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$86 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 7/17. 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 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 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 Midway to Portland (MDW-PDX)

 
These are the cheapest deals for flights from Midway to Portland 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 Midway to Portland

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

Recent one-way flight deals from Midway to Portland

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

Recent last minute flight deals from Midway to Portland

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

Recent direct flight deals from Midway to Portland

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

Cheap bus & train deals from Midway to Portland

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

All round-trip flight deals to Portland

The cheapest plane tickets to Portland found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
$172Frontier
Find Deal
Wed, Aug 21 - Tue, Aug 27
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
$173Frontier
Find Deal
Fri, Sep 6 - Mon, Sep 9
9:45 pm - 6:49 amMDW-PDX
11h 04m1 stop
11:43 am - 4:45 amPDX-MDW
15h 02m1 stop
$175Frontier
Find Deal
Tue, Jul 23 - Tue, Jul 30
12:23 pm - 7:32 pmMDW-PDX
9h 09m1 stop
10:21 pm - 11:13 amPDX-MDW
10h 52m1 stop
$178Frontier
Find Deal
Wed, Jul 17 - Fri, Aug 2
10:20 am - 4:34 pmMDW-PDX
8h 14m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$179Frontier
Find Deal
Sat, Aug 10 - Wed, Aug 14
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$180Frontier
Find Deal
Thu, Aug 15 - Mon, Aug 19
12:23 pm - 9:31 pmMDW-PDX
11h 08m1 stop
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
$188Frontier
Find Deal
Mon, Aug 12 - Thu, Aug 15
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$189Frontier
Find Deal
Thu, Aug 22 - Mon, Aug 26
6:00 am - 1:34 pmMDW-PDX
9h 34m1 stop
11:45 am - 9:44 pmPDX-MDW
7h 59m1 stop
$277Delta
Find Deal
Sat, Nov 2 - Sat, Nov 16
2:00 pm - 7:58 pmMDW-PDX
7h 58m1 stop
12:50 am - 10:31 amPDX-MDW
7h 41m1 stop
$307Delta
Find Deal
Wed, Oct 23 - Fri, Nov 1
12:23 pm - 7:32 pmMDW-PDX
9h 09m1 stop
$86Frontier
Find Deal
Wed, Jul 17
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
$93Frontier
Find Deal
Sun, Jun 9
8:20 pm - 5:46 pmMDW-PDX
23h 26m1 stop
$100Frontier
Find Deal
Sun, Jun 30
7:19 pm - 11:17 pmMDW-PDX
5h 58m1 stop
$151Delta
Find Deal
Mon, Jun 17
7:19 pm - 11:29 pmMDW-PDX
6h 10m1 stop
$226Delta
Find Deal
Fri, Jul 19
2:14 pm - 11:08 amMDW-PDX
22h 54m3 stops
Mon, Jul 1
8:25 pm - 10:51 pmMDW-PDX
28h 26m3 stops
Sun, Jun 16
10:12 am - 8:35 amMDW-PDX
24h 23m2 stops
$408Allegiant Air
Find Deal
Thu, Jun 27
7:21 pm - 7:47 pmMDW-PDX
26h 26m3 stops
$624WestJet
Find Deal
Wed, Jul 3
7:11 pm - 7:32 pmMDW-PDX
26h 21m3 stops
$656WestJet
Find Deal
Sat, Jun 29
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
12:49 am - 12:00 pmPDX-MDW
9h 11m1 stop
$223Frontier
Find Deal
Sun, Jun 9 - Tue, Jun 11
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
8:52 am - 9:45 pmPDX-MDW
10h 53m1 stop
$249Frontier
Find Deal
Sat, Jun 8 - Thu, Jun 13
10:26 pm - 8:45 amMDW-PDX
12h 19m1 stop
12:52 am - 9:45 pmPDX-MDW
18h 53m1 stop
$259Frontier
Find Deal
Sat, Jun 8 - Wed, Jun 12
8:58 pm - 9:42 pmMDW-PDX
26h 44m1 stop
12:59 am - 11:12 amPDX-MDW
8h 13m1 stop
$278Frontier
Find Deal
Fri, Jun 7 - Sat, Jun 8
5:40 am - 8:45 amMDW-PDX
29h 05m1 stop
8:52 am - 12:00 pmPDX-MDW
25h 08m1 stop
$279Frontier
Find Deal
Sat, Jun 8 - Thu, Jun 13
8:58 pm - 5:20 pmMDW-PDX
22h 22m2 stops
12:59 am - 11:12 amPDX-MDW
8h 13m1 stop
$283Frontier
Find Deal
Fri, Jun 7 - Sat, Jun 8
7:19 pm - 11:17 pmMDW-PDX
5h 58m1 stop
12:30 am - 8:54 amPDX-MDW
6h 24m1 stop
$770Delta
Find Deal
Fri, Jun 7 - Sun, Jun 9
6:00 am - 1:19 pmMDW-PDX
9h 19m1 stop
9:45 pm - 9:51 amPDX-MDW
10h 06m1 stop
$918Delta
Find Deal
Tue, Jun 11 - Tue, Jun 11
9:34 am - 4:55 pmMDW-PDX
9h 21m2 stops
9:45 pm - 9:51 amPDX-MDW
10h 06m1 stop
$1,091Delta
Find Deal
Tue, Jun 11 - Tue, Jun 11
7:35 pm - 2:39 pmMDW-PDX
45h 04m3 stops
5:20 am - 9:47 amPDX-MDW
26h 27m3 stops
$1,098
Find Deal
Fri, Jun 7 - Mon, Jun 10

