14 days in Chicago, East Coast of USA & Philadelphia Itinerary

14 days in Chicago, East Coast of USA & Philadelphia Itinerary

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Route & dates

14 days in Chicago, East Coast of USA & Philadelphia Itinerary

Start: San Francisco
Fly:  6​h 15​min
1
Chicago
— 2 nights
Fly:  4​h
2
Boston
— 1 night
Drive:  2​h
3
Eastham
— 2 nights
Drive:  1​h 45​min
4
Nantucket
— 1 night
Fly:  4​h 30​min
5
New York City
— 2 nights
train:  1​h 45​min
6
Philadelphia
— 1 night
train:  1​h 15​min
7
Baltimore
— 1 night
Fly:  3​h 45​min
8
Charleston
— 1 night
Fly:  6​h
9
Key West
— 1 night
Fly:  3​h
10
Miami Beach
— 1 night
Fly:  7​h 30​min
End: San Francisco

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 20th (Sat), you'll have a packed day of sightseeing: wander the streets of The Magnificent Mile, explore the world behind art at The Art Institute of Chicago, then appreciate the history behind Cloud Gate, and finally get to know the fascinating history of Millennium Park.

For other places to visit and other tourist information, read Chicago tour planning website .

San Francisco to Chicago is an approximately 6.5-hour flight. You can also do a combination of subway and flight; or drive. Due to the time zone difference, you'll lose 2 hours traveling from San Francisco to Chicago. Expect a bit warmer temperatures when traveling from San Francisco in July; daily highs in Chicago reach 83°F and lows reach 67°F. Wrap up your sightseeing on the 21st (Sun) to allow time to travel to Boston.

Things to do in Chicago

Shopping Neighborhoods Parks

Side Trip

Rosewood Beach
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Swedish American Museum ©
Swedish American Museum

1
night
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
On the 22nd (Mon), browse the different shops at Faneuil Hall Marketplace, admire the masterpieces at Museum of Fine Arts, and then admire all the interesting features of Fenway Park.

To see where to stay, more things to do, reviews, and other tourist information, read our Boston trip planning website .

You can do a combination of flight and bus from Chicago to Boston in 4 hours. Alternatively, you can do a combination of flight, taxi, and bus; or drive. Traveling from Chicago to Boston, you'll lose 1 hour due to the time zone difference. In July, daytime highs in Boston are 83°F, while nighttime lows are 67°F. Finish up your sightseeing early on the 22nd (Mon) so you can go by car to Eastham.

Things to do in Boston

Museums Shopping
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Faneuil Hall Marketplace ©
Faneuil Hall Marketplace
Fenway Park ©
Fenway Park

2
nights
Eastham

Eastham ©
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Start off your visit on the 23rd (Tue): get engrossed in the history at Salt Pond Visitor Center and then kick back and relax at Cape Cod National Seashore. Here are some ideas for day two: kick back and relax at Coast Guard Beach, then contemplate the long history of First Encounter Beach, and then kick back and relax at Nauset Beach.

To see photos, reviews, traveler tips, and other tourist information, go to the Eastham trip planning tool .

You can drive from Boston to Eastham in 2 hours. Other options are to take a bus; or do a combination of ferry and bus. Expect a daytime high around 79°F in July, and nighttime lows around 65°F. Finish up your sightseeing early on the 24th (Wed) so you can travel to Nantucket.

Things to do in Eastham

Outdoors Beaches Parks

Side Trips

Cape Cod National Seashore, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Nauset Beach ©
Nauset Beach
Coast Guard Beach ©
Coast Guard Beach

1
night
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. On the 25th (Thu), examine the collection at Whaling Museum, then enjoy the sand and surf at Jetties Beach, and then enjoy the sea views from Sankaty Head Lighthouse.

To see reviews, ratings, more things to do, and tourist information, refer to the Nantucket day trip site .

Getting from Eastham to Nantucket by combination of taxi and ferry takes about 2 hours. Other options: do a combination of bus and ferry. In July, daily temperatures in Nantucket can reach 76°F, while at night they dip to 64°F. Finish up your sightseeing early on the 25th (Thu) so you can travel to New York City.

Things to do in Nantucket

Outdoors Beaches Parks
Highlights from your plan
Jetties Beach ©
Jetties Beach
Whaling Museum ©
Whaling Museum
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse

2
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.
Kick off your visit on the 26th (Fri): browse the exhibits of The Metropolitan Museum of Art, make a trip to Times Square, and then enjoy breathtaking views from Empire State Building. On the 27th (Sat), you'll have a packed day of sightseeing: wander the streets of SoHo, then make a trip to Statue of Liberty National Monument, then stop by Kalustyan's, and finally make a trip to Fifth Avenue.

