$64 Cheap flight deals from Portland (PWM) to Winchester (CHA)

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This Weekend's Flight Deals from Portland to Winchester

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 11 - Thu, May 29
PWM
Portland Intl. Jetport
BNA
Nashville Intl.
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, May 11 from Portland Intl. Jetport to Nashville Intl., returning Thu, May 29, priced at $200 found 2 days ago

Airfares from $64 One Way, $169 Round Trip from Portland to Winchester

Prices starting at $169 for return flights and $64 for one-way flights to Winchester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jun 2 - Thu, Jun 5
PWM
Portland
BNA
Nashville
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Jun 2 from Portland to Nashville, returning Thu, Jun 5, priced at $169 found 1 day ago
Sat, Jun 7 - Sat, Jun 14
PWM
Portland
BNA
Nashville
$171 Roundtrip, found 10 hours ago
$171
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sat, Jun 7 from Portland to Nashville, returning Sat, Jun 14, priced at $171 found 10 hours ago
Tue, Jun 24 - Wed, Jun 25
PWM
Portland
BNA
Nashville
$174 Roundtrip, found 10 hours ago
$174
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Tue, Jun 24 from Portland to Nashville, returning Wed, Jun 25, priced at $174 found 10 hours ago
Mon, Jun 2 - Fri, Jun 6
PWM
Portland
BNA
Nashville
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jun 2 from Portland to Nashville, returning Fri, Jun 6, priced at $217 found 1 day ago
Wed, Oct 29 - Sun, Nov 2
PWM
Portland
BNA
Nashville
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Portland to Nashville, returning Sun, Nov 2, priced at $217 found 2 days ago

Winchester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Nashville
4.5-star property

Virgin Hotels Nashville

9.4/10 Exceptional! (2,004 reviews)

Jun 16 - Jun 19

3 night stay

Portland (PWM) to Nashville (BNA)

Delta • Non-stop roundtrip • Coach
per person
found 1 day ago
The hotel is nice .Cleanliness was average .Alot of staff was around but no matter what we asked about they could not complete the task. The valet was excellent and fast. The Door greeter was entertaining .

Reviewed on Feb 15, 2025

Bobby Hotel
4.0-star property

Bobby Hotel

9.2/10 Wonderful! (1,006 reviews)

Jun 16 - Jun 19

3 night stay

Portland (PWM) to Nashville (BNA)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The location was very good and close to everything and the staff were excellent. I will say it was a little eclectic for my taste. The glass enclosed bathroom left a bit to be desired. There was a curtain to pull around it to give you some privacy but that did not work well with a bathroom sliding door that would not stay shut. I also found the layout could have been much better in my opinion. This was a room with over 500 square feet and it was all open with no divided spaces that would allow a person to sleep while you were up. One last thing the pool is small and only 3 feet deep. That being said this is a very clean nice hotel, just not my style

Reviewed on Sep 27, 2024

Brentwood Suites, Ascend Hotel Collection
3.0-star property

Brentwood Suites, Ascend Hotel Collection

8.8/10 Excellent! (1,709 reviews)

Jun 21 - Jun 27

6 night stay

Portland (PWM) to Nashville (BNA)

United • Non-stop roundtrip • Coach
per person
found 2 hours ago
Properly was conveniently located. Front desk employees were friendly and efficient. Bed was comfortable. I did not like that the floor of the shower was mildewy and not cleaned properly. I’m glad that I remembered to bring flip flops to shower in. I appreciated that a hot breakfast was prepared. Unfortunately , there was a strand of hair in my scrambled eggs.

Reviewed on Apr 11, 2025

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More About Flying To Winchester from Portland

Route Information for Flights from Portland to Winchester

Origin Airport IATA Code
PWM
Destination Airport IATA Code
CHA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Portland to Winchester

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.