$112+ Cheap flights from Dallas 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.
DFW — MDW
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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Find cheap flights from Dallas 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 Dallas to Chicago Midway are usually found in December or January, booked 49 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday
Cheap flight deals from Dallas to Midway
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Cheapest flights from Dallas to MidwayExplore the most affordable flight options available from Dallas to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
Explore the most affordable flight options available from Dallas to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:12 pm -
Nonstop2h 23m
Wed 10/213:30 pm -
Nonstop2h 42m
Deal found 9/21![Frontier logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Wed 10/2112:12 pm -
Nonstop2h 23m
Sat 10/243:30 pm -
Nonstop2h 42m
Deal found 9/19![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Thu 10/229:54 am -
Nonstop2h 23m
Tue 10/2712:27 pm -
Nonstop2h 42m
Deal found 9/19![Frontier logo]()
$201
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Sat 10/1012:12 pm -
Nonstop2h 23m
Tue 10/133:30 pm -
Nonstop2h 42m
Deal found 9/17![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:08 pm -
1 stop10h 35m
Thu 10/221:12 pm -
Nonstop2h 33m
Deal found 9/19![Frontier logo]()
$204
This Super.com deal was found by Cheapflights users on 9/18. 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.
Mon 10/59:36 am -
Nonstop2h 23m
Wed 10/76:25 am -
1 stop5h 47m
Deal found 9/18![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:54 am -
Nonstop2h 31m
Mon 11/212:20 pm -
Nonstop2h 42m
Deal found 9/18![Frontier logo]()
$206
This Super.com deal was found by Cheapflights users on 9/17. 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.
Mon 10/129:54 am -
Nonstop2h 23m
Wed 10/143:30 pm -
Nonstop2h 42m
Deal found 9/17![Frontier logo]()
$208
This Super.com deal was found by Cheapflights users on 9/17. 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 11/68:54 am -
Nonstop2h 31m
Mon 11/912:20 pm -
Nonstop2h 42m
Deal found 9/17![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:12 pm -
Nonstop2h 23m
Mon 10/191:12 pm -
Nonstop2h 33m
Deal found 9/17![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Mon 10/199:54 am -
Nonstop2h 23m
Sat 10/243:30 pm -
Nonstop2h 42m
Deal found 9/19![Frontier logo]()
$211
This Southwest deal was found by Cheapflights users on 9/18. 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 10/136:25 pm -
Nonstop2h 15m
Tue 10/204:45 pm -
Nonstop2h 15m
Deal found 9/18![Southwest logo]()
$233
Best flights from Dallas to MidwayDiscover carefully curated flight deals from Dallas to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Dallas to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/20. 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 1/198:50 pm -
Nonstop2h 10m
Sat 1/231:35 pm -
Nonstop2h 25m
Deal found 9/20![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/17. 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 10/205:20 am -
1 stop7h 27m
Tue 10/205:09 pm -
1 stop7h 13m
Deal found 9/17![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 9/19. 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 12/38:25 pm -
Nonstop2h 15m
Mon 12/78:45 pm -
Nonstop2h 25m
Deal found 9/19![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/17. 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 10/295:20 am -
1 stop7h 27m
Sat 10/311:27 pm -
2 stops10h 55m
Deal found 9/17![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 9/21. 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 10/1210:55 pm -
Nonstop2h 15m
Wed 10/149:20 pm -
Nonstop2h 10m
Deal found 9/21![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/21. 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.
Wed 12/25:30 am -
1 stop6h 34m
Sat 12/511:28 am -
1 stop6h 01m
Deal found 9/21![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 9/21. 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 10/231:55 pm -
Nonstop2h 15m
Mon 10/265:15 am -
Nonstop2h 15m
Deal found 9/21![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/19. 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 12/35:30 am -
2 stops7h 31m
Mon 12/75:12 pm -
1 stop7h 04m
Deal found 9/19![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 9/19. 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 10/2210:55 pm -
Nonstop2h 15m
Mon 10/266:25 pm -
1 stop4h 30m
Deal found 9/19![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/19. 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 10/315:20 am -
2 stops9h 57m
Tue 11/311:39 am -
2 stops10h 26m
Deal found 9/19![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 9/21. 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 10/3112:05 pm -
1 stop4h 40m
Mon 11/210:15 am -
1 stop4h 15m
Deal found 9/21![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 9/19. 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 11/236:50 pm -
Nonstop2h 10m
Fri 11/278:20 pm -
Nonstop2h 30m
Deal found 9/19![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:00 am -
1 stop6h 05m
Sun 10/189:15 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 9/18. 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 10/179:00 am -
2 stops5h 50m
Sat 10/242:20 pm -
1 stop3h 55m
Deal found 9/18![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 9/18. 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.
