$95+ Cheap flights from Maryland to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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Find cheap flights from Maryland to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Maryland to Midway
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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 September 8, 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 September 8, 2026.
This Frontier deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:50 am -
1 stop10h 56m
Wed 9/306:25 am -
1 stop9h 53m
Deal found 9/4![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/215:22 pm -
1 stop7h 21m
Wed 10/286:16 am -
1 stop11h 03m
Deal found 9/4![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:36 pm -
1 stop5h 51m
Wed 10/286:42 pm -
1 stop11h 29m
Deal found 9/6![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/205:22 pm -
1 stop7h 21m
Tue 10/279:53 am -
1 stop7h 26m
Deal found 9/5![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:39 am -
1 stop10h 08m
Fri 11/136:42 pm -
1 stop11h 39m
Deal found 9/6![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/267:50 am -
1 stop11h 01m
Tue 9/296:25 am -
1 stop9h 53m
Deal found 9/3![Frontier logo]()
$195
This Expedia deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/2912:40 pm -
1 stop6h 06m
Wed 9/306:25 am -
1 stop10h 49m
Deal found 9/3![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/45:22 pm -
1 stop7h 25m
Mon 11/96:16 am -
1 stop24h 05m
Deal found 9/4![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:50 am -
1 stop11h 01m
Tue 9/296:25 am -
1 stop9h 53m
Deal found 9/4![Frontier logo]()
$200
This Expedia deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Wed 11/45:22 pm -
1 stop7h 25m
Thu 11/56:42 pm -
1 stop11h 39m
Deal found 9/3![Frontier logo]()
$205
This Expedia deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Fri 9/2512:40 pm -
1 stop12h 04m
Mon 9/286:46 pm -
1 stop11h 30m
Deal found 9/3![Frontier logo]()
$209
This Expedia deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Sat 10/37:50 am -
1 stop11h 01m
Tue 10/66:25 am -
1 stop9h 53m
Deal found 9/3![Frontier logo]()
$210
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 September 8, 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 September 8, 2026.
This Southwest deal was found by Cheapflights users on 9/7. 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 10/25:15 pm -
1 stop8h 00m
Mon 10/56:30 pm -
1 stop4h 25m
Deal found 9/7![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:12 pm -
1 stop5h 21m
Mon 10/266:44 pm -
1 stop3h 32m
Deal found 9/7![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/75:30 pm -
Nonstop2h 05m
Fri 10/96:55 pm -
Nonstop2h 00m
Deal found 9/3![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
1 stop5h 03m
Thu 10/156:44 pm -
1 stop3h 32m
Deal found 9/7![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/243:15 pm -
Nonstop2h 00m
Tue 9/296:30 am -
Nonstop1h 45m
Deal found 9/3![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/176:55 am -
Nonstop2h 00m
Mon 10/1912:50 pm -
Nonstop1h 50m
Deal found 9/3![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/126:05 am -
1 stop4h 27m
Wed 10/146:44 pm -
1 stop3h 32m
Deal found 9/4![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/33:05 pm -
1 stop3h 45m
Sat 10/109:55 am -
Nonstop1h 50m
Deal found 9/3![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:05 am -
1 stop4h 27m
Tue 10/136:44 pm -
1 stop3h 32m
Deal found 9/4![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 9/7. 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 10/78:20 pm -
Nonstop2h 05m
Sat 10/109:55 am -
Nonstop1h 50m
Deal found 9/7![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:05 am -
1 stop4h 27m
Sat 10/176:44 pm -
1 stop3h 32m
Deal found 9/6![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/69:15 pm -
Nonstop2h 05m
Sat 11/73:30 pm -
Nonstop1h 45m
Deal found 9/3![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:12 pm -
1 stop5h 21m
Fri 10/236:44 pm -
1 stop3h 32m
Deal found 9/5![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/26:15 am -
Nonstop2h 00m
Wed 10/77:45 am -
1 stop4h 05m
Deal found 9/3![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 9/8. 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 10/126:05 am -
1 stop4h 27m
Thu 10/156:44 pm -
1 stop3h 32m
Deal found 9/8![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 9/7. 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 10/3010:40 am -
1 stop3h 05m
Mon 11/25:05 am -
Nonstop1h 50m
Deal found 9/7![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/56:05 am -
1 stop4h 27m
Sun 11/86:44 pm -
1 stop3h 32m
Deal found 9/3![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/1212:00 pm -
2 stops6h 50m
Mon 11/1611:30 am -
1 stop3h 50m
Deal found 9/3![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 11/1210:45 am -
Nonstop2h 05m
Sat 11/141:05 pm -
Nonstop1h 50m
Deal found 9/6![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:27 pm -
1 stop4h 47m
Sun 11/16:44 pm -
1 stop3h 32m
Deal found 9/7![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/296:00 pm -
Nonstop2h 00m
Mon 11/212:25 pm -
Nonstop1h 50m
Deal found 9/5![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am -
1 stop6h 54m
Tue 9/296:05 am -
1 stop7h 06m
Deal found 9/6![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 9/7. 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 10/237:55 am -
Nonstop2h 00m
Fri 10/305:00 pm -
Nonstop1h 50m
Deal found 9/7![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/296:00 am -
1 stop6h 54m
Sun 11/16:44 pm -
1 stop3h 32m
Deal found 9/4![Delta logo]()
$420
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 11/42:40 pm -
1 stop4h 05m
Sat 11/71:05 pm -
Nonstop1h 50m
Deal found 9/5![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 9/7. 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 10/301:05 pm -
Nonstop2h 00m
Sat 10/313:30 pm -
Nonstop1h 45m
Deal found 9/7![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 9/7. 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 10/306:00 pm -
Nonstop2h 00m
Mon 11/25:10 pm -
Nonstop1h 45m
Deal found 9/7![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 11/124:40 pm -
1 stop4h 25m
Sat 11/148:00 am -
1 stop3h 55m
Deal found 9/6![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 9/6. 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.
Tue 9/298:00 am -
Nonstop2h 00m
Wed 10/73:25 pm -
Nonstop1h 45m
Deal found 9/6![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/510:00 pm -
Nonstop2h 05m
Mon 11/97:30 am -
Nonstop1h 50m
Deal found 9/4![Southwest logo]()
$339
Last-minute flights from Maryland to MidwayDiscover last-minute flight deals from Maryland to Midway. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Maryland to Midway. Data last updated September 8, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:50 am -
1 stop11h 01m
Tue 9/296:25 am -
1 stop9h 53m
Deal found 9/4![Frontier logo]()
$200
This Expedia deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Thu 9/2412:40 pm -
1 stop6h 06m
Mon 9/286:46 pm -
1 stop11h 30m
Deal found 9/3![Frontier logo]()
$209
This Orbitz deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:50 am -
1 stop11h 01m
Tue 9/296:25 am -
1 stop9h 53m
Deal found 9/3![Frontier logo]()
$195
This CheapOair deal was found by Cheapflights users on 9/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:50 am -
1 stop11h 01m
Wed 9/306:25 am -
1 stop9h 53m
Deal found 9/6![Frontier logo]()
$213
This Frontier deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:50 am -
1 stop10h 56m
Wed 9/306:25 am -
1 stop9h 53m
Deal found 9/4![Frontier logo]()
$180
This Expedia deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/2912:40 pm -
1 stop6h 06m
Wed 9/306:25 am -
1 stop10h 49m
Deal found 9/3![Frontier logo]()
$195
This CheapOair deal was found by Cheapflights users on 9/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:50 am -
1 stop10h 56m
Tue 10/66:25 am -
1 stop9h 53m
Deal found 9/7![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:50 am -
1 stop11h 01m
Wed 10/146:21 am -
1 stop9h 52m
Deal found 9/4![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/205:22 pm -
1 stop7h 21m
Tue 10/279:53 am -
1 stop7h 26m
Deal found 9/5![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/215:22 pm -
1 stop7h 21m
Wed 10/286:16 am -
1 stop11h 03m
Deal found 9/4![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:36 pm -
1 stop5h 51m
Wed 10/286:42 pm -
1 stop11h 29m
Deal found 9/6![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:39 am -
1 stop10h 08m
Fri 11/136:42 pm -
1 stop11h 39m
Deal found 9/6![Frontier logo]()
$192
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 September 8, 2026.
Search for one-way flight options from Maryland to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Super.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/297:50 am -
1 stop10h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$95
This Expedia deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Wed 9/307:50 am -
1 stop11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$96
This CheapOair deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:36 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$99
This Trip.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Tue 10/612:40 pm -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Wed 10/1412:35 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$102
This CheapOair deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:41 am -
1 stop10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$104
This Priceline deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:46 am -
1 stop5h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/168:30 am -
1 stop10h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 9/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:40 pm -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/267:50 am -
1 stop11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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.
Wed 9/2312:40 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$110
This Gotogate deal was found by Cheapflights users on 9/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:50 am -
1 stop11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$111
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 September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $180 (Frontier) |
One-way from | $95 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $272 |
Good round-trip deal | $306 or less |
Good one-way deal | $148 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 7,457,451 searches. Data last updated September 8, 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
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Sat 9/26
7:50 am-5:51 pm
1 stop11h 01m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$110
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 10/23
7:10 pm-8:15 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$128
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Thu 12/3
9:14 am-7:02 pm
1 stop10h 48m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Sun 11/8
7:40 am-5:47 pm
1 stop11h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$136
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 10/15
1:55 pm-3:00 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Quickest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 9/30
2:50 pm-3:50 pm
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Tue 10/20
7:15 am-8:15 am
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 10/3
5:45 pm-6:45 pm
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 10/7
7:30 am-8:30 am
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Sat 10/3
1:00 pm-2:00 pm
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
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
PHL-MDW
DCA-MDW
BWI-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
PHL-MDW
DCA-MDW
BWI-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 $188). Flying from Maryland to Chicago Midway Airport in May is currently the most expensive (average of $407). 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 September 8, 2026.
It’s optimal to fly from Maryland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 29% 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?
Airfare is below average for this route at the moment.
Maryland to Chicago Midway Airport flights typically cost between $222 and $382 in October.The cheapest round-trip price found within the last 5 days was $219 on Frontier (Oct 28-Oct 31).
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 29 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 September 5, 2026.
Travelers seeking maximum savings on their Maryland to Chicago Midway Airport flight should consider departing on Saturday 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
Merrillville
Lansing
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 September 8, 2026.
Maryland and Midway flights
Browse other Maryland and Midway flight options. Last updated on September 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Maryland to Midway flights
Consider these flights traveling from Maryland to Midway.
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 7,457,451 searches. Data last updated September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$223 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$360 | FlexibilityNo cancel fee | On-time63% |