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MDW - PWM

Find cheap flights from Chicago Midway Airport to Portland from $59

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 5/6. 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
0 bags
Sun 5/19
Sun 5/26

Search 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
In the last 7 days travelers have searched 44,212,662 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
1:13 pm - 9:02 amMDW-PWM
18h 49m1 stop
11:46 am - 10:48 amPWM-MDW
24h 02m1 stop
$160Frontier
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Fri, Sep 20 - Sun, Sep 22
1:13 pm - 9:02 amMDW-PWM
18h 49m1 stop
9:52 am - 9:55 pmPWM-MDW
13h 03m1 stop
$177Frontier
Find Deal
Fri, Sep 6 - Mon, Sep 9
11:38 am - 9:02 amMDW-PWM
20h 24m1 stop
9:52 am - 9:55 pmPWM-MDW
13h 03m1 stop
$189Frontier
Find Deal
Mon, Aug 19 - Fri, Aug 23
1:24 pm - 11:00 pmMDW-PWM
8h 36m2 stops
5:37 am - 8:48 amPWM-MDW
4h 11m1 stop
$203Delta
Find Deal
Tue, Jun 11 - Wed, Jun 26
5:05 am - 12:00 pmMDW-PWM
29h 55m1 stop
9:11 am - 10:36 pmPWM-MDW
14h 25m1 stop
$239Frontier
Find Deal
Thu, May 9 - Mon, May 13
10:28 am - 8:02 pmMDW-PWM
8h 34m1 stop
11:40 am - 11:11 amPWM-MDW
24h 31m1 stop
$246Frontier
Find Deal
Thu, Jun 6 - Sun, Jun 9
10:28 am - 8:02 pmMDW-PWM
8h 34m1 stop
11:40 am - 11:11 amPWM-MDW
24h 31m1 stop
$250Frontier
Find Deal
Thu, Jun 6 - Sun, Jun 9
11:38 am - 9:02 amMDW-PWM
20h 24m1 stop
11:46 am - 10:48 amPWM-MDW
24h 02m1 stop
$253Frontier
Find Deal
Mon, Aug 12 - Sun, Aug 18
5:47 pm - 11:44 pmMDW-PWM
4h 57m1 stop
5:37 am - 8:48 amPWM-MDW
4h 11m1 stop
$267Delta
Find Deal
Sat, Jun 1 - Sun, Jun 9
12:45 pm - 9:59 pmMDW-PWM
8h 14m1 stop
5:37 am - 8:48 amPWM-MDW
4h 11m1 stop
$269Delta
Find Deal
Tue, Jun 11 - Wed, Jun 26

Flights from Midway to Portland - Travel Insights & Trends

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 flights from Chicago Midway Airport to Portland, Maine 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 Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Portland, Monday is the cheapest day to fly and Thursday is the most expensive.

What is the cheapest month to fly from Chicago Midway Airport to Portland, Maine?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Portland, Maine, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Portland, Maine is April, where tickets cost $335 on average. On the other hand, the most expensive months are November and December, where the average cost of tickets is $490 and $443 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Portland, Maine?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Portland, Maine, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Portland, Maine, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 65 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Portland?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $59. KAYAK users also found Chicago Midway Airport to Portland round-trip flights on Frontier from $160 and on Delta from $203.

Good to know

Cheapest flight

$59
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, Maine?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Portland, Maine was $59 for a one-way ticket and $160 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 aircraft models fly most regularly from Chicago Midway Airport to Portland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Portland?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Portland.

  • 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.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to Portland?

Find which airlines fly direct from Midway to Portland, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Portland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Portland to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

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
DeltaOverall score based on 11094 reviews
8.2boarding
8.6crew
7.5food
7.9comfort
8.0entertainment
Airline reviews

Seat back monitors and outlets were dead and not working.

8.0 ExcellentCarl, Apr 2024JFK - FLL
Read more about Delta reviews

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

It was a crowded flight. They did the best they could.

Service was good for such a short flight. Small plane but smooth flight.

Worst flight in my life. Only was scheduled for a 45 min flight to get our connection flight. It was late by 40 minutes and we missed our connection. Delta was totally useless trying to help and unable to get my family on the next flight because they overbooked it Thus had to get a hotel at my expense and lost a day at Disney as a result. Cost me about a $1000 if you add 2 hotels meals shuttles etc to get thru the day Awful customer service by Delta in Detroit totally useless people

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

Boarding was great. The flight landed early. It took the crew over an hour and a half to bring out drinks. I paid to upgrade my seat to Comfort+ only to be near a crying/screaming baby who was seldom quiet. Noise-cancelling earbuds didn’t even help. Waste of money to upgrade.

Book cheap flights from Chicago to Portland

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Portland found on KAYAK in the last 72 hours.
5/6Mon
1 stopFrontier
19h 26mMDW-PWM
$59
5/15Wed
1 stopFrontier
16h 54mMDW-PWM
$60
5/5Sun
1 stopFrontier
12h 40mMDW-PWM
$65
5/20Mon
1 stopFrontier
21h 36mMDW-PWM
$83
5/6Mon
1 stopFrontier
19h 26mMDW-PWM
$85
6/11Tue
2 stopsDelta
8h 36mMDW-PWM
$104
6/11Tue
1 stopDelta
8h 14mMDW-PWM
$149
6/11Tue
1 stopDelta
8h 14mMDW-PWM
$170
7/11Thu
1 stopDelta
4h 39mMDW-PWM
$210
5/6Mon
3 stopsWestJet
22h 42mMDW-PWM
$737

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Last minute flights from Midway to Portland

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Portland that are departing in the next 10 days.
4/23Tue
multi-stopDelta
4h 44mMDW-PWM
4/30Tue
multi-stopDelta
4h 50mPWM-MDW
$493
4/23Tue
multi-stopDelta
11h 27mMDW-PWM
4/30Tue
multi-stopDelta
4h 50mPWM-MDW
$498
4/23Tue
multi-stopDelta
8h 02mMDW-PWM
4/30Tue
multi-stopDelta
12h 10mPWM-MDW
$503

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Chicago Midway Airport - Portland Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Portland (PWM)United States

Return flight deals:

Portland - Chicago Midway Airport

Cabin classes:

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