$69+ Cheap flights from Pittsburgh (PIT) 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
aug. 28 — sep. 41
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Midway with Cheapflights
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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 Pittsburgh to Midway
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Cheapest flights from Pittsburgh to MidwayExplore the most affordable flight options available from Pittsburgh to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juli 29, 2026.
Explore the most affordable flight options available from Pittsburgh to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juli 29, 2026.
This Delta deal was found by Cheapflights users on 7/26. 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.
ons. 9/2311:35 am
PIT
- MDW
1 stop7h 44m
Delta
man. 9/287:01 pm
MDW
- PIT
1 stop3h 57m
Delta
Deal found 7/26![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 7/24. 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.
lør. 8/156:10 am
PIT
- MDW
2 stops7h 55m
Southwest
tir. 8/188:15 am
MDW
- PIT
1 stop3h 50m
Southwest
Deal found 7/24![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 7/24. 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.
lør. 9/125:40 pm
PIT
- MDW
1 stop6h 04m
Delta
tor. 9/171:19 pm
MDW
- PIT
1 stop4h 39m
Delta
Deal found 7/24![Delta logo]()
$193
This KAYAK deal was found by Cheapflights users on 7/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 8/177:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
tor. 8/207:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/27![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/28. 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.
fre. 9/47:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
lør. 9/53:10 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/28![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 7/28. 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.
fre. 9/42:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
søn. 9/69:10 am
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/28![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 7/29. 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.
tor. 8/275:50 am
PIT
- MDW
1 stop7h 01m
Delta
man. 8/315:45 pm
MDW
- PIT
1 stop5h 19m
Delta
Deal found 7/29![Delta logo]()
$218
Best flights from Pittsburgh to MidwayDiscover carefully curated flight deals from Pittsburgh to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated juli 29, 2026.
Discover carefully curated flight deals from Pittsburgh to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated juli 29, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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.
fre. 9/42:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
søn. 9/69:10 am
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/28![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 7/25. 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.
fre. 10/238:55 pm
PIT
- MDW
1 stop4h 00m
Southwest
man. 10/264:20 pm
MDW
- PIT
2 stops6h 10m
Southwest
Deal found 7/25![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/28. 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.
tor. 9/177:20 pm
PIT
- MDW
1 stop3h 40m
Southwest
lør. 9/199:55 am
MDW
- PIT
2 stops9h 55m
Southwest
Deal found 7/28![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/27. 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.
fre. 9/186:10 am
PIT
- MDW
2 stops7h 05m
Southwest
man. 9/213:15 pm
MDW
- PIT
1 stop6h 05m
Southwest
Deal found 7/27![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/25. 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.
ons. 8/1910:10 am
PIT
- MDW
2 stops7h 40m
Southwest
tor. 8/2012:20 pm
MDW
- PIT
2 stops9h 25m
Southwest
Deal found 7/25![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 7/26. 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.
tir. 8/1812:40 pm
PIT
- MDW
2 stops10h 10m
Southwest
ons. 8/191:00 pm
MDW
- PIT
2 stops7h 30m
Southwest
Deal found 7/26![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 7/27. 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.
fre. 9/47:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
man. 9/77:40 pm
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 7/27![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 7/26. 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.
tor. 8/206:10 am
PIT
- MDW
2 stops10h 15m
Southwest
man. 8/2412:20 pm
MDW
- PIT
2 stops9h 25m
Southwest
Deal found 7/26![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 7/24. 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.
fre. 8/282:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
ons. 9/23:05 pm
MDW
- PIT
1 stop4h 45m
Southwest
Deal found 7/24![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 7/25. 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.
tor. 10/228:20 pm
PIT
- MDW
1 stop3h 45m
Southwest
søn. 10/258:15 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 7/25![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 7/28. 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.
lør. 10/106:30 pm
PIT
- MDW
1 stop4h 10m
Southwest
søn. 10/1812:55 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 7/28![Southwest logo]()
$266
Last-minute flights from Pittsburgh to MidwayDiscover last-minute flight deals from Pittsburgh to Midway. Data last updated juli 29, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Midway. Data last updated juli 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/24. 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.
lør. 8/156:10 am
PIT
- MDW
2 stops7h 55m
Southwest
man. 8/1710:30 am
MDW
- PIT
1 stop6h 10m
Southwest
Deal found 7/24![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 7/24. 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.
lør. 8/156:10 am
PIT
- MDW
2 stops7h 55m
Southwest
tir. 8/1810:30 am
MDW
- PIT
2 stops7h 10m
Southwest
Deal found 7/24![Southwest logo]()
$194
This KAYAK deal was found by Cheapflights users on 7/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 8/177:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
tor. 8/207:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/27![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/29. 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.
fre. 8/217:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
ons. 9/98:45 am
MDW
- PIT
Nonstop1h 35m
Southwest
Deal found 7/29![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 7/28. 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.
fre. 8/216:19 pm
PIT
- MDW
1 stop5h 17m
Delta
man. 8/2412:46 pm
MDW
- PIT
1 stop6h 44m
Delta
Deal found 7/28![Delta logo]()
$230
This Delta deal was found by Cheapflights users on 7/29. 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.
tor. 8/275:50 am
PIT
- MDW
1 stop7h 01m
Delta
man. 8/315:45 pm
MDW
- PIT
1 stop5h 19m
Delta
Deal found 7/29![Delta logo]()
$218
One-way flights from Pittsburgh to MidwaySearch for one-way flight options from Pittsburgh to Midway. Find affordable one-way fares based on user searches. Data last updated juli 29, 2026.
