$122+ Cheap flights from Pittsburgh (PIT) 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh 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 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 October 30, 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 October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. 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.
Sat 12/52:20 pm -
1 stop6h 15m
Mon 12/78:15 am -
Nonstop1h 25m
Deal found 10/26![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 10/25. 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.
Fri 12/114:00 pm -
Nonstop1h 35m
Mon 12/141:40 pm -
Nonstop1h 25m
Deal found 10/25![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1912:20 pm -
2 stops8h 25m
Mon 11/2312:45 pm -
2 stops5h 50m
Deal found 10/26![Southwest logo]()
$273
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
1 stop23h 48m
Sun 12/138:37 pm -
1 stop19h 56m
Deal found 10/30![Frontier logo]()
$274
This Southwest deal was found by Cheapflights users on 10/30. 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 11/234:00 pm -
Nonstop1h 35m
Tue 12/18:15 am -
Nonstop1h 25m
Deal found 10/30![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 11/1812:20 pm -
2 stops8h 25m
Fri 11/206:50 pm -
Nonstop1h 30m
Deal found 10/27![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/28. 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.
Sat 12/55:45 am -
2 stops12h 40m
Tue 12/81:15 pm -
2 stops7h 25m
Deal found 10/28![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 10/28. 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.
Sat 12/122:20 pm -
1 stop6h 15m
Sat 12/196:55 pm -
Nonstop1h 30m
Deal found 10/28![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 12/411:17 am -
1 stop6h 33m
Tue 12/85:30 pm -
1 stop4h 48m
Deal found 10/29![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 10/29. 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.
Tue 12/112:20 pm -
2 stops8h 25m
Sat 12/126:35 am -
1 stop5h 35m
Deal found 10/29![Southwest logo]()
$285
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 October 30, 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 October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. 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.
Sat 12/55:45 am -
2 stops12h 40m
Tue 12/81:15 pm -
2 stops7h 25m
Deal found 10/26![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 10/26. 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.
Thu 12/176:10 am -
1 stop4h 27m
Mon 12/216:15 pm -
1 stop3h 44m
Deal found 10/26![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 10/27. 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.
Sat 12/124:35 pm -
Nonstop1h 30m
Thu 1/77:45 am -
1 stop4h 15m
Deal found 10/27![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 12/36:10 am -
1 stop4h 27m
Sun 12/66:41 pm -
1 stop3h 16m
Deal found 10/28![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 10/29. 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.
Mon 12/288:15 pm -
1 stop3h 45m
Wed 12/301:05 pm -
Nonstop1h 20m
Deal found 10/29![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 1/152:01 pm -
1 stop4h 59m
Mon 1/186:40 pm -
1 stop3h 33m
Deal found 10/29![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/28. 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.
Thu 12/1012:20 pm -
2 stops8h 25m
Sun 12/136:30 am -
1 stop5h 20m
Deal found 10/28![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 12/1212:50 pm -
1 stop5h 00m
Sat 1/99:38 am -
1 stop4h 30m
Deal found 10/28![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 10/28. 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.
Mon 11/3012:30 pm -
2 stops8h 45m
Wed 12/28:15 am -
Nonstop1h 25m
Deal found 10/28![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 10/28. 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.
Fri 1/12:20 pm -
Nonstop1h 35m
Sun 1/37:40 am -
Nonstop1h 20m
Deal found 10/28![Southwest logo]()
$396
Last-minute flights from Pittsburgh to MidwayDiscover last-minute flight deals from Pittsburgh to Midway. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Midway. Data last updated October 30, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/26. 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.
Tue 11/174:00 pm -
1 stop6h 30m
Thu 11/196:10 pm -
Nonstop1h 35m
Deal found 10/26![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 11/1812:20 pm -
2 stops8h 25m
Fri 11/206:50 pm -
Nonstop1h 30m
Deal found 10/27![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/1912:20 pm -
2 stops8h 25m
Mon 11/2312:45 pm -
2 stops5h 50m
Deal found 10/26![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/1910:24 am -
1 stop3h 27m
Fri 11/2012:30 pm -
1 stop5h 05m
Deal found 10/29![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 10/30. 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 11/234:00 pm -
Nonstop1h 35m
Tue 12/18:15 am -
Nonstop1h 25m
Deal found 10/30![Southwest logo]()
$277
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 October 30, 2026.
Search for one-way flight options from Pittsburgh to Midway. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. 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.
Mon 11/162:20 pm -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$122
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/16:10 am -
1 stop4h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 12/77:59 pm -
2 stops16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$133
This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:11 pm -
1 stop26h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$134
This Southwest deal was found by Cheapflights users on 10/26. 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.
Tue 11/1712:20 pm -
2 stops8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 1/188:27 pm -
2 stops40h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$141
This Southwest deal was found by Cheapflights users on 10/28. 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.
Sat 12/125:35 am -
2 stops12h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$143
This Orbitz deal was found by Cheapflights users on 10/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:59 pm -
1 stop25h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$145
This Southwest deal was found by Cheapflights users on 10/28. 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.
Thu 11/197:25 pm -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 11/167:12 pm -
2 stops29h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 10/26. 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.
Sat 11/216:10 am -
1 stop4h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 10/26. 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.
Wed 11/252:00 pm -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$163
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (Southwest) |
One-way from | $122 (Southwest) |
Popular in | August |
Cheapest in | November |
Average price | $423 |
Good round-trip deal | $346 or less |
Good one-way deal | $168 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 7,457,451 searches. Data last updated October 30, 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
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Mon 11/16
5:35 am-9:00 am
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Wed 12/16
7:10 pm-10:45 pm
1 stop4h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Sat 11/21
6:10 am-9:46 am
1 stop4h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Fri 11/27
6:10 am-11:25 am
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Mon 12/21
11:15 am-8:20 pm
2 stops10h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
Quickest round-trip
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Sun 11/22
4:00 pm-4:35 pm
Nonstop1h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$169
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Tue 4/27
6:45 am-11:51 am
1 stop6h 06m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$217
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Sat 1/2
6:25 am-11:03 am
1 stop5h 38m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$217
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Sat 12/5
5:45 am-5:25 pm
2 stops12h 40m
Chicago Midway
Tue 12/8
1:15 pm-9:40 pm
2 stops7h 25m
$279
PittsburghChicago
PIT Pittsburgh - MDW Chicago Midway
PITMDW
Pittsburgh
Sat 12/12
4:35 pm-5:05 pm
Nonstop1h 30m
Chicago Midway
Thu 1/7
7:45 am-1:00 pm
1 stop4h 15m
$280
Showing 1-10 of 18 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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, November is the cheapest month in which you can book a flight from Pittsburgh to Chicago Midway Airport (average of $303). Flying from Pittsburgh to Chicago Midway Airport in August is currently the most expensive (average of $519). 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 October 30, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 16% 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 October 24, 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. Sunday afternoons 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 16% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 98 minutes.
What is the most punctual flight time for Pittsburgh to Chicago flights?
Historically, flights departing at night 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?
Wednesday 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 16% 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 October 30, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.4
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.4
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
Merrillville
Lansing
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 October 30, 2026.
Pittsburgh and Midway flights
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Other flights from Pittsburgh
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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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$384 | FlexibilityNo cancel fee | On-time63% |