$69+ Cheap flights from Midway (MDW) to Pennsylvania
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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Jun 19 — Jun 261
Round-trip
1 adult, Economy
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Cheapest flights from Midway to PennsylvaniaExplore the most affordable flight options available from Midway to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.
Explore the most affordable flight options available from Midway to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.
This Southwest deal was found by Cheapflights users on 5/18. 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 7/27:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Tue 7/77:25 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/18![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 5/17. 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.
Thu 7/27:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Fri 7/106:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/17![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/16. 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 6/35:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sat 6/66:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 5/18. 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 7/25:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sun 7/56:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/18![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 5/18. 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 8/65:55 am
MDW
- PIT
1 stop5h 40m
Southwest
Thu 8/132:45 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 5/18![Southwest logo]()
$187
This deal was found by Cheapflights users on 5/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/71:18 pm
MDW
- PIT
1 stop4h 44m
Delta
Wed 7/156:30 am
PIT
- MDW
1 stop3h 38m
Delta
Deal found 5/15![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 5/16. 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.
Fri 5/295:40 pm
MDW
- LGA
1 stop4h 45m
Southwest
Sat 5/303:35 pm
LGA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/16![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 5/18. 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 7/35:15 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Sun 7/56:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/18![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 5/19. 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 8/69:20 am
MDW
- PIT
2 stops7h 20m
Southwest
Mon 8/107:30 pm
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 5/19![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 6/172:35 pm
MDW
- LGA
1 stop7h 45m
Southwest
Sat 6/206:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/15![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 5/19. 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 7/2911:50 am
MDW
- PIT
2 stops6h 50m
Southwest
Wed 8/510:10 am
PIT
- MDW
2 stops9h 55m
Southwest
Deal found 5/19![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 5/16. 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 6/24:40 pm
MDW
- LGA
1 stop5h 20m
Southwest
Sat 6/66:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$195
Best flights from Midway to PennsylvaniaDiscover carefully curated flight deals from Midway to Pennsylvania that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 20, 2026.
Discover carefully curated flight deals from Midway to Pennsylvania that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 20, 2026.
This Southwest deal was found by Cheapflights users on 5/15. 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 6/196:00 pm
MDW
- LGA
1 stop4h 20m
Southwest
Sat 6/206:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/15![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 5/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:05 am
MDW
- EWR
1 stop7h 09m
Delta
Tue 8/183:20 pm
EWR
- MDW
1 stop8h 16m
Delta
Deal found 5/16![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/16. 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 7/147:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Sat 7/186:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 5/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:27 pm
MDW
- EWR
1 stop4h 58m
Delta
Wed 8/129:39 am
EWR
- MDW
1 stop4h 00m
Delta
Deal found 5/16![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/18. 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 8/225:55 am
MDW
- PIT
1 stop5h 15m
Southwest
Thu 8/274:10 pm
PIT
- MDW
1 stop5h 50m
Southwest
Deal found 5/18![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 5/19. 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 8/69:20 am
MDW
- PIT
2 stops7h 20m
Southwest
Mon 8/106:10 am
PIT
- MDW
2 stops7h 05m
Southwest
Deal found 5/19![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 5/17. 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.
Fri 5/296:36 pm
MDW
- EWR
1 stop3h 42m
Delta
Wed 6/36:00 am
EWR
- MDW
1 stop3h 43m
Delta
Deal found 5/17![Delta logo]()
$232
This Delta deal was found by Cheapflights users on 5/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Wed 8/129:39 am
EWR
- MDW
1 stop4h 00m
Delta
Deal found 5/16![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 5/15. 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.
Sat 8/156:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Tue 8/186:30 am
LGA
- MDW
1 stop6h 20m
Southwest
Deal found 5/15![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 5/18. 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 6/309:17 am
MDW
- EWR
1 stop5h 42m
Delta
Sun 7/51:00 pm
EWR
- MDW
1 stop6h 31m
Delta
Deal found 5/18![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/275:25 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Tue 6/307:25 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/17![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 5/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:00 pm
MDW
- DCA
1 stop4h 59m
Delta
Sat 10/248:00 am
DCA
- MDW
1 stop4h 56m
Delta
Deal found 5/16![Delta logo]()
$238
This Southwest deal was found by Cheapflights users on 5/16. 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 6/35:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sun 6/76:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 5/18. 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 7/72:35 pm
MDW
- LGA
1 stop7h 45m
Southwest
Wed 7/87:25 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/18![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Mon 8/317:00 am
IAD
- MDW
1 stop5h 54m
Delta
Deal found 5/15![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 5/16. 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 8/65:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Tue 8/117:15 am
LGA
- MDW
1 stop7h 15m
Southwest
Deal found 5/16![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 5/19. 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 7/256:00 am
MDW
- PIT
1 stop5h 42m
Delta
Tue 7/286:13 pm
PIT
- MDW
1 stop5h 02m
Delta
Deal found 5/19![Delta logo]()
$260
This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:23 am
MDW
- EWR
1 stop6h 32m
Delta
Tue 6/23:28 pm
EWR
- MDW
1 stop6h 41m
Delta
Deal found 5/15![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 5/17. 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.
Thu 7/26:00 pm
MDW
- LGA
1 stop4h 20m
Southwest
Sun 7/56:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/17![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 5/19. 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 7/2211:05 am
MDW
- PHL
1 stop5h 07m
Delta
Tue 7/286:25 am
PHL
- MDW
1 stop4h 40m
Delta
Deal found 5/19![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/15. 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.
Sat 6/610:15 am
MDW
- LGA
1 stop5h 05m
Southwest
Mon 6/89:30 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/15![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 5/17. 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 7/291:18 pm
MDW
- EWR
1 stop5h 11m
Delta
Tue 8/49:39 am
EWR
- MDW
1 stop4h 00m
Delta
Deal found 5/17![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/20. 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 7/135:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sun 7/196:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/20![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 5/17. 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 6/279:54 am
MDW
- EWR
1 stop6h 01m
Delta
Tue 6/306:00 am
EWR
- MDW
1 stop4h 14m
Delta
Deal found 5/17![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/19. 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 7/119:15 am
MDW
- DCA
1 stop3h 50m
Southwest
Tue 8/49:00 pm
DCA
- MDW
Nonstop2h 05m
Southwest
Deal found 5/19![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 5/18. 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 7/216:00 am
MDW
- IAD
1 stop4h 37m
Delta
Fri 7/245:46 pm
IAD
- MDW
1 stop5h 29m
Delta
Deal found 5/18![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 5/19. 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 7/185:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Tue 7/216:10 pm
PHL
- MDW
1 stop6h 55m
Southwest
Deal found 5/19![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 5/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Tue 8/119:39 am
EWR
- MDW
1 stop4h 00m
Delta
Deal found 5/16![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 5/17. 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 7/205:05 pm
MDW
- DCA
Nonstop1h 50m
Southwest
Tue 7/281:00 pm
DCA
- MDW
1 stop5h 05m
Southwest
Deal found 5/17![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 5/19. 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 6/275:05 pm
MDW
- DCA
Nonstop1h 50m
Southwest
Wed 7/811:45 am
DCA
- MDW
2 stops6h 20m
Southwest
Deal found 5/19![Southwest logo]()
$258
Last-minute flights from Midway to PennsylvaniaDiscover last-minute flight deals from Midway to Pennsylvania. Data last updated May 20, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pennsylvania. Data last updated May 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/16. 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.
Fri 5/295:40 pm
MDW
- LGA
1 stop4h 45m
Southwest
Sat 5/303:35 pm
LGA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/16![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 5/305:30 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sat 6/66:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 5/16. 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 6/24:40 pm
MDW
- LGA
1 stop5h 20m
Southwest
Sat 6/66:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 5/16. 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 6/35:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sat 6/66:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$186
This Delta deal was found by Cheapflights users on 5/17. 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 6/66:23 am
MDW
- EWR
1 stop7h 59m
Delta
Tue 6/166:00 am
EWR
- MDW
1 stop4h 14m
Delta
Deal found 5/17![Delta logo]()
$212
This Southwest deal was found by Cheapflights users on 5/18. 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 6/136:40 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Wed 6/176:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/18![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 5/18. 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 6/136:40 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Mon 6/156:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/18![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 6/172:35 pm
MDW
- LGA
1 stop7h 45m
Southwest
Sat 6/206:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/15![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 5/15. 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 6/196:00 pm
MDW
- LGA
1 stop4h 20m
Southwest
Sat 6/206:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/15![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 5/18. 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 6/205:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Wed 6/246:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/18![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 5/17. 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 6/279:54 am
MDW
- EWR
1 stop6h 01m
Delta
Tue 7/77:05 am
EWR
- MDW
1 stop5h 51m
Delta
Deal found 5/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/19. 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 6/307:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Sun 7/56:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/19![Southwest logo]()
$182
One-way flights from Midway to PennsylvaniaSearch for one-way flight options from Midway to Pennsylvania. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
Search for one-way flight options from Midway to Pennsylvania. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
This Southwest deal was found by Cheapflights users on 5/18. 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 6/912:50 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 5/18![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 5/18. 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 6/96:58 pm
MDW
- PIT
1 stop4h 09m
Delta
Deal found 5/18![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 5/18. 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 6/245:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/18![Southwest logo]()
$89
This Southwest deal was found by Cheapflights users on 5/17. 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.
Thu 8/138:15 am
MDW
- PIT
Nonstop1h 30m
Southwest
Deal found 5/17![Southwest logo]()
$89
This Southwest deal was found by Cheapflights users on 5/18. 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 7/35:15 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 5/18![Southwest logo]()
$94
This Southwest deal was found by Cheapflights users on 5/18. 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 6/107:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 5/18![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 5/18. 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 6/279:54 am
MDW
- EWR
1 stop6h 01m
Delta
Deal found 5/18![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 5/305:30 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/16![Southwest logo]()
$102
This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Deal found 5/15![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 5/18. 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 5/2710:15 am
MDW
- LGA
1 stop5h 25m
Southwest
Deal found 5/18![Southwest logo]()
$104
This Delta deal was found by Cheapflights users on 5/18. 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 6/1912:50 pm
MDW
- EWR
1 stop6h 54m
Delta
Deal found 5/18![Delta logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Wed 6/106:00 am
MDW
- LGA
1 stop10h 53m
Frontier
Deal found 5/19![Frontier logo]()
$105
Find flight deals from Midway to Pennsylvania
Keep the following information in mind while searching for Midway to Pennsylvania flight deals. Data was last updated May 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | March |
Cheapest in | October |
Average price | $311 |
Good round-trip deal | $251 or less |
Good one-way deal | $115 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Pennsylvania 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 May 20, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pennsylvania that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Fri 6/19
6:00 pm-11:20 pm
1 stop4h 20m
New York LaGuardia
Sat 6/20
6:00 am-7:20 am
Nonstop2h 20m
$192
ChicagoNewark
MDW - EWR
MDWEWR
Chicago Midway
Thu 8/13
6:05 am-2:14 pm
1 stop7h 09m
Newark
Tue 8/18
3:20 pm-10:36 pm
1 stop8h 16m
$197
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 7/14
7:45 pm-10:55 pm
Nonstop2h 10m
New York LaGuardia
Sat 7/18
6:00 am-7:20 am
Nonstop2h 20m
$197
ChicagoNewark
MDW - EWR
MDWEWR
Chicago Midway
Thu 8/6
1:27 pm-7:25 pm
1 stop4h 58m
Newark
Wed 8/12
9:39 am-12:39 pm
1 stop4h 00m
$197
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Sat 8/22
5:55 am-12:10 pm
1 stop5h 15m
Pittsburgh
Thu 8/27
4:10 pm-9:00 pm
1 stop5h 50m
$197
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Thu 8/6
9:20 am-5:40 pm
2 stops7h 20m
Pittsburgh
Mon 8/10
6:10 am-12:15 pm
2 stops7h 05m
$207
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Sat 8/15
6:00 am-9:00 am
Nonstop2h 00m
New York LaGuardia
Tue 8/18
6:30 am-11:50 am
1 stop6h 20m
$217
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Sat 6/27
5:25 pm-8:30 pm
Nonstop2h 05m
New York LaGuardia
Tue 6/30
7:25 am-8:50 am
Nonstop2h 25m
$217
Quickest round-trip
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Wed 6/3
5:15 am-8:15 am
Nonstop2h 00m
New York LaGuardia
Sun 6/7
6:00 am-7:20 am
Nonstop2h 20m
$222
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 7/7
2:35 pm-11:20 pm
1 stop7h 45m
New York LaGuardia
Wed 7/8
7:25 am-8:50 am
Nonstop2h 25m
$223
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Pennsylvania
Have a flexible travel schedule? Discover the best time to fly to Pennsylvania from Midway with our price prediction graph.
MDW-LGA
MDW-EWR
MDW-PIT
MDW-DCA
MDW-IAD
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 Chicago Midway Airport to Pennsylvania
MDW-USPA
MDW-LGA
MDW-EWR
MDW-PIT
MDW-DCA
What is the cheapest month to book a flight from Chicago Midway Airport to Pennsylvania?
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Pennsylvania (average of $67). Flying from Chicago Midway Airport to Pennsylvania in February is currently the most expensive (average of $321). 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 MDW to PA?
Find hourly flight availability from Midway to Pennsylvania. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 20, 2026.
It’s typically best to fly out from Chicago Midway Airport to Pennsylvania in the afternoon. Doing so could potentially save you 19% on the flight price compared to flying at noon, which is usually more expensive.
How much does it cost to fly round-trip from Chicago Midway Airport to Pennsylvania?
What is the cheapest day to fly from Chicago Midway Airport to Pennsylvania?
Use this chart to determine the cheapest time to fly round-trip from Midway to Pennsylvania. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Pennsylvania flight should consider departing on Saturday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Pennsylvania
Get insights into the airlines that provide service to Pennsylvania. 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 Pennsylvania. Reviews last updated May 20, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Pennsylvania, such as Southwest and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Pennsylvania. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Pennsylvania
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Complete your trip
Complete your trip to Pennsylvania by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Pennsylvania by cabin class
Find flights from Midway to Pennsylvania, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Pennsylvania flights
Browse other Midway and Pennsylvania flight options. Last updated on May 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Pennsylvania flights
Consider these flights traveling from Midway to Pennsylvania.
Top 2 airlines flying from Midway to Pennsylvania
Discover the top 2 airlines that operate flights from Midway to Pennsylvania. 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 May 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$159 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$116 | Average$355 | FlexibilityNo cancel fee | On-time63% |