Fri 12/186:20 am -
1 stop5h 39m
Fri 12/253:30 pm -
1 stop7h 29m
Deal found 9/18![Delta logo]()
$479
This Southwest deal was found by Cheapflights users on 9/18. 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 12/57:15 am -
Nonstop2h 15m
Sun 12/62:35 pm -
1 stop4h 20m
Deal found 9/18![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 9/21. 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.
Sat 10/35:20 am -
1 stop7h 19m
Sat 10/104:19 pm -
1 stop8h 03m
Deal found 9/21![Delta logo]()
$517
This Southwest deal was found by Cheapflights users on 9/21. 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.
Tue 11/31:20 pm -
1 stop3h 50m
Sun 11/810:15 am -
1 stop4h 15m
Deal found 9/21![Southwest logo]()
$373
This Delta deal was found by Cheapflights users on 9/22. 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 12/157:15 am -
1 stop4h 49m
Sat 12/199:30 am -
1 stop5h 01m
Deal found 9/22![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 9/18. 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.
Mon 11/95:10 am -
1 stop7h 41m
Mon 11/95:13 pm -
1 stop7h 04m
Deal found 9/18![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 12/55:05 am -
1 stop7h 56m
Sun 12/612:39 pm -
1 stop7h 56m
Deal found 9/18![Delta logo]()
$587
Last-minute flights from Dallas to MidwayDiscover last-minute flight deals from Dallas to Midway. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Dallas to Midway. Data last updated September 22, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 9/18. 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.
Mon 10/59:36 am -
Nonstop2h 23m
Wed 10/76:25 am -
1 stop5h 47m
Deal found 9/18![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Sat 10/1012:12 pm -
Nonstop2h 23m
Tue 10/133:30 pm -
Nonstop2h 42m
Deal found 9/17![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Sun 10/119:54 am -
Nonstop2h 23m
Tue 10/133:30 pm -
Nonstop2h 42m
Deal found 9/17![Frontier logo]()
$209
This Super.com deal was found by Cheapflights users on 9/17. 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.
Mon 10/129:54 am -
Nonstop2h 23m
Wed 10/143:30 pm -
Nonstop2h 42m
Deal found 9/17![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 9/18. 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 10/136:25 pm -
Nonstop2h 15m
Tue 10/204:45 pm -
Nonstop2h 15m
Deal found 9/18![Southwest logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:12 pm -
Nonstop2h 23m
Mon 10/191:12 pm -
Nonstop2h 33m
Deal found 9/17![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:12 pm -
Nonstop2h 23m
Wed 10/213:30 pm -
Nonstop2h 42m
Deal found 9/21![Frontier logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Mon 10/199:54 am -
Nonstop2h 23m
Sat 10/243:30 pm -
Nonstop2h 42m
Deal found 9/19![Frontier logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:08 pm -
1 stop10h 35m
Thu 10/221:12 pm -
Nonstop2h 33m
Deal found 9/19![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Wed 10/2112:12 pm -
Nonstop2h 23m
Sat 10/243:30 pm -
Nonstop2h 42m
Deal found 9/19![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Thu 10/229:54 am -
Nonstop2h 23m
Tue 10/2712:27 pm -
Nonstop2h 42m
Deal found 9/19![Frontier logo]()
$201
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:54 am -
Nonstop2h 31m
Mon 11/212:20 pm -
Nonstop2h 42m
Deal found 9/18![Frontier logo]()
$206
One-way flights from Dallas to MidwaySearch for one-way flight options from Dallas to Midway. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Dallas to Midway. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:01 am -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$112
This Frontier deal was found by Cheapflights users on 9/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:54 am -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:08 pm -
1 stop10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$115
This Southwest deal was found by Cheapflights users on 9/17. 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 10/289:35 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/275:35 am -
2 stops18h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:05 am -
1 stop15h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:38 am -
1 stop15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Sat 10/1012:12 pm -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$120
This Southwest deal was found by Cheapflights users on 9/17. 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 11/41:20 pm -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:54 am -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 11/178:05 am -
1 stop9h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$123
This Southwest deal was found by Cheapflights users on 9/17. 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 12/511:45 am -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$127
Find flight deals from Dallas to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Dallas (A78) 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 September 22, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $199 (Kiwi.com) |
One-way from | $112 (Cheapflightsfares) |
Popular in | June |
Cheapest in | December |
Average price | $304 |
Cheapflights Fare Finder
Customize your flight search to find flights from Dallas 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 22, 2026.
Use the filters below to find and compare flights from Dallas to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Tue 1/19
8:50 pm-11:00 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Mon 11/2
6:50 pm-9:00 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Mon 12/14
8:35 am-12:25 pm
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
DallasChicago
DFW Dallas/Fort Worth - MDW Chicago Midway
DFWMDW
Dallas/Fort Worth
Thu 12/17
6:20 am-11:59 am
1 stop5h 39m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
DallasChicago
DFW Dallas/Fort Worth - MDW Chicago Midway
DFWMDW
Dallas/Fort Worth
Thu 11/26
5:10 am-11:25 am
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 10/23
6:00 am-8:10 am
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
DallasChicago
DFW Dallas/Fort Worth - MDW Chicago Midway
DFWMDW
Dallas/Fort Worth
Wed 10/28
7:05 am-6:00 pm
2 stops10h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$151
DallasChicago
DFW Dallas/Fort Worth - MDW Chicago Midway
DFWMDW
Dallas/Fort Worth
Sat 10/17
5:30 am-12:47 pm
2 stops7h 17m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$151
DallasChicago
DFW Dallas/Fort Worth - MDW Chicago Midway
DFWMDW
Dallas/Fort Worth
Tue 11/17
6:25 am-6:04 pm
2 stops11h 39m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$154
DallasChicago
DFW Dallas/Fort Worth - MDW Chicago Midway
DFWMDW
Dallas/Fort Worth
Tue 10/20
5:30 am-12:47 pm
2 stops7h 17m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$154
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Dallas to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Dallas with our price prediction graph.
A78-MDW
DAL-MDW
DFW-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 Dallas to Chicago Midway Airport
A78-MDW
DAL-MDW
DFW-MDW
What is the cheapest month to book a flight from Dallas to Chicago Midway Airport?
Currently, December is the cheapest month in which you can book a flight from Dallas to Chicago Midway Airport (average of $176). Flying from Dallas to Chicago Midway Airport in July is currently the most expensive (average of $386). 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 DFW to MDW?
Find hourly flight availability from Dallas 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 22, 2026.
When flying from Dallas to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 20% versus a flight in the afternoon.
How much does it cost to fly round-trip from Dallas to Chicago Midway Airport?
Airfare is typical for this route at the moment.
Dallas to Chicago Midway Airport flights typically cost between $192 and $336 in October.The cheapest round-trip price found within the last 5 days was $199 on Frontier (Oct 17-Oct 21).
How often are flights from Dallas to Chicago delayed?
About 25% of weekly flights between Dallas and Chicago have experienced delays in the past year, with the average delay time being 151 minutes.
What is the most punctual flight time for Dallas to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Friday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Dallas to Chicago flights?
Over the last year, Frontier have had the lowest number of delays on this route, with just 25% of flights being delayed.
How far ahead should I book a flight from Dallas to Chicago Midway Airport?
Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Dallas to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Dallas to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Dallas to Midway. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Dallas to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Dallas 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 Dallas 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 September 22, 2026.
See what other customers who have flown with Southwest and Frontier from Dallas to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Dallas 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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Other flights to Midway
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Dallas and Midway flights
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Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Dallas to Midway
Discover the top 2 airlines that operate flights from Dallas 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$404 | FlexibilityNo cancel fee | On-time63% |