11 days in Oregon, Chicago & New York City Itinerary

11 days in Oregon, Chicago & New York City Itinerary

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Route & dates

11 days in Oregon, Chicago & New York City Itinerary

Start: Tokyo
+2
Fly + tram + bus:  15​h 30​min
1
Cannon Beach
— 1 night
Drive:  2​h 15​min
2
Lincoln City
— 2 nights
Drive:  3​h 45​min
3
Bandon
— 2 nights
bus + Fly:  11​h
4
Chicago
— 1 night
Fly + bus:  4​h 45​min
5
New York City
— 1 night
Fly:  16​h 15​min
End: Tokyo

1
night
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Start off your visit on the 29th (Mon): examine the collection at International Police Museum, then get some fabulous bargains at The Myrtlewood Factory Outlet, then browse for treasures at Wheeler Station Antiques, and finally enjoy the sand and surf at Cannon Beach. Get ready for a full day of sightseeing on the 30th (Tue): take in the exciting artwork at Icefire Glassworks, then take in the dramatic natural features at Haystack Rock, and then look for gifts at Tillamook Country Smoker.

For where to stay, reviews, more things to do, and other tourist information, you can read our Cannon Beach trip planner .

Tokyo, Japan to Cannon Beach is an approximately 15.5-hour combination of flight and bus. You can also do a combination of flight, train, and bus. You'll gain 17 hours traveling from Tokyo to Cannon Beach due to the time zone difference. Plan for slightly colder temperatures traveling from Tokyo in April, with highs in Cannon Beach at 17°C and lows at 7°C. Finish your sightseeing early on the 30th (Tue) to allow enough time to drive to Lincoln City.

Things to do in Cannon Beach

Parks Beaches Outdoors

Side Trips

International Police Museum, Tillamook Country Smoker, The Myrtlewood Factory, Wheeler Station Antiques
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Wheeler Station Antiques ©
Wheeler Station Antiques

2
nights
Lincoln City

Lincoln City ©
Lincoln City is a city in Lincoln County, Oregon, United States. Kick off your visit on the 1st (Wed): take in the exciting artwork at Freed Gallery, take in the exciting artwork at Rock Your World: Pacific Northwest Gem & Jewelry Gallery, take in the exciting artwork at Alderhouse Glass Blowers, shop like a local with Mossy Creek Pottery, then get engrossed in the history at North Lincoln County Historical Museum, and finally take in the exciting artwork at Lincoln City Glass Center. Get ready for a full day of sightseeing on the 2nd (Thu): get engrossed in the history at Prehistoric, then buy something for everyone on your list at Little Antique Mall, then shop like a local with The Edge Art Gallery, and finally pick up some local products at Newport Farmer's Market.

To see photos, traveler tips, and tourist information, go to the Lincoln City day trip website .

Traveling by car from Cannon Beach to Lincoln City takes 2.5 hours. Alternatively, you can take a bus. In April, daytime highs in Lincoln City are 15°C, while nighttime lows are 6°C. Finish up your sightseeing early on the 2nd (Thu) so you can go by car to Bandon.

Things to do in Lincoln City

Shopping Museums

Side Trips

The Edge Art Gallery, Newport Farmer's Market
Highlights from your plan
Mossy Creek Pottery ©
Mossy Creek Pottery
The Edge Art Gallery ©
The Edge Art Gallery
Lincoln City Glass Center ©
Lincoln City Glass Center

2
nights
Bandon

Bandon ©
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. On the 3rd (Fri), look for gifts at Langlois Market, admire the majestic nature at Bandon State Park, then take in the exciting artwork at Second Street Gallery, then view the masterpieces at Washed Ashore - Gallery & Workshop, and finally view the masterpieces at Art by the Sea Gallery and Studio. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Bandon Historical Society Museum, shop like a local with Hawthorne Gallery, and then see the interesting displays at Port Orford Lifeboat Station Museum.

For other places to visit, where to stay, maps, and more tourist information, read our Bandon trip website .

Drive from Lincoln City to Bandon in 4 hours. Alternatively, you can take a bus; or do a combination of bus and train. May in Bandon sees daily highs of 19°C and lows of 11°C at night. Finish up your sightseeing early on the 4th (Sat) so you can travel to Chicago.

Things to do in Bandon

Museums Shopping Parks

Side Trips

Port Orford, Langlois Market
Highlights from your plan
Hawthorne Gallery ©
Hawthorne Gallery
Bandon State Park ©
Bandon State Park
Langlois Market ©
Langlois Market

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 5th (Sun): look for gifts at Woodman's and then get a taste of the local shopping with The Magnificent Mile. Get ready for a full day of sightseeing on the next day: explore the engaging exhibits at Dupage Children's Museum and then buy something for everyone on your list at Southlake Mall.

Plan a Chicago trip in moments using our itinerary builder.

Traveling by combination of bus and flight from Bandon to Chicago takes 11 hours. Alternatively, you can drive; or do a combination of bus and train. You'll lose 2 hours traveling from Bandon to Chicago due to the time zone difference. Traveling from Bandon in May, expect nights in Chicago to be about the same, around 13°C, while days are a bit warmer, around 25°C. Cap off your sightseeing on the 6th (Mon) early enough to travel to New York City.

Things to do in Chicago

Shopping Neighborhoods Museums

Side Trips

Dupage Children's Museum, Woodman's, Southlake Mall
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Dupage Children's Museum ©
Dupage Children's Museum
Southlake Mall ©
Southlake Mall

1
night
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.
On the 7th (Tue), examine the collection at United States Golf Association Museum, examine the collection at Golf House Museum, then pick up some local products at Goffle Road Poultry Farm, and finally browse the eclectic array of goods at Chelsea Market. Get ready for a full day of sightseeing on the 8th (Wed): grab your bike and head to Bliss Price Arboretum and Wildlife Sanctuary and then stop by Bridgewater Commons.

For traveler tips, ratings, other places to visit, and other tourist information, go to the New York City trip planner.

Getting from Chicago to New York City by combination of flight and bus takes about 5 hours. Other options: fly; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to New York City. In May, daily temperatures in New York City can reach 24°C, while at night they dip to 15°C. Wrap up your sightseeing on the 8th (Wed) early enough to travel back home.

Things to do in New York City

Museums Parks Trails

Side Trips

Far Hills, Bridgewater Commons, Bliss Price Arboretum and Wildlife Sanctuary, Goffle Road Poultry Farm
Highlights from your plan
Golf House Museum ©
Golf House Museum
Chelsea Market ©
Chelsea Market

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