15 days in Portland, Chicago & New York City Itinerary

15 days in Portland, Chicago & New York City Itinerary

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Route & dates

15 days in Portland, Chicago & New York City Itinerary

Start: Copenhagen
Fly:  15​h 30​min
1
Portland
— 4 nights
Fly:  6​h 45​min
2
Chicago
— 2 nights
Fly + bus:  4​h 45​min
3
New York City
— 5 nights
bus + Fly:  11​h
End: Copenhagen

4
nights
Portland

Portland ©
A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Escape the urban bustle at Hug Point State Recreation Site and Forest Park. Head to Powell's City of Books and Northwest (Nob Hill)for some retail therapy. Get out of town with these interesting Portland side-trips: Haystack Rock (in Cannon Beach) and Astoria Column (in Astoria). And it doesn't end there: head outdoors with Portland Timbers, tour the pleasant surroundings at Wildwood Trail, look for all kinds of wild species at Hyland Forest Park, and relax in the rural setting at Fiala Farms.

To see reviews, ratings, maps, and other tourist information, read our Portland trip builder app .

Copenhagen, Denmark to Portland is an approximately 15.5-hour flight. You can also do a combination of train, bus, and flight; or do a combination of train and flight. The time zone difference when traveling from Copenhagen to Portland is minus 9 hours. Traveling from Copenhagen in January, expect nights in Portland to be about the same, around 1°C, while days are somewhat warmer, around 9°C. Finish your sightseeing early on the 19th (Sat) so you can travel to Chicago.

Things to do in Portland

Outdoors Parks Beaches

Side Trips

West Linn, Hug Point State Recreation Site, Haystack Rock, Astoria Column, Hyland Forest Park
Highlights from your plan
Haystack Rock ©
Haystack Rock
Powell's City of Books ©
Powell's City of Books
Oaks Bottom Wildlife Refuge ©
Oaks Bottom Wildlife Refuge

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Escape the urban bustle at Lincoln Park Zoo and Deer Grove Forest Preserve. The Art Institute of Chicago and Fourth Presbyterian Church are good opportunities to explore the local culture. Get out of town with these interesting Chicago side-trips: Little Red Schoolhouse (in Willow Springs) and Swallow Cliff Stairs (in Palos Park). The adventure continues: admire all the interesting features of Millennium Park.

To see other places to visit, where to stay, maps, and more tourist information, read our Chicago day trip planner .

You can fly from Portland to Chicago in 7 hours. Other options are to do a combination of flight and train; or drive. Due to the time zone difference, you'll lose 2 hours traveling from Portland to Chicago. Expect a bit cooler temperatures when traveling from Portland in January; daily highs in Chicago reach 0°C and lows reach -9°C. Wrap up your sightseeing on the 22nd (Tue) early enough to travel to New York City.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Swallow Cliff Stairs, Little Red Schoolhouse, Deer Grove Forest Preserve
Highlights from your plan
Lincoln Park Zoo ©
Lincoln Park Zoo
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park

5
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.
You'll explore and learn at The Metropolitan Museum of Art and 9/11 Memorial. Get outdoors at Bronx Zoo and Edwin B. Forsythe National Wildlife Refuge. There's still lots to do: don't miss a visit to Fifth Avenue, explore and take pictures at Hamilton Grange National Memorial, stop by Tiffany & Co., and explore the activities along Jacqueline Kennedy Onassis Reservoir.

To find other places to visit, reviews, photos, and tourist information, read our New York City route planner.

Do a combination of flight and bus from Chicago to New York City in 5 hours. Alternatively, you can fly; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to New York City. Expect somewhat warmer temperatures when traveling from Chicago in January; daily highs in New York City reach 5°C and lows reach -5°C. Wrap up your sightseeing on the 28th (Mon) early enough to travel back home.

Things to do in New York City

Parks Museums Outdoors

Side Trips

Edwin B. Forsythe National Wildlife Refuge, Bronx Zoo
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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