$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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PHL
Aug 26 — Sep 21
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Pennsylvania with Cheapflights
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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 July 27, 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 July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:15 am
MDW
- PIT
1 stop3h 50m
Southwest
Tue 9/156:10 am
PIT
- MDW
2 stops8h 45m
Southwest
Deal found 7/24![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:55 am
MDW
- PIT
2 stops8h 20m
Southwest
Mon 11/212:30 pm
PIT
- MDW
2 stops8h 35m
Southwest
Deal found 7/26![Southwest logo]()
$172
This Delta deal was found by Cheapflights users on 7/23. 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 8/156:42 pm
MDW
- PIT
1 stop3h 09m
Delta
Tue 8/185:50 am
PIT
- MDW
1 stop7h 01m
Delta
Deal found 7/23![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:15 pm
MDW
- PIT
1 stop6h 30m
Southwest
Sat 8/226:10 am
PIT
- MDW
2 stops7h 55m
Southwest
Deal found 7/25![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:50 am
MDW
- DCA
2 stops6h 00m
Southwest
Thu 8/209:15 pm
DCA
- MDW
Nonstop1h 55m
Southwest
Deal found 7/27![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:42 pm
MDW
- PIT
1 stop3h 09m
Delta
Mon 8/176:19 pm
PIT
- MDW
1 stop5h 17m
Delta
Deal found 7/24![Delta logo]()
$193
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:35 am
MDW
- DCA
1 stop4h 20m
Southwest
Sat 10/176:00 am
DCA
- MDW
1 stop5h 45m
Southwest
Deal found 7/24![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:35 am
MDW
- IAD
1 stop4h 36m
Delta
Wed 9/1612:26 pm
IAD
- MDW
1 stop4h 49m
Delta
Deal found 7/26![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:05 am
MDW
- DCA
2 stops8h 35m
Southwest
Tue 11/32:40 pm
DCA
- MDW
1 stop4h 05m
Southwest
Deal found 7/25![Southwest logo]()
$198
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:03 pm
MDW
- IAD
1 stop11h 25m
Frontier
Sat 9/267:00 am
IAD
- MDW
1 stop4h 58m
Frontier
Deal found 7/22![Frontier logo]()
$200
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:50 am
MDW
- IAD
1 stop10h 02m
Frontier
Tue 9/157:50 am
IAD
- MDW
1 stop10h 56m
Frontier
Deal found 7/25![Frontier logo]()
$201
This Southwest deal was found by Cheapflights users on 7/22. 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 8/205:55 am
MDW
- DCA
1 stop5h 25m
Southwest
Mon 8/241:00 pm
DCA
- MDW
2 stops5h 50m
Southwest
Deal found 7/22![Southwest logo]()
$202
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 July 27, 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 July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:45 pm
MDW
- PIT
2 stops7h 10m
Southwest
Thu 9/177:20 pm
PIT
- MDW
1 stop3h 40m
Southwest
Deal found 7/27![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:35 am
MDW
- DCA
1 stop6h 57m
Delta
Wed 10/79:32 am
DCA
- MDW
1 stop4h 15m
Delta
Deal found 7/27![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:44 pm
MDW
- IAD
1 stop3h 32m
Delta
Wed 10/146:00 am
IAD
- MDW
1 stop5h 03m
Delta
Deal found 7/26![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:55 pm
MDW
- DCA
1 stop6h 00m
Southwest
Thu 9/241:00 pm
DCA
- MDW
2 stops5h 50m
Southwest
Deal found 7/26![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:37 pm
MDW
- IAD
1 stop4h 37m
Delta
Sat 9/266:10 am
IAD
- MDW
1 stop3h 57m
Delta
Deal found 7/25![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:55 am
MDW
- DCA
1 stop5h 25m
Southwest
Mon 8/241:00 pm
DCA
- MDW
2 stops5h 50m
Southwest
Deal found 7/25![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:44 pm
MDW
- IAD
1 stop3h 32m
Delta
Sat 10/246:12 pm
IAD
- MDW
1 stop5h 21m
Delta
Deal found 7/26![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Tue 9/87:25 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 7/25![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:03 pm
MDW
- DCA
1 stop4h 59m
Delta
Mon 9/146:30 pm
DCA
- MDW
1 stop5h 14m
Delta
Deal found 7/27![Delta logo]()
$202
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:50 am
MDW
- DCA
2 stops6h 00m
Southwest
Tue 9/156:00 am
DCA
- MDW
2 stops7h 05m
Southwest
Deal found 7/26![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:50 pm
MDW
- DCA
1 stop4h 05m
Southwest
Mon 9/141:00 pm
DCA
- MDW
2 stops5h 50m
Southwest
Deal found 7/24![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 7/22. 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 9/1011:35 am
MDW
- IAD
1 stop4h 36m
Delta
Tue 9/156:10 am
IAD
- MDW
1 stop3h 57m
Delta
Deal found 7/22![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:46 pm
MDW
- IAD
1 stop4h 42m
Delta
Mon 8/245:47 pm
IAD
- MDW
1 stop5h 49m
Delta
Deal found 7/25![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:20 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Fri 8/218:40 am
PIT
- MDW
Nonstop1h 20m
Southwest
Deal found 7/25![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:05 am
MDW
- IAD
1 stop7h 06m
Delta
Wed 10/710:07 am
IAD
- MDW
1 stop7h 13m
Delta
Deal found 7/24![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:35 am
MDW
- LGA
Nonstop2h 05m
Southwest
Tue 8/187:05 am
LGA
- MDW
1 stop7h 25m
Southwest
Deal found 7/25![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:10 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Sun 9/136:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Mon 8/315:47 pm
IAD
- MDW
1 stop5h 49m
Delta
Deal found 7/26![Delta logo]()
$238
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:40 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Thu 10/2212:30 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 7/24![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 7/22. 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 10/16:05 am
MDW
- IAD
1 stop4h 25m
Delta
Mon 10/512:26 pm
IAD
- MDW
1 stop4h 49m
Delta
Deal found 7/22![Delta logo]()
$238
This Southwest deal was found by Cheapflights users on 7/23. 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 9/28:55 am
MDW
- LGA
1 stop5h 55m
Southwest
Wed 9/25:40 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Deal found 7/23![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 7/23. 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 8/216:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Wed 8/2612:00 pm
EWR
- MDW
1 stop5h 15m
Delta
Deal found 7/23![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 pm
MDW
- LGA
1 stop4h 50m
Southwest
Sat 9/197:35 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 7/25![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Tue 8/257:05 am
EWR
- MDW
1 stop5h 46m
Delta
Deal found 7/26![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:15 am
MDW
- LGA
1 stop5h 40m
Southwest
Sun 9/206:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:35 pm
MDW
- PIT
2 stops6h 20m
Southwest
Sat 9/196:20 am
PIT
- MDW
2 stops8h 00m
Southwest
Deal found 7/26![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Fri 8/286:00 am
EWR
- MDW
1 stop4h 17m
Delta
Deal found 7/26![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:10 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Sat 10/176:00 am
LGA
- MDW
2 stops10h 15m
Southwest
Deal found 7/27![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:00 pm
MDW
- IAD
1 stop7h 30m
Delta
Mon 10/126:00 am
IAD
- MDW
1 stop4h 18m
Delta
Deal found 7/24![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:45 pm
MDW
- PIT
2 stops7h 10m
Southwest
Wed 9/166:30 am
PIT
- MDW
2 stops11h 20m
Southwest
Deal found 7/26![Southwest logo]()
$246
Last-minute flights from Midway to PennsylvaniaDiscover last-minute flight deals from Midway to Pennsylvania. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pennsylvania. Data last updated July 27, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/23. 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 8/156:42 pm
MDW
- PIT
1 stop3h 09m
Delta
Tue 8/185:50 am
PIT
- MDW
1 stop7h 01m
Delta
Deal found 7/23![Delta logo]()
$188
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:42 pm
MDW
- PIT
1 stop3h 09m
Delta
Mon 8/176:19 pm
PIT
- MDW
1 stop5h 17m
Delta
Deal found 7/24![Delta logo]()
$193
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:42 pm
MDW
- DCA
1 stop3h 17m
Delta
Wed 8/199:39 am
DCA
- MDW
1 stop4h 00m
Delta
Deal found 7/24![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:50 am
MDW
- DCA
2 stops6h 00m
Southwest
Thu 8/209:15 pm
DCA
- MDW
Nonstop1h 55m
Southwest
Deal found 7/27![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:15 pm
MDW
- PIT
1 stop6h 30m
Southwest
Sat 8/226:10 am
PIT
- MDW
2 stops7h 55m
Southwest
Deal found 7/25![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2010:00 am
MDW
- DCA
1 stop3h 55m
Southwest
Tue 8/257:00 pm
DCA
- MDW
1 stop4h 20m
Southwest
Deal found 7/27![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:46 pm
MDW
- IAD
1 stop4h 42m
Delta
Mon 8/245:47 pm
IAD
- MDW
1 stop5h 49m
Delta
Deal found 7/26![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/22. 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 8/205:55 am
MDW
- DCA
1 stop5h 25m
Southwest
Mon 8/241:00 pm
DCA
- MDW
2 stops5h 50m
Southwest
Deal found 7/22![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sat 8/297:35 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 7/24![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:00 am
MDW
- PIT
1 stop7h 25m
Southwest
Mon 8/316:10 am
PIT
- MDW
2 stops7h 05m
Southwest
Deal found 7/26![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:50 am
MDW
- PIT
2 stops9h 30m
Southwest
Mon 8/316:10 am
PIT
- MDW
2 stops7h 05m
Southwest
Deal found 7/24![Southwest logo]()
$167
This Frontier deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:45 am
MDW
- IAD
1 stop10h 07m
Frontier
Wed 9/26:20 am
IAD
- MDW
1 stop5h 35m
Frontier
Deal found 7/24![Frontier logo]()
$200
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 July 27, 2026.
Search for one-way flight options from Midway to Pennsylvania. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:50 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 7/26![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:42 pm
MDW
- PIT
1 stop4h 22m
Delta
Deal found 7/26![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:55 pm
MDW
- DCA
Nonstop1h 55m
Southwest
Deal found 7/27![Southwest logo]()
$94
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/223:10 pm
MDW
- PIT
Nonstop1h 20m
Southwest
Deal found 7/26![Southwest logo]()
$96
This Southwest deal was found by Cheapflights users on 7/22. 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 8/229:55 am
MDW
- DCA
1 stop5h 40m
Southwest
Deal found 7/22![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Deal found 7/26![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 7/23. 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 8/265:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 7/23![Southwest logo]()
$104
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:55 am
MDW
- DCA
2 stops8h 00m
Southwest
Deal found 7/27![Southwest logo]()
$104
This Delta deal was found by Cheapflights users on 7/22. 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 9/59:24 am
MDW
- IAD
1 stop6h 14m
Delta
Deal found 7/22![Delta logo]()
$104
This Southwest deal was found by Cheapflights users on 7/23. 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 8/177:40 pm
MDW
- PIT
Nonstop1h 25m
Southwest
Deal found 7/23![Southwest logo]()
$104
This Super.com deal was found by Cheapflights users on 7/23. 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.
Sat 8/156:05 am
MDW
- IAD
1 stop9h 29m
Frontier
Deal found 7/23![Frontier logo]()
$106
This KAYAK deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:42 pm
MDW
- PIT
1 stop4h 22m
Delta
Deal found 7/23![Delta logo]()
$108
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 July 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | June |
Cheapest in | October |
Average price | $348 |
Good round-trip deal | $240 or less |
Good one-way deal | $214 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 July 27, 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
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Tue 9/15
12:45 pm-8:55 pm
2 stops7h 10m
Pittsburgh
Thu 9/17
7:20 pm-10:00 pm
1 stop3h 40m
$162
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Sat 10/3
11:35 am-7:32 pm
1 stop6h 57m
Washington, D.C. Reagan-National
Wed 10/7
9:32 am-12:47 pm
1 stop4h 15m
$197
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Tue 10/13
6:44 pm-11:16 pm
1 stop3h 32m
Washington, D.C. Dulles Intl
Wed 10/14
6:00 am-10:03 am
1 stop5h 03m
$197
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Sat 9/12
5:37 pm-11:14 pm
1 stop4h 37m
Washington, D.C. Dulles Intl
Sat 9/26
6:10 am-9:07 am
1 stop3h 57m
$197
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Wed 10/21
6:44 pm-11:16 pm
1 stop3h 32m
Washington, D.C. Dulles Intl
Sat 10/24
6:12 pm-10:33 pm
1 stop5h 21m
$197
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Wed 9/23
1:55 pm-8:55 pm
1 stop6h 00m
Washington, D.C. Reagan-National
Thu 9/24
1:00 pm-5:50 pm
2 stops5h 50m
$202
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Thu 8/20
5:55 am-12:20 pm
1 stop5h 25m
Washington, D.C. Reagan-National
Mon 8/24
1:00 pm-5:50 pm
2 stops5h 50m
$202
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Fri 9/11
5:03 pm-11:02 pm
1 stop4h 59m
Washington, D.C. Reagan-National
Mon 9/14
6:30 pm-10:44 pm
1 stop5h 14m
$202
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Wed 9/2
7:05 pm-10:10 pm
Nonstop2h 05m
New York LaGuardia
Tue 9/8
7:25 am-8:45 am
Nonstop2h 20m
$207
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Tue 9/1
8:50 am-3:50 pm
2 stops6h 00m
Washington, D.C. Reagan-National
Tue 9/15
6:00 am-12:05 pm
2 stops7h 05m
$207
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-PIT
MDW-DCA
MDW-IAD
MDW-EWR
MDW-MDT
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-PIT
MDW-DCA
MDW-IAD
MDW-EWR
What is the cheapest month to book a flight from Chicago Midway Airport to Pennsylvania?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Pennsylvania (average of $113). Flying from Chicago Midway Airport to Pennsylvania in February is currently the most expensive (average of $461). 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 July 27, 2026.
It’s typically best to fly out from Chicago Midway Airport to Pennsylvania in the evening. Doing so could potentially save you 11% on the flight price compared to flying in the afternoon, which is usually more expensive.
How much does it cost to fly round-trip from Chicago Midway Airport to Pennsylvania?
Airfare is typical for this route at the moment.
Chicago Midway Airport to Pennsylvania flights typically cost between $184 and $291 in August.The cheapest round-trip price found within the last 5 days was $220 on Frontier (Aug 28-Sep 2).
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 July 18, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Pennsylvania flight should consider departing on Thursday afternoons 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.
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 July 27, 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.
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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 July 27, 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 July 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$148 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$364 | FlexibilityNo cancel fee | On-time63% |