$91+ Cheap flights from Washington, D.C. (WAS) 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Nov 20 — Nov 271
Round-trip
1 adult, Economy
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Find cheap flights from Washington, D.C. 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Washington, D.C. to Chicago Midway are usually found in January or February, booked 76 days in advance, depart on a Saturday or Wednesday and return on a Saturday
Cheap flight deals from Washington, D.C. to Midway
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Cheapest flights from Washington, D.C. to MidwayExplore the most affordable flight options available from Washington, D.C. to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
Explore the most affordable flight options available from Washington, D.C. to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/104:55 pm -
1 stop3h 50m
Mon 12/1412:50 pm -
Nonstop1h 40m
Deal found 10/19![Southwest logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 10/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:23 am -
1 stop10h 44m
Wed 12/912:28 pm -
1 stop9h 13m
Deal found 10/17![Frontier logo]()
$182
This Mytrip deal was found by Cheapflights users on 10/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:45 am -
1 stop13h 02m
Sat 12/512:28 pm -
1 stop9h 13m
Deal found 10/17![Frontier logo]()
$184
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:59 pm -
2 stops20h 48m
Mon 11/166:42 pm -
1 stop14h 04m
Deal found 10/20![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/142:10 pm -
1 stop3h 55m
Sun 11/158:25 pm -
Nonstop1h 55m
Deal found 10/20![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/1212:35 pm -
Nonstop2h 05m
Sun 11/157:50 am -
1 stop3h 30m
Deal found 10/20![Southwest logo]()
$190
This Mytrip deal was found by Cheapflights users on 10/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:41 pm -
2 stops26h 01m
Mon 12/75:02 pm -
1 stop15h 05m
Deal found 10/19![Frontier logo]()
$191
This Priceline deal was found by Cheapflights users on 10/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:41 am -
1 stop8h 06m
Tue 11/176:08 am -
1 stop9h 06m
Deal found 10/18![Frontier logo]()
$192
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 am -
1 stop4h 46m
Wed 12/26:00 am -
1 stop5h 54m
Deal found 10/20![Delta logo]()
$193
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:45 am -
1 stop8h 02m
Mon 11/96:42 pm -
1 stop14h 04m
Deal found 10/20![Frontier logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:48 am -
1 stop10h 59m
Mon 11/166:08 am -
1 stop10h 04m
Deal found 10/16![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:07 pm -
1 stop6h 40m
Wed 11/116:08 am -
1 stop10h 04m
Deal found 10/19![Frontier logo]()
$212
Best flights from Washington, D.C. to MidwayDiscover carefully curated flight deals from Washington, D.C. to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
Discover carefully curated flight deals from Washington, D.C. to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/246:00 am -
1 stop3h 50m
Mon 12/286:15 pm -
1 stop4h 01m
Deal found 10/20![Delta logo]()
$195
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2211:10 am -
1 stop4h 35m
Thu 1/287:50 am -
2 stops5h 45m
Deal found 10/19![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 10/18. 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 1/54:39 pm -
1 stop6h 31m
Thu 1/710:35 am -
1 stop5h 28m
Deal found 10/18![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:20 pm -
1 stop4h 10m
Mon 11/166:15 pm -
Nonstop1h 55m
Deal found 10/19![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 10/17. 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 12/34:50 pm -
2 stops5h 45m
Sat 12/58:00 am -
1 stop3h 55m
Deal found 10/17![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/2312:36 pm -
1 stop6h 08m
Fri 12/259:30 am -
1 stop5h 08m
Deal found 10/20![Delta logo]()
$323
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:10 pm -
2 stops6h 15m
Mon 11/2312:45 pm -
1 stop3h 35m
Deal found 10/19![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/247:01 am -
1 stop10h 38m
Fri 11/2712:05 pm -
1 stop3h 44m
Deal found 10/20![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/2712:40 pm -
Nonstop2h 05m
Mon 11/308:55 pm -
Nonstop1h 45m
Deal found 10/20![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/246:00 am -
1 stop4h 46m
Sat 11/286:44 pm -
1 stop3h 37m
Deal found 10/21![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/35:50 pm -
Nonstop2h 05m
Mon 11/98:15 pm -
Nonstop1h 55m
Deal found 10/20![Southwest logo]()
$311
This KAYAK deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:02 pm -
1 stop6h 52m
Thu 12/1011:28 am -
1 stop6h 13m
Deal found 10/20![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:50 am -
Nonstop2h 05m
Mon 11/309:05 pm -
Nonstop1h 50m
Deal found 10/19![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 10/16. 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.
