26 days in Chicago, Boston & New York City Itinerary

26 days in Chicago, Boston & New York City Itinerary

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Route & dates

26 days in Chicago, Boston & New York City Itinerary

Start: Cebu City, Cebu Island
Fly:  35​h 30​min
1
Chicago
— 8 nights
Fly:  2​h 30​min
2
Boston
— 4 nights
Fly + bus:  3​h
3
New York City
— 10 nights
Fly:  29​h 30​min
End: Cebu City, Cebu Island

8
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Skydeck Chicago - Willis Tower has been added to your itinerary. You'll discover tucked-away gems like Starved Rock State Park and Museum of Science and Industry. Get out of town with these interesting Chicago side-trips: Matthiessen State Park (in Utica), Milwaukee (Milwaukee Public Museum & Milwaukee Art Museum) and Lake Geneva (Geneva Lake Shore Path & Geneva Lake). There's much more to do: explore the landscape on two wheels at Lakefront Trail, pause for some serene contemplation at Basilica of the Sacred Heart, take in nature's colorful creations at Garfield Park Conservatory, and admire the local landmark of Buckingham Fountain.

To see other places to visit, photos, where to stay, and more tourist information, read our Chicago online trip itinerary planner .

Cebu City, Philippines to Chicago is an approximately 24-hour flight. You can also do a combination of ferry and flight; or do a combination of bus and flight. The time zone difference moving from Philippines Time (PHT) to Central Standard Time (CST) is minus 14 hours. Expect much colder temperatures when traveling from Cebu City in April; daily highs in Chicago reach 17°C and lows reach 5°C. On the 22nd (Wed), you'll have the morning to explore before heading off to Boston.

Things to do in Chicago

Parks Museums Nature

Side Trips

Utica, Milwaukee, Lake Geneva, Basilica of the Sacred Heart
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Lakefront Trail ©
Lakefront Trail
Museum of Science and Industry ©
Museum of Science and Industry

4
nights
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.
Explore hidden gems such as Museum of Fine Arts and Purgatory Chasm State Reservation. And it doesn't end there: take in nature's colorful creations at Boston Public Garden, explore the engaging exhibits at Boston Children's Museum, browse the different shops at Faneuil Hall Marketplace, and head off the coast to Castle Island.

For where to stay, maps, ratings, and more tourist information, use the Boston day trip planning website .

You can fly from Chicago to Boston in 4 hours. Other options are to do a combination of flight and bus; or drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In April, daytime highs in Boston are 15°C, while nighttime lows are 5°C. You will have some time to spend on the 26th (Sun) before leaving for New York City.

Things to do in Boston

Parks Museums Nature

Side Trip

Purgatory Chasm State Reservation
Highlights from your plan
Castle Island ©
Castle Island
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden

10
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.
Madison Square Garden has been added to your itinerary. You'll explore the less-touristy side of things at New York Public Library and Independence National Historical Park. You'll find plenty of places to visit near New York City: Grounds For Sculpture (in Hamilton) and Philadelphia Museum of Art (in Philadelphia). The adventure continues: go for a walk through Central Park, pause for some photo ops at Statue of Liberty National Monument, explore the world behind art at The Metropolitan Museum of Art, and settle in for a delightful tour with a horse-drawn carriage tour.

Plan a trip to New York City easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by combination of flight and bus from Boston to New York City takes 3 hours. Alternatively, you can fly; or drive. April in New York City sees daily highs of 19°C and lows of 8°C at night. Finish your sightseeing early on the 6th (Wed) to allow enough time to travel back home.

Things to do in New York City

Parks Museums Historic Sites

Side Trips

Brooklyn, Philadelphia, Grounds For Sculpture, New York Botanical Garden
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Independence National Historical Park ©

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