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 clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Portland on a Monday and more expensive on a Friday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Mondays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Portland, 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 is January, where tickets cost $313 on average. On the other hand, the most expensive months are July and June, where the average cost of tickets is $417 and $405 respectively.

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

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, 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, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 86 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 past 3 days, the cheapest one-way tickets to Portland from Chicago Midway Airport were found on Frontier ($86) and Delta ($151), and the lowest round-trip tickets were found on Frontier ($172) and Delta ($277).

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

Each day, there are between 2 and 6 nonstop flights that take off from Chicago Midway Airport and land in Portland, with an average flight time of 4h 20m. The most common departure time is 5:00 pm and most flights take off in the afternoon. Each week, there are 29 flights. The most frequent day of departure is Friday, when 21% of all weekly flights depart. The fewest flights depart on a Sunday.

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

Early birds can take the earliest flight from Chicago Midway Airport at 8:10 am and will be landing in Portland at 10:30 am.

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

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Portland jets off at 10:50 pm and lands at 1:10 am.

Good to know

Low season

January

High season

July

Cheapest flight

$86
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 16% 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 $86 for a one-way ticket and $172 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Delta and Frontier. With an average price for the route of $639 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 $218 and an overall rating of 6.2.

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

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

they made me check my carryon. There was space in the overhead bins.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

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 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.
7/17Wed
1 stopFrontier
9h 09mMDW-PDX
$86
6/9Sun
1 stopFrontier
12h 12mMDW-PDX
$93
6/30Sun
1 stopFrontier
23h 26mMDW-PDX
$100
6/17Mon
1 stopDelta
5h 58mMDW-PDX
$151
7/19Fri
1 stopDelta
6h 10mMDW-PDX
$226
7/1Mon
3 stops
22h 54mMDW-PDX
$257
6/16Sun
3 stops
28h 26mMDW-PDX
$284
6/27Thu
2 stopsAllegiant Air
24h 23mMDW-PDX
$408
7/3Wed
3 stopsWestJet
26h 26mMDW-PDX
$624
6/29Sat
3 stopsWestJet
26h 21mMDW-PDX
$656

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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.
6/9Sun
multi-stopFrontier
12h 12mMDW-PDX
6/11Tue
multi-stopFrontier
9h 11mPDX-MDW
$223
6/8Sat
multi-stopFrontier
12h 19mMDW-PDX
6/13Thu
multi-stopFrontier
10h 53mPDX-MDW
$249
6/8Sat
multi-stopFrontier
12h 19mMDW-PDX
6/12Wed
multi-stopFrontier
18h 53mPDX-MDW
$259
6/7Fri
multi-stopFrontier
26h 44mMDW-PDX
6/8Sat
multi-stopFrontier
8h 13mPDX-MDW
$278
6/8Sat
multi-stopFrontier
29h 05mMDW-PDX
6/13Thu
multi-stopFrontier
25h 08mPDX-MDW
$279
6/7Fri
multi-stopFrontier
22h 22mMDW-PDX
6/8Sat
multi-stopFrontier
8h 13mPDX-MDW
$283
6/7Fri
multi-stopDelta
5h 58mMDW-PDX
6/9Sun
multi-stopDelta
6h 24mPDX-MDW
$770
6/11Tue
multi-stopDelta
9h 19mMDW-PDX
6/11Tue
multi-stopDelta
10h 06mPDX-MDW
$918
6/11Tue
multi-stopDelta
9h 21mMDW-PDX
6/11Tue
multi-stopDelta
10h 06mPDX-MDW
$1,091
6/7Fri
multi-stop
45h 04mMDW-PDX
6/10Mon
multi-stop
26h 27mPDX-MDW
$1,098

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Chicago Midway Airport - Portland Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Chicago Midway Airport

Cabin classes: