$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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — MDW
Jul 17 — Jul 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 June 17, 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 June 17, 2026.
This Southwest deal was found by Cheapflights users on 6/15. 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 10/68:35 am
PIT
- MDW
Nonstop1h 20m
Southwest
Thu 10/82:00 pm
MDW
- PIT
1 stop7h 30m
Southwest
Deal found 6/15![Southwest logo]()
$175
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:45 am
PIT
- MDW
1 stop7h 22m
Delta
Sat 9/264:30 pm
MDW
- PIT
1 stop6h 55m
Delta
Deal found 6/12![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 6/16. 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 8/62:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Mon 8/108:15 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 6/16![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 6/14. 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 7/298:15 pm
PIT
- MDW
1 stop4h 00m
Southwest
Thu 8/61:20 pm
MDW
- PIT
2 stops7h 30m
Southwest
Deal found 6/14![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:15 pm
PIT
- MDW
1 stop3h 55m
Southwest
Fri 7/36:50 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 6/12![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 6/14. 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 10/146:00 am
PIT
- MDW
2 stops9h 30m
Southwest
Sat 10/172:20 pm
MDW
- PIT
1 stop5h 10m
Southwest
Deal found 6/14![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:35 am
PIT
- MDW
1 stop3h 42m
Delta
Mon 8/106:42 pm
MDW
- PIT
1 stop4h 22m
Delta
Deal found 6/13![Delta logo]()
$201
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 June 17, 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 June 17, 2026.
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Mon 8/107:55 am
MDW
- PIT
1 stop4h 05m
Southwest
Deal found 6/13![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 6/16. 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 7/144:45 pm
PIT
- MDW
2 stops7h 30m
Southwest
Wed 7/157:50 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 6/16![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 6/16. 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 7/214:45 pm
PIT
- MDW
2 stops7h 30m
Southwest
Sat 7/256:35 am
MDW
- PIT
1 stop5h 00m
Southwest
Deal found 6/16![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 6/14. 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 7/311:45 pm
PIT
- MDW
2 stops10h 20m
Southwest
Wed 8/51:00 pm
MDW
- PIT
2 stops7h 30m
Southwest
Deal found 6/14![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 6/16. 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 9/108:40 am
PIT
- MDW
Nonstop1h 20m
Southwest
Sun 9/138:30 am
MDW
- PIT
Nonstop1h 35m
Southwest
Deal found 6/16![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/15. 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 9/116:10 am
PIT
- MDW
2 stops7h 05m
Southwest
Mon 9/142:35 pm
MDW
- PIT
2 stops6h 15m
Southwest
Deal found 6/15![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1610:10 am
PIT
- MDW
2 stops7h 45m
Southwest
Mon 8/175:55 am
MDW
- PIT
1 stop5h 40m
Southwest
Deal found 6/12![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 6/16. 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 7/86:00 am
PIT
- MDW
2 stops6h 00m
Southwest
Sat 7/112:10 pm
MDW
- PIT
2 stops7h 55m
Southwest
Deal found 6/16![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 6/14. 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 7/18:45 am
PIT
- MDW
Nonstop1h 25m
Southwest
Wed 7/87:50 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 6/14![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:05 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Mon 7/277:45 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 6/12![Southwest logo]()
$343
Last-minute flights from Pittsburgh to MidwayDiscover last-minute flight deals from Pittsburgh to Midway. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Midway. Data last updated June 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:45 am
PIT
- MDW
Nonstop1h 25m
Southwest
Fri 7/31:35 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 6/12![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:30 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Sat 7/47:40 am
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 6/12![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:15 pm
PIT
- MDW
1 stop3h 55m
Southwest
Fri 7/36:50 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 6/12![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 6/16. 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 7/147:30 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Wed 7/156:10 pm
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 6/16![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 6/16. 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 7/217:30 pm
PIT
- MDW
Nonstop1h 30m
Southwest
Sat 7/255:45 pm
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 6/16![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 6/14. 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 7/298:15 pm
PIT
- MDW
1 stop4h 00m
Southwest
Thu 8/61:20 pm
MDW
- PIT
2 stops7h 30m
Southwest
Deal found 6/14![Southwest logo]()
$184
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 June 17, 2026.
Search for one-way flight options from Pittsburgh to Midway. Find affordable one-way fares based on user searches. Data last updated June 17, 2026.
This Southwest deal was found by Cheapflights users on 6/17. 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 7/1412:50 pm
PIT
- MDW
Nonstop1h 25m
Southwest
Deal found 6/17![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 6/17. 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.
Wed 8/55:50 am
PIT
- MDW
1 stop5h 09m
Delta
Deal found 6/17![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 6/17. 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 7/294:45 pm
PIT
- MDW
2 stops7h 30m
Southwest
Deal found 6/17![Southwest logo]()
$84
This Southwest deal was found by Cheapflights users on 6/17. 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 8/102:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 6/17![Southwest logo]()
$91
This Delta deal was found by Cheapflights users on 6/17. 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 9/125:40 pm
PIT
- MDW
1 stop6h 05m
Delta
Deal found 6/17![Delta logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Sun 9/131:30 pm
PIT
- MDW
2 stops33h 28m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 6/14. 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.
Wed 7/86:30 am
PIT
- MDW
1 stop3h 43m
Delta
Deal found 6/14![Delta logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Sun 8/231:09 pm
PIT
- MDW
2 stops23h 00m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Sun 10/116:45 am
PIT
- MDW
2 stops29h 13m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Thu 8/1312:09 pm
PIT
- MDW
2 stops22h 42m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$158
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 June 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $175 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | August |
Cheapest in | October |
Average price | $488 |
Good round-trip deal | $366 or less |
Good one-way deal | $209 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 June 17, 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 - MDW
PITMDW
Pittsburgh
Thu 8/6
2:45 pm-3:05 pm
Nonstop1h 20m
Chicago Midway
Mon 8/10
7:55 am-1:00 pm
1 stop4h 05m
$191
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Tue 7/14
4:45 pm-11:15 pm
2 stops7h 30m
Chicago Midway
Wed 7/15
7:50 am-10:20 am
Nonstop1h 30m
$222
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Tue 7/21
4:45 pm-11:15 pm
2 stops7h 30m
Chicago Midway
Sat 7/25
6:35 am-12:35 pm
1 stop5h 00m
$265
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 7/31
1:45 pm-11:05 pm
2 stops10h 20m
Chicago Midway
Wed 8/5
1:00 pm-9:30 pm
2 stops7h 30m
$270
Quickest round-trip
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Thu 9/10
8:40 am-9:00 am
Nonstop1h 20m
Chicago Midway
Sun 9/13
8:30 am-11:05 am
Nonstop1h 35m
$273
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 9/11
6:10 am-12:15 pm
2 stops7h 05m
Chicago Midway
Mon 9/14
2:35 pm-9:50 pm
2 stops6h 15m
$292
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Sun 8/16
10:10 am-4:55 pm
2 stops7h 45m
Chicago Midway
Mon 8/17
5:55 am-12:35 pm
1 stop5h 40m
$294
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Wed 7/8
6:00 am-11:00 am
2 stops6h 00m
Chicago Midway
Sat 7/11
2:10 pm-11:05 pm
2 stops7h 55m
$309
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Wed 7/1
8:45 am-9:10 am
Nonstop1h 25m
Chicago Midway
Wed 7/8
7:50 am-10:20 am
Nonstop1h 30m
$313
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Sat 7/25
7:05 pm-7:35 pm
Nonstop1h 30m
Chicago Midway
Mon 7/27
7:45 am-10:15 am
Nonstop1h 30m
$343
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 June.
| 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 June 17, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 12% 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 June 13, 2026.
Travelers seeking maximum savings on their Pittsburgh to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Saturday at noon 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 14% of weekly flights between Pittsburgh and Chicago have experienced delays in the past year, with the average delay time being 103 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 June 17, 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
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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
Hammond
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 Pittsburgh
Popular flights
Alternative routes for Pittsburgh 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 Pittsburgh to Midway by cabin class
Find flights from Pittsburgh 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 June 17, 2026.
Pittsburgh and Midway flights
Browse other Pittsburgh and Midway flight options. Last updated on June 17, 2026.
Other flights from Pittsburgh
Browse through other flights departing from Pittsburgh. Flights are based on user searches made on Cheapflights and were last updated on June 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$326 | FlexibilityNo cancel fee | On-time63% |