18 days in United States Itinerary

18 days in United States Itinerary

Created using Inspirock United States trip itinerary planner

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Route & dates

18 days in United States Itinerary

Start: Madison
Fly:  8​h 15​min
1
Portland
— 2 nights
Drive:  2​h
2
Cannon Beach
— 3 nights
Drive:  4​h 15​min
3
Seattle
— 1 night
Fly:  4​h
4
San Francisco
— 4 nights
Fly + bus:  8​h 45​min
5
Grand Canyon National Park
— 3 nights
bus + Fly:  10​h 45​min
6
Chicago
— 2 nights
Drive:  2​h 45​min
End: Madison


Learn more about your trip

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.
Kick off your visit on the 6th (Sat): take in nature's colorful creations at Portland Japanese Garden. On the 7th (Sun), you'll have a packed day of sightseeing: take in the dramatic scenery at Little Zigzag Falls, admire the sheer force of Multnomah Falls, and then look for gifts at Powell's City of Books.

To find reviews, ratings, other places to visit, and more tourist information, read Portland visit planner.

Madison to Portland is an approximately 8.5-hour flight. You can also do a combination of bus and flight; or drive. The time zone difference moving from Central Standard Time to Pacific Standard Time is minus 2 hours. Expect a bit warmer evenings in Portland when traveling from Madison in October, with lows around 49°F. Finish your sightseeing early on the 8th (Mon) so you can drive to Cannon Beach.

Things to do in Portland

Parks Nature Wildlife

Side Trips

Wintler Community Park, Multnomah Falls, Evergreen Aviation & Space Museum, Sokol Blosser Winery, Little Zigzag Falls
Highlights from your plan
Multnomah Falls ©
Multnomah Falls
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Sokol Blosser Winery ©
Sokol Blosser Winery

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Start off your visit on the 9th (Tue): stroll through Cannon Beach, savor the flavors at Seaside Candyman, then explore the activities along Columbia River Maritime Museum, and finally identify plant and animal life at Astoria Column. Here are some ideas for day two: stop by Beach Books, then take in the dramatic natural features at Haystack Rock, then admire the majestic nature at Ecola State Park, and finally stop by Bronze Coast Gallery.

To see maps, photos, and other tourist information, you can read our Cannon Beach itinerary website .

Traveling by car from Portland to Cannon Beach takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 63°F in October, and nighttime lows around 48°F. Wrap up your sightseeing on the 11th (Thu) early enough to drive to Seattle.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

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

1
night
Seattle

Seattle ©
Nicknamed the "Emerald City" because of its abundant evergreen trees, Seattle is the cultural and business center of the Pacific Northwest, as well as a popular holiday destination.
Start off your visit on the 11th (Thu): take in the exciting artwork at Glasshouse Studio, take a leisurely stroll along Hiram M. Chittenden Locks, then identify plant and animal life at Mercer Slough Nature Park, and finally explore the world behind art at Chihuly Garden and Glass. Get ready for a full day of sightseeing on the 12th (Fri): take a stroll through Pike Place Market, then wander the streets of Pioneer Square, and then tour the pleasant surroundings at Alki Beach.

To find traveler tips, more things to do, photos, and tourist information, refer to the Seattle journey maker app .

You can drive from Cannon Beach to Seattle in 4.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. October in Seattle sees daily highs of 63°F and lows of 50°F at night. Wrap up your sightseeing on the 12th (Fri) to allow time to travel to San Francisco.

Things to do in Seattle

Shopping Neighborhoods Parks

Side Trip

Mercer Slough Nature Park
Highlights from your plan
Chihuly Garden and Glass ©
Chihuly Garden and Glass
Pike Place Market ©
Pike Place Market
Alki Beach ©
Alki Beach

4
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Your inner history buff will appreciate Alcatraz Island and SS Jeremiah O'Brien. Fisherman's Wharf and Union Square are good opportunities to explore the local culture. When in San Francisco, make a side trip to see Fitzgerald J V Marine Reserve in Moss Beach, approximately 40 minutes away. And it doesn't end there: enjoy the sand and surf at Marshall’s Beach, browse the different shops at Ferry Building Marketplace, stroll through China Beach, and look for all kinds of wild species at Fort Funston National Park.

To find more things to do, ratings, maps, and other tourist information, read our San Francisco road trip planning app .

Traveling by combination of flight and subway from Seattle to San Francisco takes 4 hours. Alternatively, you can fly; or drive. Traveling from Seattle in October, things will get a bit warmer in San Francisco: highs are around 73°F and lows about 56°F. Finish your sightseeing early on the 16th (Tue) to allow enough time to travel to Grand Canyon National Park.

Things to do in San Francisco

Parks Beaches Outdoors

Side Trip

Fitzgerald J V Marine Reserve
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Golden Gate Bridge ©
Golden Gate Bridge
Fisherman's Wharf ©
Fisherman's Wharf

3
nights
Grand Canyon National Park

Grand Canyon National Park ©
The size, shape, and color of Grand Canyon National Park combine to leave an impression on visitors as deep as the canyon itself.
Step out of the city life by going to Nature & Wildlife Tours and Bright Angel Trail. For shopping fun, head to Canyon Village Marketplace or Lookout Studio. There's much more to do: trek along Rim Trail, admire the striking features of Grand Canyon Railway Depot, take in breathtaking views at Grand Canyon South Rim, and stop by Tusayan General Store.

To find where to stay, other places to visit, traveler tips, and other tourist information, go to the Grand Canyon National Park trip itinerary planner.

Do a combination of flight and bus from San Francisco to Grand Canyon National Park in 9 hours. Alternatively, you can do a combination of subway, flight, and bus; or drive. The time zone difference when traveling from San Francisco to Grand Canyon National Park is 1 hour. When traveling from San Francisco in October, plan for slightly colder days and cooler nights in Grand Canyon National Park: temperatures range from 66°F by day to 31°F at night. Finish up your sightseeing early on the 20th (Sat) so you can travel to Chicago.

Things to do in Grand Canyon National Park

Outdoors Parks Trails

Side Trip

Tusayan General Store
Highlights from your plan
Grand Canyon South Rim ©
Grand Canyon South Rim
Rim Trail ©
Rim Trail
Bright Angel Trail ©
Bright Angel Trail

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll enjoy a bit of beach vacationing at Oak Street Beach and North Avenue Beach. Get a sense of the local culture at The Art Institute of Chicago and Millennium Park. Go for a jaunt from Chicago to Willow Springs to see Little Red Schoolhouse about 34 minutes away. There's still lots to do: don't miss a visit to The Magnificent Mile, admire the striking features of Skydeck Chicago - Willis Tower, and try your luck at Horseshoe Hammond.

To find ratings, photos, and other tourist information, read our Chicago trip planner .

Traveling by combination of bus and flight from Grand Canyon National Park to Chicago takes 11 hours. Alternatively, you can drive. Due to the time zone difference, you'll lose 1 hour traveling from Grand Canyon National Park to Chicago. Traveling from Grand Canyon National Park in October, expect somewhat warmer with lows of 49°F in Chicago. Wrap up your sightseeing on the 23rd (Tue) early enough to drive back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Little Red Schoolhouse, Horseshoe Hammond
Highlights from your plan
Millennium Park ©
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile

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