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

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The best prices from Portland to Chicago Midway are usually found in February or August, booked 43 days in advance, depart on a Monday or Tuesday and return on a Saturday

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

PDX - MDW
Price
$283 - $490
MDW
Temperature
33.8 - 84.2 °F
MDW
Rainfall
0.7 - 4.3 inches
Popular in December High demand for flights, 19% potential price rise
Cheapest in February Best time to find cheap flights, 29% potential price drop
Round-trip from $283 From Portland to Chicago Midway
One-way from $121 One-way flight from Portland to Chicago Midway
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Portland to Chicago Midway?

Flights from Portland to Chicago Midway are found to be more expensive on Wednesday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway.

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

Travelers have found it’s best to book a flight 37 days in advance to save up to 10% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 37 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Portland to Chicago Midway 1-2 weeks in advance for as low as $177, or $177 for flights within the next 24 hours.

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

It’s typically best to fly out from Portland to Chicago Midway in the noon. Doing so could potentially save you 23% on the flight price compared to flying in the evening, which is usually more expensive.

Cheap flights from Portland to Chicago Midway in August, September 2020

The best prices found for PDX to MDW flights for August, September
2 Aug - 7 Aug
$344pp
PDX
Portland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
PDX
Portland
2 Aug - 7 Aug
$6522pp
PDX
Portland
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
PDX
Portland

Portland to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from Portland found for this year
15 Sep - 23 Sep
$204pp
PDX
Portland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
PDX
Portland
18 Sep - 20 Sep
$242pp
PDX
Portland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
PDX
Portland
29 Oct - 2 Nov
$244pp
PDX
Portland
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
PDX
Portland

One-way flights to Chicago Midway from Portland

The cheapest one-way flights from Portland to Chicago Midway
1:45 am - 12:51 pm
Delta
2 Stops
9h 06m
PDX - MDW
Delta
$121
Delta
4:10 am - 9:48 am
Multiple Airlines
3 Stops
51h 38m
PDX - MDW
Multiple Airlines
$122
Kiwi.com
4:59 pm - 1:30 pm
Multiple Airlines
3 Stops
42h 31m
PDX - MDW
Multiple Airlines
$137
Kiwi.com

Related info for your journey

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

Flight FAQs

From Portland to Chicago Midway

Are flight prices decreasing from Portland to Chicago Midway due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Portland and Chicago Midway for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Portland to Chicago Midway for under $300 on Cheapflights?

Yes, there are multiple flights from Portland to Chicago Midway for under $300. The cheapest flight booked recently is on Delta for just $204, but on average you can expect to pay $297.

Are there nonstop flights from Portland to Chicago Midway for under $200 on Cheapflights?

There are no nonstop flights from Portland to Chicago Midway, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

What days are nonstop flights available from Portland to Chicago Midway?

Days when nonstop flights are available for this flight are: Sunday, Monday.

Does it rain more in Portland or Chicago Midway?

The rainfall in Portland is generally more than the rainfall in Chicago Midway. This will continue over the next 8 days.

Is Portland weather warmer or cooler than Chicago Midway?

We forecast the temperature to be around the 84 °F's in July, on average. The temperature in Chicago Midway is generally hotter than in Portland. Book flights in a timely manner in correlation to your departure date.

How long is the flight from Portland to Chicago Midway?

Delta and Spirit Airlines can get you from Portland to Chicago Midway in just under 5h 29m. Your travel time can differ by up to 1h 18m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Portland to Chicago Midway round-trip?

Cheapflights users have booked flights from Portland to Chicago Midway round-trip from $204. Another airline that can offer you cheap pricing is Spirit Airlines. These flights start at 48% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Portland to Chicago Midway one-way?

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $121.

Alternative routes for Portland to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Portland to Chicago Midway
Average temperature for August in Chicago Midway
82.4 °F
Avg rainfall for August in Chicago Midway
3.9 ″

Airports servicing Portland

Airports servicing Chicago

Hourly flight availability from Portland to Chicago Midway

Morning 6 AM to noon 100% of PDX to MDW departures
Early morning Midnight to 6 AM 0% of PDX to MDW departures
Afternoon Noon to 6 PM 0% of PDX to MDW departures
Evening 6 PM to midnight 0% of PDX to MDW departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Portland to Chicago Midway
Sunday
1 daily flight
Monday
1 daily flight
Tuesday
0 flights
Wednesday
0 flights
Thursday
0 flights
Friday
1 daily flight
Saturday
1 daily flight
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