$94+ Cheap flights from Maryland to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Aug 12 — Aug 191
Round-trip
1 adult, Economy
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Find cheap flights from Maryland to Midway with Cheapflights
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Cheapest flights from Maryland to MidwayExplore the most affordable flight options available from Maryland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 13, 2026.
Explore the most affordable flight options available from Maryland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 13, 2026.
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 8/197:15 am
PHL
- MDW
2 stops9h 10m
Southwest
Tue 8/2512:35 pm
MDW
- PHL
2 stops8h 15m
Southwest
Deal found 7/9![Southwest logo]()
$213
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.
Thu 8/276:35 pm
PHL
- MDW
1 stop4h 20m
Southwest
Mon 8/319:20 am
MDW
- PHL
2 stops11h 40m
Southwest
Deal found 7/9![Southwest logo]()
$214
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.
Mon 8/31:32 pm
PHL
- MDW
1 stop9h 31m
Frontier
Fri 8/711:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Deal found 7/10![Frontier logo]()
$215
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 8/277:10 am
PHL
- MDW
2 stops7h 35m
Southwest
Thu 8/272:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/10![Southwest logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Sat 9/511:45 am
MDW
- PHL
1 stop7h 43m
Frontier
Deal found 7/12![Frontier logo]()
$217
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.
Thu 8/66:20 am
PHL
- MDW
1 stop10h 05m
Southwest
Thu 8/139:20 am
MDW
- PHL
2 stops11h 40m
Southwest
Deal found 7/9![Southwest logo]()
$219
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 9/312:45 pm
PHL
- MDW
Nonstop2h 00m
Southwest
Sat 9/511:45 am
MDW
- PHL
Nonstop1h 55m
Southwest
Deal found 7/10![Southwest logo]()
$220
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.
Sun 8/232:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Sun 8/306:05 am
MDW
- PHL
1 stop13h 23m
Frontier
Deal found 7/9![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
PHL
- MDW
1 stop7h 07m
Frontier
Tue 9/157:25 am
MDW
- PHL
1 stop9h 50m
Frontier
Deal found 7/12![Frontier logo]()
$222
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 10/1010:15 am
PHL
- MDW
Nonstop2h 10m
Southwest
Mon 10/127:50 am
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/8![Southwest logo]()
$223
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 11/131:50 pm
PHL
- MDW
Nonstop2h 15m
Southwest
Mon 11/1611:30 am
MDW
- PHL
2 stops9h 30m
Southwest
Deal found 7/9![Southwest logo]()
$224
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 8/66:20 am
PHL
- MDW
1 stop10h 05m
Southwest
Fri 8/72:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/10![Southwest logo]()
$225
Best flights from Maryland to MidwayDiscover carefully curated flight deals from Maryland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 13, 2026.
Discover carefully curated flight deals from Maryland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 13, 2026.
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 8/51:45 pm
PHL
- MDW
Nonstop2h 05m
Southwest
Sat 8/88:10 am
MDW
- PHL
Nonstop2h 05m
Southwest
Deal found 7/9![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:32 pm
DCA
- MDW
1 stop5h 25m
Delta
Fri 9/181:19 pm
MDW
- DCA
1 stop4h 20m
Delta
Deal found 7/12![Delta logo]()
$263
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 8/144:05 pm
PHL
- MDW
1 stop8h 40m
Southwest
Tue 8/1812:35 pm
MDW
- PHL
2 stops8h 15m
Southwest
Deal found 7/9![Southwest logo]()
$235
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 9/47:15 pm
BWI
- MDW
1 stop4h 05m
Southwest
Sat 9/511:15 am
MDW
- BWI
2 stops6h 15m
Southwest
Deal found 7/9![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:15 am
BWI
- MDW
1 stop4h 02m
Delta
Sat 8/89:24 am
MDW
- BWI
1 stop6h 25m
Delta
Deal found 7/12![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:55 pm
DCA
- MDW
Nonstop2h 10m
Southwest
Fri 12/49:15 am
MDW
- DCA
Nonstop1h 45m
Southwest
Deal found 7/12![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.
Thu 9/176:00 am
IAD
- MDW
1 stop4h 50m
Delta
Sun 9/206:05 am
MDW
- IAD
1 stop4h 26m
Delta
Deal found 7/8![Delta logo]()
$290
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 9/59:40 am
BWI
- MDW
Nonstop2h 00m
Southwest
Mon 9/77:30 am
MDW
- BWI
Nonstop1h 45m
Southwest
Deal found 7/10![Southwest logo]()
$244
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.
Thu 10/86:00 am
IAD
- MDW
1 stop4h 18m
Delta
Sun 10/116:45 pm
MDW
- IAD
1 stop3h 26m
Delta
Deal found 7/9![Delta logo]()
$292
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.
Thu 9/36:30 am
BWI
- MDW
Nonstop2h 00m
Southwest
Sun 9/61:45 pm
MDW
- BWI
1 stop3h 30m
Southwest
Deal found 7/8![Southwest logo]()
$245
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.
Sun 8/238:00 am
DCA
- MDW
1 stop4h 51m
Delta
Wed 8/265:10 pm
MDW
- DCA
1 stop5h 38m
Delta
Deal found 7/10![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:20 pm
BWI
- MDW
Nonstop1h 55m
Southwest
Mon 8/248:15 am
MDW
- BWI
1 stop3h 10m
Southwest
Deal found 7/12![Southwest logo]()
$249
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 8/15:28 pm
IAD
- MDW
1 stop5h 47m
Delta
Tue 8/46:05 am
MDW
- IAD
1 stop4h 28m
Delta
Deal found 7/10![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:05 am
PHL
- MDW
Nonstop2h 05m
Southwest
Mon 8/176:45 pm
MDW
- PHL
Nonstop1h 55m
Southwest
Deal found 7/13![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.
Fri 9/116:09 pm
IAD
- MDW
1 stop5h 36m
Delta
Sun 9/136:05 am
MDW
- IAD
1 stop4h 26m
Delta
Deal found 7/8![Delta logo]()
$315
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.
Tue 8/47:30 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Sun 8/95:00 am
MDW
- BWI
Nonstop1h 45m
Southwest
Deal found 7/9![Southwest logo]()
$264
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.
Mon 8/36:30 pm
DCA
- MDW
1 stop5h 06m
Delta
Fri 8/76:42 pm
MDW
- DCA
1 stop3h 17m
Delta
Deal found 7/10![Delta logo]()
$323
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:05 pm
PHL
- MDW
Nonstop2h 05m
Southwest
Sat 8/298:05 am
MDW
- PHL
1 stop7h 05m
Southwest
Deal found 7/13![Southwest logo]()
$267
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 9/32:05 pm
PHL
- MDW
Nonstop2h 05m
Southwest
Sat 9/58:05 am
MDW
- PHL
1 stop4h 25m
Southwest
Deal found 7/11![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 am
IAD
- MDW
1 stop4h 59m
Delta
Mon 8/176:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Deal found 7/12![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
DCA
- MDW
2 stops8h 20m
Southwest
Sat 8/2910:05 am
MDW
- DCA
2 stops9h 45m
Southwest
Deal found 7/12![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.
Sun 8/28:27 am
IAD
- MDW
1 stop4h 29m
Delta
Wed 8/56:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Deal found 7/10![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:00 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Sun 8/308:00 am
MDW
- BWI
1 stop3h 30m
Southwest
Deal found 7/12![Southwest logo]()
$269
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.
Sun 8/28:27 am
IAD
- MDW
1 stop4h 29m
Delta
Thu 8/66:42 pm
MDW
- IAD
1 stop3h 44m
Delta
Deal found 7/10![Delta logo]()
$352
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 8/176:05 pm
PHL
- MDW
Nonstop2h 05m
Southwest
Tue 8/184:40 pm
MDW
- PHL
1 stop4h 10m
Southwest
Deal found 7/10![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:30 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Wed 8/56:30 am
MDW
- BWI
Nonstop1h 45m
Southwest
Deal found 7/12![Southwest logo]()
$273
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.
Wed 7/296:00 am
IAD
- MDW
1 stop4h 13m
Delta
Thu 7/309:19 am
MDW
- IAD
1 stop6h 22m
Delta
Deal found 7/8![Delta logo]()
$389
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 8/16:15 am
BWI
- MDW
Nonstop2h 00m
Southwest
Wed 8/56:30 am
MDW
- BWI
Nonstop1h 45m
Southwest
Deal found 7/10![Southwest logo]()
$274
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 8/156:10 am
DCA
- MDW
Nonstop1h 55m
Southwest
Sun 8/165:35 pm
MDW
- DCA
1 stop4h 20m
Southwest
Deal found 7/11![Southwest logo]()
$278
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 7/2412:37 pm
IAD
- MDW
1 stop4h 38m
Delta
Wed 7/296:00 am
MDW
- IAD
1 stop4h 37m
Delta
Deal found 7/8![Delta logo]()
$426
Last-minute flights from Maryland to MidwayDiscover last-minute flight deals from Maryland to Midway. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from Maryland to Midway. Data last updated July 13, 2026 and is based on user searches.
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 7/314:40 pm
PHL
- MDW
1 stop6h 23m
Frontier
Sun 8/96:05 am
MDW
- PHL
1 stop24h 10m
Frontier
Deal found 7/10![Frontier logo]()
$217
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 8/14:30 pm
PHL
- MDW
1 stop6h 33m
Frontier
Wed 8/126:05 am
MDW
- PHL
1 stop15h 23m
Frontier
Deal found 7/9![Frontier logo]()
$226
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.
Mon 8/31:32 pm
PHL
- MDW
1 stop9h 31m
Frontier
Fri 8/711:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Deal found 7/10![Frontier logo]()
$215
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 8/49:16 pm
PHL
- MDW
2 stops13h 35m
Frontier
Tue 8/1111:06 am
MDW
- PHL
1 stop19h 09m
Frontier
Deal found 7/10![Frontier logo]()
$227
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.
Thu 8/66:20 am
PHL
- MDW
1 stop10h 05m
Southwest
Thu 8/139:20 am
MDW
- PHL
2 stops11h 40m
Southwest
Deal found 7/9![Southwest logo]()
$219
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 8/66:20 am
PHL
- MDW
1 stop10h 05m
Southwest
Fri 8/72:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/10![Southwest logo]()
$225
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.
Fri 8/74:40 pm
PHL
- MDW
1 stop6h 23m
Frontier
Mon 8/1011:06 am
MDW
- PHL
1 stop7h 14m
Frontier
Deal found 7/9![Frontier logo]()
$220
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 8/84:30 pm
PHL
- MDW
1 stop6h 33m
Frontier
Thu 8/1311:06 am
MDW
- PHL
1 stop10h 22m
Frontier
Deal found 7/9![Frontier logo]()
$224
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 8/197:15 am
PHL
- MDW
2 stops9h 10m
Southwest
Tue 8/2512:35 pm
MDW
- PHL
2 stops8h 15m
Southwest
Deal found 7/9![Southwest logo]()
$213
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.
Sun 8/232:45 pm
PHL
- MDW
1 stop9h 02m
Frontier
Sun 8/306:05 am
MDW
- PHL
1 stop13h 23m
Frontier
Deal found 7/9![Frontier logo]()
$221
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.
Thu 8/276:35 pm
PHL
- MDW
1 stop4h 20m
Southwest
Mon 8/319:20 am
MDW
- PHL
2 stops11h 40m
Southwest
Deal found 7/9![Southwest logo]()
$214
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 8/277:10 am
PHL
- MDW
2 stops7h 35m
Southwest
Thu 8/272:55 pm
MDW
- PHL
Nonstop2h 00m
Southwest
Deal found 7/10![Southwest logo]()
$216
One-way flights from Maryland to MidwaySearch for one-way flight options from Maryland to Midway. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
Search for one-way flight options from Maryland to Midway. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:00 pm
BWI
- MDW
1 stop3h 15m
Southwest
Deal found 7/13![Southwest logo]()
$94
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
IAD
- MDW
1 stop6h 51m
Delta
Deal found 7/12![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:20 pm
BWI
- MDW
1 stop5h 16m
Delta
Deal found 7/12![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:00 am
DCA
- MDW
1 stop4h 50m
Southwest
Deal found 7/12![Southwest logo]()
$99
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 8/244:35 pm
BWI
- MDW
1 stop4h 15m
Southwest
Deal found 7/10![Southwest logo]()
$100
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 10/77:30 am
BWI
- MDW
2 stops5h 35m
Southwest
Deal found 7/9![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.
Mon 8/246:30 pm
DCA
- MDW
1 stop5h 06m
Delta
Deal found 7/8![Delta logo]()
$101
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 8/56:10 am
IAD
- MDW
1 stop4h 07m
Delta
Deal found 7/9![Delta logo]()
$103
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.
Tue 8/43:50 pm
DCA
- MDW
1 stop5h 20m
Southwest
Deal found 7/9![Southwest logo]()
$103
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.
Thu 8/137:48 am
IAD
- MDW
1 stop15h 15m
Frontier
Deal found 7/11![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
DCA
- MDW
2 stops8h 20m
Southwest
Deal found 7/12![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.
Sat 8/84:30 pm
PHL
- MDW
1 stop6h 33m
Frontier
Deal found 7/11![Frontier logo]()
$105
Find flight deals from Maryland to Midway
Keep the following information in mind while searching for Maryland to Midway flight deals. Data was last updated July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $213 (Southwest) |
One-way from | $94 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $325 |
Good round-trip deal | $328 or less |
Good one-way deal | $188 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Maryland to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 13, 2026.
Use the filters below to find and compare flights from Maryland to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Wed 8/5
1:45 pm-2:50 pm
Nonstop2h 05m
Chicago Midway
Sat 8/8
8:10 am-11:15 am
Nonstop2h 05m
$235
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Fri 8/14
4:05 pm-11:45 pm
1 stop8h 40m
Chicago Midway
Tue 8/18
12:35 pm-9:50 pm
2 stops8h 15m
$235
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Fri 9/4
7:15 pm-10:20 pm
1 stop4h 05m
Chicago Midway
Sat 9/5
11:15 am-6:30 pm
2 stops6h 15m
$242
Washington, D.C.Chicago
DCA - MDW
DCAMDW
Washington, D.C. Reagan-National
Tue 12/1
8:55 pm-10:05 pm
Nonstop2h 10m
Chicago Midway
Fri 12/4
9:15 am-12:00 pm
Nonstop1h 45m
$243
Quickest round-trip
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Sat 9/5
9:40 am-10:40 am
Nonstop2h 00m
Chicago Midway
Mon 9/7
7:30 am-10:15 am
Nonstop1h 45m
$244
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Thu 9/3
6:30 am-7:30 am
Nonstop2h 00m
Chicago Midway
Sun 9/6
1:45 pm-6:15 pm
1 stop3h 30m
$245
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Fri 8/21
5:20 pm-6:15 pm
Nonstop1h 55m
Chicago Midway
Mon 8/24
8:15 am-12:25 pm
1 stop3h 10m
$249
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Sat 8/15
8:05 am-9:10 am
Nonstop2h 05m
Chicago Midway
Mon 8/17
6:45 pm-9:40 pm
Nonstop1h 55m
$257
Washington, D.C.Chicago
DCA - MDW
DCAMDW
Washington, D.C. Reagan-National
Sat 9/12
12:32 pm-4:57 pm
1 stop5h 25m
Chicago Midway
Fri 9/18
1:19 pm-6:39 pm
1 stop4h 20m
$263
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Tue 8/4
7:30 pm-8:30 pm
Nonstop2h 00m
Chicago Midway
Sun 8/9
5:00 am-7:45 am
Nonstop1h 45m
$264
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Maryland to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Maryland with our price prediction graph.
IAD-MDW
BWI-MDW
DCA-MDW
PHL-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Maryland to Chicago Midway Airport
USMD-MDW
IAD-MDW
BWI-MDW
DCA-MDW
PHL-MDW
What is the cheapest month to book a flight from Maryland to Chicago Midway Airport?
Currently, November is the cheapest month in which you can book a flight from Maryland to Chicago Midway Airport (average of $50). Flying from Maryland to Chicago Midway Airport in April is currently the most expensive (average of $222). 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 MD to MDW?
Find hourly flight availability from Maryland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 13, 2026.
It’s optimal to fly from Maryland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Maryland to Chicago Midway Airport?
How far ahead should I book a flight from Maryland to Chicago Midway Airport?
The price you pay for your flight from Maryland to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 35 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Maryland to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Maryland to Midway. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Maryland to Chicago Midway Airport flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Maryland to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Maryland to Midway
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Complete your trip
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Search flights from Maryland to Midway by cabin class
Find flights from Maryland to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 13, 2026.
Maryland and Midway flights
Browse other Maryland and Midway flight options. Last updated on July 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Maryland to Midway
Discover the top 2 airlines that operate flights from Maryland to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$174 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$169 | Average$337 | FlexibilityNo cancel fee | On-time63% |