Flights from Portland Airport PDX to Chicago Airport MDW
We've found the cheapest flights to Chicago
Flying to Midway is very easy as there are 2 airliners who offer flights from Portland International including Presidential Aviation and Southwest Airlines. The flight time is approximately 4 Hours 7 Minutes.
The exact cost of the flight we vary quite significantly base on the dates you travel, the time of day you will depart and how long in advance you pre book the flights. The cheapest flights available will generally be mid week or late in the evening, so if you are on a budget then these are the flight times you should consider. Alternatively, you could book well in advance and you flight could be up to 50% cheaper, especially with budget airliners. The ticket prices for most airliners will increase the closer you get the departure date, so as soon as you know the date you will travel you should book your flights.
The time zone at Midway is different from Portland International, so please be aware of this when making travel arrangements.
If you plan on flying to Midway Airport from Portland International Airport you can pre-arrange your long or short term parking at Portland International Airport.
If you are renting a car at Midway Airport it is recommended to fill up the fuel tank before returning the vehicle at the nearest fuel station to Midway Airport in order to avoid incurring additional costs. *Please check your rental agreement to understand the fuel policy for your vehicle.
Organise and book your choice of transport to Portland International Airport:
- Private Transfers to Portland International Airport
- Buses to Portland International Airport
- Taxis to Portland International Airport
- Train Services to/near Portland International Airport
Ensure your arrival at Midway Airport is as stress-free as possible by pre-booking your onwards transport - booking early may also save you money:
- Compare car rental at Midway Airport
- Private transfers at Midway Airport
- Buses from Midway Airport
- Taxis from Midway Airport
- Train services at or near Midway Airport
You can also research and pre-book a hotel near Midway Airport
For a full summary of all the airliners that fly from Portland International to Midway, please see the table below.

Airliner | Mo | Tu | We | Th | Fr | Sa | Su | First Flight | Last Flight | Flights |
---|---|---|---|---|---|---|---|---|---|---|
Southwest Airlines | 3 | 3 | 3 | 3 | 3 | 2 | 2 | 06:00 | 13:35 | VIEW FLIGHTS |
Presidential Aviation | 0 | 0 | 0 | 0 | 0 | 0 | 1 | 08:00 | 08:00 | VIEW FLIGHTS |
Most people choose to fly with Southwest Airlines. They offer the largest number of flights so they have times which are most likely to suite you. The flights they offer will go by the flight numbers WN2149, WN2248, WN2668 and WN2678 with times between 06:00 and 13:35.
If you would like more information on this flight the please visit the website for Southwest Airlines at www.southwest.com/?ref=southwestairlines.com. You will be able to find the latest availability, prices and make your booking online.
Flight times for the route are summarised in the table below. These time were correct at the time of writing, but please be aware that times may vary from time to time so please check their website for exact times and the dates you wish to fly.

Day | Flight Times | Flights | ||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Monday | 06:10
08:15
13:35
| VIEW FLIGHTS | ||||||||||||
Tuesday | 06:00
09:20
13:30
| VIEW FLIGHTS | ||||||||||||
Wednesday | 06:00
09:20
13:30
| VIEW FLIGHTS | ||||||||||||
Thursday | 06:10
08:15
13:35
| VIEW FLIGHTS | ||||||||||||
Friday | 06:10
08:15
13:35
| VIEW FLIGHTS | ||||||||||||
Saturday | 06:00
10:35
| VIEW FLIGHTS | ||||||||||||
Sunday | 06:55
08:00
13:20
| VIEW FLIGHTS |
If you are flexible on the airport you depart from, then there are other airports that offer direct flights to Midway. You can see full details of these below.

Route | Stops | Distance | Flying Time |
---|---|---|---|
Seattle to Chicago Midway | 0 | 4 Hours 5 Minutes |
Please remember to leave plenty of time to get though customers when you are departing form the airports. Flights regulations are getting very strict these days so getting through customs can take in excess of 1 hour in some cases.