Search for one-way flight options from Pittsburgh to Midway. Find affordable one-way fares based on user searches. Data last updated juli 29, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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.
tor. 8/277:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 7/28![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 7/28. 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.
lør. 8/296:29 pm
PIT
- MDW
1 stop5h 07m
Delta
Deal found 7/28![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 7/27. 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.
ons. 8/2612:40 pm
PIT
- MDW
2 stops10h 10m
Southwest
Deal found 7/27![Southwest logo]()
$84
This Southwest deal was found by Cheapflights users on 7/24. 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.
man. 8/171:50 pm
PIT
- MDW
2 stops9h 30m
Southwest
Deal found 7/24![Southwest logo]()
$90
This Delta deal was found by Cheapflights users on 7/24. 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.
tor. 10/226:00 am
PIT
- MDW
1 stop4h 18m
Delta
Deal found 7/24![Delta logo]()
$140
This Southwest deal was found by Cheapflights users on 7/28. 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.
fre. 8/287:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 7/28![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 7/28. 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.
fre. 8/284:55 pm
PIT
- MDW
1 stop6h 41m
Delta
Deal found 7/28![Delta logo]()
$152
This Delta deal was found by Cheapflights users on 7/24. 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.
fre. 8/216:19 pm
PIT
- MDW
1 stop5h 17m
Delta
Deal found 7/24![Delta logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
søn. 8/307:49 pm
PIT
- MDW
2 stops40h 06m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
søn. 8/237:49 pm
PIT
- MDW
2 stops40h 06m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$164
Find flight deals from Pittsburgh to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) 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 juli 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $188 (Delta) |
One-way from | $69 (Southwest) |
Popular in | August |
Cheapest in | October |
Average price | $494 |
Good round-trip deal | $344 or less |
Good one-way deal | $184 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pittsburgh 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 juli 29, 2026.
Use the filters below to find and compare flights from Pittsburgh to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
fre. 9/4
2:45 pm-3:05 pm
Nonstop1h 20m
Chicago Midway
søn. 9/6
9:10 am-11:35 am
Nonstop1h 25m
$215
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
fre. 10/23
8:55 pm-11:55 pm
1 stop4h 00m
Chicago Midway
man. 10/26
4:20 pm-11:30 pm
2 stops6h 10m
$235
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
tor. 9/17
7:20 pm-10:00 pm
1 stop3h 40m
Chicago Midway
lør. 9/19
9:55 am-8:50 pm
2 stops9h 55m
$235
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
fre. 9/18
6:10 am-12:15 pm
2 stops7h 05m
Chicago Midway
man. 9/21
3:15 pm-10:20 pm
1 stop6h 05m
$235
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
ons. 8/19
10:10 am-4:50 pm
2 stops7h 40m
Chicago Midway
tor. 8/20
12:20 pm-10:45 pm
2 stops9h 25m
$240
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
tir. 8/18
12:40 pm-9:50 pm
2 stops10h 10m
Chicago Midway
ons. 8/19
1:00 pm-9:30 pm
2 stops7h 30m
$240
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
fre. 9/4
7:30 pm-7:50 pm
Nonstop1h 20m
Chicago Midway
man. 9/7
7:40 pm-10:10 pm
Nonstop1h 30m
$245
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
tor. 8/20
6:10 am-3:25 pm
2 stops10h 15m
Chicago Midway
man. 8/24
12:20 pm-10:45 pm
2 stops9h 25m
$246
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
fre. 8/28
2:45 pm-3:05 pm
Nonstop1h 20m
Chicago Midway
ons. 9/2
3:05 pm-8:50 pm
1 stop4h 45m
$255
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
tor. 10/22
8:20 pm-11:05 pm
1 stop3h 45m
Chicago Midway
søn. 10/25
8:15 pm-10:35 pm
Nonstop1h 20m
$266
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Pittsburgh 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 Pittsburgh to Midway in July.
| 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 Pittsburgh-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 Pittsburgh-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Pittsburgh-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 Pittsburgh-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 Pittsburgh to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Pittsburgh with our price prediction graph.
PIT-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 Pittsburgh to Chicago Midway Airport
Prices
Delays
What is the cheapest month to book a flight from Pittsburgh to Chicago Midway Airport?
Currently, October is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $200). Flying from Pittsburgh to Chicago Midway Airport in August is currently the most expensive (average of $546). 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 PIT to MDW?
Find hourly flight availability from Pittsburgh 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 juli 29, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 18% on flights from Pittsburgh to Chicago Midway Airport by exploring options for tickets at noon.
What is the cheapest day to fly from Pittsburgh to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Midway. Price data was last updated on July 25, 2026.
Travelers seeking maximum savings on their Pittsburgh to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Pittsburgh to Chicago delayed?
About 15% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 102 minutes.
What is the most punctual flight time for Pittsburgh to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Pittsburgh to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 14% of flights being delayed.
The best insider tips for Pittsburgh to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Pittsburgh to Chicago Midway Airport trip
Our travel experts
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 juli 29, 2026.
Read through reviews of airlines operating flights from Pittsburgh to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Overall
8.0
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 Pittsburgh 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
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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 juli 29, 2026.
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Top airline flying from Pittsburgh to Midway
Discover the top airline that operate flights from Pittsburgh 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 juli 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$351 | FlexibilityNo cancel fee | On-time63% |