$105+ Cheap flights from Midway (MDW) to Mexico
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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Mar 23 — Mar 301
1 adult, Economy
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Find cheap flights from Midway to Mexico with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Midway to MexicoExplore the most affordable flight options available from Midway to Mexico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2026.
Explore the most affordable flight options available from Midway to Mexico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2026.
This Frontier deal was found by Cheapflights users on 2/19. 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.
Sat 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/19![Frontier logo]()
$248
This Trip.com deal was found by Cheapflights users on 2/19. 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.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$259
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Sat 3/1410:39 am
CUN
- MDW
1 stop7h 55m
Volaris
Deal found 2/19![Volaris logo]()
$284
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/32:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Tue 3/178:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/19![Volaris logo]()
$284
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Tue 3/1010:39 am
CUN
- MDW
1 stop7h 55m
Volaris
Deal found 2/20![Volaris logo]()
$286
This Trip.com deal was found by Cheapflights users on 2/17. 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.
Mon 3/26:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$288
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Fri 3/61:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/19![Volaris logo]()
$289
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Tue 3/101:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/18![Volaris logo]()
$290
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Fri 3/1310:39 am
CUN
- MDW
1 stop7h 55m
Volaris
Deal found 2/20![Volaris logo]()
$290
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Wed 3/188:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/19![Volaris logo]()
$290
This Gotogate deal was found by Cheapflights users on 2/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:09 pm
MDW
- GDL
Nonstop4h 10m
Volaris
Fri 4/171:36 pm
GDL
- MDW
Nonstop4h 04m
Volaris
Deal found 2/19![Volaris logo]()
$292
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:09 pm
MDW
- GDL
Nonstop4h 10m
Volaris
Wed 4/221:36 pm
GDL
- MDW
Nonstop4h 04m
Volaris
Deal found 2/19![Volaris logo]()
$294
Best flights from Midway to MexicoDiscover carefully curated flight deals from Midway to Mexico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 21, 2026.
Discover carefully curated flight deals from Midway to Mexico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 21, 2026.
This Southwest deal was found by Cheapflights users on 2/17. 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 3/71:25 pm
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 3/138:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/17![Southwest logo]()
$298
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Tue 3/34:31 pm
MDW
- DGO
Nonstop4h 07m
Volaris
Tue 3/1010:42 am
DGO
- MDW
Nonstop3h 27m
Volaris
Deal found 2/19![Volaris logo]()
$299
This Delta deal was found by Cheapflights users on 2/20. 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.
Sun 5/1010:46 am
MDW
- CUN
1 stop9h 17m
Delta
Sat 5/168:15 am
CUN
- MDW
1 stop7h 11m
Delta
Deal found 2/20![Delta logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Tue 3/176:00 am
MDW
- MTY
2 stops35h 10m
Multiple Airlines
Tue 3/2411:30 am
MTY
- MDW
1 stop21h 55m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$407
This Aeromexico deal was found by Cheapflights users on 2/20. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:45 am
MDW
- DGO
2 stops13h 13m
Aeromexico
Wed 5/137:40 pm
DGO
- MDW
2 stops19h 37m
Aeromexico
Deal found 2/20![Aeromexico logo]()
$450
This Trip.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/162:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Wed 3/188:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/19![Volaris logo]()
$301
This CheapOair deal was found by Cheapflights users on 2/17. 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.
Wed 3/47:15 am
MDW
- OAX
2 stops32h 57m
Frontier
Wed 3/118:40 am
OAX
- MDW
2 stops30h 12m
Frontier
Deal found 2/17![Frontier logo]()
$609
This Southwest deal was found by Cheapflights users on 2/18. 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 4/139:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 4/223:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/18![Southwest logo]()
$337
This CheapOair deal was found by Cheapflights users on 2/19. 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.
Tue 3/104:31 pm
MDW
- DGO
Nonstop4h 07m
Volaris
Tue 3/1710:42 am
DGO
- MDW
Nonstop3h 27m
Volaris
Deal found 2/19![Volaris logo]()
$321
This Delta deal was found by Cheapflights users on 2/17. 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.
Wed 3/410:49 am
MDW
- CUN
1 stop9h 22m
Delta
Mon 3/911:10 am
CUN
- MDW
1 stop7h 30m
Delta
Deal found 2/17![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 2/17. 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 4/116:10 am
MDW
- CUN
Nonstop3h 35m
Southwest
Thu 4/164:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/17![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 2/17. 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 3/1712:47 pm
MDW
- CUN
1 stop7h 33m
Delta
Wed 3/2510:00 am
CUN
- MDW
1 stop7h 22m
Delta
Deal found 2/17![Delta logo]()
$358
This CheapOair deal was found by Cheapflights users on 2/18. 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 4/142:32 pm
MDW
- MLM
Nonstop4h 00m
Volaris
Thu 5/78:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/18![Volaris logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Wed 3/47:15 am
MDW
- MTY
2 stops16h 50m
Multiple Airlines
Tue 3/1011:30 am
MTY
- MDW
1 stop21h 55m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 2/18. 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 4/139:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 4/173:05 pm
CUN
- MDW
1 stop7h 15m
Southwest
Deal found 2/18![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 2/18. 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 3/231:10 pm
MDW
- CUN
2 stops19h 50m
Delta
Wed 3/2511:15 am
CUN
- MDW
1 stop6h 07m
Delta
Deal found 2/18![Delta logo]()
$362
This Mytrip deal was found by Cheapflights users on 2/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:32 pm
MDW
- MLM
Nonstop4h 00m
Volaris
Sat 5/98:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/18![Volaris logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/304:09 pm
MDW
- MTY
2 stops16h 01m
Multiple Airlines
Mon 5/411:30 am
MTY
- MDW
1 stop9h 51m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 2/18. 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 3/49:15 am
MDW
- CUN
Nonstop3h 40m
Southwest
Wed 3/111:10 pm
CUN
- MDW
1 stop6h 30m
Southwest
Deal found 2/18![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
MDW
- CUN
1 stop5h 30m
Delta
Wed 4/228:00 am
CUN
- MDW
1 stop8h 26m
Delta
Deal found 2/20![Delta logo]()
$363
This Mytrip deal was found by Cheapflights users on 2/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:15 pm
MDW
- DGO
Nonstop3h 46m
Volaris
Thu 4/1610:16 am
DGO
- MDW
Nonstop3h 35m
Volaris
Deal found 2/18![Volaris logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/74:09 pm
MDW
- MEX
1 stop7h 36m
Multiple Airlines
Thu 5/146:20 am
MEX
- MDW
2 stops12h 11m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$419
This Booking.com deal was found by Cheapflights users on 2/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:09 pm
MDW
- GDL
Nonstop4h 10m
Volaris
Sat 5/302:25 pm
GDL
- MDW
Nonstop4h 04m
Volaris
Deal found 2/17![Volaris logo]()
$343
This Southwest deal was found by Cheapflights users on 2/17. 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 3/194:05 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Tue 3/248:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/17![Southwest logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Tue 3/177:30 am
MDW
- GDL
1 stop28h 14m
Multiple Airlines
Tue 3/2411:48 am
GDL
- MDW
2 stops21h 37m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$431
This CheapOair deal was found by Cheapflights users on 2/17. 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.
Tue 4/144:15 pm
MDW
- DGO
Nonstop3h 46m
Volaris
Tue 4/2810:16 am
DGO
- MDW
Nonstop3h 35m
Volaris
Deal found 2/17![Volaris logo]()
$343
This Aeromexico deal was found by Cheapflights users on 2/17. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/276:00 am
MDW
- CZM
1 stop7h 45m
Aeromexico
Wed 4/12:00 pm
CZM
- MDW
1 stop7h 31m
Aeromexico
Deal found 2/17![Aeromexico logo]()
$611
This Delta deal was found by Cheapflights users on 2/18. 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.
