$118+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
May 21 — May 281
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Mexico with Cheapflights
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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 April 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 April 21, 2026.
This Frontier deal was found by Cheapflights users on 4/18. 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 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Fri 5/83:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/18![Frontier logo]()
$271
This Priceline deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Mon 5/113:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/16![Frontier logo]()
$286
This Expedia deal was found by Cheapflights users on 4/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Fri 5/83:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/19![Frontier logo]()
$293
This Priceline deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:15 pm
MDW
- CUN
1 stop24h 41m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/16![Frontier logo]()
$303
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/16![Frontier logo]()
$311
This Trip.com deal was found by Cheapflights users on 4/17. 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 5/186:00 am
MDW
- CUN
1 stop8h 07m
Multiple Airlines
Sat 5/2312:45 pm
CUN
- MDW
1 stop8h 24m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$318
This Expedia deal was found by Cheapflights users on 4/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/19![Frontier logo]()
$319
This Priceline deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:30 am
MDW
- CUN
2 stops29h 16m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/17![Frontier logo]()
$322
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/16![Frontier logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/63:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Tue 5/1211:05 am
MEX
- MDW
2 stops33h 57m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$337
This FlightHub deal was found by Cheapflights users on 4/19. 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 5/68:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Thu 5/142:25 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/19![Volaris logo]()
$362
This FlightHub deal was found by Cheapflights users on 4/19. 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 5/158:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Fri 5/222:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/19![Volaris logo]()
$363
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 April 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 April 21, 2026.
This FlightHub deal was found by Cheapflights users on 4/20. 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 5/162:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Thu 5/288:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/20![Volaris logo]()
$373
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2910:30 am
MDW
- CUN
Nonstop3h 30m
Southwest
Mon 5/184:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/19![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 4/20. 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 5/2910:59 am
MDW
- CUN
1 stop9h 17m
Delta
Fri 6/58:09 am
CUN
- MDW
2 stops13h 00m
Delta
Deal found 4/20![Delta logo]()
$398
This Justfly.com deal was found by Cheapflights users on 4/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:59 am
MDW
- MLM
2 stops33h 10m
Frontier
Tue 5/268:04 am
MLM
- MDW
2 stops36h 58m
Frontier
Deal found 4/19![Frontier logo]()
$533
This Delta deal was found by Cheapflights users on 4/20. 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 6/512:53 pm
MDW
- CUN
1 stop7h 23m
Delta
Mon 6/88:00 am
CUN
- MDW
1 stop14h 17m
Delta
Deal found 4/20![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Sat 5/2310:35 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/20![Southwest logo]()
$403
This FlightHub deal was found by Cheapflights users on 4/20. 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 6/122:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Fri 6/198:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/20![Volaris logo]()
$436
This Delta deal was found by Cheapflights users on 4/20. 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 6/99:17 am
MDW
- CUN
2 stops11h 08m
Delta
Tue 6/168:00 am
CUN
- MDW
1 stop8h 16m
Delta
Deal found 4/20![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 4/19. 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.
Sun 5/36:50 am
MDW
- CUN
1 stop6h 20m
Southwest
Thu 5/74:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/19![Southwest logo]()
$405
This Delta deal was found by Cheapflights users on 4/18. 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 6/169:17 am
MDW
- CUN
2 stops11h 08m
Delta
Tue 6/238:00 am
CUN
- MDW
1 stop8h 16m
Delta
Deal found 4/18![Delta logo]()
$402
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Mon 9/148:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/16![Volaris logo]()
$446
This Southwest deal was found by Cheapflights users on 4/18. 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 7/710:05 am
MDW
- CUN
Nonstop3h 35m
Southwest
Thu 7/161:20 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 4/18![Southwest logo]()
$428
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Mon 5/48:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/16![Volaris logo]()
$452
This Delta deal was found by Cheapflights users on 4/20. 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 4/299:27 am
MDW
- CUN
2 stops10h 48m
Delta
Wed 5/63:15 pm
CUN
- MDW
1 stop7h 13m
Delta
Deal found 4/20![Delta logo]()
$420
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Mon 5/182:15 pm
CUN
- MDW
1 stop7h 40m
Southwest
Deal found 4/20![Southwest logo]()
$447
This Volaris deal was found by Cheapflights users on 4/20. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:23 pm
MDW
- MTY
1 stop12h 07m
Volaris
Thu 5/286:00 am
MTY
- MDW
1 stop12h 20m
Volaris
Deal found 4/20![Volaris logo]()
$461
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- CUN
1 stop6h 40m
Delta
Tue 5/58:00 am
CUN
- MDW
1 stop8h 26m
Delta
Deal found 4/17![Delta logo]()
$433
This Frontier deal was found by Cheapflights users on 4/20. 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 6/113:04 pm
MDW
- BJX
Nonstop3h 55m
Frontier
Thu 6/258:44 am
BJX
- MDW
Nonstop3h 55m
Frontier
Deal found 4/20![Frontier logo]()
$669
This Gotogate deal was found by Cheapflights users on 4/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Tue 6/98:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/18![Volaris logo]()
$469
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:18 am
MDW
- MEX
1 stop11h 32m
Delta
Sat 5/97:05 am
MEX
- MDW
1 stop8h 27m
Delta
Deal found 4/16![Delta logo]()
$434
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Sat 6/138:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/17![Volaris logo]()
$472
This Delta deal was found by Cheapflights users on 4/17. 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.
Sat 5/910:45 am
MDW
- MEX
1 stop12h 05m
Delta
Tue 5/128:40 am
MEX
- MDW
1 stop11h 29m
Delta
Deal found 4/17![Delta logo]()
$434
This Southwest deal was found by Cheapflights users on 4/17. 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 6/275:25 am
MDW
- PVR
1 stop8h 35m
Southwest
Sat 7/44:55 pm
PVR
- MDW
1 stop11h 30m
Southwest
Deal found 4/17![Southwest logo]()
$564
This Delta deal was found by Cheapflights users on 4/19. 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 5/612:52 pm
MDW
- MEX
1 stop9h 58m
Delta
Sat 5/161:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/19![Delta logo]()
$434
This CheapOair deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/144:15 pm
MDW
- DGO
Nonstop3h 59m
Volaris
Sat 5/2310:26 am
DGO
- MDW
Nonstop3h 25m
Volaris
Deal found 4/20![Volaris logo]()
$483
This Southwest deal was found by Cheapflights users on 4/18. 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 6/26:10 am
MDW
- PVR
1 stop8h 10m
Southwest
Tue 6/92:00 pm
PVR
- MDW
2 stops9h 05m
Southwest
Deal found 4/18![Southwest logo]()
$569
This Delta deal was found by Cheapflights users on 4/18. 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 5/46:00 am
MDW
- MEX
1 stop8h 55m
Delta
Fri 5/81:20 pm
MEX
- MDW
1 stop7h 06m
Delta
Deal found 4/18![Delta logo]()
$434
This Justfly.com deal was found by Cheapflights users on 4/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Mon 5/118:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/20![Volaris logo]()
$502
This Delta deal was found by Cheapflights users on 4/19. 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.
Tue 5/56:00 am
MDW
- MEX
1 stop8h 55m
Delta
Sat 5/91:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/19![Delta logo]()
$434
This Southwest deal was found by Cheapflights users on 4/17. 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 6/255:45 am
MDW
- SJD
1 stop7h 15m
Southwest
Sat 6/2712:55 pm
SJD
- MDW
1 stop7h 00m
Southwest
Deal found 4/17![Southwest logo]()
$586
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated April 21, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated April 21, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/16![Frontier logo]()
$324
This Priceline deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:15 pm
MDW
- CUN
1 stop24h 41m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/16![Frontier logo]()
$303
This Priceline deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:30 am
MDW
- CUN
2 stops29h 16m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/17![Frontier logo]()
$322
This Expedia deal was found by Cheapflights users on 4/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Fri 5/83:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/19![Frontier logo]()
$293
This Frontier deal was found by Cheapflights users on 4/18. 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 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Fri 5/83:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/18![Frontier logo]()
$271
This Priceline deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Mon 5/113:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/16![Frontier logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/63:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Tue 5/1211:05 am
MEX
- MDW
2 stops33h 57m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$337
This FlightHub deal was found by Cheapflights users on 4/19. 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 5/68:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Thu 5/142:25 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/19![Volaris logo]()
$362
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/16![Frontier logo]()
$311
This Expedia deal was found by Cheapflights users on 4/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/19![Frontier logo]()
$319
This FlightHub deal was found by Cheapflights users on 4/19. 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 5/158:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Fri 5/222:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/19![Volaris logo]()
$363
This Trip.com deal was found by Cheapflights users on 4/17. 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 5/186:00 am
MDW
- CUN
1 stop8h 07m
Multiple Airlines
Sat 5/2312:45 pm
CUN
- MDW
1 stop8h 24m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$318
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 April 21, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated April 21, 2026.
