MDW - PWM

$111 Find Cheap Flights from Chicago Midway Airport to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Portland departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Portland (MDW-PWM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Portland

Tue, Mar 3 - Wed, Mar 4
Delta Logo
1:05 pm - 11:49 pmMDW-PWM
9h 44m2 stops
Delta Logo
6:00 am - 12:35 pmPWM-MDW
7h 35m2 stops
$259Delta
Find Deal
Mon, Jan 26 - Thu, Jan 29
Southwest Logo
6:50 am - 2:55 pmMDW-PWM
7h 05m1 stop
Southwest Logo
5:45 am - 11:35 amPWM-MDW
6h 50m1 stop
$269Southwest
Find Deal
Fri, Nov 14 - Wed, Nov 19
Delta Logo
1:15 pm - 11:54 pmMDW-PWM
9h 39m2 stops
Delta Logo
6:00 am - 11:52 amPWM-MDW
6h 52m1 stop
$274Delta
Find Deal
Fri, Nov 14 - Wed, Nov 19
Delta Logo
1:15 pm - 11:54 pmMDW-PWM
9h 39m2 stops
Delta Logo
2:30 pm - 11:40 pmPWM-MDW
10h 10m2 stops
$279Delta
Find Deal
Fri, Feb 27 - Tue, Mar 3
Southwest Logo
5:25 am - 4:15 pmMDW-PWM
9h 50m2 stops
Southwest Logo
5:45 am - 11:35 amPWM-MDW
6h 50m1 stop
$284Southwest
Find Deal
Fri, Feb 27 - Tue, Mar 3
Southwest Logo
5:25 am - 4:15 pmMDW-PWM
9h 50m2 stops
Southwest Logo
5:45 am - 1:25 pmPWM-MDW
8h 40m2 stops
$289Southwest
Find Deal
Fri, Nov 14 - Wed, Nov 19
Southwest Logo
5:05 am - 11:10 amMDW-PWM
5h 05m1 stop
Southwest Logo
5:30 am - 10:10 amPWM-MDW
5h 40m1 stop
$299Southwest
Find Deal
Wed, Nov 12 - Sat, Nov 15
Delta Logo
1:15 pm - 10:19 pmMDW-PWM
8h 04m2 stops
Delta Logo
12:48 pm - 6:08 pmPWM-MDW
6h 20m1 stop
$304Delta
Find Deal
Fri, Nov 14 - Wed, Nov 19
Delta Logo
9:34 am - 10:19 pmMDW-PWM
11h 45m2 stops
Delta Logo
6:00 am - 4:39 pmPWM-MDW
11h 39m2 stops
$309Delta
Find Deal
Fri, Dec 19 - Mon, Dec 29
Multiple Airlines Logo
3:10 pm - 10:36 amMDW-PWM
18h 26m1 stop
Multiple Airlines Logo
11:21 am - 10:12 pmPWM-MDW
35h 51m2 stops
$510Multiple Airlines
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $259 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$259
Delta
Tue 3/3Wed 3/4
MDW - PWM • 2 stops
Cheapest one-way
$111
Multiple Airlines
Fri 12/5
MDW - PWM • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Booking Insights

KAYAK's insights & trends for Midway to Portland flights

Get data-powered insights and trends into flights from Midway to Portland to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Portland?

The average price of all round-trip flights from Chicago Midway Airport to Portland clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Portland, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Portland, Thursday is the cheapest day to fly and Sunday is the most expensive.

Can I save money by flying with a layover from Chicago Midway Airport to Portland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $591 on average.

Good to know

Low seasonFebruary
Cheapest flight$111
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Chicago Midway Airport to Portland

When to book flights from Midway to Portland

Are your dates flexible? Find out the best times to travel from Midway to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Portland flights

  • What is the cheapest flight from Chicago Midway Airport to Portland?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Portland was $111 for a one-way ticket and $259 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Portland?

    No, a passport isn't needed to fly from Chicago Midway Airport to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago Midway Airport to Portland?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Portland is Portland.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Portland?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Portland flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Portland?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Portland flight route.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PWM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4240 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Everything you need to know for your flight from Midway to Portland

Information on your arrival and departure airports

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