Cheap flights from Portland (PDX) to Midway (MDW)

PDX — MDW
Oct 4 — Oct 111

How to find the cheapest flight from Portland (PDX) to Midway (MDW)

All the information you need to plan the best PDX to MDW flight in 2022: compare Portland to Midway flight prices with the expected peak season, weather and rainfall in Midway.

PDX - MDW

Price

$255 - $666

MDW

Temperature

23 - 73.4 °F

MDW

Rainfall

1.7 - 4.9 inches

Popular inJulyHigh demand for flights, 42% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 34% potential price drop
Round-trip from$255From Portland to Chicago Midway
One-way from$148One-way flight from Portland to Chicago Midway

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

To save on the cost of your flight from Portland to Chicago Midway Airport, book at least 61 days before your planned departure. Booking around this time can save you about 43% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $488 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $637.

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

The best pricing can be found in the month of October. Prices to Chicago Midway Airport from Portland average $406. You can even find prices in October for less than $406, as users have found deals to Chicago Midway Airport from as low as $158. The month of July appears to be one of the more expensive times to travel to Chicago Midway Airport from Portland. Flying in the targeted month can save you up to 61%.

When is the cheapest time to fly from Portland to Chicago Midway Airport (PDX - MDW)?

When flying from Portland to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Portland to Midway in September, October 2022

The best prices found for PDX to MDW flights for September, October
Oct 1 - Oct 4
PDX

Portland

MDW

Chicago Midway

1 stop

10h 01m
MDW

Chicago Midway

PDX

Portland

1 stop

15h 57m
$164

Frontier

Pick Dates

Deal found 9/26/22

Oct 28 - Nov 2
PDX

Portland

MDW

Chicago Midway

1 stop

11h 17m
MDW

Chicago Midway

PDX

Portland

1 stop

10h 09m
$165

Frontier

Pick Dates

Deal found 9/26/22

Oct 25 - Nov 2
PDX

Portland

MDW

Chicago Midway

1 stop

17h 44m
MDW

Chicago Midway

PDX

Portland

1 stop

10h 09m
$166

Frontier

Pick Dates

Deal found 9/26/22

Portland to Midway 2022 flight deals

Cheap flights to Midway from Portland found for this year
Oct 1 - Oct 4
PDX

Portland

MDW

Chicago Midway

1 stop

10h 01m
MDW

Chicago Midway

PDX

Portland

1 stop

15h 57m
$164

Frontier

Pick Dates

Deal found 9/26/22

Oct 28 - Nov 2
PDX

Portland

MDW

Chicago Midway

1 stop

11h 17m
MDW

Chicago Midway

PDX

Portland

1 stop

10h 09m
$165

Frontier

Pick Dates

Deal found 9/26/22

Oct 25 - Nov 2
PDX

Portland

MDW

Chicago Midway

1 stop

17h 44m
MDW

Chicago Midway

PDX

Portland

1 stop

10h 09m
$166

Frontier

Pick Dates

Deal found 9/26/22

Cheap Frontier flights from Portland to Midway

Oct 4 - Oct 11
PDX

Portland

MDW

Chicago Midway

1 stop

10h 16m
MDW

Chicago Midway

PDX

Portland

1 stop

15h 24m
$164

Frontier

Pick Dates

Deal found 9/27/22

Oct 28 - Nov 2
PDX

Portland

MDW

Chicago Midway

1 stop

11h 17m
MDW

Chicago Midway

PDX

Portland

1 stop

10h 09m
$165

Frontier

Pick Dates

Deal found 9/26/22

Oct 25 - Nov 2
PDX

Portland

MDW

Chicago Midway

1 stop

17h 44m
MDW

Chicago Midway

PDX

Portland

1 stop

10h 09m
$166

Frontier

Pick Dates

Deal found 9/26/22

Last minute flights from Portland to Midway

Late deals on return flights to Midway from Portland, departing today and this week
Oct 4 - Oct 11
PDX

Portland

MDW

Chicago Midway

1 stop

10h 16m
MDW

Chicago Midway

PDX

Portland

1 stop

15h 24m
$164

Frontier

Pick Dates

Deal found 9/27/22

Oct 4 - Oct 12
PDX

Portland

MDW

Chicago Midway

1 stop

10h 16m
MDW

Chicago Midway

PDX

Portland

1 stop

15h 54m
$168

Frontier

Pick Dates

Deal found 9/27/22

Oct 8 - Oct 11
PDX

Portland

MDW

Chicago Midway

1 stop

10h 18m
MDW

Chicago Midway

PDX

Portland

1 stop

15h 24m
$172

Frontier

Pick Dates

Deal found 9/27/22

One-way flights to Midway from Portland

The cheapest one-way flights from Portland to Midway
Oct 8
PDX

Portland

MDW

Chicago Midway

1 stop

10h 18m
$86

Frontier

Pick Dates

Deal found 9/26/22

Oct 11
PDX

Portland

MDW

Chicago Midway

1 stop

10h 28m
$87

Frontier

Pick Dates

Deal found 9/28/22

Oct 4
PDX

Portland

MDW

Chicago Midway

1 stop

10h 16m
$90

Frontier

Pick Dates

Deal found 9/28/22

Related info for your journey

Useful info, stats and facts about Portland to Midway flights.

What airport do you fly from for flights from Portland to Chicago Midway?

If you book a flight to Chicago Midway from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PDX) is located 6.0 mi from the center of Portland. There are 0 flights from Portland to Chicago Midway per day from 7 different airlines.

Which airlines flying from Portland to Chicago Midway have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Portland to Chicago Midway that may be offering flexible cancellation policies are Delta, Frontier, and Alaska Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Portland to Chicago Midway Airport for under $200 on Cheapflights?

Yes, there are multiple flights from Portland to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Frontier for just $164, but on average you can expect to pay $183.

Are there last-minute flights available from Portland to Chicago Midway Airport for under $200?

There are currently 20+ open flights from Portland to Chicago Midway Airport within the next 7 days for less than $200.

What is the cheapest airline to fly from Portland to Chicago Midway Airport round-trip?

Currently priced at $164, Frontier will fly you from Portland to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. This flight start at 57% lower than the current average price 3 months from now.

What are the most popular airlines that fly from Portland to Chicago Midway Airport?

Consider American Airlines, Alaska Airlines or Delta when booking your flight. These represent the most popular airlines when flying from Portland to Chicago Midway Airport.

What are the cheapest flights from Portland to Chicago Midway Airport?

Looking at all options, your cheapest flight can be booked for $86. While the most popular route (Portland - Chicago Midway) can be booked for $164 on average our data indicates $322 when flying from Portland to Chicago Midway Airport.

Alternative routes for Portland to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Portland to Midway

The chart below displays the airlines Cheapflights users traveling from Portland to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
FrontierCheapest$174Average$262FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
DeltaCheapest$214Average$555FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
Alaska AirlinesCheapest$262Average$479FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
United AirlinesCheapest$364Average$546FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Portland to Midway

See what time of day planes typically take off from Portland to Midway
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Portland to Midway

See how many times per day planes take to the skies headed from Portland to Midway
Sunday0daily flights
Monday1daily flight
Tuesday1daily flight
Wednesday1daily flight
Thursday1daily flight
Friday1daily flight
Saturday0daily flights