This Super.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/16![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/186:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/15![Frontier logo]()
$120
This FlightHub deal was found by Cheapflights users on 4/20. 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 6/18:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 4/20![Volaris logo]()
$123
This Super.com deal was found by Cheapflights users on 4/17. 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 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/17![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- CUN
1 stop23h 05m
Frontier
Deal found 4/16![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 4/20. 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 5/96:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/20![Frontier logo]()
$130
This Expedia deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:52 pm
MDW
- CUN
1 stop23h 05m
Frontier
Deal found 4/17![Frontier logo]()
$131
This Priceline deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:19 pm
MDW
- CUN
1 stop25h 48m
Frontier
Deal found 4/16![Frontier logo]()
$137
This Trip.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$142
This Jetabroad deal was found by Cheapflights users on 4/20. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 4/20![Volaris logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:07 pm
MDW
- GDL
1 stop24h 13m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$152
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 April 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $271 (Frontier) |
One-way from | $118 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $333 |
Good round-trip deal | $349 or less |
Good one-way deal | $115 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 April 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Mexico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Sat 5/16
2:32 pm-5:41 pm
Nonstop4h 09m
Morelia
Thu 5/28
8:22 am-1:15 pm
Nonstop3h 53m
$373
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 4/29
10:30 am-2:00 pm
Nonstop3h 30m
Cancun
Mon 5/18
4:10 pm-7:50 pm
Nonstop3h 40m
$386
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/29
10:59 am-8:16 pm
1 stop9h 17m
Cancun
Fri 6/5
8:09 am-9:09 pm
2 stops13h 00m
$398
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 6/5
12:53 pm-8:16 pm
1 stop7h 23m
Cancun
Mon 6/8
8:00 am-10:17 pm
1 stop14h 17m
$398
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 6/9
9:17 am-8:25 pm
2 stops11h 08m
Cancun
Tue 6/16
8:00 am-4:16 pm
1 stop8h 16m
$402
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 6/16
9:17 am-8:25 pm
2 stops11h 08m
Cancun
Tue 6/23
8:00 am-4:16 pm
1 stop8h 16m
$402
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/8
9:35 am-1:10 pm
Nonstop3h 35m
Cancun
Sat 5/23
10:35 am-2:15 pm
Nonstop3h 40m
$403
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 5/3
6:50 am-1:10 pm
1 stop6h 20m
Cancun
Thu 5/7
4:10 pm-7:50 pm
Nonstop3h 40m
$405
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 4/29
9:27 am-8:15 pm
2 stops10h 48m
Cancun
Wed 5/6
3:15 pm-10:28 pm
1 stop7h 13m
$420
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 7/7
10:05 am-1:40 pm
Nonstop3h 35m
Cancun
Thu 7/16
1:20 pm-4:55 pm
Nonstop3h 35m
$428
Showing 1-10 of 60 resultsSorted by cheapest first
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-MEX
MDW-GDL
MDW-MLM
MDW-MTY
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-MEX
MDW-GDL
MDW-MLM
What is the cheapest month to book a flight from Chicago Midway Airport to Mexico?
Currently, January 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 June is currently the most expensive (average of $631). 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 April 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 in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 23% on airfare.
How often are flights from Chicago to Mexico delayed?
About 17% of weekly flights between Chicago and Mexico have experienced delays in the past year, with the average delay time being 151 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, Volaris have had the lowest number of delays on this route, with just 16% 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 April 21, 2026.
See what other customers who have flown with Southwest,Delta, andAeromexico 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.
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
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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
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Midway and Mexico flights
Browse other Midway and Mexico flight options. Last updated on April 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 5 airlines flying from Midway to Mexico
Discover the top 5 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 April 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$402 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$416 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$193 | Average$2,092 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$475 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$290 | Average$620 | FlexibilityNo cancel fee | On-time63% |