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Alternative Airports in United States with Connections from Portland International Airport
- airplanemode_active Portland Oregon Airport to Seattle Tacoma International 142 flights per week
- airplanemode_active Portland Oregon Airport to Los Angeles 88 flights per week
- airplanemode_active Portland Oregon Airport to Las Vegas 69 flights per week
- airplanemode_active Portland Oregon Airport to Phoenix 60 flights per week
- airplanemode_active Portland Oregon Airport to Salt Lake City 56 flights per week
- airplanemode_active Portland Oregon Airport to Sacramento International 51 flights per week
- airplanemode_active Portland Oregon Airport to Anchorage Ted Stevens Anchorage International 39 flights per week
- airplanemode_active Portland Oregon Airport to Medford Rogue Valley International Medford 39 flights per week
- airplanemode_active Portland Oregon Airport to Oakland International 37 flights per week
- airplanemode_active Portland Oregon Airport to Santa Ana John Wayne 36 flights per week
- airplanemode_active Portland Oregon Airport to San Diego International 32 flights per week
- airplanemode_active Portland Oregon Airport to Ontario International 25 flights per week
- airplanemode_active Portland Oregon Airport to Houston 21 flights per week
- airplanemode_active Portland Oregon Airport to Pendleton 21 flights per week
- airplanemode_active Portland Oregon Airport to Burbank 20 flights per week
- airplanemode_active Portland Oregon Airport to Honolulu International 17 flights per week
- airplanemode_active Portland Oregon Airport to Eugene 15 flights per week
- airplanemode_active Portland Oregon Airport to Maui 14 flights per week
- airplanemode_active Portland Oregon Airport to Austin bergstrom International 12 flights per week
- airplanemode_active Portland Oregon Airport to Klamath Falls 10 flights per week
- airplanemode_active Portland Oregon Airport to Kansas City International 8 flights per week
- airplanemode_active Portland Oregon Airport to Billings 7 flights per week
- airplanemode_active Portland Oregon Airport to Baltimore Washington International Thurgood Marshall 7 flights per week
- airplanemode_active Portland Oregon Airport to Dallas Love Field 7 flights per week
- airplanemode_active Portland Oregon Airport to Kalispell 7 flights per week
- airplanemode_active Portland Oregon Airport to Kona 7 flights per week
- airplanemode_active Portland Oregon Airport to North Bend 7 flights per week
- airplanemode_active Portland Oregon Airport to Palm Springs Municipal 7 flights per week
- airplanemode_active Portland Oregon Airport to San Luis Obispo 7 flights per week
- airplanemode_active Portland Oregon Airport to Fort Worth Alliance 6 flights per week
- airplanemode_active Portland Oregon Airport to San Bernardino Norton Afb 6 flights per week
- airplanemode_active Portland Oregon Airport to Roseburg 5 flights per week
- airplanemode_active Portland Oregon Airport to Provo 4 flights per week
- airplanemode_active Portland Oregon Airport to Hermiston 3 flights per week
- airplanemode_active Portland Oregon Airport to Appleton 2 flights per week
- airplanemode_active Portland Oregon Airport to Flint 2 flights per week
- airplanemode_active Portland Oregon Airport to Modesto 2 flights per week
- airplanemode_active Portland Oregon Airport to Teterboro 2 flights per week
- airplanemode_active Portland Oregon Airport to Aspen 1 flights per week
- airplanemode_active Portland Oregon Airport to Chehalis 1 flights per week
- airplanemode_active Portland Oregon Airport to Grand Canyon Pulliam Field 1 flights per week
- airplanemode_active Portland Oregon Airport to Hayward Air Terminal 1 flights per week
- airplanemode_active Portland Oregon Airport to Milwaukee General Mitchell International 1 flights per week
- airplanemode_active Portland Oregon Airport to Everett 1 flights per week
- airplanemode_active Portland Oregon Airport to Rancho 1 flights per week
- airplanemode_active Portland Oregon Airport to Sacramento Executive 1 flights per week
- airplanemode_active Portland Oregon Airport to Sitka 1 flights per week
- airplanemode_active Portland Oregon Airport to Las Vegas North Air Terminal 1 flights per week