Fri 12/2512:36 pm -
1 stop6h 08m
Thu 12/316:00 am -
1 stop5h 43m
Deal found 10/16![Delta logo]()
$343
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/191:55 pm -
2 stops7h 15m
Sun 12/207:20 am -
1 stop4h 15m
Deal found 10/20![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 10/16. 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.
Thu 11/126:00 am -
1 stop4h 46m
Mon 11/166:44 pm -
1 stop3h 37m
Deal found 10/16![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 10/16. 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.
Mon 11/166:10 am -
Nonstop2h 05m
Sat 12/1210:25 am -
2 stops8h 30m
Deal found 10/16![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 10/18. 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 12/2212:36 pm -
1 stop6h 08m
Mon 12/286:15 pm -
1 stop3h 55m
Deal found 10/18![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 10/16. 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 1/229:40 am -
1 stop4h 25m
Thu 1/281:45 pm -
1 stop3h 45m
Deal found 10/16![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 10/16. 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.
Fri 1/226:10 am -
1 stop3h 35m
Sun 1/246:00 am -
1 stop4h 59m
Deal found 10/16![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 10/17. 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 12/22:40 pm -
1 stop4h 10m
Wed 12/98:35 pm -
Nonstop1h 45m
Deal found 10/17![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 10/17. 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.
Thu 11/198:05 am -
1 stop4h 54m
Sat 11/216:44 pm -
1 stop3h 37m
Deal found 10/17![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 10/16. 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 11/69:15 pm -
Nonstop2h 05m
Sun 11/87:20 am -
Nonstop1h 50m
Deal found 10/16![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 10/16. 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.
Fri 12/115:00 pm -
1 stop6h 54m
Sun 12/136:41 pm -
1 stop3h 42m
Deal found 10/16![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 10/16. 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.
Wed 11/259:00 pm -
Nonstop2h 05m
Sat 11/285:30 am -
Nonstop1h 50m
Deal found 10/16![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 12/236:00 am -
1 stop3h 50m
Fri 12/259:30 am -
1 stop6h 09m
Deal found 10/19![Delta logo]()
$389
This Southwest deal was found by Cheapflights users on 10/17. 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 1/97:15 am -
2 stops8h 30m
Mon 1/111:40 pm -
Nonstop1h 50m
Deal found 10/17![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 10/16. 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.
Fri 12/186:00 am -
1 stop4h 37m
Sat 1/96:00 am -
1 stop7h 41m
Deal found 10/16![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/299:30 pm -
Nonstop2h 05m
Thu 12/31:30 pm -
Nonstop1h 45m
Deal found 10/20![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 10/17. 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.
Fri 11/206:00 am -
1 stop4h 46m
Mon 11/236:00 am -
1 stop4h 37m
Deal found 10/17![Delta logo]()
$393
Last-minute flights from Washington, D.C. to MidwayDiscover last-minute flight deals from Washington, D.C. to Midway. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Washington, D.C. to Midway. Data last updated October 21, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:45 am -
1 stop8h 02m
Mon 11/96:42 pm -
1 stop14h 04m
Deal found 10/20![Frontier logo]()
$196
This Priceline deal was found by Cheapflights users on 10/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:41 am -
1 stop8h 06m
Tue 11/176:08 am -
1 stop9h 06m
Deal found 10/18![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:07 pm -
1 stop6h 40m
Wed 11/116:08 am -
1 stop10h 04m
Deal found 10/19![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/1110:41 am -
1 stop8h 06m
Sat 11/147:15 am -
1 stop7h 59m
Deal found 10/21![Frontier logo]()
$197
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:45 am -
1 stop5h 15m
Sun 11/157:50 am -
1 stop3h 30m
Deal found 10/19![Southwest logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:48 am -
1 stop10h 59m
Mon 11/166:08 am -
1 stop10h 04m
Deal found 10/16![Frontier logo]()
$211
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/1212:35 pm -
Nonstop2h 05m
Sun 11/157:50 am -
1 stop3h 30m
Deal found 10/20![Southwest logo]()
$190
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:59 pm -
2 stops20h 48m
Mon 11/166:42 pm -
1 stop14h 04m
Deal found 10/20![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/142:10 pm -
1 stop3h 55m
Sun 11/158:25 pm -
Nonstop1h 55m
Deal found 10/20![Southwest logo]()
$189
This Mytrip deal was found by Cheapflights users on 10/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:45 am -
1 stop13h 02m
Sat 12/512:28 pm -
1 stop9h 13m
Deal found 10/17![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:07 am -
1 stop10h 40m
Tue 12/112:33 pm -
1 stop8h 50m
Deal found 10/20![Frontier logo]()
$199
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:30 pm -
1 stop5h 24m
Wed 11/256:44 pm -
1 stop3h 43m
Deal found 10/20![Delta logo]()
$193
One-way flights from Washington, D.C. to MidwaySearch for one-way flight options from Washington, D.C. to Midway. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
Search for one-way flight options from Washington, D.C. to Midway. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This WAYA deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:40 pm -
1 stop14h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$91
This Priceline deal was found by Cheapflights users on 10/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:26 pm -
1 stop5h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:50 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$95
