$106+ Cheap flights from New York, NY (NYC) 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — MDW
Sep 22 — Sep 291
Round-trip
1 adult, Economy
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Find cheap flights from New York 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 New York to Chicago Midway are usually found in January or February, booked 53 days in advance, depart on a Thursday or Tuesday and return on a Thursday
Cheap flight deals from New York to Midway
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Cheapest flights from New York to MidwayExplore the most affordable flight options available from New York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 23, 2026.
Explore the most affordable flight options available from New York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 23, 2026.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:15 am -
1 stop12h 36m
Tue 9/296:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$218
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 am -
1 stop12h 36m
Sat 9/126:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$219
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:55 pm -
1 stop7h 49m
Mon 10/56:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$221
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 10/305:55 am -
1 stop6h 03m
Mon 11/212:03 pm -
1 stop8h 25m
Deal found 8/18![Frontier logo]()
$223
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:55 am -
1 stop5h 55m
Wed 9/211:50 am -
1 stop12h 13m
Deal found 8/18![Frontier logo]()
$228
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.
Sat 9/266:15 am -
1 stop12h 36m
Mon 9/286:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$228
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.
Tue 10/204:59 pm -
1 stop7h 44m
Tue 10/277:25 am -
1 stop9h 10m
Deal found 8/18![Frontier logo]()
$229
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:55 am -
1 stop6h 00m
Fri 8/2811:50 am -
1 stop12h 13m
Deal found 8/18![Frontier logo]()
$230
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:15 am -
1 stop12h 31m
Mon 9/146:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$233
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:55 am -
1 stop6h 03m
Thu 11/1212:03 pm -
1 stop11h 56m
Deal found 8/18![Frontier logo]()
$234
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:15 am -
1 stop12h 36m
Mon 9/146:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$234
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.
Wed 9/236:15 am -
1 stop12h 36m
Tue 9/296:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$235
Best flights from New York to MidwayDiscover carefully curated flight deals from New York to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 23, 2026.
Discover carefully curated flight deals from New York to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 23, 2026.
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.
Thu 9/107:25 am -
Nonstop2h 20m
Mon 9/217:50 pm -
Nonstop2h 05m
Deal found 8/20![Southwest logo]()
$247
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
1 stop4h 42m
Tue 11/176:44 pm -
1 stop3h 31m
Deal found 8/18![Delta logo]()
$267
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:06 am -
1 stop8h 56m
Sun 12/66:10 pm -
1 stop13h 42m
Deal found 8/19![Multiple Airlines logo]()
$390
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 10/169:00 pm -
Nonstop2h 20m
Sun 10/185:05 am -
Nonstop2h 05m
Deal found 8/22![Southwest logo]()
$247
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop4h 42m
Mon 11/166:44 pm -
1 stop3h 31m
Deal found 8/18![Delta logo]()
$267
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 10/39:25 am -
Nonstop2h 30m
Sun 10/45:05 am -
Nonstop2h 05m
Deal found 8/20![Southwest logo]()
$247
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 10/36:00 am -
1 stop4h 07m
Sat 10/36:40 pm -
1 stop3h 35m
Deal found 8/22![Delta logo]()
$267
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.
Wed 9/307:25 am -
Nonstop2h 20m
Fri 10/97:35 pm -
Nonstop2h 05m
Deal found 8/21![Southwest logo]()
$257
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.
Wed 9/1612:05 pm -
1 stop5h 45m
Mon 9/215:00 am -
Nonstop2h 00m
Deal found 8/20![Southwest logo]()
$257
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.
Tue 10/209:40 am -
1 stop4h 07m
Sat 10/245:31 pm -
1 stop5h 17m
Deal found 8/21![Delta logo]()
$287
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 11/135:35 pm -
1 stop8h 30m
Sun 11/155:00 am -
Nonstop2h 05m
Deal found 8/22![Southwest logo]()
$257
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.
Wed 10/2812:57 pm -
1 stop6h 03m
Sat 10/316:04 am -
1 stop4h 56m
Deal found 8/22![Delta logo]()
$297
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:00 pm -
1 stop7h 19m
Thu 10/11:00 pm -
1 stop8h 03m
Deal found 8/20![Delta logo]()
$302
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.
Tue 11/179:30 am -
1 stop8h 55m
Thu 11/199:40 am -
1 stop4h 30m
Deal found 8/20![Southwest logo]()
$277
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 9/174:25 pm -
1 stop6h 10m
Fri 9/185:50 pm -
1 stop4h 30m
Deal found 8/18![Southwest logo]()
$277
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
1 stop4h 17m
Mon 11/96:44 pm -
1 stop3h 31m
Deal found 8/20![Delta logo]()
$307
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.
Mon 9/216:00 am -
Nonstop2h 15m
Wed 9/238:50 am -
2 stops7h 15m
Deal found 8/22![Southwest logo]()
$282
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 12/316:00 am -
1 stop3h 45m
Sat 1/236:00 am -
1 stop5h 20m
Deal found 8/21![Delta logo]()
$317
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 9/53:40 pm -
1 stop7h 56m
Sat 9/124:30 pm -
1 stop7h 29m
Deal found 8/19![Delta logo]()
$317
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 9/187:25 am -
Nonstop2h 20m
Mon 9/215:00 am -
Nonstop2h 00m
Deal found 8/22![Southwest logo]()
$291
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 9/268:35 am -
1 stop7h 49m
Thu 10/11:00 pm -
1 stop8h 03m
Deal found 8/19![Delta logo]()
$317
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 9/148:55 pm -
Nonstop2h 25m
Tue 9/157:15 am -
1 stop7h 35m
Deal found 8/18![Southwest logo]()
$292
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.
Thu 12/1011:06 am -
1 stop8h 56m
Sun 12/138:07 pm -
2 stops14h 29m
Deal found 8/18![Multiple Airlines logo]()
$689
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:10 am -
1 stop7h 10m
Sat 10/31:19 pm -
1 stop5h 50m
Deal found 8/20![Delta logo]()
$317
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 10/106:45 am -
2 stops10h 25m
Tue 10/132:45 pm -
1 stop7h 15m
Deal found 8/20![Southwest logo]()
$292
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.
Wed 9/91:00 pm -
1 stop4h 57m
Sat 9/124:48 pm -
1 stop6h 37m
Deal found 8/19![Delta logo]()
$317
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.
Fri 11/134:05 pm -
1 stop7h 49m
Sun 11/155:29 pm -
1 stop5h 29m
Deal found 8/22![Delta logo]()
$317
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 2/136:00 am -
1 stop3h 45m
Mon 2/155:59 pm -
1 stop4h 04m
Deal found 8/22![Delta logo]()
$321
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop4h 17m
Mon 10/266:44 pm -
1 stop3h 32m
Deal found 8/20![Delta logo]()
$330
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:00 pm -
1 stop4h 57m
Wed 9/94:30 pm -
1 stop6h 27m
Deal found 8/18![Delta logo]()
$367
Last-minute flights from New York to MidwayDiscover last-minute flight deals from New York to Midway. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from New York to Midway. Data last updated August 23, 2026 and is based on user searches.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:55 am -
1 stop6h 00m
Fri 8/2811:50 am -
1 stop12h 13m
Deal found 8/18![Frontier logo]()
$230
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:55 am -
1 stop5h 55m
Wed 9/211:50 am -
1 stop12h 13m
Deal found 8/18![Frontier logo]()
$228
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 am -
1 stop12h 36m
Sat 9/126:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$219
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:15 am -
1 stop12h 31m
Mon 9/146:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$233
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.
Thu 9/106:15 am -
1 stop12h 31m
Sat 9/126:25 am -
1 stop8h 35m
Deal found 8/19![Frontier logo]()
$236
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:15 am -
1 stop12h 36m
Mon 9/146:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$234
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:15 am -
1 stop12h 36m
Mon 9/286:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$220
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.
Wed 9/236:15 am -
1 stop12h 36m
Tue 9/296:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$235
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:55 pm -
1 stop7h 49m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$221
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.
Fri 9/254:55 pm -
1 stop7h 49m
Tue 9/296:25 am -
1 stop8h 35m
Deal found 8/19![Frontier logo]()
$232
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:15 am -
1 stop12h 36m
Tue 9/296:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$218
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.
Sat 9/266:15 am -
1 stop12h 36m
Mon 9/286:25 am -
1 stop8h 35m
Deal found 8/18![Frontier logo]()
$228
One-way flights from New York to MidwaySearch for one-way flight options from New York to Midway. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
Search for one-way flight options from New York to Midway. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:35 am -
1 stop7h 10m
Deal found 8/20![Frontier logo]()
$106
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.
Sat 11/711:35 am -
1 stop7h 12m
Deal found 8/20![Frontier logo]()
$107
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:35 am -
1 stop7h 16m
Deal found 8/22![Frontier logo]()
$108
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:00 pm -
1 stop5h 51m
Deal found 8/18![Frontier logo]()
$108
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:35 am -
1 stop7h 11m
Deal found 8/20![Frontier logo]()
$109
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:00 pm -
1 stop5h 51m
Deal found 8/19![Frontier logo]()
$109
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:55 pm -
1 stop7h 49m
Deal found 8/19![Frontier logo]()
$109
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:35 am -
1 stop7h 11m
Deal found 8/18![Frontier logo]()
$110
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.
Wed 9/231:00 pm -
1 stop5h 51m
Deal found 8/18![Frontier logo]()
$110
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:00 pm -
1 stop5h 46m
Deal found 8/19![Frontier logo]()
$111
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:55 pm -
1 stop7h 49m
Deal found 8/18![Frontier logo]()
$112
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:55 am -
1 stop6h 00m
Deal found 8/19![Frontier logo]()
$113
Find flight deals from New York to Midway
Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) 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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $218 (Expedia) |
One-way from | $106 (Frontier) |
Popular in | July |
Cheapest in | January |
Average price | $385 |
Good round-trip deal | $202 or less |
Good one-way deal | $150 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from New York 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 23, 2026.
Use the filters below to find and compare flights from New York to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Thu 9/10
7:25 am-8:45 am
Nonstop2h 20m
Chicago Midway
Mon 9/21
7:50 pm-10:55 pm
Nonstop2h 05m
$247
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Fri 10/16
9:00 pm-10:20 pm
Nonstop2h 20m
Chicago Midway
Sun 10/18
5:05 am-8:10 am
Nonstop2h 05m
$247
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Sat 10/3
9:25 am-10:55 am
Nonstop2h 30m
Chicago Midway
Sun 10/4
5:05 am-8:10 am
Nonstop2h 05m
$247
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 9/30
7:25 am-8:45 am
Nonstop2h 20m
Chicago Midway
Fri 10/9
7:35 pm-10:40 pm
Nonstop2h 05m
$257
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 9/16
12:05 pm-4:50 pm
1 stop5h 45m
Chicago Midway
Mon 9/21
5:00 am-8:00 am
Nonstop2h 00m
$257
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Fri 11/13
5:35 pm-1:05 am
1 stop8h 30m
Chicago Midway
Sun 11/15
5:00 am-8:05 am
Nonstop2h 05m
$257
NewarkChicago
EWR Newark - MDW Chicago Midway
EWRMDW
Newark
Tue 11/10
6:00 am-9:42 am
1 stop4h 42m
Chicago Midway
Tue 11/17
6:44 pm-11:15 pm
1 stop3h 31m
$267
NewarkChicago
EWR Newark - MDW Chicago Midway
EWRMDW
Newark
Fri 11/13
6:00 am-9:42 am
1 stop4h 42m
Chicago Midway
Mon 11/16
6:44 pm-11:15 pm
1 stop3h 31m
$267
NewarkChicago
EWR Newark - MDW Chicago Midway
EWRMDW
Newark
Sat 10/3
6:00 am-9:07 am
1 stop4h 07m
Chicago Midway
Sat 10/3
6:40 pm-11:15 pm
1 stop3h 35m
$267
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Tue 11/17
9:30 am-5:25 pm
1 stop8h 55m
Chicago Midway
Thu 11/19
9:40 am-3:10 pm
1 stop4h 30m
$277
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from New York 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 New York to Midway in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on New York-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 New York-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on New York-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 New York-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 New York to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from New York with our price prediction graph.
NYC-MDW
LGA-MDW
EWR-MDW
SWF-MDW
JFK-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 New York to Chicago Midway Airport
NYC-MDW
LGA-MDW
EWR-MDW
SWF-MDW
JFK-MDW
What is the cheapest month to book a flight from New York to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from New York to Chicago Midway Airport (average of $177). Flying from New York to Chicago Midway Airport in August is currently the most expensive (average of $369). 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 NYC to MDW?
Find hourly flight availability from New York 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 23, 2026.
It’s optimal to fly from New York to Chicago Midway Airport in the evening. By choosing this option you can save up to 37% on the cost of your flight, compared to a flight in the afternoon.
How much does it cost to fly round-trip from New York to Chicago Midway Airport?
Airfare is below average for this route at the moment.
New York to Chicago Midway Airport flights typically cost between $272 and $436 in September.The cheapest round-trip price found within the last 5 days was $218 on Frontier (Sep 26-Sep 29).
How often are flights from New York to Chicago delayed?
About 23% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 136 minutes.
What is the most punctual flight time for New York 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?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on New York to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.
How far ahead should I book a flight from New York to Chicago Midway Airport?
The price you pay for your flight from New York to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 62 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 New York to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from New York to Midway. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their New York to Chicago Midway Airport flight should consider departing on Wednesday 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 New York 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 New York 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 23, 2026.
Read through reviews of airlines operating flights from New York to Chicago Midway Airport, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
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 New York 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
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 23, 2026.
New York and Midway flights
Browse other New York and Midway flight options. Last updated on August 23, 2026.
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Browse through other flights departing from New York. Flights are based on user searches made on Cheapflights and were last updated on August 23, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from New York to Midway
Discover the top 4 airlines that operate flights from New York 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$55 | Average$171 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$306 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$313 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$186 | Average$444 | FlexibilityNo cancel fee | On-timeN/A |