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$90 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 6/12. 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 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 42,686,544 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
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
$179Frontier
Find Deal
Sat, Aug 17 - Sat, Aug 24
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
$180Frontier
Find Deal
Wed, Sep 18 - Mon, Sep 23
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$181Frontier
Find Deal
Thu, Aug 22 - Mon, Aug 26
4:09 pm - 2:50 pmMDW-PDX
24h 41m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$182Frontier
Find Deal
Fri, Aug 23 - Mon, Aug 26
10:00 pm - 3:54 pmMDW-PDX
19h 54m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$183Frontier
Find Deal
Tue, Aug 20 - Fri, Aug 23
4:09 pm - 2:50 pmMDW-PDX
24h 41m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$184Frontier
Find Deal
Fri, Aug 23 - Mon, Aug 26
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$190Frontier
Find Deal
Wed, Aug 14 - Mon, Aug 19
8:02 pm - 3:17 pmMDW-PDX
21h 15m2 stops
12:52 am - 11:08 amPDX-MDW
8h 16m1 stop
$194Frontier
Find Deal
Tue, Jun 11 - Wed, Jun 12
10:41 pm - 11:59 pmMDW-PDX
27h 18m1 stop
8:52 am - 9:45 pmPDX-MDW
10h 53m1 stop
$198Frontier
Find Deal
Thu, Jun 13 - Thu, Jul 4
7:19 pm - 11:17 pmMDW-PDX
5h 58m1 stop
12:30 am - 8:54 amPDX-MDW
6h 24m1 stop
$343Delta
Find Deal
Mon, Jun 10 - Tue, Jun 11
11:26 am - 6:58 pmMDW-PDX
9h 32m1 stop
$90Frontier
Find Deal
Wed, Jun 12
11:56 am - 10:07 pmMDW-PDX
12h 11m1 stop
$96Frontier
Find Deal
Sat, Jun 15
6:35 am - 4:35 pmMDW-PDX
12h 00m1 stop
$100Frontier
Find Deal
Thu, Jun 13
6:35 am - 4:26 pmMDW-PDX
11h 51m1 stop
$104Frontier
Find Deal
Thu, Jun 6
2:49 pm - 8:26 pmMDW-PDX
7h 37m1 stop
$144Delta
Find Deal
Fri, Jul 19
12:08 pm - 10:40 amMDW-PDX
24h 32m2 stops
Mon, Aug 12
2:14 pm - 2:39 pmMDW-PDX
26h 25m3 stops
Fri, Jun 7
7:19 pm - 11:29 pmMDW-PDX
6h 10m1 stop
$325Delta
Find Deal
Fri, Jul 26
9:46 am - 1:10 pmMDW-PDX
29h 24m3 stops
$520WestJet
Find Deal
Tue, Jun 4
2:24 pm - 7:31 pmMDW-PDX
31h 07m3 stops
$540WestJet
Find Deal
Tue, Jun 11
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
8:39 am - 9:30 pmPDX-MDW
10h 51m1 stop
$180Frontier
Find Deal
Sat, Jun 1 - Sat, Jun 8
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
6:25 pm - 5:21 amPDX-MDW
8h 56m2 stops
$185Frontier
Find Deal
Sat, Jun 1 - Sat, Jun 8
11:31 am - 9:22 pmMDW-PDX
11h 51m1 stop
8:07 am - 5:12 pmPDX-MDW
7h 05m1 stop
$188Frontier
Find Deal
Fri, May 31 - Tue, Jun 4
10:01 pm - 11:58 pmMDW-PDX
27h 57m1 stop
12:49 am - 9:30 pmPDX-MDW
18h 41m1 stop
$190Frontier
Find Deal
Sat, Jun 1 - Fri, Jun 7
5:01 am - 11:58 pmMDW-PDX
20h 57m1 stop
7:45 am - 11:47 amPDX-MDW
26h 02m1 stop
$239Frontier
Find Deal
Sun, Jun 2 - Fri, Jun 7
10:01 pm - 9:11 amMDW-PDX
13h 10m1 stop
12:48 am - 11:09 amPDX-MDW
8h 21m1 stop
$259Frontier
Find Deal
Sat, Jun 1 - Sun, Jun 2
7:10 pm - 11:23 pmMDW-PDX
6h 13m1 stop
12:40 am - 8:47 amPDX-MDW
6h 07m1 stop
$458Delta
Find Deal
Mon, Jun 3 - Wed, Jun 5
11:59 am - 5:07 pmMDW-PDX
7h 08m1 stop
10:47 pm - 7:55 amPDX-MDW
7h 08m1 stop
$764Delta
Find Deal
Sat, Jun 1 - Mon, Jun 3
5:00 pm - 1:10 pmMDW-PDX
22h 10m3 stops
5:20 am - 9:47 amPDX-MDW
26h 27m3 stops
Sat, Jun 1 - Sat, Jun 8
7:10 pm - 11:23 pmMDW-PDX
6h 13m1 stop
6:36 am - 6:07 pmPDX-MDW
9h 31m2 stops
$1,014Delta
Find Deal
Sun, Jun 2 - Tue, Jun 4
10:50 pm - 1:10 amMDW-PDX
4h 20mnonstop
5:15 am - 11:10 amPDX-MDW
3h 55mnonstop
$372Southwest
Find Deal
Mon, Jun 10 - Wed, Jun 12

