$89+ Cheap flights from Washington, D.C. (WAS) 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Sep 21 — Sep 281
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 September or January, booked 76 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
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 August 22, 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 August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:35 am -
Nonstop2h 00m
Wed 9/306:30 am -
Nonstop1h 45m
Deal found 8/21![Southwest logo]()
$177
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:20 am -
1 stop5h 35m
Fri 9/116:25 am -
1 stop9h 53m
Deal found 8/17![Frontier logo]()
$181
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 am -
1 stop11h 01m
Mon 9/146:25 am -
1 stop9h 53m
Deal found 8/18![Frontier logo]()
$182
This CheapOair deal was found by Cheapflights users on 8/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:22 am -
1 stop8h 23m
Mon 10/196:15 am -
1 stop9h 32m
Deal found 8/21![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 8/17. 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 9/266:35 am -
Nonstop2h 00m
Sat 9/2611:45 am -
1 stop3h 15m
Deal found 8/17![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:40 pm -
1 stop4h 05m
Wed 11/1812:05 pm -
Nonstop1h 50m
Deal found 8/18![Southwest logo]()
$183
This Kissandfly.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:22 am -
1 stop8h 29m
Mon 9/146:25 am -
1 stop9h 21m
Deal found 8/22![Frontier logo]()
$184
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:50 am -
1 stop11h 01m
Fri 9/256:25 am -
1 stop9h 53m
Deal found 8/19![Frontier logo]()
$185
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 am -
1 stop11h 01m
Sat 9/126:25 am -
1 stop9h 53m
Deal found 8/17![Frontier logo]()
$187
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:40 pm -
1 stop4h 55m
Mon 10/55:00 am -
Nonstop1h 45m
Deal found 8/18![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 8/17. 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 9/266:40 pm -
Nonstop2h 00m
Wed 9/3011:10 am -
1 stop5h 50m
Deal found 8/17![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 8/17. 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 11/55:20 pm -
1 stop4h 10m
Tue 11/101:15 pm -
1 stop3h 20m
Deal found 8/17![Southwest logo]()
$188
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 August 22, 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 August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:15 am -
Nonstop2h 00m
Sat 10/34:50 pm -
Nonstop1h 50m
Deal found 8/21![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 8/17. 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 10/226:05 am -
1 stop4h 12m
Mon 10/269:29 am -
1 stop5h 59m
Deal found 8/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/21. 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 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 11/96:10 pm -
Nonstop1h 50m
Deal found 8/21![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/176:05 am -
1 stop4h 12m
Sat 10/176:44 pm -
1 stop3h 32m
Deal found 8/22![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:45 pm -
Nonstop2h 05m
Tue 9/2212:35 pm -
1 stop3h 05m
Deal found 8/18![Southwest logo]()
$183
This Delta deal was found by Cheapflights users on 8/21. 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.
Mon 11/96:00 am -
1 stop4h 42m
Mon 11/95:09 pm -
1 stop6h 30m
Deal found 8/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:00 pm -
Nonstop2h 00m
Mon 9/289:20 am -
1 stop4h 20m
Deal found 8/18![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/17. 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.
Tue 10/206:12 pm -
1 stop5h 21m
Sat 10/246:44 pm -
1 stop3h 32m
Deal found 8/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:50 am -
1 stop4h 30m
Thu 10/1511:00 am -
Nonstop1h 45m
Deal found 8/22![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/21. 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.
Thu 11/56:05 am -
1 stop4h 12m
Mon 11/95:09 pm -
1 stop6h 30m
Deal found 8/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:30 am -
Nonstop2h 00m
Mon 10/53:45 pm -
1 stop5h 20m
Deal found 8/21![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop5h 03m
Thu 10/156:44 pm -
1 stop3h 32m
Deal found 8/22![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/20. 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 11/79:25 am -
Nonstop2h 05m
Mon 11/98:45 am -
1 stop6h 30m
Deal found 8/20![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:37 pm -
1 stop6h 23m
Mon 10/2612:49 pm -
1 stop4h 45m
Deal found 8/19![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:00 pm -
1 stop5h 20m
Mon 9/148:15 am -
1 stop5h 40m
Deal found 8/18![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 8/21. 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.
Mon 11/96:10 am -
1 stop4h 32m
Mon 11/95:09 pm -
1 stop4h 35m
Deal found 8/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 8/19. 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.
Mon 10/58:05 pm -
1 stop6h 00m
Wed 10/78:05 am -
2 stops5h 25m
Deal found 8/19![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:10 am -
1 stop6h 47m
Mon 9/145:10 pm -
1 stop6h 31m
Deal found 8/19![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 8/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:00 pm -
Nonstop2h 00m
Mon 10/268:45 pm -
Nonstop1h 45m
Deal found 8/21![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 8/21. 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.
Fri 10/25:12 pm -
1 stop6h 32m
Wed 10/710:59 am -
1 stop5h 11m
Deal found 8/21![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 8/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:45 am -
2 stops6h 25m
Mon 9/289:20 am -
1 stop4h 20m
Deal found 8/21![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 8/22![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 8/19. 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 9/255:20 pm -
Nonstop1h 55m
Mon 9/289:20 am -
1 stop4h 20m
Deal found 8/19![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 8/17. 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.
Tue 9/1510:15 am -
1 stop7h 00m
Wed 4/216:00 am -
1 stop7h 41m
Deal found 8/17![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:50 pm -
1 stop4h 10m
Fri 9/255:50 pm -
1 stop4h 05m
Deal found 8/17![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 12m
Thu 10/156:44 pm -
1 stop3h 32m
Deal found 8/22![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 8/17. 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 10/14:40 pm -
1 stop4h 55m
Mon 10/52:45 pm -
2 stops5h 50m
Deal found 8/17![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/114:50 pm -
1 stop3h 45m
Sat 9/127:40 am -
1 stop3h 25m
Deal found 8/22![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/19. 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 10/96:00 pm -
1 stop3h 15m
Mon 10/125:00 am -
Nonstop1h 45m
Deal found 8/19![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 8/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:15 pm -
Nonstop2h 00m
Fri 9/254:30 pm -
1 stop5h 50m
Deal found 8/21![Southwest logo]()
$265
Last-minute flights from Washington, D.C. to MidwayDiscover last-minute flight deals from Washington, D.C. to Midway. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Washington, D.C. to Midway. Data last updated August 22, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:20 am -
1 stop5h 35m
Fri 9/116:25 am -
1 stop9h 53m
Deal found 8/17![Frontier logo]()
$181
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 am -
1 stop11h 01m
Mon 9/146:25 am -
1 stop9h 53m
Deal found 8/18![Frontier logo]()
$182
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 am -
1 stop11h 01m
Sat 9/126:25 am -
1 stop9h 53m
Deal found 8/17![Frontier logo]()
$187
This Expedia deal was found by Cheapflights users on 8/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:22 am -
1 stop8h 29m
Mon 9/146:25 am -
1 stop9h 21m
Deal found 8/21![Frontier logo]()
$187
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:50 am -
1 stop11h 01m
Fri 9/256:25 am -
1 stop9h 53m
Deal found 8/19![Frontier logo]()
$185
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:20 am -
1 stop3h 30m
Tue 9/2212:45 pm -
1 stop3h 15m
Deal found 8/18![Southwest logo]()
$188
This CheapOair deal was found by Cheapflights users on 8/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:22 am -
1 stop8h 24m
Sat 9/266:25 am -
1 stop9h 21m
Deal found 8/20![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 8/21. 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.