This Trip.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/307:26 pm -
1 stop5h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$96
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:30 pm -
1 stop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$97
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/112:22 pm -
1 stop6h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$98
This Trip.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 2/246:30 pm -
1 stop6h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$99
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/104:50 pm -
2 stops5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$102
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/96:00 pm -
2 stops5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$103
This Super.com deal was found by Cheapflights users on 10/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:48 am -
1 stop10h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$114
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:10 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$114
Find flight deals from Washington, D.C. to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Washington, D.C. (WAS) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $181 (Southwest) |
One-way from | $91 (WAYA) |
Popular in | March |
Cheapest in | January |
Average price | $378 |
Good round-trip deal | $322 or less |
Good one-way deal | $213 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Washington, D.C. 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 October 21, 2026.
Use the filters below to find and compare flights from Washington, D.C. to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 12/7
4:55 pm-7:45 pm
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$93
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Thu 11/26
8:25 am-2:55 pm
1 stop7h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$98
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 11/11
4:50 pm-9:35 pm
2 stops5h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$102
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Tue 12/1
8:55 pm-10:10 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$114
Quickest round-trip
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Mon 12/14
7:55 am-9:00 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$120
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Wed 11/25
6:00 am-9:46 am
1 stop4h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Tue 11/24
6:00 am-9:46 am
1 stop4h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Wed 12/23
12:36 pm-5:44 pm
1 stop6h 08m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 11/25
6:10 am-9:46 am
1 stop4h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Mon 12/28
6:00 am-8:50 am
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
Showing 1-10 of 55 resultsSorted by cheapest first
Compare providers for flights from Washington, D.C. to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Washington, D.C. to Midway in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Washington, D.C.-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C.-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Washington, D.C.-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C.-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Washington, D.C. to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Washington, D.C. with our price prediction graph.
WAS-MDW
BWI-MDW
IAD-MDW
DCA-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 Washington, D.C. to Chicago Midway Airport
WAS-MDW
BWI-MDW
IAD-MDW
DCA-MDW
What is the cheapest month to book a flight from Washington, D.C. to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $302). Flying from Washington, D.C. to Chicago Midway Airport in June is currently the most expensive (average of $425). 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 WAS to MDW?
Find hourly flight availability from Washington, D.C. 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 October 21, 2026.
It’s optimal to fly from Washington, D.C. to Chicago Midway Airport in the evening. By choosing this option you can save up to 9% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Washington, D.C. to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Washington, D.C. to Chicago Midway Airport flights typically cost between $266 and $474 in December.The cheapest round-trip price found within the last 5 days was $181 on Southwest (Dec 10-Dec 14).
How far ahead should I book a flight from Washington, D.C. to Chicago Midway Airport?
The price you pay for your flight from Washington, D.C. to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 39 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 Washington, D.C. to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Washington, D.C. to Midway. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Washington, D.C. 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.
The best insider tips for Washington, D.C. to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated October 21, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andFrontier from Washington, D.C. to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Washington, D.C. 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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Top 2 airlines flying from Washington, D.C. to Midway
Discover the top 2 airlines that operate flights from Washington, D.C. 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 October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$264 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$376 | FlexibilityNo cancel fee | On-time63% |