12 days in Chicago, Philadelphia & Washington DC Itinerary

12 days in Chicago, Philadelphia & Washington DC Itinerary

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Route & dates

12 days in Chicago, Philadelphia & Washington DC Itinerary

Start: Auckland
Fly:  20​h 15​min
1
Chicago
— 3 nights
Fly:  4​h
2
Philadelphia
— 2 nights
train:  1​h 45​min
3
Washington DC
— 2 nights
Fly:  3​h 45​min
4
Chicago
— 2 nights
Fly:  20​h 15​min
End: Auckland

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 9th (Sat): admire the landmark architecture of Frank Lloyd Wright Home and Studio, steep yourself in history at Pleasant Home, explore the world behind art at The Art Institute of Chicago, then admire the striking features of Chicago Cultural Center, and finally admire the striking features of Marquette Building. Keep things going the next day: admire the striking features of Frank Lloyd Wright's Robie House, then stroll through Swallow Cliff Stairs, then shop like a local with L.H. Selman Ltd, and finally take in the spiritual surroundings of Fourth Presbyterian Church.

For ratings, where to stay, maps, and more tourist information, use the Chicago online trip itinerary builder .

Auckland, New Zealand to Chicago is an approximately 20.5-hour flight. You can also do a combination of bus and flight. You'll gain 18 hours traveling from Auckland to Chicago due to the time zone difference. Expect little chillier weather when traveling from Auckland in November: highs in Chicago hover around 11°C, while lows dip to 1°C. Wrap up your sightseeing on the 11th (Mon) early enough to travel to Philadelphia.

Things to do in Chicago

Historic Sites Museums Parks

Side Trips

Oak Park, Swallow Cliff Stairs
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Frank Lloyd Wright Home and Studio ©
Pleasant Home ©
Pleasant Home

2
nights
Philadelphia

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Kick off your visit on the 11th (Mon): admire the masterpieces at Barnes Foundation, ponder the world of politics at Independence Hall, and then browse the eclectic array of goods at Reading Terminal Market. Get ready for a full day of sightseeing on the 12th (Tue): appreciate the history behind Liberty Bell Center, admire the masterpieces at Philadelphia Museum of Art, then get engrossed in the history at Eastern State Penitentiary, then take a stroll around Kimmel Center for the Performing Arts, and finally take a stroll through Rittenhouse Square.

To see reviews, ratings, and other tourist information, read our Philadelphia trip maker .

Getting from Chicago to Philadelphia by flight takes about 4 hours. Other options: do a combination of flight and train; or drive. You'll lose 1 hour traveling from Chicago to Philadelphia due to the time zone difference. Traveling from Chicago in November, you will find days in Philadelphia are a bit warmer (16°C), and nights are about the same (5°C). Finish your sightseeing early on the 13th (Wed) so you can take a train to Washington DC.

Things to do in Philadelphia

Museums Shopping Historic Sites
Highlights from your plan
Philadelphia Museum of Art ©
Philadelphia Museum of Art
Independence Hall ©
Independence Hall
Barnes Foundation ©
Barnes Foundation

2
nights
Washington DC

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Kick off your visit on the 13th (Wed): explore the world behind art at National Gallery of Art, see the interesting displays at National Air and Space Museum, and then pause for some serene contemplation at Washington National Cathedral. On the 14th (Thu), you'll have a packed day of sightseeing: explore the different monuments and memorials at Arlington National Cemetery, then get engrossed in the history at United States Holocaust Memorial Museum, and then learn more about the world around you at Smithsonian National Museum of Natural History.

Plan a Washington DC trip in moments using our itinerary builder.

Take a train from Philadelphia to Washington DC in 2 hours. Alternatively, you can drive; or take a bus. In November, daytime highs in Washington DC are 17°C, while nighttime lows are 6°C. Finish up your sightseeing early on the 15th (Fri) so you can travel to Chicago.

Things to do in Washington DC

Museums Historic Sites

Side Trip

Arlington National Cemetery
Highlights from your plan
National Air and Space Museum ©
National Air and Space Museum
Arlington National Cemetery ©
Arlington National Cemetery
National Gallery of Art ©
National Gallery of Art

2
nights
Chicago

Chicago ©
The Magnificent Mile and Ernest Hemingway Birthplace are good opportunities to explore the local culture. Visit Fourth Presbyterian Church and Marquette Building for their historical value. Venture out of the city with trips to Little Red Schoolhouse (in Willow Springs) and Swallow Cliff Stairs (in Palos Park). Enjoy Chicago some more: hike along Lakefront Trail, admire the striking features of Reliance Building, enjoy breathtaking views from 360 Chicago Observation Deck, and take in the waterfront at Navy Pier.

To see maps, other places to visit, reviews, and tourist information, use the Chicago online trip planner .

Traveling by flight from Washington DC to Chicago takes 4 hours. Alternatively, you can do a combination of train and flight; or drive. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Traveling from Washington DC in November, expect Chicago to be a bit cooler, temps between 11°C and 1°C. Finish your sightseeing early on the 17th (Sun) so you can travel back home.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Little Red Schoolhouse, Ernest Hemingway Birthplace, Swallow Cliff Stairs
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace
Fourth Presbyterian Church ©
Fourth Presbyterian Church

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