$123+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Aug 13 — Aug 201
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 July 14, 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 July 14, 2026.
This Justfly.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Fri 10/98:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 10/1610:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/10![Volaris logo]()
$342
This CheapOair deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/268:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 9/210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$345
This FlightHub deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/98:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Sun 9/1310:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/10![Volaris logo]()
$350
This Justfly.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/268:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/3110:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:02 pm
MDW
- MEX
1 stop10h 43m
Multiple Airlines
Sun 10/410:05 am
MEX
- MDW
2 stops23h 53m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$356
This FlightHub deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 10/168:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 10/2310:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$359
This Super.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/168:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Sun 7/1910:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/9![Volaris logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Fri 8/76:17 pm
MDW
- QRO
1 stop29h 08m
Multiple Airlines
Wed 8/1211:20 pm
QRO
- MDW
2 stops20h 12m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$361
This Super.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 7/178:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Wed 7/2210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$362
This FlightHub deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/148:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 9/2110:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/10![Volaris logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Fri 8/218:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Fri 9/49:38 pm
GDL
- MDW
1 stop19h 27m
Volaris
Deal found 7/9![Volaris logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Fri 8/218:23 pm
MDW
- GDL
Nonstop4h 07m
Multiple Airlines
Fri 8/287:57 am
GDL
- MDW
2 stops13h 50m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$375
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 July 14, 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 July 14, 2026.
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/175:25 am
MDW
- CUN
1 stop9h 35m
Southwest
Wed 8/2612:40 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/9![Southwest logo]()
$405
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/269:24 am
MDW
- CUN
2 stops10h 41m
Delta
Wed 9/29:11 am
CUN
- MDW
2 stops13h 25m
Delta
Deal found 7/9![Delta logo]()
$443
This Frontier deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/276:05 am
MDW
- MLM
2 stops23h 50m
Frontier
Mon 8/316:40 am
MLM
- MDW
1 stop12h 51m
Frontier
Deal found 7/11![Frontier logo]()
$459
This CheapOair deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Mon 9/78:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 7/13![Volaris logo]()
$499
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/188:49 pm
MDW
- QRO
1 stop11h 08m
Multiple Airlines
Fri 7/2411:20 pm
QRO
- MDW
2 stops17h 06m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/235:10 am
MDW
- CUN
1 stop6h 40m
Southwest
Sun 8/302:40 pm
CUN
- MDW
1 stop6h 30m
Southwest
Deal found 7/9![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/248:25 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 9/212:40 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/13![Southwest logo]()
$432
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/46:05 am
MDW
- MEX
1 stop6h 50m
Delta
Sat 10/101:10 pm
MEX
- MDW
1 stop8h 15m
Delta
Deal found 7/10![Delta logo]()
$477
This CheapOair deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/209:26 pm
MDW
- MLM
1 stop23h 43m
Frontier
Thu 9/177:58 am
MLM
- MDW
2 stops26h 00m
Frontier
Deal found 7/12![Frontier logo]()
$500
This CheapOair deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/209:26 pm
MDW
- MLM
1 stop23h 43m
Multiple Airlines
Thu 9/178:14 am
MLM
- MDW
Nonstop4h 01m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$513
This Volaris deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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.
Wed 7/298:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Tue 8/410:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 7/11![Volaris logo]()
$519
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 9/1111:35 am
MDW
- MTY
1 stop5h 57m
Delta
Wed 9/1612:16 pm
MTY
- MDW
1 stop9h 29m
Delta
Deal found 7/9![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/107:55 am
MDW
- CUN
1 stop5h 35m
Southwest
Thu 8/271:05 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/13![Southwest logo]()
$467
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:35 am
MDW
- MEX
1 stop11h 15m
Delta
Sun 10/117:05 am
MEX
- MDW
1 stop8h 15m
Delta
Deal found 7/12![Delta logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:23 pm
MDW
- MLM
2 stops18h 40m
Volaris
Thu 8/278:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 7/12![Volaris logo]()
$558
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/68:49 pm
MDW
- MLM
2 stops19h 16m
Multiple Airlines
Tue 8/118:14 am
MLM
- MDW
Nonstop4h 01m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 9/141:00 pm
MDW
- MEX
1 stop7h 15m
Delta
Tue 9/291:20 pm
MEX
- MDW
1 stop8h 25m
Delta
Deal found 7/11![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/268:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 9/212:40 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/12![Southwest logo]()
$488
This CheapOair deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Sat 10/38:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 7/14![Volaris logo]()
$561
This Frontier deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:32 pm
MDW
- MLM
Nonstop3h 59m
Frontier
Fri 8/286:40 am
MLM
- MDW
1 stop12h 51m
Frontier
Deal found 7/10![Frontier logo]()
$635
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/171:00 pm
MDW
- MEX
1 stop9h 50m
Delta
Sun 9/201:20 pm
MEX
- MDW
1 stop8h 25m
Delta
Deal found 7/12![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/137:10 am
MDW
- CUN
1 stop6h 40m
Southwest
Sat 9/1910:10 am
CUN
- MDW
2 stops9h 00m
Southwest
Deal found 7/12![Southwest logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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.
Sun 8/98:23 pm
MDW
- MLM
2 stops19h 42m
Multiple Airlines
Sun 8/168:14 am
MLM
- MDW
Nonstop4h 01m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$604
This Volaris deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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.