Thu 4/210:45 am
MDW
- MTY
1 stop8h 05m
Delta
Wed 4/88:00 am
MTY
- MDW
1 stop8h 22m
Delta
Deal found 2/18![Delta logo]()
$426
This Aeromexico deal was found by Cheapflights users on 2/19. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- CZM
1 stop7h 45m
Aeromexico
Sat 4/182:14 pm
CZM
- MDW
1 stop7h 14m
Aeromexico
Deal found 2/19![Aeromexico logo]()
$611
This FlightHub deal was found by Cheapflights users on 2/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:32 pm
MDW
- MLM
Nonstop4h 00m
Volaris
Sun 5/38:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/17![Volaris logo]()
$347
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated February 21, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated February 21, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Fri 3/61:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/19![Volaris logo]()
$289
This Trip.com deal was found by Cheapflights users on 2/17. 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.
Mon 3/26:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$288
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Tue 3/101:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/18![Volaris logo]()
$290
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/32:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Tue 3/178:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/19![Volaris logo]()
$284
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Tue 3/34:31 pm
MDW
- DGO
Nonstop4h 07m
Volaris
Tue 3/1010:42 am
DGO
- MDW
Nonstop3h 27m
Volaris
Deal found 2/19![Volaris logo]()
$299
This Mytrip deal was found by Cheapflights users on 2/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Sat 3/71:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/18![Volaris logo]()
$299
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Tue 3/1010:39 am
CUN
- MDW
1 stop7h 55m
Volaris
Deal found 2/20![Volaris logo]()
$286
This Frontier deal was found by Cheapflights users on 2/19. 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.
Sat 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/19![Frontier logo]()
$248
This Trip.com deal was found by Cheapflights users on 2/19. 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.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$259
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Sat 3/1410:39 am
CUN
- MDW
1 stop7h 55m
Volaris
Deal found 2/19![Volaris logo]()
$284
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Fri 3/1310:39 am
CUN
- MDW
1 stop7h 55m
Volaris
Deal found 2/20![Volaris logo]()
$290
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Wed 3/188:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/19![Volaris logo]()
$290
One-way flights from Midway to MexicoSearch for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated February 21, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated February 21, 2026.
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/20![Volaris logo]()
$105
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/20![Volaris logo]()
$108
This Expedia deal was found by Cheapflights users on 2/21. 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.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Deal found 2/21![Frontier logo]()
$114
This FlightHub deal was found by Cheapflights users on 2/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/17![Volaris logo]()
$116
This Trip.com deal was found by Cheapflights users on 2/19. 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.
Sat 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Deal found 2/19![Frontier logo]()
$117
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:09 pm
MDW
- CUN
1 stop13h 39m
Volaris
Deal found 2/20![Volaris logo]()
$118
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:09 pm
MDW
- CUN
1 stop13h 39m
Volaris
Deal found 2/19![Volaris logo]()
$119
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/257:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Deal found 2/19![Volaris logo]()
$120
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Deal found 2/18![Volaris logo]()
$121
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/42:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Deal found 2/19![Volaris logo]()
$121
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Deal found 2/18![Volaris logo]()
$122
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/82:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Deal found 2/20![Volaris logo]()
$123
Find flight deals from Midway to Mexico
Keep the following information in mind while searching for Midway to Mexico flight deals. Data was last updated February 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $248 (Frontier) |
One-way from | $105 (FlightHub) |
Popular in | December |
Cheapest in | January |
Average price | $306 |
Good round-trip deal | $251 or less |
Good one-way deal | $128 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Mexico 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 2,558,603 searches. Data last updated February 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Mexico that are best for you.
