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$86 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 7/1. 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 7/6
Sat 7/13

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 43,995,393 times on KAYAK, and here is why:

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

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

 
These are the cheapest deals for flights from Portland to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 flight deals from Portland to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Portland to Midway.

Recent one-way flight deals from Portland to Midway

Only flying one-way? Below are some of the best one-way flight deals from Portland to Midway found on KAYAK recently.

Recent last minute flight deals from Portland to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Portland to Midway.

Recent direct flight deals from Portland to Midway

The latest deals for direct flights from Portland to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Portland to Midway

Find recent round-trip train or bus tickets from Portland to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
4:28 pm - 4:45 amPDX-MDW
10h 17m1 stop
7:00 am - 4:06 pmMDW-PDX
11h 06m1 stop
$171Frontier
Find Deal
Thu, Jul 18 - Tue, Jul 30
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
$172Frontier
Find Deal
Fri, Sep 6 - Wed, Sep 11
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
$173Frontier
Find Deal
Tue, Aug 20 - Fri, Aug 23
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
$178Frontier
Find Deal
Mon, Sep 9 - Tue, Sep 17
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
$180Frontier
Find Deal
Tue, Sep 17 - Sun, Sep 22
11:43 am - 4:45 amPDX-MDW
15h 02m1 stop
12:23 pm - 5:37 pmMDW-PDX
31h 14m2 stops
$185Frontier
Find Deal
Tue, Jul 30 - Wed, Jul 31
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
$187Frontier
Find Deal
Mon, Sep 9 - Wed, Sep 18
4:28 pm - 4:45 amPDX-MDW
10h 17m1 stop
6:15 am - 11:53 pmMDW-PDX
19h 38m1 stop
$188Frontier
Find Deal
Thu, Jul 18 - Mon, Jul 29
12:39 am - 8:42 amPDX-MDW
6h 03m1 stop
5:45 pm - 10:07 pmMDW-PDX
6h 22m1 stop
$307Delta
Find Deal
Thu, Sep 5 - Sun, Sep 15
12:39 am - 8:42 amPDX-MDW
6h 03m1 stop
9:20 am - 4:03 pmMDW-PDX
8h 43m1 stop
$337Delta
Find Deal
Thu, Sep 5 - Mon, Sep 16
6:36 pm - 5:29 amPDX-MDW
8h 53m1 stop
$86Frontier
Find Deal
Mon, Jul 1
11:43 am - 4:45 amPDX-MDW
15h 02m1 stop
$92Frontier
Find Deal
Tue, Jul 23
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
$93Frontier
Find Deal
Mon, Sep 2
12:39 am - 8:42 amPDX-MDW
6h 03m1 stop
$109Delta
Find Deal
Thu, Aug 29
12:39 am - 8:42 amPDX-MDW
6h 03m1 stop
$118Delta
Find Deal
Thu, Aug 15
11:59 pm - 7:40 pmPDX-MDW
17h 41m2 stops
Sun, Aug 11
5:55 pm - 1:00 pmPDX-MDW
17h 05m2 stops
Thu, Aug 29
12:15 pm - 11:28 amPDX-MDW
21h 13m3 stops
$455WestJet
Find Deal
Fri, Jul 5
6:29 pm - 9:52 amPDX-MDW
13h 23m1 stop
$473Volaris
Find Deal
Tue, Jul 2
8:15 am - 6:30 pmPDX-MDW
32h 15m3 stops
$641WestJet
Find Deal
Fri, Jun 14
12:49 am - 1:09 pmPDX-MDW
10h 20m1 stop
10:41 pm - 11:59 pmMDW-PDX
27h 18m1 stop
$187Frontier
Find Deal
Mon, Jun 10 - Thu, Jun 13
12:49 am - 1:09 pmPDX-MDW
10h 20m1 stop
7:00 am - 5:11 pmMDW-PDX
12h 11m1 stop
$200Frontier
Find Deal
Mon, Jun 10 - Tue, Jun 18
12:49 am - 1:09 pmPDX-MDW
10h 20m1 stop
11:26 am - 9:30 pmMDW-PDX
12h 04m1 stop
$214Frontier
Find Deal
Mon, Jun 10 - Mon, Jun 17
8:39 am - 11:12 amPDX-MDW
24h 33m1 stop
8:58 pm - 3:59 pmMDW-PDX
21h 01m1 stop
$215Frontier
Find Deal
Sat, Jun 8 - Mon, Jun 24
12:49 am - 12:00 pmPDX-MDW
9h 11m1 stop
11:56 am - 10:07 pmMDW-PDX
12h 11m1 stop
$223Frontier
Find Deal
Tue, Jun 11 - Sat, Jun 15
7:53 am - 5:10 pmPDX-MDW
7h 17m1 stop
10:41 pm - 11:59 pmMDW-PDX
27h 18m1 stop
$224Frontier
Find Deal
Tue, Jun 11 - Thu, Jun 13
5:41 pm - 4:33 amPDX-MDW
8h 52m2 stops
10:41 pm - 11:59 pmMDW-PDX
27h 18m1 stop
$230Frontier
Find Deal
Tue, Jun 11 - Thu, Jun 13
7:53 am - 5:10 pmPDX-MDW
7h 17m1 stop
7:00 am - 5:11 pmMDW-PDX
12h 11m1 stop
$233Frontier
Find Deal
Tue, Jun 11 - Tue, Jun 18
12:30 am - 8:54 amPDX-MDW
6h 24m1 stop
12:07 pm - 5:42 pmMDW-PDX
7h 35m1 stop
$352Delta
Find Deal
Mon, Jun 10 - Sat, Jun 15
6:20 am - 5:59 pmPDX-MDW
9h 39m1 stop
7:19 pm - 11:17 pmMDW-PDX
5h 58m1 stop
$377Delta
Find Deal
Fri, Jun 7 - Mon, Jun 10
5:00 am - 10:55 amPDX-MDW
3h 55mnonstop
8:55 pm - 11:15 pmMDW-PDX
4h 20mnonstop
$572Southwest
Find Deal
Sun, Jun 16 - Tue, Jun 18

