Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

PWM - MDW

$62 Find cheap flights from Portland to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Midway departing on 6/11. 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
Sat 6/29
Sat 7/6

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago, 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 Portland to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Portland to Midway (PWM-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Midway 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
4:04 pm - 7:56 pmPWM-MDW
4h 52m1 stop
12:57 pm - 10:49 amMDW-PWM
20h 52m1 stop
$139Frontier
Find Deal
Thu, Jun 13 - Mon, Jun 17
9:52 am - 9:55 pmPWM-MDW
13h 03m1 stop
1:13 pm - 9:02 amMDW-PWM
18h 49m1 stop
$188Frontier
Find Deal
Fri, Sep 6 - Fri, Sep 13
1:57 pm - 5:15 pmPWM-MDW
28h 18m1 stop
12:57 pm - 10:49 amMDW-PWM
20h 52m1 stop
$209Frontier
Find Deal
Thu, Jun 13 - Mon, Jun 17
1:57 pm - 5:15 pmPWM-MDW
28h 18m1 stop
12:57 pm - 10:49 amMDW-PWM
20h 52m1 stop
$239Frontier
Find Deal
Thu, Jun 13 - Mon, Jun 17
1:04 pm - 7:13 pmPWM-MDW
7h 09m1 stop
12:15 pm - 10:56 amMDW-PWM
21h 41m1 stop
$255Frontier
Find Deal
Sun, Aug 18 - Wed, Aug 21
9:52 am - 9:55 pmPWM-MDW
13h 03m1 stop
1:13 pm - 9:02 amMDW-PWM
18h 49m1 stop
$257Frontier
Find Deal
Fri, Aug 23 - Fri, Aug 30
12:55 pm - 5:03 pmPWM-MDW
5h 08m1 stop
5:59 pm - 11:06 pmMDW-PWM
4h 07m1 stop
$258Delta
Find Deal
Wed, Sep 18 - Mon, Sep 23
11:59 am - 6:39 pmPWM-MDW
7h 40m1 stop
5:45 pm - 11:26 pmMDW-PWM
4h 41m1 stop
$268Delta
Find Deal
Wed, Jul 31 - Sat, Aug 3
5:30 am - 1:02 pmPWM-MDW
8h 32m2 stops
5:59 pm - 11:06 pmMDW-PWM
4h 07m1 stop
$272Delta
Find Deal
Wed, Sep 18 - Mon, Sep 23
1:02 pm - 5:05 pmPWM-MDW
5h 03m1 stop
5:45 pm - 11:21 pmMDW-PWM
4h 36m1 stop
$273Delta
Find Deal
Wed, Jul 3 - Sun, Jul 7

Flights from Portland to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Portland to Midway 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 Portland to Chicago Midway Airport?

The average price of all flights from Portland, Maine to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Portland to Chicago Midway Airport, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago Midway Airport back to Portland, the best deals are generally found on Thursday, with Monday being the most expensive.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($62) and Delta ($98). The cheapest round-trip tickets were found on Frontier ($139) and Delta ($258).

How many flights are there between Portland, Maine and Chicago Midway Airport per day?

There is a maximum of 1 nonstop flight a day that takes off from Portland, Maine and lands in Chicago Midway Airport, with an average flight time of 2h 35m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

What’s the earliest departure time from Portland to Chicago Midway Airport?

Early birds can take the earliest flight from Portland, Maine at 3:45 pm and will be landing in Chicago Midway Airport at 5:20 pm.

What’s the latest departure time from Portland to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Portland, Maine to Chicago Midway Airport jets off at 7:00 pm and lands at 8:35 pm.

Good to know

High season

September

Cheapest flight

$62
Most popular time to fly and prices are also 10% lower on average.
Flight from Portland to Chicago Midway Airport

When to book flights from Portland to Midway

Are your dates flexible? Find out the best times to travel from Portland to Midway 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 Portland to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Portland, Maine to Chicago Midway Airport was $62 for a one-way ticket and $139 for a round-trip.

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

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

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

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

  • On which days can I fly direct from Portland to Chicago Midway Airport?

    There are nonstop flights from Portland to Chicago Midway Airport on a daily basis.

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

    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 Portland to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Portland 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 Portland to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Portland with another airline. Booking your flights between Portland and MDW 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 Portland to Chicago Midway Airport?

    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 Chicago Midway Airport from Portland 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 Portland to Chicago Midway Airport?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top airline flying from Portland to Midway

 
See real verified KAYAK customer reviews for airlines flying from Portland to Chicago. 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 Portland to Midway? 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 10457 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

Book cheap flights from Portland to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Portland to Chicago found on KAYAK in the last 72 hours.
6/11Tue
1 stopFrontier
6h 57mPWM-MDW
$62
6/11Tue
2 stopsFrontier
12h 21mPWM-MDW
$74
7/9Tue
2 stopsFrontier
12h 33mPWM-MDW
$91
8/27Tue
1 stopDelta
4h 01mPWM-MDW
$98
8/27Tue
2 stopsDelta
11h 06mPWM-MDW
$103
6/12Wed
1 stopDelta
7h 39mPWM-MDW
$128
6/10Mon
1 stopDelta
5h 14mPWM-MDW
$139
8/6Tue
3 stopsWestJet
33h 06mPWM-MDW
$557
6/9Sun
3 stopsWestJet
31h 56mPWM-MDW
$794
7/7Sun
3 stopsWestJet
23h 11mPWM-MDW
$905

Search by stops

Search by airline

Search by price

Last minute flights from Portland to Midway

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 Portland to Chicago that are departing in the next 10 days.
6/4Tue
multi-stopDelta
5h 06mPWM-MDW
6/11Tue
multi-stopDelta
8h 36mMDW-PWM
$297
6/4Tue
multi-stopDelta
9h 35mPWM-MDW
6/11Tue
multi-stopDelta
8h 36mMDW-PWM
$302
5/31Fri
multi-stopDelta
5h 06mPWM-MDW
6/2Sun
multi-stopDelta
4h 57mMDW-PWM
$448
5/31Fri
multi-stopDelta
10h 24mPWM-MDW
6/2Sun
multi-stopDelta
4h 57mMDW-PWM
$453
6/3Mon
multi-stopDelta
8h 34mPWM-MDW
6/4Tue
multi-stopDelta
8h 29mMDW-PWM
$568
6/4Tue
multi-stopDelta
5h 06mPWM-MDW
6/4Tue
multi-stopDelta
8h 29mMDW-PWM
$601
6/3Mon
multi-stopDelta
5h 06mPWM-MDW
6/4Tue
multi-stopDelta
8h 29mMDW-PWM
$603
6/4Tue
multi-stopDelta
5h 06mPWM-MDW
6/4Tue
multi-stopDelta
4h 57mMDW-PWM
$686
6/3Mon
multi-stopDelta
5h 06mPWM-MDW
6/4Tue
multi-stopDelta
4h 57mMDW-PWM
$688
5/31Fri
multi-stopDelta
8h 26mPWM-MDW
6/2Sun
multi-stopDelta
8h 29mMDW-PWM
$734

Search by stops

Search by airline

Search by price

Portland - Chicago Midway Airport Flights

Departure:

Portland (PWM)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Portland

Cabin classes: