PWM - MDW
$59 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 6/18. 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.
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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.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?
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 Monday, with Wednesday being the most expensive.
Which airlines provide the cheapest flights from Portland to Chicago Midway Airport?
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($59) and Delta ($158). The cheapest round-trip tickets were found on Frontier ($167) and Delta ($227).
How many flights are there between Portland and Chicago Midway Airport per day?
Each day, there are between 1 and 2 nonstop flights that take off from Portland and land 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 11 flights. The most frequent day of departure is Wednesday, when 18% of all weekly flights depart. The fewest flights depart on a Tuesday.
What’s the earliest departure time from Portland to Chicago Midway Airport?
Early birds can take the earliest flight from Portland 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 to Chicago Midway Airport jets off at 7:00 pm and lands at 8:35 pm.
When to book flights from Portland to Midway
FAQs for booking Portland to Chicago Midway Airport flights
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
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
Top airline flying from Portland to Midway
3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.
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!
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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:
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