$123+ Cheap flights from Portland, ME (PWM) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Nov 12 — Nov 191
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to MidwayExplore the most affordable flight options available from Portland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
Explore the most affordable flight options available from Portland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:10 pm -
1 stop7h 05m
Sun 11/155:05 am -
1 stop4h 25m
Deal found 10/8![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:20 pm -
1 stop6h 55m
Tue 12/16:00 am -
1 stop7h 45m
Deal found 10/8![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:10 pm -
2 stops6h 35m
Mon 11/95:05 am -
1 stop4h 25m
Deal found 10/8![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:25 pm -
2 stops9h 35m
Tue 12/16:00 am -
1 stop7h 45m
Deal found 10/8![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:45 pm -
1 stop6h 19m
Wed 11/119:30 am -
1 stop5h 40m
Deal found 10/12![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 pm -
Nonstop2h 35m
Tue 10/277:45 am -
Nonstop2h 10m
Deal found 10/8![Southwest logo]()
$390
Best flights from Portland to MidwayDiscover carefully curated flight deals from Portland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
Discover carefully curated flight deals from Portland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:25 pm -
2 stops9h 35m
Tue 12/16:00 am -
1 stop7h 45m
Deal found 10/8![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:00 am -
2 stops11h 25m
Mon 1/256:00 am -
2 stops9h 59m
Deal found 10/11![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:25 pm -
1 stop7h 00m
Sun 12/65:05 am -
1 stop4h 25m
Deal found 10/8![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2112:50 pm -
1 stop6h 47m
Sat 1/236:00 am -
2 stops9h 59m
Deal found 10/11![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/243:25 pm -
1 stop7h 00m
Tue 1/55:20 am -
2 stops8h 25m
Deal found 10/12![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:27 am -
2 stops10h 51m
Thu 11/126:00 am -
1 stop6h 01m
Deal found 10/10![Delta logo]()
$414
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2212:50 pm -
1 stop6h 40m
Sun 1/246:25 am -
1 stop7h 15m
Deal found 10/11![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/312:50 pm -
1 stop6h 47m
Sun 4/119:30 am -
1 stop5h 43m
Deal found 10/10![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:25 pm -
1 stop6h 40m
Sun 11/225:05 am -
1 stop4h 25m
Deal found 10/11![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:10 pm -
1 stop7h 05m
Sun 11/85:05 am -
1 stop4h 25m
Deal found 10/12![Southwest logo]()
$427
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated October 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 pm -
Nonstop2h 35m
Tue 10/277:45 am -
Nonstop2h 10m
Deal found 10/8![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:10 pm -
2 stops6h 35m
Mon 11/95:05 am -
1 stop4h 25m
Deal found 10/8![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:45 pm -
1 stop6h 19m
Wed 11/119:30 am -
1 stop5h 40m
Deal found 10/12![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:10 pm -
1 stop7h 05m
Sun 11/155:05 am -
1 stop4h 25m
Deal found 10/8![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:25 pm -
2 stops9h 35m
Tue 12/16:00 am -
1 stop7h 45m
Deal found 10/8![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:20 pm -
1 stop6h 55m
Tue 12/16:00 am -
1 stop7h 45m
Deal found 10/8![Southwest logo]()
$346
One-way flights from Portland to MidwaySearch for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:55 am -
1 stop5h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$123
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:10 pm -
2 stops6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 pm -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:12 pm -
2 stops20h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:12 pm -
2 stops20h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:12 pm -
2 stops22h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:09 pm -
2 stops25h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:35 pm -
3 stops42h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$176
Find flight deals from Portland to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $345 (Southwest) |
One-way from | $123 (Delta) |
Popular in | July |
Cheapest in | May |
Average price | $417 |
Good round-trip deal | $632 or less |
Good one-way deal | $336 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 13, 2026.
Use the filters below to find and compare flights from Portland to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 12/8
12:49 pm-6:01 pm
1 stop6h 12m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 11/12
5:10 pm-11:15 pm
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Fri 1/8
12:50 pm-6:37 pm
1 stop6h 47m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
Quickest round-trip
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 11/11
5:15 am-9:00 am
1 stop4h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 12/16
12:49 pm-6:01 pm
1 stop6h 12m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 12/15
6:00 am-12:04 pm
1 stop7h 04m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 4/10
12:50 pm-6:37 pm
1 stop6h 47m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Mon 11/9
5:20 am-4:00 pm
1 stop11h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 12/17
1:40 pm-8:10 pm
2 stops7h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 1/13
6:00 am-4:50 pm
2 stops11h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Portland to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Midway in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland, Maine-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland, Maine-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Portland with our price prediction graph.
PWM-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Chicago Midway Airport
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated October 13, 2026.
See what other customers who have flown with Southwest from Portland to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Portland to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Complete your trip
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 13, 2026.
Portland and Midway flights
Browse other Portland and Midway flight options. Last updated on October 13, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on October 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Portland to Midway
Discover the top airline that operate flights from Portland to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$267 | Average$378 | FlexibilityNo cancel fee | On-time63% |