15 days in Oregon Itinerary

15 days in Oregon Itinerary

Created using Inspirock Oregon itinerary maker

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

Route & dates

15 days in Oregon Itinerary

Start: Chicago
Fly + bus:  10​h
1
Ashland
— 3 nights
Drive:  4​h 15​min
2
Florence
— 3 nights
Drive:  4​h
3
Cannon Beach
— 3 nights
Drive:  1​h 30​min
4
Portland
— 5 nights
Fly:  6​h 45​min
End: Chicago

3
nights
Ashland

Ashland ©
Ashland is a city in Jackson County, in the State of Oregon. Your day-by-day itinerary now includes Noah's River Adventures. Get out of town with these interesting Ashland side-trips: Grants Pass (Wildlife Images - Rehabilitation & Education Center & The Glass Forge), Lost Creek Covered Bridge (in Eagle Point) and Crater Lake National Park (in Crater Lake National Park). There's lots more to do: explore the activities along Rogue River, look for gifts at Rogue Creamery, and Head underground at Oregon Caves National Monument and Preserve.

To find reviews, photos, and other tourist information, you can read our Ashland road trip planning tool .

Chicago to Ashland is an approximately 10-hour combination of flight and bus. You can also do a combination of subway, bus, and flight; or drive. You'll gain 2 hours traveling from Chicago to Ashland due to the time zone difference. Expect a bit cooler evenings in Ashland when traveling from Chicago in June, with lows around 55°F. Wrap up your sightseeing on the 8th (Sat) to allow time to drive to Florence.

Things to do in Ashland

Parks Nature Adventure

Side Trips

Grants Pass, Rogue River, Lost Creek Covered Bridge, Crater Lake National Park, Rogue Creamery
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Noah's River Adventures ©
Noah's River Adventures
Rogue River ©
Rogue River

3
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Bring the kids along to Sandland Adventures and Devils Punchbowl State Natural Area. Change things up with these side-trips from Florence: Newport (Yaquina Head Outstanding Natural Area, Newport's Historic Bayfront, & more) and Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline). There's still lots to do: tour or see a game at Sand Master Park and take in the dramatic natural features at Thor's Well.

To find other places to visit, ratings, maps, and more tourist information, you can read our Florence trip planner .

Traveling by car from Ashland to Florence takes 4.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. Expect colder weather when traveling from Ashland in June: highs in Florence hover around 65°F, while lows dip to 52°F. Wrap up your sightseeing on the 11th (Tue) early enough to drive to Cannon Beach.

Things to do in Florence

Parks Outdoors Nature

Side Trips

Newport, Yachats
Highlights from your plan
Sand Master Park - Sandboarding ©
Sand Master Park - Sandboarding
Oregon Coast Aquarium ©
Oregon Coast Aquarium

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Bring the kids along to Haystack Rock and Cannon Beach. Explore Cannon Beach's surroundings by going to Astoria (Astoria Column, Astoria-Megler Bridge, & more). There's still lots to do: admire the majestic nature at Ecola State Park, see the interesting displays at Seaside Inverted Experience, get up close and personal with brilliant marine life at Seaside Aquarium, and stop by Seaside Candyman.

Make your Cannon Beach itinerary with Inspirock to find out what to see and where to go.

Getting from Florence to Cannon Beach by car takes about 4 hours. Other options: do a combination of bus and flight; or take a bus. Expect a daytime high around 66°F in June, and nighttime lows around 52°F. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Portland.

Things to do in Cannon Beach

Parks Nature Outdoors

Side Trips

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

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.
Escape Games PDX has been added to your itinerary. Family-friendly places like Powell's City of Books and Oregon Zoo will thrill your kids. Explore the numerous day-trip ideas around Portland: Historic Columbia River Highway State Trail (in Mosier), Big Winds (in Hood River) and Multnomah Falls (in Bridal Veil). Next up on the itinerary: explore the activities along Columbia River Gorge National Scenic Area, admire the natural beauty at Lan Su Chinese Garden, get a sense of history and politics at Portland City Hall, and steep yourself in history at Timberline Lodge and Ski Area.

For more things to do, reviews, maps, and tourist information, use the Portland trip itinerary maker app .

Traveling by car from Cannon Beach to Portland takes 1.5 hours. Alternatively, you can take a bus. Expect somewhat warmer weather when traveling from Cannon Beach in June: highs in Portland hover around 77°F, while lows dip to 56°F. Wrap up your sightseeing by early afternoon on the 19th (Wed) to allow time for travel back home.

Things to do in Portland

Parks Nature Wildlife

Side Trips

Multnomah Falls, Camassia Natural Area, Timberline Lodge and Ski Area, Columbia River Gorge National Scenic Area, Big Winds
Highlights from your plan
Multnomah Falls ©
Multnomah Falls
Powell's City of Books ©
Powell's City of Books

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