, which meet to form the Ohio River.
Get out of town with these interesting Pittsburgh side-trips: Mister Rogers' Park Bench (in Latrobe) and Fallingwater (in Mill Run). Next up on the itinerary: see the interesting displays at Bicycle Heaven, take a stroll through Mount Washington, take an in-depth tour of Soldiers & Sailors Memorial Hall & Museum, and explore the world behind art at The Butler Institute of American Art.

To see ratings, where to stay, reviews, and more tourist information, read Pittsburgh trip planner .

Fly from Chicago to Pittsburgh in 4 hours. Alternatively, you can drive; or take a train. The time zone difference when traveling from Chicago to Pittsburgh is 1 hour. April in Pittsburgh sees daily highs of 20°C and lows of 7°C at night. Wrap up your sightseeing on the 13th (Mon) to allow time to travel to New York City.

Things to do in Pittsburgh

Museums Parks Historic Sites

Side Trips

Youngstown, Mister Rogers' Park Bench, Fallingwater
Find places to stay Apr 10 — 13:
Highlights from your plan
Bicycle Heaven ©
Bicycle Heaven
Fellows Riverside Gardens ©
Fellows Riverside Gardens

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.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: tour the pleasant surroundings at Central Park, enjoy breathtaking views from Empire State Building, walk around The High Line, and admire the landmark architecture of Grand Central Terminal.

For reviews, other places to visit, maps, and other tourist information, you can read our New York City road trip app .

You can fly from Pittsburgh to New York City in 4.5 hours. Other options are to fly; or drive. In April, plan for daily highs up to 19°C, and evening lows to 8°C. Cap off your sightseeing on the 21st (Tue) early enough to travel back home.

Things to do in New York City

Museums Parks Historic Sites
Find places to stay Apr 13 — 21:
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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