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 to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Portland to Chicago Midway Airport, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Mondays and the most expensive ones on Fridays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Portland to Chicago Midway Airport, 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 Portland to Chicago Midway Airport is October, where tickets cost $257 on average. On the other hand, the most expensive months are January and February, where the average cost of tickets is $527 and $453 respectively.

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 ($86) and Delta ($109). The cheapest round-trip tickets were found on Frontier ($171) and Delta ($307).

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

Each day, there are between 2 and 6 nonstop flights that take off from Portland and land in Chicago Midway Airport, with an average flight time of 3h 54m. The most common departure time is 2:00 pm and most flights take off in the afternoon. Each week, there are 28 flights. The most frequent day of departure is Friday, when 21% of all weekly flights depart. The fewest flights depart on a Sunday.

How long does a flight from Portland to Chicago Midway Airport take?

The average nonstop flight takes 3h 55m, covering a distance of 1,746 miles.

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

Early birds can take the earliest flight from Portland at 5:00 am and will be landing in Chicago Midway Airport at 10:55 am.

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

If you prefer to fly at night, the latest flight from Portland to Chicago Midway Airport jets off at 6:50 pm and lands at 12:45 am.

Good to know

Low season

February

High season

May

Cheapest flight

$86
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly and prices are also 18% 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 to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Portland to Chicago Midway Airport was $86 for a one-way ticket and $171 for a round-trip.

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

    No

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

    When flying out of Portland you will be using Portland. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • 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.

  • Which is the best airline for flights from Portland to Chicago, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Delta and Frontier. With an average price for the route of $584 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $266 and an overall rating of 6.2.

  • 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 3 airlines serving 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 10368 reviews
7.9Comfort
8.2Boarding
7.4Food
8.0Entertainment
8.6Crew
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

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.
7/1Mon
1 stopFrontier
8h 53mPDX-MDW
$86
7/23Tue
1 stopFrontier
15h 02mPDX-MDW
$92
9/2Mon
1 stopFrontier
9h 04mPDX-MDW
$93
8/29Thu
1 stopDelta
6h 03mPDX-MDW
$109
8/15Thu
1 stopDelta
6h 03mPDX-MDW
$118
8/11Sun
2 stops
17h 41mPDX-MDW
$190
8/29Thu
2 stops
17h 05mPDX-MDW
$243
7/5Fri
3 stopsWestJet
21h 13mPDX-MDW
$455
7/2Tue
1 stopVolaris
13h 23mPDX-MDW
$473
6/14Fri
3 stopsWestJet
32h 15mPDX-MDW
$641

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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.
6/10Mon
multi-stopFrontier
10h 20mPDX-MDW
6/13Thu
multi-stopFrontier
27h 18mMDW-PDX
$187
6/10Mon
multi-stopFrontier
10h 20mPDX-MDW
6/18Tue
multi-stopFrontier
12h 11mMDW-PDX
$200
6/10Mon
multi-stopFrontier
10h 20mPDX-MDW
6/17Mon
multi-stopFrontier
12h 04mMDW-PDX
$214
6/8Sat
multi-stopFrontier
24h 33mPDX-MDW
6/24Mon
multi-stopFrontier
21h 01mMDW-PDX
$215
6/11Tue
multi-stopFrontier
9h 11mPDX-MDW
6/15Sat
multi-stopFrontier
12h 11mMDW-PDX
$223
6/11Tue
multi-stopFrontier
7h 17mPDX-MDW
6/13Thu
multi-stopFrontier
27h 18mMDW-PDX
$224
6/11Tue
multi-stopFrontier
8h 52mPDX-MDW
6/13Thu
multi-stopFrontier
27h 18mMDW-PDX
$230
6/11Tue
multi-stopFrontier
7h 17mPDX-MDW
6/18Tue
multi-stopFrontier
12h 11mMDW-PDX
$233
6/10Mon
multi-stopDelta
6h 24mPDX-MDW
6/15Sat
multi-stopDelta
7h 35mMDW-PDX
$352
6/7Fri
multi-stopDelta
9h 39mPDX-MDW
6/10Mon
multi-stopDelta
5h 58mMDW-PDX
$377

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Portland - Chicago Midway Airport Flights

Departure:

Portland (PDX)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Portland

Cabin classes:

$737