Fly from
Midway
Fly to
Mexico
Route
Depart
Return
Price
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 3/7
1:25 pm-6:00 pm
Nonstop3h 35m
Cancun
Fri 3/13
8:30 am-12:10 pm
Nonstop3h 40m
$298
ChicagoDurango
MDW - DGO
MDWDGO
Chicago Midway
Tue 3/3
4:31 pm-8:38 pm
Nonstop4h 07m
Durango Guadalupe Victoria
Tue 3/10
10:42 am-3:09 pm
Nonstop3h 27m
$299
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Mon 3/16
2:32 pm-5:48 pm
Nonstop4h 16m
Morelia
Wed 3/18
8:15 am-1:04 pm
Nonstop3h 49m
$301
ChicagoDurango
MDW - DGO
MDWDGO
Chicago Midway
Tue 3/10
4:31 pm-7:38 pm
Nonstop4h 07m
Durango Guadalupe Victoria
Tue 3/17
10:42 am-3:09 pm
Nonstop3h 27m
$321
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Tue 4/14
2:32 pm-5:32 pm
Nonstop4h 00m
Morelia
Thu 5/7
8:15 am-1:15 pm
Nonstop4h 00m
$331
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Thu 4/30
2:32 pm-5:32 pm
Nonstop4h 00m
Morelia
Sat 5/9
8:15 am-1:15 pm
Nonstop4h 00m
$335
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 4/13
9:35 am-1:10 pm
Nonstop3h 35m
Cancun
Wed 4/22
3:15 pm-6:55 pm
Nonstop3h 40m
$337
ChicagoDurango
MDW - DGO
MDWDGO
Chicago Midway
Thu 4/9
4:15 pm-7:01 pm
Nonstop3h 46m
Durango Guadalupe Victoria
Thu 4/16
10:16 am-2:51 pm
Nonstop3h 35m
$339
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 4/11
6:10 am-9:45 am
Nonstop3h 35m
Cancun
Thu 4/16
4:10 pm-7:50 pm
Nonstop3h 40m
$342
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 5/10
10:46 am-8:03 pm
1 stop9h 17m
Cancun
Sat 5/16
8:15 am-3:26 pm
1 stop7h 11m
$343
Showing 1-10 of 60 results
Best time to book a flight from Midway to Mexico
Have a flexible travel schedule? Discover the best time to fly to Mexico from Midway with our price prediction graph.
MDW-CUN
MDW-MLM
MDW-GDL
MDW-MTY
MDW-SJD
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 Chicago Midway Airport to Mexico
MDW-MX0
MDW-CUN
MDW-MLM
MDW-GDL
MDW-MTY
What is the cheapest month to book a flight from Chicago Midway Airport to Mexico?
Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $101). Flying from Chicago Midway Airport to Mexico in November is currently the most expensive (average of $243). 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 MDW to MX?
Find hourly flight availability from Midway to Mexico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 21, 2026.
One of the essential ways to save on airfare from Chicago Midway Airport to Mexico is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 28% on airfare.
How often are flights from Chicago to Mexico delayed?
About 16% of weekly flights between Chicago and Mexico have experienced delays in the past year, with the average delay time being 147 minutes.
What is the most punctual flight time for Chicago to Mexico flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon 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 Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Mexico flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 13% of flights being delayed.
Reviews of airlines servicing Mexico
Get insights into the airlines that provide service to Mexico. 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 Mexico. Reviews last updated February 21, 2026.
See what other customers who have flown with Southwest, Delta, and Aeromexico from Chicago Midway Airport to Mexico 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
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway to Mexico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Mexico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Mexico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Mexico by cabin class
Find flights from Midway to Mexico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Mexico flights
Browse other Midway and Mexico flight options. Last updated on February 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Mexico flights
Consider these flights traveling from Midway to Mexico.
Fly to Mexico regions
Consider these flights traveling to Mexico regions.
Top 6 airlines flying from Midway to Mexico
Discover the top 6 airlines that operate flights from Midway to Mexico. 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 2,558,603 searches. Data last updated February 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$400 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$190 | Average$339 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$195 | Average$417 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$198 | Average$397 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$293 | Average$620 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$358 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |