13 days in Chicago, New York City & Portland Itinerary

13 days in Chicago, New York City & Portland Itinerary

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Route & dates

13 days in Chicago, New York City & Portland Itinerary

Start: Monson
Drive + Fly:  7​h 15​min
1
Chicago
— 3 nights
Fly + bus:  4​h 45​min
2
New York City
— 3 nights
foot + Fly:  9​h
3
Portland
— 5 nights
Fly:  4​h 30​min
End: Missoula

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll explore the less-touristy side of things at Illinois Railway Museum and Kenosha Public Museum. Give yourself a bit of retail therapy at Pleasant Prairie Premium Outlets and Kernel's Gourmet Popcorn & More. Get out of town with these interesting Chicago side-trips: Baha'i House of Worship (in Wilmette) and Civil War Museum (in Kenosha). Next up on the itinerary: shop like a local with Skokie Northshore Sculpture Park and paddle through the water with a kayaking and canoeing tour.

For more things to do, traveler tips, other places to visit, and more tourist information, refer to the Chicago online trip itinerary maker .

Monson to Chicago is an approximately 7.5-hour flight. You can also drive. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Plan for somewhat warmer nights when traveling from Monson in July since evenings lows in Chicago dip to 67°F. Cap off your sightseeing on the 4th (Thu) early enough to travel to New York City.

Things to do in Chicago

Museums Shopping Outdoors

Side Trips

Kenosha, Pleasant Prairie Premium Outlets, Illinois Railway Museum, Baha'i House of Worship, Kernel's Gourmet Popcorn & More
Highlights from your plan
Illinois Railway Museum ©
Illinois Railway Museum
Baha'i House of Worship ©
Baha'i House of Worship
Kenosha Public Museum ©
Kenosha Public Museum

3
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.
Escape the urban bustle at Ocean Grove Beach and Lakota Wolf Preserve. You'll explore the less-touristy side of things at DM Weil Gallery and Quiet Valley Living Historical Farm. Explore the numerous day-trip ideas around New York City: Boscobel House and Gardens (in Garrison), Historic Huguenot Street (in New Paltz) and Hudson Beach Glass (in Beacon). And it doesn't end there: take an in-depth tour of Hudson River Maritime Museum, get some fabulous bargains at Jersey Shore Premium Outlets, and get a taste of the local shopping with Barsky Gallery.

To see photos, more things to do, other places to visit, and tourist information, use the New York City day trip planning tool .

Traveling by combination of flight and bus from Chicago to New York City takes 5 hours. Alternatively, you can fly; or drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Expect a daytime high around 86°F in July, and nighttime lows around 72°F. Wrap up your sightseeing on the 7th (Sun) to allow time to travel to Portland.

Things to do in New York City

Museums Shopping Parks

Side Trips

New Paltz, Lakota Wolf Preserve, Barsky Gallery, Ocean Grove Beach, Hudson Beach Glass
Highlights from your plan
DM Weil Gallery ©
DM Weil Gallery
Boscobel House and Gardens ©
Boscobel House and Gardens
Hudson Beach Glass ©
Hudson Beach Glass

5
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.
Head to Woodburn Premium Outlets and Made Here PDXfor plenty of shopping. Timberline Lodge and Ski Area and Willamette Valley Vineyards are good opportunities to explore the local culture. Explore Portland's surroundings by going to The Lewis And Clark National And State Historical Parks (in Astoria), Seaside (Camp 18 Logging Museum & Restaurant & Seaside Inverted Experience) and Mt. Hood National Forest (in Welches). There's much more to do: take in the architecture and atmosphere at St. Mary's Catholic Church, steep yourself in history at Officers' Row, examine the collection at Columbia Gorge Interpretive Center, and identify plant and animal life at Bonneville Hatchery.

For more things to do, other places to visit, and other tourist information, use the Portland trip tool .

You can fly from New York City to Portland in 9 hours. Other options are to fly; or drive. You'll gain 3 hours traveling from New York City to Portland due to the time zone difference. Traveling from New York City in July, expect a bit cooler with lows of 59°F in Portland. On the 13th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Portland

Parks Nature Historic Sites

Side Trips

Corbett, Seaside, The Lewis And Clark National And State Historical Parks, Officers' Row, Woodburn Premium Outlets
Highlights from your plan

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