$115+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
May 31 — Jun 71
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 May 1, 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 May 1, 2026.
This Expedia deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 5/116:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/27![Frontier logo]()
$296
This Priceline deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Sat 5/166:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Sun 5/173:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 5/1![Frontier logo]()
$297
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/189:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 5/224:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/29![Southwest logo]()
$333
This Priceline deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/1512:04 pm
MDW
- CUN
1 stop26h 03m
Frontier
Mon 5/183:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/26![Frontier logo]()
$338
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1110:59 am
MDW
- CUN
1 stop9h 17m
Delta
Wed 5/2012:45 pm
CUN
- MDW
1 stop8h 24m
Delta
Deal found 4/27![Delta logo]()
$340
This Frontier deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/166:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Sat 5/2311:05 am
CUN
- MDW
2 stops10h 57m
Frontier
Deal found 5/1![Frontier logo]()
$342
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1710:59 am
MDW
- CUN
1 stop9h 17m
Delta
Wed 5/208:00 am
CUN
- MDW
1 stop13h 09m
Delta
Deal found 4/27![Delta logo]()
$348
This FlightHub deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/116:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Mon 5/183:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/26![Frontier logo]()
$351
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/176:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Sat 5/2311:05 am
CUN
- MDW
1 stop27h 07m
Frontier
Deal found 4/29![Frontier logo]()
$354
This FlightHub deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/128:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 6/1910:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 4/30![Volaris logo]()
$356
This FlightHub deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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
- GDL
Nonstop4h 07m
Volaris
Sat 6/62:31 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 4/26![Volaris logo]()
$370
This FlightHub deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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
- GDL
Nonstop4h 07m
Volaris
Tue 6/92:31 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 4/26![Volaris logo]()
$371
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 May 1, 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 May 1, 2026.
This FlightHub deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/82:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Fri 5/158:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/26![Volaris logo]()
$392
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/279:22 am
MDW
- CUN
2 stops10h 54m
Delta
Wed 6/38:00 am
CUN
- MDW
1 stop8h 12m
Delta
Deal found 4/26![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/1610:40 am
MDW
- CUN
Nonstop3h 30m
Southwest
Thu 5/214:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/26![Southwest logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/283:07 pm
MDW
- PVR
2 stops17h 33m
Multiple Airlines
Thu 6/410:20 am
PVR
- MDW
1 stop8h 14m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$553
This FlightHub deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/242:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Sun 5/318:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/26![Volaris logo]()
$435
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1010:59 am
MDW
- MEX
1 stop9h 01m
Delta
Tue 5/121:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/27![Delta logo]()
$444
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/286:55 am
MDW
- CUN
1 stop8h 25m
Southwest
Thu 6/44:10 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 4/30![Southwest logo]()
$473
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/810:59 am
MDW
- MEX
1 stop11h 51m
Delta
Tue 5/121:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/28![Delta logo]()
$444
This Volaris deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
Fri 9/258:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Mon 9/282:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 4/30![Volaris logo]()
$488
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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
Tue 5/121:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/27![Delta logo]()
$444
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/117:30 am
MDW
- CUN
Nonstop3h 35m
Southwest
Sat 7/1812:10 pm
CUN
- MDW
1 stop7h 10m
Southwest
Deal found 4/28![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/81:22 pm
MDW
- MEX
2 stops9h 53m
Delta
Mon 5/186:45 am
MEX
- MDW
2 stops13h 24m
Delta
Deal found 4/27![Delta logo]()
$449
This Super.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/52:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Wed 6/108:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/30![Volaris logo]()
$516
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/57:25 am
MDW
- CUN
1 stop5h 55m
Southwest
Mon 5/112:15 pm
CUN
- MDW
2 stops9h 40m
Southwest
Deal found 4/30![Southwest logo]()
$529
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/1110:59 am
MDW
- MEX
1 stop11h 51m
Delta
Tue 5/191:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/30![Delta logo]()
$454
This Flightnetwork deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:23 pm
MDW
- MTY
2 stops15h 35m
Multiple Airlines
Sun 6/218:09 am
MTY
- MDW
1 stop9h 55m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$676
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/32:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Sun 6/78:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/29![Volaris logo]()
$518
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/76:30 am
MDW
- CUN
1 stop6h 20m
Southwest
Thu 6/1111:40 am
CUN
- MDW
2 stops8h 40m
Southwest
Deal found 4/27![Southwest logo]()
$543
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/1910:59 am
MDW
- MEX
1 stop11h 51m
Delta
Fri 6/51:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/29![Delta logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/145:53 pm
MDW
- AGU
Nonstop4h 10m
Multiple Airlines
Thu 5/283:22 pm
AGU
- MDW
2 stops53h 40m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$678
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 9/157:30 pm
MDW
- DGO
2 stops23h 24m
Volaris
Tue 9/2210:16 am
DGO
- MDW
Nonstop3h 35m
Volaris
Deal found 4/26![Volaris logo]()
$544
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/157:45 am
MDW
- CUN
2 stops7h 35m
Southwest
Fri 5/223:15 pm
CUN
- MDW
1 stop8h 40m
Southwest
Deal found 4/27![Southwest logo]()
$545
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/106:23 am
MDW
- MEX
1 stop8h 32m
Delta
Sat 5/161:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 4/30![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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
Wed 5/138:40 am
MEX
- MDW
1 stop11h 29m
Delta
Deal found 4/29![Delta logo]()
$454
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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
Mon 5/114:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/30![Southwest logo]()
$551
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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
Thu 5/288:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/26![Volaris logo]()
$553
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/239:19 am
MDW
- CUN
2 stops10h 56m
Delta
Tue 7/288:00 am
CUN
- MDW
2 stops10h 25m
Delta
Deal found 4/29![Delta logo]()
$457
This Volaris deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Fri 5/152:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Sun 5/178:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/27![Volaris logo]()
$559
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 8/58:50 pm
MDW
- PVR
2 stops16h 30m
Southwest
Sun 8/92:45 pm
PVR
- MDW
1 stop8h 40m
Southwest
Deal found 4/29![Southwest logo]()
$579
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/16:23 am
MDW
- MEX
2 stops13h 37m
Delta
Mon 6/87:05 am
MEX
- MDW
1 stop8h 11m
Delta
Deal found 4/26![Delta logo]()
$459
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated May 1, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated May 1, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Wed 5/68:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Thu 5/142:25 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/26![Volaris logo]()
$373
This Expedia deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 5/116:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/27![Frontier logo]()
$296
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1110:59 am
MDW
- CUN
1 stop9h 17m
Delta
Wed 5/2012:45 pm
CUN
- MDW
1 stop8h 24m
Delta
Deal found 4/27![Delta logo]()
$340
This FlightHub deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/116:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Mon 5/183:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/26![Frontier logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/123:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Wed 5/2710:05 am
MEX
- MDW
2 stops10h 57m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$374
This Priceline deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/1512:04 pm
MDW
- CUN
1 stop26h 03m
Frontier
Mon 5/183:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/26![Frontier logo]()
$338
This Priceline deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Sat 5/166:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Sun 5/173:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 5/1![Frontier logo]()
$297
This Frontier deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/166:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Sat 5/2311:05 am
CUN
- MDW
2 stops10h 57m
Frontier
Deal found 5/1![Frontier logo]()
$342
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1710:59 am
MDW
- CUN
1 stop9h 17m
Delta
Wed 5/208:00 am
CUN
- MDW
1 stop13h 09m
Delta
Deal found 4/27![Delta logo]()
$348
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/176:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Sat 5/2311:05 am
CUN
- MDW
1 stop27h 07m
Frontier
Deal found 4/29![Frontier logo]()
$354
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/189:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 5/224:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/29![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/1910:30 am
MDW
- CUN
Nonstop3h 30m
Southwest
Sat 5/2310:35 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/28![Southwest logo]()
$358
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 May 1, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated May 1, 2026.
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 4/27![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/266:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/29![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/166:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/30![Frontier logo]()
$125
This FlightHub deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/278:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 4/30![Volaris logo]()
$140
This Flightnetwork deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork 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 4/27![Frontier logo]()
$141
This FlightHub deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/102:32 pm
MDW
- MTY
1 stop7h 09m
Volaris
Deal found 4/27![Volaris logo]()
$157
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/168:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 4/29![Volaris logo]()
$159
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/189:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Deal found 4/28![Southwest logo]()
$160
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/68:23 pm
MDW
- MTY
1 stop12h 07m
Volaris
Deal found 4/29![Volaris logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/206:00 am
MDW
- CUN
2 stops27h 09m
Frontier
Deal found 4/28![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/212:27 pm
MDW
- MTY
2 stops22h 53m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/123:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$164
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 May 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Expedia) |
One-way from | $115 (Frontier) |
Popular in | December |
Cheapest in | January |
Average price | $366 |
Good round-trip deal | $353 or less |
Good one-way deal | $74 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 May 1, 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
Fri 5/8
2:32 pm-5:41 pm
Nonstop4h 09m
Morelia
Fri 5/15
8:22 am-1:15 pm
Nonstop3h 53m
$392
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 5/27
9:22 am-8:16 pm
2 stops10h 54m
Cancun
Wed 6/3
8:00 am-4:12 pm
1 stop8h 12m
$402
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Sun 5/24
2:32 pm-5:41 pm
Nonstop4h 09m
Morelia
Sun 5/31
8:22 am-1:15 pm
Nonstop3h 53m
$435
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Sun 5/10
10:59 am-7:00 pm
1 stop9h 01m
Mexico City Benito Juarez
Tue 5/12
1:20 pm-9:09 pm
1 stop6h 49m
$444
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Fri 5/8
10:59 am-9:50 pm
1 stop11h 51m
Mexico City Benito Juarez
Tue 5/12
1:20 pm-9:09 pm
1 stop6h 49m
$444
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Tue 5/5
6:00 am-1:55 pm
1 stop8h 55m
Mexico City Benito Juarez
Tue 5/12
1:20 pm-9:09 pm
1 stop6h 49m
$444
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Fri 5/8
1:22 pm-10:15 pm
2 stops9h 53m
Mexico City Benito Juarez
Mon 5/18
6:45 am-9:09 pm
2 stops13h 24m
$449
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/16
10:40 am-2:10 pm
Nonstop3h 30m
Cancun
Thu 5/21
4:10 pm-7:50 pm
Nonstop3h 40m
$452
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Mon 5/11
10:59 am-9:50 pm
1 stop11h 51m
Mexico City Benito Juarez
Tue 5/19
1:20 pm-9:09 pm
1 stop6h 49m
$454
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Tue 5/19
10:59 am-9:50 pm
1 stop11h 51m
Mexico City Benito Juarez
Fri 6/5
1:20 pm-9:09 pm
1 stop6h 49m
$454
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-MTY
MDW-SJD
MDW-MEX
MDW-GDL
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-MTY
MDW-SJD
MDW-MEX
How far ahead should I book a flight from Chicago Midway Airport to Mexico?
The best time to book flights from Chicago Midway Airport to Mexico is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 May 1, 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 18% 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 evening 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?
Wednesday 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 17% 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 May 1, 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
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
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
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Midway and Mexico flights
Browse other Midway and Mexico flight options. Last updated on May 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Mexico flights
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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 May 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$402 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$418 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$193 | Average$2,092 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$296 | Average$620 | FlexibilityNo cancel fee | On-time63% |