For photos, more things to do, ratings, and other tourist information, use the New York City trip itinerary maker app .

You can fly from Nantucket to New York City in 4.5 hours. Alternatively, you can fly; or do a combination of flight, bus, and train. In July, New York City is somewhat warmer than Nantucket - with highs of 86°F and lows of 72°F. Finish your sightseeing early on the 27th (Sat) so you can take a train to Philadelphia.

Things to do in New York City

Neighborhoods Shopping Museums
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Times Square ©
Times Square
Fifth Avenue ©
Fifth Avenue

1
night
Philadelphia

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Kick off your visit on the 28th (Sun): take an in-depth tour of Eastern State Penitentiary, explore the world behind art at Philadelphia Museum of Art, then browse the eclectic array of goods at Reading Terminal Market, and finally get a sense of history and politics at Independence Hall.

For where to stay, photos, other places to visit, and other tourist information, go to the Philadelphia trip planner .

Take a train from New York City to Philadelphia in 2 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 88°F in July, and nighttime lows around 72°F. Finish up your sightseeing early on the 28th (Sun) so you can catch the train to Baltimore.

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
Eastern State Penitentiary ©
Eastern State Penitentiary

1
night
Baltimore

Baltimore ©
A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
Start off your visit on the 29th (Mon): pause for some serene contemplation at Saint Alphonsus Church, then wander the streets of Inner Harbor, then take in the history at Fort McHenry National Monument, and finally take a stroll through Fell's Point.

To see photos, reviews, and tourist information, refer to the Baltimore day trip tool .

You can take a train from Philadelphia to Baltimore in 1.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 89°F in July, and nighttime lows around 74°F. Finish up your sightseeing early on the 29th (Mon) so you can travel to Charleston.

Things to do in Baltimore

Parks Historic Sites Zoos & Aquariums
Highlights from your plan
Inner Harbor ©
Inner Harbor
Fell's Point ©
Fell's Point

1
night
Charleston

Charleston ©
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
Start off your visit on the 30th (Tue): get a taste of the local shopping with One Of A Kind and then enjoy the sand and surf at Folly Beach Public Beach.

To find more things to do, where to stay, reviews, and more tourist information, go to the Charleston holiday tool .

Getting from Baltimore to Charleston by flight takes about 4 hours. Other options: do a combination of train and flight; or drive. Expect a daytime high around 89°F in July, and nighttime lows around 75°F. Finish your sightseeing early on the 30th (Tue) so you can travel to Key West.

Things to do in Charleston

Outdoors Beaches Parks

Side Trip

Folly Beach Public Beach
Highlights from your plan
Folly Beach Public Beach ©
Folly Beach Public Beach
One Of A Kind ©
One Of A Kind

1
night
Key West

Key West ©
Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Start off your visit on the 31st (Wed): see the interesting displays at The Ernest Hemingway Home and Museum, then view the masterpieces at 7 Artists & Friends, then enjoy the sand and surf at Fort Zachary Taylor, and finally get a taste of the local shopping with Alan S. Maltz Gallery.

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

Traveling by flight from Charleston to Key West takes 6 hours. Alternatively, you can drive; or do a combination of car, train, and bus. Expect somewhat warmer evenings in Key West when traveling from Charleston in July, with lows around 81°F. Cap off your sightseeing on the 31st (Wed) early enough to travel to Miami Beach.

Things to do in Key West

Museums Outdoors Beaches
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©
Fort Zachary Taylor ©
Fort Zachary Taylor

1
night
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
On the 1st (Thu), take a stroll through Collins Avenue, then wander the streets of Lincoln Road, then admire the landmark architecture of Art Deco Historic District, and finally kick back and relax at South Beach.

To find more things to do, reviews, other places to visit, and more tourist information, use the Miami Beach vacation app .

Getting from Key West to Miami Beach by combination of flight, tram, and bus takes about 3 hours. Other options: drive; or take a bus. In July, daily temperatures in Miami Beach can reach 91°F, while at night they dip to 78°F. Cap off your sightseeing on the 1st (Thu) early enough to travel back home.

Things to do in Miami Beach

Neighborhoods Shopping Historic Sites
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

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