8 days in Oregon Itinerary

8 days in Oregon Itinerary

Created using Inspirock United States vacation planner

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Route & dates

8 days in Oregon Itinerary

Start: Chicago
Fly:  6​h 45​min
1
Portland
— 2 nights
Drive:  2​h
2
Cannon Beach
— 3 nights
Drive:  3​h
3
Hood River
— 2 nights
+2
bus + tram + Fly:  8​h 30​min
End: Chicago

2
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.
Visiting Multnomah Falls and Sokol Blosser Winery will get you outdoors. Get some cultural insight at Evergreen Aviation & Space Museum and Carlton Winemakers Studio. There's still lots to do: contemplate the long history of Pittock Mansion, look for gifts at Powell's City of Books, examine the collection at Oregon Museum of Science and Industry, and admire the natural beauty at International Rose Test Garden.

For other places to visit, reviews, maps, and more tourist information, refer to the Portland tour itinerary planner.

Chicago to Portland is an approximately 7-hour flight. You can also do a combination of train and flight; or drive. The time zone changes from Central Standard Time (CST) to Pacific Standard Time (PST), which is usually a -2 hour difference. Plan for a bit cooler nights when traveling from Chicago in June since evenings lows in Portland dip to 56°F. Wrap up your sightseeing on the 25th (Tue) to allow time to drive to Cannon Beach.

Things to do in Portland

Parks Nature Museums

Side Trips

Multnomah Falls, Carlton Winemakers Studio, Sokol Blosser Winery, Evergreen Aviation & Space Museum
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Multnomah Falls ©
Multnomah Falls
Powell's City of Books ©
Powell's City of Books

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Do some cultural sightseeing at Fort Clatsop National Memorial and Columbia River Maritime Museum. Visiting Haystack Rock and Ecola State Park will get you outdoors. Change things up with a short trip to Astoria Column in Astoria (about 42 minutes away). There's lots more to do: tour the pleasant surroundings at Cannon Beach, stop by Bronze Coast Gallery, and enjoy the sea views from Tillamook Rock Light.

For where to stay, other places to visit, photos, and more tourist information, read our Cannon Beach trip itinerary planner .

You can drive from Portland to Cannon Beach in 2 hours. Another option is to take a bus. While traveling from Portland, expect little chillier days and about the same nights in Cannon Beach, ranging from highs of 66°F to lows of 52°F. Wrap up your sightseeing on the 28th (Fri) early enough to drive to Hood River.

Things to do in Cannon Beach

Parks Nature Historic Sites

Side Trip

Astoria
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Ecola State Park ©
Ecola State Park

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 29th (Sat), relax in the rural setting at Hood River Lavender, then see the interesting displays at Western Antique Aeroplane & Automobile Museum, and then contemplate the waterfront views at Columbia River Gorge National Scenic Area.

To see reviews, ratings, maps, and more tourist information, read Hood River holiday planner.

Getting from Cannon Beach to Hood River by car takes about 3 hours. Other options: take a bus; or do a combination of bus and train. Traveling from Cannon Beach in June, you will find days in Hood River are a bit warmer (72°F), and nights are about the same (55°F). On the 30th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Hood River

Parks Nature Wildlife

Side Trips

Columbia River Gorge National Scenic Area, Historic Columbia River Highway State Trail
Highlights from your plan

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