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Find cheap Southwest flights to Portland from $120

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Cheap Southwest Flight Deals to Portland

 
Here are some of the best deals found on KAYAK recently from Southwest to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip Southwest flight deals to Portland

KAYAK's recommended round-trip Southwest deals departing in the coming months to Portland.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
1:50 pm - 12:05 amORD-PWM
9h 15m1 stop
Southwest Logo
7:40 am - 11:50 amPWM-ORD
5h 10m1 stop
$254Southwest
Find Deal
Fri, Oct 24 - Tue, Oct 28
Southwest Logo
5:20 am - 1:15 pmDEN-PWM
5h 55m1 stop
Southwest Logo
3:40 pm - 9:25 pmPWM-DEN
7h 45m1 stop
$273Southwest
Find Deal
Fri, Sep 12 - Tue, Sep 16
Southwest Logo
1:50 pm - 12:05 amORD-PWM
9h 15m1 stop
Southwest Logo
5:40 am - 1:05 pmPWM-ORD
8h 25m1 stop
$275Southwest
Find Deal
Fri, Jun 27 - Mon, Jun 30
Southwest Logo
7:30 am - 6:20 pmORD-PWM
9h 50m2 stops
Southwest Logo
5:50 am - 11:50 amPWM-ORD
7h 00m1 stop
$279Southwest
Find Deal
Wed, Aug 27 - Tue, Sep 2
Southwest Logo
5:50 am - 2:55 pmDEN-PWM
7h 05m1 stop
Southwest Logo
5:50 am - 12:50 pmPWM-DEN
9h 00m2 stops
$282Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
11:40 pm - 9:50 amDEN-PWM
8h 10m1 stop
Southwest Logo
5:50 am - 3:25 pmPWM-DEN
11h 35m2 stops
$294Southwest
Find Deal
Wed, Aug 20 - Tue, Aug 26
Southwest Logo
1:15 pm - 11:25 pmDEN-PWM
8h 10m2 stops
Southwest Logo
7:40 pm - 11:40 pmPWM-DEN
6h 00m1 stop
$298Southwest
Find Deal
Tue, Jun 10 - Fri, Jun 13
Southwest Logo
7:30 am - 6:20 pmORD-PWM
9h 50m2 stops
Southwest Logo
5:50 am - 5:55 pmPWM-ORD
13h 05m2 stops
$304Southwest
Find Deal
Wed, Aug 27 - Tue, Sep 2
Southwest Logo
1:50 pm - 12:05 amORD-PWM
9h 15m1 stop
Southwest Logo
5:40 am - 1:05 pmPWM-ORD
8h 25m1 stop
$310Southwest
Find Deal
Thu, Jun 26 - Mon, Jun 30
Southwest Logo
11:25 am - 12:05 amORD-PWM
11h 40m2 stops
Southwest Logo
5:40 am - 1:05 pmPWM-ORD
8h 25m1 stop
$314Southwest
Find Deal
Thu, Jun 26 - Mon, Jun 30
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$120
Average price round-trip$416
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Chicago O'Hare Airport to Portland
(price for this month)

When to book flights with Southwest to Portland

Average price per month
Flight prices as travel date approaches

FAQs for flying to Portland with Southwest

  • Which other airlines fly to Portland?

    Along with Southwest, you can also fly to Portland with Delta, Delta, Breeze Airways, Breeze Airways, American Airlines, United Airlines and United Airlines.

  • How much is a flight to Portland with Southwest?

    On average, Southwest flights to Portland cost $181 one-way.

  • Which airport do Southwest flights to Portland fly into?

    You’ll fly into Portland Airport when flying to Portland with Southwest.

Top tips for your flights to Portland with Southwest

  • The cheapest flight to Portland with Southwest found on KAYAK in the last 2 weeks departed from Baltimore and cost $122.

Southwest customer reviews

8.0
Very goodBased on 4,294 verified guest reviews
7.1Food
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
K
8.0 Very good
Start drink service earlier. We were rushed.
J
8.0 Very good
It is southwest seat was ok. Not the most comfortable seat
H
6.0 Okay
They were more than 2 hours late.
H
10.0 Wonderful
Good
J
8.0 Very good
I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight
J
6.0 Okay
The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.
A
10.0 Wonderful
Plz don't take away free bags and free seating
D
6.0 Okay
The seats were a bit cramped and worn, but otherwise okay.
D
6.0 Okay
The seats were a bit cramped, but otherwise okay.
A
8.0 Very good
It departed late
Read more about Southwest

Everything you need to know for your flight to Portland

Other airlines flying to Portland

Flight deals from the most popular airlines with KAYAK users flying the route
JetBlue flights to Portland
Delta flights to Portland
American Airlines flights to Portland
United Airlines flights to Portland

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