15 days in Portland, Chicago & New York City Itinerary

15 days in Portland, Chicago & New York City Itinerary

Created using Inspirock United States visit planner

This plan was created by another user. Make it your plan

Route & dates

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.
Visit Haystack Rock and Hug Point State Recreation Site for some beach relaxation. Escape the urban bustle at Astoria Column and Wildwood Trail. And it doesn't end there: look for gifts at Powell's City of Books, take a stroll through Northwest (Nob Hill), head outdoors with Portland Timbers, and hike along Forest Park.

To see ratings, where to stay, traveler tips, and other tourist information, you can read our Portland trip itinerary maker tool.

Copenhagen, Denmark to Portland is an approximately 15.5- hour flight. You can also do a combination of flight, bus, and train; or do a combination of train and flight. The time zone difference when traveling from Copenhagen to Portland is minus 9 hours. When traveling from Copenhagen in January, plan for somewhat warmer days and about the same nights in Portland: temperatures range from 9°C by day to 1°C at night. Cap off your sightseeing on the 19th (Sat) early enough to travel to Chicago.

Things to do in Portland

Outdoors Parks Beaches

Side Trips

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

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get a sense of the local culture at The Art Institute of Chicago and Fourth Presbyterian Church. Step out of the city life by going to Little Red Schoolhouse and Swallow Cliff Stairs. Take a break from Chicago with a short trip to Deer Grove Forest Preserve in Palatine, about 46 minutes away. The adventure continues: walk around Millennium Park and learn about wildlife with up-close encounters at Lincoln Park Zoo.

To see traveler tips, reviews, maps, and other tourist information, read Chicago trip itinerary planner.

You can fly from Portland to Chicago in 7 hours. Alternatively, you can drive; or take a train. The time zone changes from Pacific Standard Time to Central Standard Time, which is usually a 2 hour difference. Prepare for a bit cooler weather when traveling from Portland in January: high temperatures in Chicago hover around 0°C and lows are around -9°C. Finish up your sightseeing early on the 22nd (Tue) so you can travel to New York City.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

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

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.
Satisfy your inner culture vulture at 9/11 Memorial and The Metropolitan Museum of Art. Popular historic sites such as Hamilton Grange National Memorial and St. Patrick's Cathedral are in your itinerary. Venture out of the city with trips to Edwin B. Forsythe National Wildlife Refuge (in Oceanville) and Bronx Zoo (in Bronx). There's much more to do: wander the streets of Fifth Avenue, examine the collection at New York Public Library, learn more about the world around you at American Museum of Natural History, and get to know the resident critters at Central Park Zoo.

For photos, where to stay, and more tourist information, read New York City travel planner.

Getting from Chicago to New York City by combination of flight and bus takes about 5 hours. Other options: fly; or drive. You'll lose 1 hour traveling from Chicago to New York City due to the time zone difference. Expect a bit warmer temperatures when traveling from Chicago in January; daily highs in New York City reach 5°C and lows reach -5°C. Finish up your sightseeing early on the 28th (Mon) so you can travel back home.

Things to do in New York City

Parks Museums Zoos & Aquariums

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 ©
American Museum of Natural History

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