Fri 9/257:50 am -
1 stop11h 01m
Sat 9/266:25 am -
1 stop9h 53m
Deal found 8/21![Frontier logo]()
$189
This Southwest deal was found by Cheapflights users on 8/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:45 pm -
Nonstop2h 00m
Mon 9/289:00 am -
Nonstop1h 55m
Deal found 8/21![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 8/17. 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 9/266:35 am -
Nonstop2h 00m
Sat 9/2611:45 am -
1 stop3h 15m
Deal found 8/17![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 8/17. 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 9/266:40 pm -
Nonstop2h 00m
Wed 9/3011:10 am -
1 stop5h 50m
Deal found 8/17![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:22 am -
1 stop8h 29m
Mon 9/286:25 am -
1 stop9h 21m
Deal found 8/20![Frontier logo]()
$191
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 August 22, 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 August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:00 pm -
Nonstop2h 00m
Deal found 8/17![Southwest logo]()
$89
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:55 am -
Nonstop2h 00m
Deal found 8/18![Southwest logo]()
$89
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.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
Deal found 8/18![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Mon 9/2110:22 am -
1 stop8h 29m
Deal found 8/22![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 8/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:50 am -
1 stop11h 01m
Deal found 8/17![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:00 am -
1 stop14h 53m
Deal found 8/18![Frontier logo]()
$93
This Expedia deal was found by Cheapflights users on 8/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:50 am -
1 stop11h 01m
Deal found 8/17![Frontier logo]()
$94
This Southwest deal was found by Cheapflights users on 8/17. 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 11/55:20 pm -
1 stop4h 10m
Deal found 8/17![Southwest logo]()
$94
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 11/172:40 pm -
1 stop4h 05m
Deal found 8/17![Southwest logo]()
$94
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:50 am -
1 stop11h 01m
Deal found 8/17![Frontier logo]()
$95
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:22 am -
1 stop8h 29m
Deal found 8/17![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 8/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:36 am -
1 stop11h 09m
Deal found 8/21![Frontier logo]()
$98
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 August 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $89 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $354 |
Good round-trip deal | $274 or less |
Good one-way deal | $188 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 August 22, 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
Thu 10/1
6:15 am-7:15 am
Nonstop2h 00m
Chicago Midway
Sat 10/3
4:50 pm-7:40 pm
Nonstop1h 50m
$177
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Thu 11/5
10:00 pm-11:05 pm
Nonstop2h 05m
Chicago Midway
Mon 11/9
6:10 pm-9:00 pm
Nonstop1h 50m
$177
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Tue 9/15
7:45 pm-8:50 pm
Nonstop2h 05m
Chicago Midway
Tue 9/22
12:35 pm-4:40 pm
1 stop3h 05m
$183
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Thu 9/24
8:00 pm-9:00 pm
Nonstop2h 00m
Chicago Midway
Mon 9/28
9:20 am-2:40 pm
1 stop4h 20m
$187
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Tue 10/13
10:50 am-2:20 pm
1 stop4h 30m
Chicago Midway
Thu 10/15
11:00 am-1:45 pm
Nonstop1h 45m
$187
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Mon 10/5
9:30 am-10:30 am
Nonstop2h 00m
Chicago Midway
Mon 10/5
3:45 pm-10:05 pm
1 stop5h 20m
$187
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Sat 11/7
9:25 am-10:30 am
Nonstop2h 05m
Chicago Midway
Mon 11/9
8:45 am-4:15 pm
1 stop6h 30m
$187
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Thu 10/22
6:05 am-9:17 am
1 stop4h 12m
Chicago Midway
Mon 10/26
9:29 am-4:28 pm
1 stop5h 59m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Sat 10/17
6:05 am-9:17 am
1 stop4h 12m
Chicago Midway
Sat 10/17
6:44 pm-11:16 pm
1 stop3h 32m
$197
Washington, D.C.Chicago
IAD Washington, D.C. Dulles Intl - MDW Chicago Midway
IADMDW
Washington, D.C. Dulles Intl
Mon 11/9
6:00 am-9:42 am
1 stop4h 42m
Chicago Midway
Mon 11/9
5:09 pm-12:39 am
1 stop6h 30m
$197
Showing 1-10 of 60 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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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
DCA-MDW
IAD-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
DCA-MDW
IAD-MDW
What is the cheapest month to book a flight from Washington, D.C. to Chicago Midway Airport?
Currently, September is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $269). 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 August 22, 2026.
It’s optimal to fly from Washington, D.C. to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 17% 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 $262 and $392 in September.The cheapest round-trip price found within the last 5 days was $177 on Southwest (Sep 26-Sep 28).
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 56 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 August 22, 2026.
Travelers seeking maximum savings on their Washington, D.C. to Chicago Midway Airport flight should consider departing on Thursday 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 August 22, 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.
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Consider these flights traveling from Washington, D.C. to Midway.
Top 3 airlines flying from Washington, D.C. to Midway
Discover the top 3 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 August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$174 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$408 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$361 | FlexibilityNo cancel fee | On-time63% |