Wed 8/198:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/2410:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$572
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:48 am
MDW
- MEX
1 stop9h 27m
Delta
Sun 10/41:20 pm
MEX
- MDW
1 stop8h 25m
Delta
Deal found 7/11![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/257:50 am
MDW
- CUN
1 stop7h 10m
Southwest
Mon 8/311:05 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/13![Southwest logo]()
$497
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:35 am
MDW
- MEX
1 stop8h 40m
Delta
Sun 9/277:05 am
MEX
- MDW
1 stop8h 11m
Delta
Deal found 7/13![Delta logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/308:49 pm
MDW
- QRO
1 stop11h 08m
Multiple Airlines
Sun 8/211:30 pm
QRO
- MDW
2 stops18h 34m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$654
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:40 am
MDW
- SJD
1 stop9h 40m
Southwest
Fri 10/3012:25 pm
SJD
- MDW
1 stop10h 30m
Southwest
Deal found 7/10![Southwest logo]()
$498
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/21:00 pm
MDW
- MEX
1 stop9h 50m
Delta
Sun 10/117:05 am
MEX
- MDW
1 stop8h 15m
Delta
Deal found 7/10![Delta logo]()
$486
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated July 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated July 14, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/168:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Sun 7/1910:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/9![Volaris logo]()
$360
This Super.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 7/178:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Wed 7/2210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$362
This Justfly.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Fri 7/178:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Sun 7/1910:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/9![Volaris logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Fri 8/76:17 pm
MDW
- QRO
1 stop29h 08m
Multiple Airlines
Wed 8/1211:20 pm
QRO
- MDW
2 stops20h 12m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/187:50 am
MDW
- CUN
1 stop7h 10m
Southwest
Thu 8/271:05 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/9![Southwest logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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.
Fri 8/218:23 pm
MDW
- GDL
Nonstop4h 07m
Multiple Airlines
Fri 8/287:57 am
GDL
- MDW
2 stops13h 50m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Fri 8/218:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Fri 9/49:38 pm
GDL
- MDW
1 stop19h 27m
Volaris
Deal found 7/9![Volaris logo]()
$371
This Justfly.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Fri 8/218:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/2410:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/13![Volaris logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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.
Fri 8/218:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Fri 8/289:38 pm
GDL
- MDW
1 stop19h 27m
Volaris
Deal found 7/11![Volaris logo]()
$376
This CheapOair deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/268:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 9/210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$345
This Justfly.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/268:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/3110:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/12![Volaris logo]()
$351
This FlightHub deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/308:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 9/210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/11![Volaris logo]()
$371
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 July 14, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated July 14, 2026.
This Super.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/218:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 7/13![Volaris logo]()
$123
This iWofly deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/12![Volaris logo]()
$132
This oojo deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 7/13![Volaris logo]()
$136
This FlightHub deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/288:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/10![Volaris logo]()
$137
This Super.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/12![Volaris logo]()
$141
This Super.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/218:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 7/14![Volaris logo]()
$142
This iWofly deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 7/11![Volaris logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 9/101:02 pm
MDW
- GDL
2 stops30h 20m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$147
This oojo deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/13![Volaris logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/37:30 pm
MDW
- GDL
1 stop15h 57m
Volaris
Deal found 7/10![Volaris logo]()
$152
This Super.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/268:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 7/10![Volaris logo]()
$153
This Super.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Sun 7/198:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 7/13![Volaris logo]()
$154
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 July 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $342 (Justfly.com) |
One-way from | $123 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $443 |
Good round-trip deal | $337 or less |
Good one-way deal | $150 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 July 14, 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
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 8/17
5:25 am-3:00 pm
1 stop9h 35m
Cancun
Wed 8/26
12:40 pm-4:15 pm
Nonstop3h 35m
$405
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 8/23
5:10 am-11:50 am
1 stop6h 40m
Cancun
Sun 8/30
2:40 pm-9:10 pm
1 stop6h 30m
$428
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 8/24
8:25 am-12:00 pm
Nonstop3h 35m
Cancun
Wed 9/2
12:40 pm-4:15 pm
Nonstop3h 35m
$432
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 8/26
9:24 am-8:05 pm
2 stops10h 41m
Cancun
Wed 9/2
9:11 am-10:36 pm
2 stops13h 25m
$443
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Thu 8/27
6:05 am-4:55 am
2 stops23h 50m
Morelia
Mon 8/31
6:40 am-8:31 pm
1 stop12h 51m
$459
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 8/10
7:55 am-1:30 pm
1 stop5h 35m
Cancun
Thu 8/27
1:05 pm-4:40 pm
Nonstop3h 35m
$467
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Sun 10/4
6:05 am-11:55 am
1 stop6h 50m
Mexico City Benito Juarez
Sat 10/10
1:10 pm-10:25 pm
1 stop8h 15m
$477
ChicagoMonterrey
MDW - MTY
MDWMTY
Chicago Midway
Fri 9/11
11:35 am-4:32 pm
1 stop5h 57m
Monterrey Gen Mariano Escobedo
Wed 9/16
12:16 pm-10:45 pm
1 stop9h 29m
$480
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Sat 10/3
11:35 am-9:50 pm
1 stop11h 15m
Mexico City Benito Juarez
Sun 10/11
7:05 am-4:20 pm
1 stop8h 15m
$486
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Mon 9/14
1:00 pm-7:15 pm
1 stop7h 15m
Mexico City Benito Juarez
Tue 9/29
1:20 pm-10:45 pm
1 stop8h 25m
$486
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-QRO
MDW-GDL
MDW-MEX
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-QRO
MDW-GDL
MDW-MEX
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 May is currently the most expensive (average of $216). 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 July 14, 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 15% on airfare.
How often are flights from Chicago to Mexico delayed?
About 20% 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 evening are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
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.
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.
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 July 14, 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.
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
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 July 14, 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 July 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$194 | Average$425 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$518 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$207 | Average$419 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$312 | Average$633 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$327 | Average$425 | FlexibilityNo cancel fee | On-timeN/A |