- airplanemode_active Portland Oregon Airport to Denver International 93 flights per week
- airplanemode_active Portland Oregon Airport to San Francisco 81 flights per week
- airplanemode_active Portland Oregon Airport to Chicago OHare International 66 flights per week
- airplanemode_active Portland Oregon Airport to San Jose Mineta San Jose International 57 flights per week
- airplanemode_active Portland Oregon Airport to Dallas Fort Worth International 55 flights per week
- airplanemode_active Portland Oregon Airport to Minneapolis St Paul International 42 flights per week
- airplanemode_active Portland Oregon Airport to Boise 39 flights per week
- airplanemode_active Portland Oregon Airport to Spokane International 38 flights per week
- airplanemode_active Portland Oregon Airport to Redmond 37 flights per week
- airplanemode_active Portland Oregon Airport to Atlanta 35 flights per week
- airplanemode_active Portland Oregon Airport to Reno 28 flights per week
- airplanemode_active Portland Oregon Airport to Newark 21 flights per week
- airplanemode_active Portland Oregon Airport to New York John F Kennedy International 21 flights per week
- airplanemode_active Portland Oregon Airport to Boston 20 flights per week
- airplanemode_active Portland Oregon Airport to Fresno Air Terminal 20 flights per week
- airplanemode_active Portland Oregon Airport to Bozeman 15 flights per week
- airplanemode_active Portland Oregon Airport to Missoula 14 flights per week
- airplanemode_active Portland Oregon Airport to Santa Rosa Sonoma County 14 flights per week
- airplanemode_active Portland Oregon Airport to Detroit 11 flights per week
- airplanemode_active Portland Oregon Airport to Kentucky 8 flights per week
- airplanemode_active Portland Oregon Airport to Albuquerque 7 flights per week
- airplanemode_active Portland Oregon Airport to Nashville 7 flights per week
- airplanemode_active Portland Oregon Airport to Charlotte Douglas 7 flights per week
- airplanemode_active Portland Oregon Airport to Washington Ronald Reagan Washington National 7 flights per week
- airplanemode_active Portland Oregon Airport to Washington Dulles International 7 flights per week
- airplanemode_active Portland Oregon Airport to Orlando International 7 flights per week
- airplanemode_active Portland Oregon Airport to Philadelphia International 7 flights per week
- airplanemode_active Portland Oregon Airport to Santa Barbara Municipal 7 flights per week
- airplanemode_active Portland Oregon Airport to Salina 7 flights per week
- airplanemode_active Portland Oregon Airport to Fairbanks International 6 flights per week
- airplanemode_active Portland Oregon Airport to Newport 5 flights per week
- airplanemode_active Portland Oregon Airport to Crescent City 4 flights per week
- airplanemode_active Portland Oregon Airport to Seattle Boeing Field King County International 3 flights per week
- airplanemode_active Portland Oregon Airport to Napa 2 flights per week
- airplanemode_active Portland Oregon Airport to Des Moines 2 flights per week
- airplanemode_active Portland Oregon Airport to Indianapolis 2 flights per week
- airplanemode_active Portland Oregon Airport to St Louis Lambert St Louis International 2 flights per week
- airplanemode_active Portland Oregon Airport to Tulsa International 2 flights per week
- airplanemode_active Portland Oregon Airport to Carlsbad Mc Clellan Palomar 1 flights per week
- airplanemode_active Portland Oregon Airport to Cheyenne 1 flights per week
- airplanemode_active Portland Oregon Airport to Houston William P Hobby 1 flights per week
- airplanemode_active Portland Oregon Airport to Jackson Hole 1 flights per week
- airplanemode_active Portland Oregon Airport to Moses Lake Grant County 1 flights per week
- airplanemode_active Portland Oregon Airport to Page 1 flights per week
- airplanemode_active Portland Oregon Airport to Rifle 1 flights per week
- airplanemode_active Portland Oregon Airport to Phoenix Scottsdale Municipal 1 flights per week
- airplanemode_active Portland Oregon Airport to Thermal 1 flights per week
- airplanemode_active Portland Oregon Airport to Visalia 1 flights per week
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Useful Information about Portland International Airport

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