$128+ Cheap flights from Portland, ME (PWM) to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Sep 9 — Sep 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 August 10, 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 August 10, 2026.
This Southwest deal was found by Cheapflights users on 8/7. 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 9/510:30 am -
1 stop7h 10m
Sun 9/66:30 pm -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/7. 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 9/1110:30 am -
1 stop6h 45m
Mon 9/146:10 pm -
Nonstop2h 25m
Deal found 8/7![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/8. 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 9/117:40 am -
Nonstop2h 30m
Tue 9/156:50 pm -
Nonstop2h 20m
Deal found 8/8![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/7. 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 9/107:40 am -
Nonstop2h 30m
Sat 9/123:20 pm -
Nonstop2h 20m
Deal found 8/7![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 8/7. 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 10/296:30 am -
Nonstop2h 35m
Mon 11/25:05 am -
1 stop4h 25m
Deal found 8/7![Southwest logo]()
$299
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 August 10, 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 August 10, 2026.
This Southwest deal was found by Cheapflights users on 8/5. 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 9/117:40 am -
Nonstop2h 30m
Mon 9/146:10 pm -
Nonstop2h 25m
Deal found 8/5![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 8/5. 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 10/296:28 am -
2 stops10h 51m
Mon 11/26:04 am -
1 stop5h 58m
Deal found 8/5![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/7. 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 9/53:45 pm -
Nonstop2h 35m
Sun 9/66:30 pm -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 8/6. 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 10/216:00 pm -
Nonstop2h 35m
Fri 10/234:20 pm -
2 stops6h 35m
Deal found 8/6![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 8/9. 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 10/165:20 am -
2 stops9h 50m
Mon 10/196:40 pm -
Nonstop2h 10m
Deal found 8/9![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 8/9. 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 9/195:40 am -
1 stop6h 00m
Sat 9/269:05 am -
1 stop4h 55m
Deal found 8/9![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 8/6. 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 9/307:45 am -
Nonstop2h 35m
Sun 10/47:50 pm -
Nonstop2h 10m
Deal found 8/6![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 8/9. 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 11/265:15 am -
1 stop7h 40m
Tue 12/18:50 am -
1 stop4h 55m
Deal found 8/9![Southwest logo]()
$384
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated August 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/7. 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 9/510:30 am -
1 stop7h 10m
Sun 9/66:30 pm -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/7. 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 9/107:40 am -
Nonstop2h 30m
Sat 9/123:20 pm -
Nonstop2h 20m
Deal found 8/7![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 8/7. 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 9/1110:30 am -
1 stop6h 45m
Mon 9/146:10 pm -
Nonstop2h 25m
Deal found 8/7![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/8. 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 9/117:40 am -
Nonstop2h 30m
Tue 9/156:50 pm -
Nonstop2h 20m
Deal found 8/8![Southwest logo]()
$276
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 August 10, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Southwest deal was found by Cheapflights users on 8/6. 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 9/510:30 am -
1 stop7h 10m
Deal found 8/6![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:10 pm -
1 stop6h 55m
Deal found 8/10![Southwest logo]()
$140
This Southwest deal was found by Cheapflights users on 8/5. 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 9/27:45 am -
Nonstop2h 35m
Deal found 8/5![Southwest logo]()
$145
This Delta deal was found by Cheapflights users on 8/7. 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 11/512:42 pm -
1 stop6h 18m
Deal found 8/7![Delta logo]()
$155
This Southwest deal was found by Cheapflights users on 8/9. 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 9/97:45 am -
Nonstop2h 35m
Deal found 8/9![Southwest logo]()
$159
This Delta deal was found by Cheapflights users on 8/7. 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 8/296:00 am -
2 stops10h 38m
Deal found 8/7![Delta logo]()
$160
This Delta deal was found by Cheapflights users on 8/10. 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 11/711:55 am -
1 stop5h 52m
Deal found 8/10![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 8/7. 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 10/66:00 pm -
Nonstop2h 35m
Deal found 8/7![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 8/5. 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 10/55:20 am -
1 stop5h 40m
Deal found 8/5![Southwest logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Fri 9/47:00 am -
2 stops28h 50m
Deal found 8/6![Multiple Airlines logo]()
$190
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 August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (Southwest) |
One-way from | $128 (Southwest) |
Popular in | July |
Cheapest in | September |
Average price | $340 |
Good round-trip deal | $366 or less |
Good one-way deal | $260 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 2,558,603 searches. Data last updated August 10, 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
Fri 9/11
7:40 am-9:10 am
Nonstop2h 30m
Chicago Midway
Mon 9/14
6:10 pm-9:35 pm
Nonstop2h 25m
$262
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 9/5
3:45 pm-5:20 pm
Nonstop2h 35m
Chicago Midway
Sun 9/6
6:30 pm-9:45 pm
Nonstop2h 15m
$302
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 10/29
6:28 am-4:19 pm
2 stops10h 51m
Chicago Midway
Mon 11/2
6:04 am-1:02 pm
1 stop5h 58m
$314
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 10/21
6:00 pm-7:35 pm
Nonstop2h 35m
Chicago Midway
Fri 10/23
4:20 pm-11:55 pm
2 stops6h 35m
$337
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Fri 10/16
5:20 am-2:10 pm
2 stops9h 50m
Chicago Midway
Mon 10/19
6:40 pm-9:50 pm
Nonstop2h 10m
$350
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 9/19
5:40 am-10:40 am
1 stop6h 00m
Chicago Midway
Sat 9/26
9:05 am-3:00 pm
1 stop4h 55m
$363
Quickest round-trip
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 9/30
7:45 am-9:20 am
Nonstop2h 35m
Chicago Midway
Sun 10/4
7:50 pm-11:00 pm
Nonstop2h 10m
$383
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 11/26
5:15 am-11:55 am
1 stop7h 40m
Chicago Midway
Tue 12/1
8:50 am-2:45 pm
1 stop4h 55m
$384
Cheapest one-way
Quickest one-way
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 9/2
7:45 am-9:20 am
Nonstop2h 35m
$145
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 10/3
6:00 am-10:36 am
1 stop5h 36m
$155
Showing 1-10 of 18 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 August.
| 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 August 10, 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.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Other flights from Portland
Popular flights
Alternative routes for Portland to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Midway by cabin class
Find flights from Portland to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 August 10, 2026.
Portland and Midway flights
Browse other Portland and Midway flight options. Last updated on August 10, 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 August 10, 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 2,558,603 searches. Data last updated August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$267 | Average$378 | FlexibilityNo cancel fee | On-time63% |