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 Wednesday, 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 $418 and $409 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 ($90) and Delta ($144), and the lowest round-trip tickets were found on Frontier ($179) and Delta ($343).

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

Each day, there are between 2 and 3 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 morning. Each week, there are 20 flights. The most frequent day of departure is Saturday, when 15% of all weekly flights depart. The fewest flights depart on a Sunday.

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

Direct flights take on average 4h 20m to travel the 1,746 miles between Chicago Midway Airport and Portland.

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

$90
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 $90 for a one-way ticket and $179 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 $615 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 10457 reviews
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
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.

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.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

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.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

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.
6/12Wed
1 stopFrontier
9h 32mMDW-PDX
$90
6/15Sat
1 stopFrontier
12h 11mMDW-PDX
$96
6/13Thu
1 stopFrontier
12h 00mMDW-PDX
$100
6/6Thu
1 stopFrontier
11h 51mMDW-PDX
$104
7/19Fri
1 stopDelta
7h 37mMDW-PDX
$144
8/12Mon
2 stops
24h 32mMDW-PDX
$166
6/7Fri
3 stops
26h 25mMDW-PDX
$229
7/26Fri
1 stopDelta
6h 10mMDW-PDX
$325
6/4Tue
3 stopsWestJet
29h 24mMDW-PDX
$520
6/11Tue
3 stopsWestJet
31h 07mMDW-PDX
$540

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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.
6/1Sat
multi-stopFrontier
13h 10mMDW-PDX
6/8Sat
multi-stopFrontier
10h 51mPDX-MDW
$180
6/1Sat
multi-stopFrontier
13h 10mMDW-PDX
6/8Sat
multi-stopFrontier
8h 56mPDX-MDW
$185
5/31Fri
multi-stopFrontier
11h 51mMDW-PDX
6/4Tue
multi-stopFrontier
7h 05mPDX-MDW
$188
6/1Sat
multi-stopFrontier
27h 57mMDW-PDX
6/7Fri
multi-stopFrontier
18h 41mPDX-MDW
$190
6/2Sun
multi-stopFrontier
20h 57mMDW-PDX
6/7Fri
multi-stopFrontier
26h 02mPDX-MDW
$239
6/1Sat
multi-stopFrontier
13h 10mMDW-PDX
6/2Sun
multi-stopFrontier
8h 21mPDX-MDW
$259
6/3Mon
multi-stopDelta
6h 13mMDW-PDX
6/5Wed
multi-stopDelta
6h 07mPDX-MDW
$458
6/1Sat
multi-stopDelta
7h 08mMDW-PDX
6/3Mon
multi-stopDelta
7h 08mPDX-MDW
$764
6/1Sat
multi-stop
22h 10mMDW-PDX
6/8Sat
multi-stop
26h 27mPDX-MDW
$925
6/2Sun
multi-stopDelta
6h 13mMDW-PDX
6/4Tue
multi-stopDelta
9h 31mPDX-MDW
$1,014

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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: