$99+ Cheap flights from Midway (MDW) to Maryland
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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BWI
Aug 11 — Aug 181
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Maryland with Cheapflights
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Cheapest flights from Midway to MarylandExplore the most affordable flight options available from Midway to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 12, 2026.
Explore the most affordable flight options available from Midway to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 12, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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 8/248:00 am
MDW
- PHL
Nonstop2h 10m
Southwest
Mon 8/315:25 pm
PHL
- MDW
1 stop6h 55m
Southwest
Deal found 7/10![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Fri 8/2111:50 am
MDW
- PHL
1 stop7h 38m
Frontier
Tue 8/254:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/11![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Fri 8/711:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Sat 8/84:30 pm
PHL
- MDW
1 stop6h 33m
Frontier
Deal found 7/10![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/1311:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Mon 8/176:25 am
PHL
- MDW
2 stops11h 57m
Frontier
Deal found 7/10![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/1311:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Sun 8/161:32 pm
PHL
- MDW
1 stop9h 31m
Frontier
Deal found 7/9![Frontier logo]()
$197
This Southwest deal was found by Cheapflights users on 7/10. 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 10/148:05 am
MDW
- PHL
2 stops8h 55m
Southwest
Sat 10/177:55 am
PHL
- MDW
Nonstop2h 05m
Southwest
Deal found 7/10![Southwest logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/611:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Thu 8/204:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/8![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 7/9. 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.
Sat 8/1511:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Mon 8/171:32 pm
PHL
- MDW
1 stop9h 31m
Frontier
Deal found 7/9![Frontier logo]()
$202
This Delta deal was found by Cheapflights users on 7/8. 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 8/46:42 pm
MDW
- PHL
1 stop3h 44m
Delta
Tue 8/1112:10 pm
PHL
- MDW
1 stop5h 05m
Delta
Deal found 7/8![Delta logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Fri 8/2111:50 am
MDW
- PHL
1 stop7h 38m
Frontier
Wed 8/264:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/8![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Tue 8/1111:06 am
MDW
- PHL
1 stop19h 09m
Frontier
Fri 8/144:40 pm
PHL
- MDW
1 stop6h 23m
Frontier
Deal found 7/10![Frontier logo]()
$205
This Southwest deal was found by Cheapflights users on 7/10. 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 8/86:00 am
MDW
- DCA
Nonstop1h 45m
Southwest
Fri 8/214:35 pm
DCA
- MDW
1 stop4h 35m
Southwest
Deal found 7/10![Southwest logo]()
$221
Best flights from Midway to MarylandDiscover carefully curated flight deals from Midway to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 12, 2026.
Discover carefully curated flight deals from Midway to Maryland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 12, 2026.
This Delta deal was found by Cheapflights users on 7/10. 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 9/161:19 pm
MDW
- PHL
1 stop5h 00m
Delta
Thu 9/176:15 am
PHL
- MDW
1 stop3h 52m
Delta
Deal found 7/10![Delta logo]()
$203
This Southwest deal was found by Cheapflights users on 7/7. 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 9/142:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Wed 9/167:15 am
PHL
- MDW
1 stop4h 35m
Southwest
Deal found 7/7![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 7/8. 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
- PHL
1 stop3h 44m
Delta
Wed 8/269:40 am
PHL
- MDW
1 stop3h 59m
Delta
Deal found 7/8![Delta logo]()
$203
This Southwest deal was found by Cheapflights users on 7/9. 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 10/95:50 pm
MDW
- DCA
1 stop4h 00m
Southwest
Mon 10/126:55 pm
DCA
- MDW
1 stop5h 15m
Southwest
Deal found 7/9![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 7/8. 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 10/166:45 pm
MDW
- IAD
1 stop3h 26m
Delta
Tue 10/206:12 pm
IAD
- MDW
1 stop5h 13m
Delta
Deal found 7/8![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 7/11. 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 11/66:10 pm
MDW
- BWI
Nonstop1h 50m
Southwest
Mon 11/92:55 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 7/11![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 7/8. 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 10/231:00 pm
MDW
- IAD
1 stop7h 30m
Delta
Mon 10/266:00 am
IAD
- MDW
1 stop4h 52m
Delta
Deal found 7/8![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 7/7. 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 8/198:50 am
MDW
- DCA
2 stops6h 00m
Southwest
Fri 9/46:50 pm
DCA
- MDW
1 stop4h 05m
Southwest
Deal found 7/7![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 7/9. 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 8/2110:54 am
MDW
- IAD
1 stop4h 48m
Delta
Sat 8/2211:06 am
IAD
- MDW
1 stop5h 32m
Delta
Deal found 7/9![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 7/8. 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 11/214:20 pm
MDW
- BWI
2 stops7h 25m
Southwest
Tue 12/110:50 am
BWI
- MDW
1 stop5h 00m
Southwest
Deal found 7/8![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 7/9. 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
- BWI
1 stop3h 31m
Delta
Fri 8/146:15 am
BWI
- MDW
1 stop4h 02m
Delta
Deal found 7/9![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 7/7. 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 8/219:00 am
MDW
- BWI
Nonstop1h 55m
Southwest
Fri 8/285:20 pm
BWI
- MDW
Nonstop1h 55m
Southwest
Deal found 7/7![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 7/11. 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 8/201:00 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 8/246:05 pm
PHL
- MDW
Nonstop2h 05m
Southwest
Deal found 7/11![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:30 pm
MDW
- IAD
1 stop3h 32m
Delta
Tue 12/16:10 am
IAD
- MDW
1 stop3h 35m
Delta
Deal found 7/8![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 7/11. 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 10/95:15 pm
MDW
- IAD
1 stop6h 16m
Delta
Mon 10/126:00 am
IAD
- MDW
1 stop4h 18m
Delta
Deal found 7/11![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 7/10. 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 8/95:00 am
MDW
- BWI
Nonstop1h 45m
Southwest
Wed 8/127:45 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Deal found 7/10![Southwest logo]()
$264
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:30 pm
MDW
- IAD
1 stop3h 32m
Delta
Mon 11/236:00 am
IAD
- MDW
1 stop4h 52m
Delta
Deal found 7/11![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:05 am
MDW
- BWI
Nonstop1h 55m
Southwest
Sun 11/2212:35 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 7/10![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 7/11. 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 11/213:40 pm
MDW
- BWI
Nonstop1h 50m
Southwest
Mon 11/2310:00 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 7/11![Southwest logo]()
$266
This KAYAK deal was found by Cheapflights users on 7/9. 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 8/106:42 pm
MDW
- DCA
1 stop3h 17m
Delta
Wed 8/126:10 am
DCA
- MDW
1 stop4h 07m
Delta
Deal found 7/9![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 7/7. 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 9/511:15 am
MDW
- BWI
2 stops6h 15m
Southwest
Mon 9/711:45 am
BWI
- MDW
1 stop4h 10m
Southwest
Deal found 7/7![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 7/11. 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 9/55:45 pm
MDW
- DCA
1 stop4h 14m
Delta
Sun 9/66:10 am
DCA
- MDW
1 stop4h 07m
Delta
Deal found 7/11![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 7/11. 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 8/106:45 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Mon 8/175:25 pm
PHL
- MDW
1 stop6h 55m
Southwest
Deal found 7/11![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 7/11. 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 8/121:25 pm
MDW
- DCA
1 stop4h 20m
Delta
Sun 8/166:10 am
DCA
- MDW
1 stop4h 07m
Delta
Deal found 7/11![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 7/11. 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 8/61:00 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Mon 8/105:55 am
PHL
- MDW
1 stop6h 05m
Southwest
Deal found 7/11![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 7/10. 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 8/66:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Sun 8/96:10 am
IAD
- MDW
1 stop4h 07m
Delta
Deal found 7/10![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 7/6. 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 8/76:45 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Mon 8/105:55 am
PHL
- MDW
1 stop6h 05m
Southwest
Deal found 7/6![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 7/9. 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 8/126:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Sun 8/166:10 am
IAD
- MDW
1 stop4h 07m
Delta
Deal found 7/9![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 7/11. 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 8/249:20 am
MDW
- DCA
1 stop5h 50m
Southwest
Fri 8/281:00 pm
DCA
- MDW
2 stops5h 50m
Southwest
Deal found 7/11![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 7/11. 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 7/3111:05 am
MDW
- IAD
1 stop6h 25m
Delta
Tue 8/46:10 am
IAD
- MDW
1 stop4h 07m
Delta
Deal found 7/11![Delta logo]()
$293
Last-minute flights from Midway to MarylandDiscover last-minute flight deals from Midway to Maryland. Data last updated July 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Maryland. Data last updated July 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/8. 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 8/46:42 pm
MDW
- PHL
1 stop3h 44m
Delta
Thu 8/63:58 pm
PHL
- MDW
1 stop7h 38m
Delta
Deal found 7/8![Delta logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/54:45 pm
MDW
- IAD
2 stops22h 55m
Frontier
Tue 8/117:48 am
IAD
- MDW
1 stop15h 15m
Frontier
Deal found 7/10![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/611:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Thu 8/204:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/8![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Fri 8/711:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Sat 8/84:30 pm
PHL
- MDW
1 stop6h 33m
Frontier
Deal found 7/10![Frontier logo]()
$195
This Southwest deal was found by Cheapflights users on 7/10. 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 8/86:00 am
MDW
- DCA
Nonstop1h 45m
Southwest
Fri 8/214:35 pm
DCA
- MDW
1 stop4h 35m
Southwest
Deal found 7/10![Southwest logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Tue 8/1111:06 am
MDW
- PHL
1 stop19h 09m
Frontier
Fri 8/144:40 pm
PHL
- MDW
1 stop6h 23m
Frontier
Deal found 7/10![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/1311:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Mon 8/176:25 am
PHL
- MDW
2 stops11h 57m
Frontier
Deal found 7/10![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/1311:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Fri 8/144:40 pm
PHL
- MDW
1 stop6h 23m
Frontier
Deal found 7/9![Frontier logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 7/9. 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.
Sat 8/1511:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Mon 8/171:32 pm
PHL
- MDW
1 stop9h 31m
Frontier
Deal found 7/9![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Fri 8/2111:50 am
MDW
- PHL
1 stop7h 38m
Frontier
Tue 8/254:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/11![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Fri 8/2111:50 am
MDW
- PHL
1 stop7h 38m
Frontier
Wed 8/264:45 pm
PHL
- MDW
1 stop7h 02m
Frontier
Deal found 7/8![Frontier logo]()
$204
This Southwest deal was found by Cheapflights users on 7/10. 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 8/248:00 am
MDW
- PHL
Nonstop2h 10m
Southwest
Mon 8/315:25 pm
PHL
- MDW
1 stop6h 55m
Southwest
Deal found 7/10![Southwest logo]()
$193
One-way flights from Midway to MarylandSearch for one-way flight options from Midway to Maryland. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
Search for one-way flight options from Midway to Maryland. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
This Delta deal was found by Cheapflights users on 7/11. 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 8/1210:54 am
MDW
- DCA
1 stop7h 40m
Delta
Deal found 7/11![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 7/10. 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 8/226:11 am
MDW
- IAD
1 stop6h 32m
Delta
Deal found 7/10![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 7/8. 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 8/48:50 am
MDW
- DCA
1 stop5h 10m
Southwest
Deal found 7/8![Southwest logo]()
$101
This Delta deal was found by Cheapflights users on 7/8. 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 8/46:05 am
MDW
- IAD
1 stop4h 28m
Delta
Deal found 7/8![Delta logo]()
$101
This Southwest deal was found by Cheapflights users on 7/7. 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 8/53:50 pm
MDW
- DCA
1 stop5h 15m
Southwest
Deal found 7/7![Southwest logo]()
$103
This Delta deal was found by Cheapflights users on 7/9. 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 8/256:05 am
MDW
- IAD
1 stop4h 28m
Delta
Deal found 7/9![Delta logo]()
$103
This Southwest deal was found by Cheapflights users on 7/10. 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 10/131:05 pm
MDW
- DCA
2 stops5h 50m
Southwest
Deal found 7/10![Southwest logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:05 am
MDW
- IAD
1 stop10h 09m
Frontier
Deal found 7/11![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 7/8. 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 8/105:30 pm
MDW
- DCA
1 stop4h 00m
Southwest
Deal found 7/8![Southwest logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:40 am
MDW
- PHL
1 stop23h 56m
Frontier
Deal found 7/11![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 7/8. 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
Deal found 7/8![Southwest logo]()
$106
This Southwest deal was found by Cheapflights users on 7/9. 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 10/79:40 am
MDW
- PHL
2 stops7h 20m
Southwest
Deal found 7/9![Southwest logo]()
$107
Find flight deals from Midway to Maryland
Keep the following information in mind while searching for Midway to Maryland flight deals. Data was last updated July 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $193 (Southwest) |
One-way from | $99 (Delta) |
Popular in | June |
Cheapest in | August |
Average price | $271 |
Good round-trip deal | $306 or less |
Good one-way deal | $188 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Maryland 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 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Maryland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Wed 9/16
1:19 pm-7:19 pm
1 stop5h 00m
Philadelphia
Thu 9/17
6:15 am-9:07 am
1 stop3h 52m
$203
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Sat 8/22
6:42 pm-11:26 pm
1 stop3h 44m
Philadelphia
Wed 8/26
9:40 am-12:39 pm
1 stop3h 59m
$203
ChicagoPhiladelphia
MDW - PHL
MDWPHL
Chicago Midway
Mon 9/14
2:55 pm-5:55 pm
Nonstop2h 00m
Philadelphia
Wed 9/16
7:15 am-10:50 am
1 stop4h 35m
$211
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Fri 10/16
6:45 pm-11:11 pm
1 stop3h 26m
Washington, D.C. Dulles Intl
Tue 10/20
6:12 pm-10:25 pm
1 stop5h 13m
$226
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Fri 10/23
1:00 pm-9:30 pm
1 stop7h 30m
Washington, D.C. Dulles Intl
Mon 10/26
6:00 am-9:52 am
1 stop4h 52m
$226
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Fri 10/9
5:50 pm-10:50 pm
1 stop4h 00m
Washington, D.C. Reagan-National
Mon 10/12
6:55 pm-11:10 pm
1 stop5h 15m
$231
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Fri 8/21
10:54 am-4:42 pm
1 stop4h 48m
Washington, D.C. Dulles Intl
Sat 8/22
11:06 am-3:38 pm
1 stop5h 32m
$231
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Fri 11/6
6:10 pm-9:00 pm
Nonstop1h 50m
Baltimore/Washington
Mon 11/9
2:55 pm-4:00 pm
Nonstop2h 05m
$243
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Wed 8/19
8:50 am-3:50 pm
2 stops6h 00m
Washington, D.C. Reagan-National
Fri 9/4
6:50 pm-9:55 pm
1 stop4h 05m
$245
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Fri 8/7
6:42 pm-11:13 pm
1 stop3h 31m
Baltimore/Washington
Fri 8/14
6:15 am-9:17 am
1 stop4h 02m
$249
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Maryland
Have a flexible travel schedule? Discover the best time to fly to Maryland from Midway with our price prediction graph.
MDW-DCA
MDW-IAD
MDW-PHL
MDW-BWI
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 Maryland
MDW-USMD
MDW-DCA
MDW-IAD
MDW-PHL
MDW-BWI
What is the cheapest month to book a flight from Chicago Midway Airport to Maryland?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Maryland (average of $59). Flying from Chicago Midway Airport to Maryland in March is currently the most expensive (average of $245). 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 MD?
Find hourly flight availability from Midway to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 12, 2026.
It’s optimal to fly from Chicago Midway Airport to Maryland at noon. By choosing this option you can save up to 42% on the cost of your flight, compared to a flight in the evening.
How much does it cost to fly round-trip from Chicago Midway Airport to Maryland?
What is the cheapest day to fly from Chicago Midway Airport to Maryland?
Use this chart to determine the cheapest time to fly round-trip from Midway to Maryland. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Maryland flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Maryland
Get insights into the airlines that provide service to Maryland. 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 Maryland. Reviews last updated July 12, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Maryland, 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.
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Food
7.0
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 Maryland. 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 Maryland
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Complete your trip
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Search flights from Midway to Maryland by cabin class
Find flights from Midway to Maryland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Maryland flights
Browse other Midway and Maryland flight options. Last updated on July 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Maryland flights
Consider these flights traveling from Midway to Maryland.
Top 2 airlines flying from Midway to Maryland
Discover the top 2 airlines that operate flights from Midway to Maryland. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$179 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$326 | FlexibilityNo cancel fee | On-time63% |