$113+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
mar. 12 — mar. 191
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
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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
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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 febrero 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 febrero 10, 2026.
This Southwest deal was found by Cheapflights users on 2/7. 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.
lun. 3/232:50 pm
PWM
- MDW
1 stop6h 25m
Southwest
mié. 3/259:20 am
MDW
- PWM
1 stop5h 35m
Southwest
Deal found 2/7![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/76:03 am
PWM
- MDW
2 stops7h 26m
Delta
dom. 4/129:35 am
MDW
- PWM
1 stop5h 31m
Delta
Deal found 2/9![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 2/9. 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.
vie. 2/274:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
jue. 3/56:35 am
MDW
- PWM
1 stop4h 20m
Southwest
Deal found 2/9![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 2/9. 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.
jue. 2/265:30 am
PWM
- MDW
2 stops8h 50m
Southwest
jue. 3/55:00 pm
MDW
- PWM
1 stop6h 05m
Southwest
Deal found 2/9![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 2/8. 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.
jue. 2/266:00 am
PWM
- MDW
2 stops7h 46m
Delta
lun. 3/29:50 am
MDW
- PWM
2 stops12h 30m
Delta
Deal found 2/8![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 2/9. 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.
lun. 4/132:50 pm
PWM
- MDW
1 stop6h 30m
Southwest
mié. 4/157:00 am
MDW
- PWM
1 stop4h 20m
Southwest
Deal found 2/9![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 2/8. 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.
lun. 2/235:35 am
PWM
- MDW
1 stop7h 30m
Southwest
vie. 2/274:55 pm
MDW
- PWM
1 stop5h 55m
Southwest
Deal found 2/8![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 2/9. 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.
vie. 2/274:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
mié. 3/45:00 am
MDW
- PWM
2 stops8h 50m
Southwest
Deal found 2/9![Southwest logo]()
$274
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 febrero 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 febrero 10, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/812:51 pm
PWM
- MDW
1 stop6h 03m
Delta
dom. 4/129:35 am
MDW
- PWM
1 stop5h 31m
Delta
Deal found 2/9![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 2/7. 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.
lun. 3/232:50 pm
PWM
- MDW
1 stop6h 25m
Southwest
mié. 3/259:20 am
MDW
- PWM
1 stop5h 35m
Southwest
Deal found 2/7![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 2/9. 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.
jue. 2/264:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
jue. 3/56:35 am
MDW
- PWM
1 stop6h 40m
Southwest
Deal found 2/9![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 2/8. 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.
jue. 4/912:51 pm
PWM
- MDW
1 stop6h 03m
Delta
lun. 4/1312:53 pm
MDW
- PWM
2 stops10h 53m
Delta
Deal found 2/8![Delta logo]()
$254
This Delta deal was found by Cheapflights users on 2/8. 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.
jue. 2/266:00 am
PWM
- MDW
2 stops7h 46m
Delta
lun. 3/29:50 am
MDW
- PWM
2 stops12h 30m
Delta
Deal found 2/8![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 2/8. 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.
lun. 2/235:35 am
PWM
- MDW
1 stop7h 30m
Southwest
vie. 2/274:55 pm
MDW
- PWM
1 stop5h 55m
Southwest
Deal found 2/8![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 2/9. 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.
vie. 2/274:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
mié. 3/45:00 am
MDW
- PWM
2 stops8h 50m
Southwest
Deal found 2/9![Southwest logo]()
$274
This Southwest deal was found by Cheapflights users on 2/9. 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.
vie. 2/272:25 pm
PWM
- MDW
2 stops7h 20m
Southwest
jue. 3/56:35 am
MDW
- PWM
1 stop4h 20m
Southwest
Deal found 2/9![Southwest logo]()
$279
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated febrero 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated febrero 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/8. 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.
lun. 2/235:35 am
PWM
- MDW
1 stop7h 30m
Southwest
vie. 2/274:55 pm
MDW
- PWM
1 stop5h 55m
Southwest
Deal found 2/8![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 2/9. 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.
jue. 2/265:30 am
PWM
- MDW
2 stops8h 50m
Southwest
jue. 3/55:00 pm
MDW
- PWM
1 stop6h 05m
Southwest
Deal found 2/9![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 2/8. 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.
jue. 2/266:00 am
PWM
- MDW
2 stops7h 46m
Delta
lun. 3/29:50 am
MDW
- PWM
2 stops12h 30m
Delta
Deal found 2/8![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 2/9. 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.
vie. 2/274:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
mié. 3/49:50 am
MDW
- PWM
1 stop4h 00m
Southwest
Deal found 2/9![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 2/9. 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.
vie. 2/272:25 pm
PWM
- MDW
2 stops7h 20m
Southwest
jue. 3/56:35 am
MDW
- PWM
1 stop4h 20m
Southwest
Deal found 2/9![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 2/7. 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.
vie. 2/274:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
lun. 3/21:40 pm
MDW
- PWM
2 stops8h 05m
Southwest
Deal found 2/7![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 2/8. 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.
sáb. 3/2112:51 pm
PWM
- MDW
1 stop6h 03m
Delta
mar. 3/2412:47 pm
MDW
- PWM
2 stops10h 12m
Delta
Deal found 2/8![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 2/8. 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.
sáb. 3/215:20 pm
PWM
- MDW
1 stop6h 40m
Southwest
mar. 3/245:40 pm
MDW
- PWM
1 stop4h 25m
Southwest
Deal found 2/8![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 2/7. 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.
lun. 3/232:50 pm
PWM
- MDW
1 stop6h 25m
Southwest
mié. 3/259:20 am
MDW
- PWM
1 stop5h 35m
Southwest
Deal found 2/7![Southwest logo]()
$229
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 febrero 10, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated febrero 10, 2026.
This Southwest deal was found by Cheapflights users on 2/8. 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.
sáb. 3/75:20 pm
PWM
- MDW
1 stop6h 40m
Southwest
Deal found 2/8![Southwest logo]()
$113
This Delta deal was found by Cheapflights users on 2/8. 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.
mié. 4/812:51 pm
PWM
- MDW
1 stop6h 03m
Delta
Deal found 2/8![Delta logo]()
$115
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/75:23 am
PWM
- MDW
2 stops8h 06m
Delta
Deal found 2/9![Delta logo]()
$120
This Delta deal was found by Cheapflights users on 2/8. 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.
mié. 3/45:31 am
PWM
- MDW
1 stop7h 28m
Delta
Deal found 2/8![Delta logo]()
$126
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/912:51 pm
PWM
- MDW
1 stop6h 03m
Delta
Deal found 2/9![Delta logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
lun. 5/45:06 pm
PWM
- MDW
2 stops44h 54m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 2/8. 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.
jue. 5/72:50 pm
PWM
- MDW
2 stops6h 55m
Southwest
Deal found 2/8![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 2/6. 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.
mié. 5/63:55 pm
PWM
- MDW
1 stop4h 35m
Southwest
Deal found 2/6![Southwest logo]()
$160
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/512:13 pm
PWM
- MDW
1 stop6h 24m
Delta
Deal found 2/9![Delta logo]()
$170
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 febrero 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $229 (Southwest) |
One-way from | $113 (Southwest) |
Popular in | March |
Cheapest in | February |
Average price | $267 |
Good round-trip deal | $482 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 febrero 10, 2026.
Use the filters below to find and compare flights from Portland to Chicago Midway Airport that are best for you.
Fly from
Portland
Fly to
Midway
Route
Depart
Return
Price
PortlandChicago
PWM - MDW
PWMMDW
Portland
mié. 4/8
12:51 pm-5:54 pm
1 stop6h 03m
Chicago Midway
dom. 4/12
9:35 am-4:06 pm
1 stop5h 31m
$229
PortlandChicago
PWM - MDW
PWMMDW
Portland
lun. 3/23
2:50 pm-8:15 pm
1 stop6h 25m
Chicago Midway
mié. 3/25
9:20 am-3:55 pm
1 stop5h 35m
$229
PortlandChicago
PWM - MDW
PWMMDW
Portland
jue. 2/26
4:50 pm-10:45 pm
1 stop6h 55m
Chicago Midway
jue. 3/5
6:35 am-2:15 pm
1 stop6h 40m
$249
PortlandChicago
PWM - MDW
PWMMDW
Portland
jue. 4/9
12:51 pm-5:54 pm
1 stop6h 03m
Chicago Midway
lun. 4/13
12:53 pm-12:46 am
2 stops10h 53m
$254
PortlandChicago
PWM - MDW
PWMMDW
Portland
jue. 2/26
6:00 am-12:46 pm
2 stops7h 46m
Chicago Midway
lun. 3/2
9:50 am-11:20 pm
2 stops12h 30m
$259
PortlandChicago
PWM - MDW
PWMMDW
Portland
lun. 2/23
5:35 am-12:05 pm
1 stop7h 30m
Chicago Midway
vie. 2/27
4:55 pm-11:50 pm
1 stop5h 55m
$269
PortlandChicago
PWM - MDW
PWMMDW
Portland
vie. 2/27
4:50 pm-10:45 pm
1 stop6h 55m
Chicago Midway
mié. 3/4
5:00 am-2:50 pm
2 stops8h 50m
$274
PortlandChicago
PWM - MDW
PWMMDW
Portland
vie. 2/27
2:25 pm-8:45 pm
2 stops7h 20m
Chicago Midway
jue. 3/5
6:35 am-11:55 am
1 stop4h 20m
$279
PortlandChicago
PWM - MDW
PWMMDW
Portland
sáb. 3/7
5:20 pm-11:00 pm
1 stop6h 40m
$113
PortlandChicago
PWM - MDW
PWMMDW
Portland
sáb. 5/9
1:40 pm-9:09 pm
1 stop8h 29m
$115
Showing 1-10 of 18 results
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 February.
| 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
What is the cheapest month to book a flight from Portland, Maine to Chicago Midway Airport?
Currently, June is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $97). Flying from Portland, Maine to Chicago Midway Airport in April is currently the most expensive (average of $175). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PWM to MDW?
Find hourly flight availability from Portland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 10, 2026.
One of the essential ways to save on airfare from Portland, Maine to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 10% on airfare.
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 febrero 10, 2026.
See what other customers who have flown with Southwest and Delta 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.
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next 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 febrero 10, 2026.
Portland and Midway flights
Browse other Portland and Midway flight options. Last updated on febrero 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 febrero 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Portland to Midway
Discover the top 2 airlines 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 febrero 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$246 | Average$397 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$262 | Average$329 | FlexibilityNo cancel fee | On-timeN/A |