Cheap Flights to Winston from $69

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How Much Does it Cost To Fly To Winston?

The cheapest prices found with in the last 7 days for return flights were $93 and $69 for one-way flights to Winston for the period specified. Prices and availability are subject to change. Additional terms apply

Sat, Aug 30 - Sat, Sep 6
SEA
Seattle - Tacoma Intl.
EUG
Eugene
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Alaska Airlines flight, departing Sat, Aug 30 from Seattle - Tacoma Intl. to Eugene, returning Sat, Sep 6, priced at $117 just found
Sun, Aug 31 - Tue, Sep 9
PHX
Sky Harbor Intl.
EUG
Eugene
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Aug 31 from Sky Harbor Intl. to Eugene, returning Tue, Sep 9, priced at $143 found 1 day ago
OriginDestinationTravel DatesFlights From*
PDXEugeneAugust 20 to August 20$93
SEAEugeneAugust 30 to September 6$117
SANEugeneOctober 14 to October 14$131
PDXMedfordSeptember 2 to September 6$137
SFOEugeneOctober 4 to October 4$161
SFOMedfordOctober 8 to October 8$183
OAKMedfordSeptember 6 to September 9$222
LASMedfordAugust 23 to August 23$229
SLCMedfordSeptember 9 to September 9$236
LASNorth BendSeptember 13 to September 22$253
LAXNorth BendOctober 9 to October 13$329
SFONorth BendOctober 3 to October 6$349
SLCNorth BendOctober 8 to October 11$497
SANNorth BendAugust 11 to August 18$608
DENNorth BendAugust 9 to August 16$656
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
SFOMedfordAugust 8 to August 13$228
PDXEugeneAugust 10 to August 21$242
DENMedfordAugust 9 to August 24$257
LASMedfordAugust 9 to August 23$266
PHXEugeneAugust 9 to August 12$269
SEAEugeneAugust 8 to August 10$277
LAXEugeneAugust 10 to August 19$314
LAXMedfordAugust 9 to August 23$341
DENEugeneAugust 10 to August 23$366
OAKMedfordAugust 8 to August 19$379
LASEugeneAugust 8 to August 11$400
SLCMedfordAugust 9 to August 20$402
DENNorth BendAugust 9 to August 16$656
PHXNorth BendAugust 8 to August 9$679
SFONorth BendAugust 10 to August 17$1,378
*Prices include taxes and fees

Winston Flight Information

Traveling to
Winston
Lowest Price
$93
Number of Airlines Serving
Airlines Serving
Alaska Airlines, Delta
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Winston Accommodation Deals

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street, Winston, OR
$70 nightly
The price is $76 total per night from Aug 4 to Aug 5
$76 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this motel in Winston. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.6/10 Good! (354 reviews)
"A quiet little place . Just right down the street from wildlife Safari ."

Reviewed on Jun 30, 2025

Safari Inn
Wildlife Inn

Wildlife Inn

2 out of 5
251 N Main St, Winston, OR
Book a stay at this business-friendly hotel in Winston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions South Umpqua River and Wildlife ...
"This property was closed for renovations. We arrived and had to find other accomodations. The staff were very friendly in pointing us to other options."

Reviewed on Apr 16, 2021

Get rates
Wildlife Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Winston

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street, Winston, OR
$70 nightly
The price is $76 total per night from Aug 4 to Aug 5
$76 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this motel in Winston. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.6/10 Good! (354 reviews)
"A quiet little place . Just right down the street from wildlife Safari ."

Reviewed on Jun 30, 2025

Safari Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Winston

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street, Winston, OR
$70 nightly
The price is $76 total per night from Aug 4 to Aug 5
$76 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this motel in Winston. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.6/10 Good! (354 reviews)
"A quiet little place . Just right down the street from wildlife Safari ."

Reviewed on Jun 30, 2025

Safari Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Winston Flight and Hotel Packages

Winston flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Bay Point Landing

Bay Point Landing

3.5 out of 5
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to North Bend (OTH)
Bandon Inn

Bandon Inn

3 out of 5
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to North Bend (OTH)
Castillo di Sabbia

Castillo di Sabbia

2 out of 5
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to North Bend (OTH)
Don't see what you're looking for?
See all available trips from Chicago to Winston
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Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Winston?
All ready to book the ticket for your exciting trip to Winston? 8 airlines offer flights to this destination. Some of the most reputable carriers are:

  • United Airlines
  • Alaska Airlines
  • Delta Air Lines

Places to visit in Winston
Wildlife Safari is a fun day for wildlife enthusiasts. After more ideas? A visit to Abacela Winery will be an experience for your tastebuds. That's not all there is to do here. Whether you have trained taste buds or simply enjoy sipping wine with your loved ones, Spangler Vineyards is a fabulous place to try the regional flavors.
How to get through airport security fast when traveling to Winston
These clever hints and tips about airport security procedures will save you a lot of time on your trip to Winston:

  • Airport security will request to see your travel ID and boarding pass as part of their checks. Put them in an accessible place, ready for inspection.
  • You'll need to put your music on pause for a short while. Earphones need to be taken off and put in a tray to be X-rayed. The same goes for items such as keys and coins.
  • Electronic devices such as tablets, laptops and phones are always sent through the X-ray machine separately. Make sure they're within easy reach.
  • When it comes to flying with gels or liquids, all passengers are permitted a quart-sized clear resealable bag to keep containers no bigger than 3.4 ounces (100 milliliters).
  • Construction boots and other heavy shoes are most often X-rayed at the security checkpoint. We suggest wearing lightweight sneakers instead.
  • The list of non-permissible items is forever updating. Check with your carrier's website to learn about what is not allowed on board their aircraft.

Plane Tickets To Winston

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winston. Browse through our inventory to explore a wide range of cheap flights to Winston to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winston as you anxiously await to exit the plane and explore what Winston has to offer. Considering all the amazing local food and culture in Winston, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winston to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winston without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winston with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winston today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.