31 days in Oregon & Chicago Itinerary

31 days in Oregon & Chicago Itinerary

Created using Inspirock United States travel route builder

Make it your trip
Fly
1
Hood River
— 4 nights
Drive
2
Portland
— 5 nights
Drive
3
Cannon Beach
— 2 nights
Drive
4
Yachats
— 1 night
Drive
5
Ashland
— 2 nights
Drive
6
Crater Lake National Park
— 4 nights
Drive
7
Bend
— 4 nights
Fly
8
Chicago
— 8 nights
Fly

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Hood River

— 4 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. You'll find plenty of places to visit near Hood River: Timberline Lodge and Ski Area (in Timberline Lodge) and Bonneville Lock & Dam (in Cascade Locks). There's still lots to do: explore the activities along Columbia River Gorge National Scenic Area, see the interesting displays at Western Antique Aeroplane & Automobile Museum, tour the pleasant surroundings at Mitchell Point Trail, and explore and take pictures at Hood River County Fruit Loop.

Plan my trip to Hood River with suggested itineraries provided by Inspirock.

Philadelphia to Hood River is an approximately 10.5-hour flight. You can also drive; or do a combination of train and subway. The time zone difference when traveling from Philadelphia to Hood River is minus 3 hours. In July, Hood River is slightly colder than Philadelphia - with highs of 79°F and lows of 58°F. Wrap up your sightseeing on the 5th (Mon) to allow time to drive to Portland.

Things to do in Hood River

Parks · Nature · Outdoors · Winter Sports

Side Trips

Portland

— 5 nights

City of Roses

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.
Explore Portland's surroundings by going to McMinnville (Evergreen Aviation & Space Museum & Memorial to Yamhill County Soldiers of the World War), Multnomah Falls (in Bridal Veil) and Cellar Door Wine Tours (in Lafayette). There's still lots to do: admire the natural beauty at International Rose Test Garden, tour the pleasant surroundings at Wildwood Trail, learn about wildlife with up-close encounters at Oregon Zoo, and sample some tasty brews at a beer tour and tasting.

To find more things to do, ratings, photos, and tourist information, use the Portland road trip app.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. In July, daytime highs in Portland are 83°F, while nighttime lows are 59°F. Wrap up your sightseeing on the 10th (Sat) to allow time to drive to Cannon Beach.

Things to do in Portland

Parks · Tours · Outdoors · Wineries

Side Trips

Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 11th (Sun), enjoy the sand and surf at Cannon Beach, take in the dramatic natural features at Haystack Rock, then admire the majestic nature at Oswald West State Park, and finally tour the pleasant surroundings at Cedar Wetlands Preserve. On your second day here, admire the majestic nature at Nehalem Bay State Park, tour the pleasant surroundings at Manzanita Beach, then stop by Cloud and Leaf Bookstore, and finally admire the majestic nature at Ecola State Park.

For reviews, traveler tips, ratings, and more tourist information, read Cannon Beach trip site.

You can drive from Portland to Cannon Beach in 1.5 hours. Another option is to take a bus. Traveling from Portland in July, expect nights in Cannon Beach to be about the same, around 55°F, while days are little chillier, around 69°F. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Yachats.

Things to do in Cannon Beach

Parks · Nature · Outdoors · Beaches

Side Trips

Yachats

— 1 night
Yachats is a small coastal city in Lincoln County, Oregon, United States. Start off your visit on the 13th (Tue): take a leisurely stroll along Yachats coastline, then cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, then explore the striking landscape at Thor's Well, and finally enjoy the sea views from Heceta Head Lighthouse.

To find maps, reviews, traveler tips, and other tourist information, read Yachats road trip planning tool.

Traveling by car from Cannon Beach to Yachats takes 3.5 hours. Alternatively, you can fly; or take a bus. Traveling from Cannon Beach in July, things will get slightly colder in Yachats: highs are around 63°F and lows about 50°F. Cap off your sightseeing on the 13th (Tue) early enough to go by car to Ashland.

Things to do in Yachats

Nature · Parks · Scenic Drive · Outdoors

Side Trip

Ashland

— 2 nights
Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 14th (Wed): get a taste of the local shopping with Gathering Glass Studio, walk around Lithia Park, then catch a live performance at Oregon Shakespeare Festival, and finally relax and float downstream with a rafting and tubing tour. Get ready for a full day of sightseeing on the 15th (Thu): hike along Natural Bridge Loop, explore the activities along Rogue River, then shop like a local with The Glass Forge, and finally examine the collection at Bear Hotel Artworks Museum.

For photos, maps, traveler tips, and tourist information, use the Ashland online travel planner.

Traveling by car from Yachats to Ashland takes 5 hours. Alternatively, you can fly; or take a bus. When traveling from Yachats in July, plan for warmer days and a bit warmer nights in Ashland: temperatures range from 94°F by day to 61°F at night. Finish up your sightseeing early on the 15th (Thu) so you can go by car to Crater Lake National Park.

Things to do in Ashland

Parks · Outdoors · Nightlife · Nature

Side Trips

Crater Lake National Park

— 4 nights
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
When in Crater Lake National Park, make a side trip to see Collier Memorial State Park in Chiloquin, approximately Chiloquin away. Spend the 16th (Fri) exploring nature at Crater Lake National Park. There's still lots to do: tour the pleasant surroundings at Cleetwood Cove Trail, step off the mainland to explore Wizard Island, hike along Sun Notch Trail, and admire the sheer force of Whitehorse Falls.

To see maps, photos, reviews, and other tourist information, read Crater Lake National Park trip planner.

Drive from Ashland to Crater Lake National Park in 2 hours. Alternatively, you can do a combination of bus and taxi. July in Crater Lake National Park sees daily highs of 94°F and lows of 61°F at night. Finish your sightseeing early on the 19th (Mon) to allow enough time to drive to Bend.

Things to do in Crater Lake National Park

Parks · Nature · Outdoors · Trails

Side Trips

Bend

— 4 nights
An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.
You'll find plenty of places to visit near Bend: Dee Wright Observatory (in Blue River), McKenzie Pass-Santiam Pass loop (in Sisters) and Smith Rock State Park (in Redmond). The adventure continues: let the river carry you with a rafting and tubing tour, stroll around Drake Park, explore the wealth of natural beauty at Deschutes National Forest, and trek along Oregon Badlands Wilderness Trails.

For maps, ratings, photos, and more tourist information, refer to the Bend trip planner.

Drive from Crater Lake National Park to Bend in 2.5 hours. Alternatively, you can do a combination of taxi and bus. In July, Bend is a bit cooler than Crater Lake National Park - with highs of 85°F and lows of 52°F. You will have some time to spend on the 23rd (Fri) before leaving for Chicago.

Things to do in Bend

Parks · Nature · Outdoors · Childrens Museums

Side Trips

Chicago

— 8 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, meet the residents at Lincoln Park Zoo, get a new perspective on nature at Field Museum, and take a leisurely stroll along Navy Pier.

To see photos, traveler tips, other places to visit, and more tourist information, go to the Chicago trip itinerary site.

You can fly from Bend to Chicago in 10 hours. Other options are to drive; or do a combination of bus and train. Traveling from Bend to Chicago, you'll lose 2 hours due to the time zone difference. Traveling from Bend in July, you can expect nighttime temperatures to be somewhat warmer in Chicago, with lows of 67°F. Finish up your sightseeing early on the 31st (Sat) so you can travel back home.

Things to do in Chicago

Parks · Museums · Historic Sites · Childrens Museums

Side Trips

Oregon travel guide

4.5
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.