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$80 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 6/18. 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
Wed 7/10
Wed 7/17

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 42,898,604 times on KAYAK, and here is why:

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

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
12:23 pm - 9:31 pmMDW-PDX
11h 08m1 stop
3:40 pm - 3:14 pmPDX-MDW
21h 34m1 stop
$176Frontier
Find Deal
Mon, Aug 12 - Fri, Aug 23
5:54 am - 4:06 pmMDW-PDX
12h 12m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$177Frontier
Find Deal
Thu, Sep 19 - Wed, Sep 25
2:06 pm - 11:28 pmMDW-PDX
11h 22m1 stop
4:28 pm - 4:45 amPDX-MDW
10h 17m1 stop
$178Frontier
Find Deal
Tue, Jul 2 - Thu, Jul 11
11:32 am - 8:36 pmMDW-PDX
11h 04m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$179Frontier
Find Deal
Wed, Aug 21 - Mon, Aug 26
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
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
9:26 pm - 10:42 amPDX-MDW
11h 16m1 stop
$181Frontier
Find Deal
Thu, Sep 26 - Mon, Sep 30
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
12:48 am - 11:52 amPDX-MDW
9h 04m1 stop
$182Frontier
Find Deal
Thu, Sep 26 - Sun, Sep 29
6:00 am - 11:40 pmMDW-PDX
19h 40m1 stop
4:30 pm - 6:33 amPDX-MDW
12h 03m1 stop
$184Frontier
Find Deal
Thu, Sep 19 - Sun, Sep 22
12:08 pm - 10:00 pmMDW-PDX
11h 52m1 stop
10:21 pm - 10:42 amPDX-MDW
10h 21m1 stop
$186Frontier
Find Deal
Sat, Aug 3 - Mon, Aug 12
12:08 pm - 10:00 pmMDW-PDX
11h 52m1 stop
10:21 pm - 11:13 amPDX-MDW
10h 52m1 stop
$187Frontier
Find Deal
Sat, Aug 3 - Fri, Aug 9

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.

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

$80
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 $80 for a one-way ticket and $176 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 10295 reviews
7.4Food
7.9Comfort
8.0Entertainment
8.2Boarding
8.6Crew
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

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!

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.

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

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.

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.
6/18Tue
1 stopFrontier
26h 50mMDW-PDX
$80
8/10Sat
1 stopFrontier
8h 14mMDW-PDX
$87
7/8Mon
1 stopFrontier
26h 34mMDW-PDX
$93
12/3Tue
1 stopDelta
7h 58mMDW-PDX
$199
11/7Thu
1 stopDelta
9h 34mMDW-PDX
$229
6/17Mon
3 stops
26h 01mMDW-PDX
$257
7/18Thu
3 stops
31h 40mMDW-PDX
$405
6/27Thu
2 stopsAllegiant Air
24h 23mMDW-PDX
$444
6/18Tue
3 stopsWestJet
12h 03mMDW-PDX
$584
6/29Sat
3 stopsWestJet
26h 21mMDW-PDX
$723

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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.
6/15Sat
multi-stopFrontier
29h 05mMDW-PDX
6/22Sat
multi-stopFrontier
8h 09mPDX-MDW
$204
6/15Sat
multi-stopFrontier
29h 05mMDW-PDX
6/22Sat
multi-stopFrontier
8h 56mPDX-MDW
$209
6/13Thu
multi-stopFrontier
10h 04mMDW-PDX
6/27Thu
multi-stopFrontier
11h 12mPDX-MDW
$238
6/15Sat
multi-stopFrontier
20h 18mMDW-PDX
6/21Fri
multi-stopFrontier
18h 41mPDX-MDW
$258
6/14Fri
multi-stopFrontier
20h 04mMDW-PDX
6/16Sun
multi-stopFrontier
10h 49mPDX-MDW
$286
6/15Sat
multi-stopFrontier
20h 13mMDW-PDX
6/22Sat
multi-stopFrontier
8h 56mPDX-MDW
$298
6/15Sat
multi-stopDelta
7h 35mMDW-PDX
6/29Sat
multi-stopDelta
7h 36mPDX-MDW
$488
6/12Wed
multi-stopDelta
10h 10mMDW-PDX
6/14Fri
multi-stopDelta
7h 37mPDX-MDW
$673
6/15Sat
multi-stopDelta
7h 52mMDW-PDX
6/28Fri
multi-stopDelta
8h 57mPDX-MDW
$762
6/13Thu
multi-stop
24h 23mMDW-PDX
6/16Sun
multi-stop
36h 58mPDX-MDW
$905

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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: