$104+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BWI
Jun 18 — Jun 251
Round-trip
1 adult, Economy
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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 May 19, 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 May 19, 2026.
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1712:50 pm
MDW
- BWI
1 stop4h 05m
Southwest
Wed 6/248:30 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/14![Southwest logo]()
$207
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:27 pm
MDW
- BWI
1 stop9h 30m
Frontier
Wed 6/247:27 pm
BWI
- MDW
1 stop16h 45m
Frontier
Deal found 5/18![Frontier logo]()
$209
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:04 pm
MDW
- BWI
1 stop5h 28m
Frontier
Sun 6/289:43 pm
BWI
- MDW
1 stop14h 26m
Frontier
Deal found 5/15![Frontier logo]()
$210
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/911:05 am
MDW
- BWI
1 stop5h 14m
Delta
Tue 6/235:40 am
BWI
- MDW
1 stop5h 29m
Delta
Deal found 5/14![Delta logo]()
$216
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 9/2310:35 am
MDW
- BWI
1 stop5h 33m
Delta
Tue 9/297:00 am
BWI
- MDW
1 stop5h 54m
Delta
Deal found 5/17![Delta logo]()
$217
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Sat 7/181:32 pm
PHL
- MDW
1 stop9h 36m
Frontier
Deal found 5/18![Frontier logo]()
$218
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:11 pm
MDW
- BWI
1 stop5h 22m
Frontier
Wed 8/196:35 am
BWI
- MDW
1 stop5h 34m
Frontier
Deal found 5/18![Frontier logo]()
$218
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Thu 8/134:30 pm
PHL
- MDW
1 stop6h 38m
Frontier
Deal found 5/19![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/611:59 am
MDW
- BWI
1 stop5h 31m
Frontier
Tue 6/91:29 pm
BWI
- MDW
1 stop9h 42m
Frontier
Deal found 5/14![Frontier logo]()
$219
This Trip.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Tue 6/96:30 am
PHL
- MDW
1 stop5h 42m
Frontier
Deal found 5/14![Frontier logo]()
$220
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:35 pm
MDW
- BWI
Nonstop1h 50m
Southwest
Wed 6/178:30 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/14![Southwest logo]()
$220
This Trip.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:04 pm
MDW
- BWI
1 stop5h 28m
Frontier
Tue 6/306:28 am
BWI
- MDW
1 stop5h 44m
Frontier
Deal found 5/14![Frontier 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 May 19, 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 May 19, 2026.
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:25 pm
MDW
- BWI
Nonstop1h 45m
Southwest
Tue 10/276:55 am
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/14![Southwest logo]()
$233
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 5/17. 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 8/155:55 am
MDW
- BWI
Nonstop1h 45m
Southwest
Wed 8/1910:50 am
BWI
- MDW
1 stop4h 15m
Southwest
Deal found 5/17![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:00 pm
MDW
- DCA
Nonstop1h 50m
Southwest
Mon 8/176:40 pm
DCA
- MDW
Nonstop1h 55m
Southwest
Deal found 5/14![Southwest logo]()
$239
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 5/15. 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.
Thu 9/38:05 am
MDW
- BWI
1 stop3h 15m
Southwest
Tue 9/810:50 am
BWI
- MDW
1 stop3h 15m
Southwest
Deal found 5/15![Southwest logo]()
$248
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.
Thu 9/246:00 am
MDW
- IAD
1 stop4h 59m
Delta
Mon 9/285:30 pm
IAD
- MDW
1 stop5h 16m
Delta
Deal found 5/19![Delta logo]()
$279
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 7/168:55 am
MDW
- BWI
Nonstop1h 50m
Southwest
Tue 7/214:50 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/18![Southwest logo]()
$253
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 6/1712:50 pm
MDW
- DCA
1 stop4h 40m
Delta
Sun 6/216:00 am
DCA
- MDW
1 stop4h 14m
Delta
Deal found 5/16![Delta logo]()
$298
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 6/188:50 pm
MDW
- BWI
Nonstop1h 55m
Southwest
Tue 6/304:50 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/18![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Tue 8/116:00 am
IAD
- MDW
1 stop4h 59m
Delta
Deal found 5/14![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:50 pm
MDW
- BWI
Nonstop1h 55m
Southwest
Wed 7/86:30 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/14![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:24 am
MDW
- IAD
1 stop6h 13m
Delta
Sun 8/166:00 am
IAD
- MDW
1 stop4h 17m
Delta
Deal found 5/14![Delta logo]()
$298
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 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.
Wed 6/106:00 am
MDW
- IAD
1 stop4h 39m
Delta
Sun 6/146:05 am
IAD
- MDW
1 stop4h 09m
Delta
Deal found 5/18![Delta logo]()
$303
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 9/248:10 am
MDW
- BWI
1 stop3h 35m
Southwest
Mon 9/285:20 pm
BWI
- MDW
Nonstop1h 55m
Southwest
Deal found 5/17![Southwest logo]()
$275
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 6/206:35 pm
MDW
- IAD
1 stop3h 39m
Delta
Mon 6/226:05 am
IAD
- MDW
1 stop4h 09m
Delta
Deal found 5/17![Delta logo]()
$317
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.
Sun 7/56:00 am
MDW
- DCA
Nonstop1h 45m
Southwest
Wed 7/89:30 pm
DCA
- MDW
Nonstop2h 00m
Southwest
Deal found 5/17![Southwest logo]()
$278
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.
Mon 7/136:00 am
MDW
- IAD
1 stop4h 37m
Delta
Mon 7/206:00 am
IAD
- MDW
1 stop4h 08m
Delta
Deal found 5/16![Delta logo]()
$317
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.
Wed 7/89:10 am
MDW
- PHL
Nonstop2h 00m
Southwest
Sat 7/116:05 pm
PHL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/17![Southwest logo]()
$279
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 8/226:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Sun 8/236:00 am
IAD
- MDW
1 stop4h 59m
Delta
Deal found 5/19![Delta logo]()
$319
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 6/65:55 am
MDW
- DCA
Nonstop1h 45m
Southwest
Tue 6/96:55 pm
DCA
- MDW
Nonstop2h 10m
Southwest
Deal found 5/17![Southwest logo]()
$279
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 6/269:17 am
MDW
- IAD
1 stop6h 25m
Delta
Sat 7/412:35 pm
IAD
- MDW
1 stop5h 32m
Delta
Deal found 5/15![Delta logo]()
$319
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 10/169:00 am
MDW
- BWI
Nonstop1h 45m
Southwest
Mon 10/1911:05 am
BWI
- MDW
Nonstop2h 00m
Southwest
Deal found 5/16![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:50 pm
MDW
- PHL
1 stop4h 47m
Delta
Wed 6/246:10 am
PHL
- MDW
1 stop4h 04m
Delta
Deal found 5/14![Delta logo]()
$321
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 7/25:20 pm
MDW
- BWI
Nonstop1h 55m
Southwest
Fri 7/36:10 am
BWI
- MDW
Nonstop2h 00m
Southwest
Deal found 5/16![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2412:41 pm
MDW
- DCA
1 stop4h 56m
Delta
Mon 7/279:39 am
DCA
- MDW
1 stop3h 59m
Delta
Deal found 5/14![Delta logo]()
$323
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 7/38:50 pm
MDW
- BWI
Nonstop1h 55m
Southwest
Mon 7/68:55 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/16![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:59 pm
MDW
- IAD
1 stop4h 00m
Delta
Mon 9/76:00 am
IAD
- MDW
1 stop6h 54m
Delta
Deal found 5/14![Delta logo]()
$323
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 7/1111:15 am
MDW
- PHL
Nonstop1h 55m
Southwest
Mon 7/135:20 pm
PHL
- MDW
Nonstop2h 10m
Southwest
Deal found 5/17![Southwest logo]()
$295
Last-minute flights from Midway to MarylandDiscover last-minute flight deals from Midway to Maryland. Data last updated May 19, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Maryland. Data last updated May 19, 2026 and is based on user searches.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:27 pm
MDW
- BWI
1 stop9h 30m
Frontier
Wed 6/247:27 pm
BWI
- MDW
1 stop16h 45m
Frontier
Deal found 5/18![Frontier logo]()
$209
This Trip.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Tue 6/96:30 am
PHL
- MDW
1 stop5h 42m
Frontier
Deal found 5/14![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
MDW
- PHL
1 stop5h 25m
Frontier
Wed 6/106:25 am
PHL
- MDW
1 stop5h 44m
Frontier
Deal found 5/14![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/611:59 am
MDW
- BWI
1 stop5h 31m
Frontier
Tue 6/91:29 pm
BWI
- MDW
1 stop9h 42m
Frontier
Deal found 5/14![Frontier logo]()
$219
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/911:05 am
MDW
- BWI
1 stop5h 14m
Delta
Tue 6/235:40 am
BWI
- MDW
1 stop5h 29m
Delta
Deal found 5/14![Delta logo]()
$216
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- BWI
1 stop10h 32m
Frontier
Wed 6/101:29 pm
BWI
- MDW
1 stop9h 42m
Frontier
Deal found 5/17![Frontier logo]()
$218
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:35 pm
MDW
- BWI
Nonstop1h 50m
Southwest
Wed 6/178:30 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/14![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:50 pm
MDW
- BWI
1 stop7h 35m
Delta
Tue 6/235:40 am
BWI
- MDW
1 stop5h 29m
Delta
Deal found 5/14![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1712:50 pm
MDW
- BWI
1 stop4h 05m
Southwest
Wed 6/248:30 pm
BWI
- MDW
Nonstop2h 05m
Southwest
Deal found 5/14![Southwest logo]()
$207
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:04 pm
MDW
- BWI
1 stop5h 28m
Frontier
Sun 6/289:43 pm
BWI
- MDW
1 stop14h 26m
Frontier
Deal found 5/15![Frontier logo]()
$210
This Trip.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:04 pm
MDW
- BWI
1 stop5h 28m
Frontier
Tue 6/306:28 am
BWI
- MDW
1 stop5h 44m
Frontier
Deal found 5/14![Frontier logo]()
$221
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/276:00 am
MDW
- PHL
1 stop12h 17m
Frontier
Mon 6/294:40 pm
PHL
- MDW
1 stop6h 31m
Frontier
Deal found 5/18![Frontier logo]()
$222
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 May 19, 2026.
Search for one-way flight options from Midway to Maryland. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
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 Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
MDW
- BWI
1 stop15h 57m
Frontier
Deal found 5/18![Frontier logo]()
$105
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:00 am
MDW
- PHL
1 stop5h 22m
Frontier
Deal found 5/16![Frontier logo]()
$108
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
MDW
- BWI
1 stop9h 22m
Frontier
Deal found 5/15![Frontier logo]()
$108
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:23 pm
MDW
- IAD
1 stop21h 41m
Allegiant Air
Deal found 5/15![Allegiant Air logo]()
$108
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 6/1612:50 pm
MDW
- BWI
1 stop4h 43m
Delta
Deal found 5/18![Delta logo]()
$109
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.
Wed 6/241:26 pm
MDW
- DCA
1 stop4h 33m
Delta
Deal found 5/18![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MDW
- IAD
1 stop4h 37m
Delta
Deal found 5/14![Delta logo]()
$109
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.
Tue 6/1612:27 pm
MDW
- PHL
1 stop9h 02m
Frontier
Deal found 5/15![Frontier logo]()
$110
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
MDW
- BWI
1 stop24h 35m
Frontier
Deal found 5/18![Frontier logo]()
$110
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
MDW
- IAD
1 stop27h 22m
Frontier
Deal found 5/15![Frontier logo]()
$110
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:00 am
MDW
- BWI
1 stop24h 36m
Frontier
Deal found 5/16![Frontier logo]()
$111
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 May 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Southwest) |
One-way from | $104 (Super.com) |
Popular in | March |
Cheapest in | August |
Average price | $303 |
Good round-trip deal | $277 or less |
Good one-way deal | $154 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 May 19, 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
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Sat 10/24
5:25 pm-8:10 pm
Nonstop1h 45m
Baltimore/Washington
Tue 10/27
6:55 am-8:00 am
Nonstop2h 05m
$233
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Sat 8/15
5:55 am-8:40 am
Nonstop1h 45m
Baltimore/Washington
Wed 8/19
10:50 am-2:05 pm
1 stop4h 15m
$239
Quickest round-trip
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Thu 8/13
12:00 pm-2:50 pm
Nonstop1h 50m
Washington, D.C. Reagan-National
Mon 8/17
6:40 pm-7:35 pm
Nonstop1h 55m
$239
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Thu 9/3
8:05 am-12:20 pm
1 stop3h 15m
Baltimore/Washington
Tue 9/8
10:50 am-1:05 pm
1 stop3h 15m
$248
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Thu 7/16
8:55 am-11:45 am
Nonstop1h 50m
Baltimore/Washington
Tue 7/21
4:50 pm-5:55 pm
Nonstop2h 05m
$253
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Thu 6/18
8:50 pm-11:45 pm
Nonstop1h 55m
Baltimore/Washington
Tue 6/30
4:50 pm-5:55 pm
Nonstop2h 05m
$253
ChicagoBaltimore
MDW - BWI
MDWBWI
Chicago Midway
Mon 7/6
8:50 pm-11:45 pm
Nonstop1h 55m
Baltimore/Washington
Wed 7/8
6:30 pm-7:35 pm
Nonstop2h 05m
$253
ChicagoWashington, D.C.
MDW - DCA
MDWDCA
Chicago Midway
Mon 7/20
5:05 pm-7:55 pm
Nonstop1h 50m
Washington, D.C. Reagan-National
Tue 7/28
1:00 pm-5:05 pm
1 stop5h 05m
$257
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Thu 8/27
6:42 pm-11:26 pm
1 stop3h 44m
Washington, D.C. Dulles Intl
Mon 8/31
7:00 am-11:54 am
1 stop5h 54m
$259
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Tue 7/21
6:00 am-11:37 am
1 stop4h 37m
Washington, D.C. Dulles Intl
Fri 7/24
5:46 pm-10:15 pm
1 stop5h 29m
$273
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-BWI
MDW-DCA
MDW-IAD
MDW-PHL
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-BWI
MDW-DCA
MDW-IAD
MDW-PHL
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 May 19, 2026.
It’s optimal to fly from Chicago Midway Airport to Maryland at noon. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight in the evening.
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 May 16, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Maryland flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Chicago Midway Airport to Maryland?
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 May 19, 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.
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
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 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 May 19, 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 May 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$95 | Average$172 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$307 | FlexibilityNo cancel fee | On-time63% |