$124+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Jul 28 — Aug 41
Round-trip
1 adult, Economy
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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 June 28, 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 June 28, 2026.
This FlightHub deal was found by Cheapflights users on 6/27. 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.
Sat 7/188:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/27![Volaris logo]()
$351
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/178:25 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 8/2612:40 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/25![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
Tue 8/2512:50 pm
CUN
- MDW
1 stop6h 20m
Southwest
Deal found 6/24![Southwest logo]()
$373
This FlightHub deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/68:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 7/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/25![Volaris logo]()
$383
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/208:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Mon 8/312:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/23![Volaris logo]()
$386
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Fri 8/282:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/27![Volaris logo]()
$389
This FlightHub deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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.
Thu 7/168:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 7/2010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/25![Volaris logo]()
$390
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Mon 8/312:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/27![Volaris logo]()
$392
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Sun 8/302:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/27![Volaris logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/168:49 pm
MDW
- MEX
1 stop11h 36m
Volaris
Sat 7/257:00 am
MEX
- MDW
1 stop9h 26m
Volaris
Deal found 6/25![Volaris logo]()
$400
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 10/46:55 am
MDW
- CUN
1 stop6h 05m
Southwest
Wed 10/72:45 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 6/25![Southwest logo]()
$400
This CheapOair deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
- MEX
1 stop12h 02m
Volaris
Sun 8/308:10 am
MEX
- MDW
1 stop9h 54m
Volaris
Deal found 6/24![Volaris logo]()
$401
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 June 28, 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 June 28, 2026.
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/178:25 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 8/261:10 pm
CUN
- MDW
1 stop7h 35m
Southwest
Deal found 6/25![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 6/27. 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 9/146:05 am
MDW
- MEX
1 stop6h 50m
Delta
Tue 9/297:05 am
MEX
- MDW
1 stop8h 11m
Delta
Deal found 6/27![Delta logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/197:25 am
MDW
- MLM
2 stops13h 58m
Multiple Airlines
Fri 9/258:14 am
MLM
- MDW
Nonstop4h 01m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$511
This Volaris deal was found by Cheapflights users on 6/26. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:49 pm
MDW
- MTY
1 stop11h 42m
Volaris
Thu 8/138:09 am
MTY
- MDW
1 stop10h 25m
Volaris
Deal found 6/26![Volaris logo]()
$513
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:05 am
MDW
- MLM
2 stops39h 04m
Frontier
Sun 9/136:40 am
MLM
- MDW
1 stop28h 27m
Frontier
Deal found 6/27![Frontier logo]()
$610
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:54 am
MDW
- MEX
1 stop9h 11m
Delta
Tue 9/227:05 am
MEX
- MDW
1 stop8h 11m
Delta
Deal found 6/25![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 11/912:25 pm
MDW
- CUN
1 stop6h 20m
Southwest
Sun 11/158:20 am
CUN
- MDW
2 stops9h 40m
Southwest
Deal found 6/24![Southwest logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Sun 8/92:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Thu 8/278:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 6/27![Volaris logo]()
$519
This Delta deal was found by Cheapflights users on 6/27. 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.
Sat 8/226:11 am
MDW
- MEX
1 stop6h 44m
Delta
Wed 8/261:20 pm
MEX
- MDW
1 stop8h 16m
Delta
Deal found 6/27![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
Mon 8/311:05 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/24![Southwest logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Wed 8/192:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Tue 8/258:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 6/27![Volaris logo]()
$529
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/136:05 am
MDW
- MEX
1 stop8h 50m
Delta
Tue 9/227:05 am
MEX
- MDW
1 stop14h 40m
Delta
Deal found 6/23![Delta logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/102:32 pm
MDW
- MLM
Nonstop3h 59m
Multiple Airlines
Mon 8/179:06 am
MLM
- MDW
2 stops24h 49m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$614
This Delta deal was found by Cheapflights users on 6/27. 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.
Thu 9/106:05 am
MDW
- MTY
1 stop11h 27m
Delta
Wed 9/168:42 am
MTY
- MDW
2 stops13h 03m
Delta
Deal found 6/27![Delta logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 8/184:15 pm
MDW
- DGO
Nonstop3h 40m
Volaris
Wed 9/26:31 pm
DGO
- MDW
2 stops22h 34m
Volaris
Deal found 6/27![Volaris logo]()
$536
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:05 am
MDW
- MLM
2 stops39h 18m
Frontier
Mon 8/176:40 am
MLM
- MDW
2 stops14h 23m
Frontier
Deal found 6/27![Frontier logo]()
$655
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/207:55 pm
MDW
- CUN
2 stops16h 05m
Southwest
Mon 8/241:00 pm
CUN
- MDW
2 stops9h 20m
Southwest
Deal found 6/24![Southwest logo]()
$542
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Fri 7/248:23 pm
MDW
- MLM
2 stops19h 42m
Multiple Airlines
Tue 7/288:14 am
MLM
- MDW
Nonstop4h 01m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$618
This Volaris deal was found by Cheapflights users on 6/27. 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 7/318:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Tue 8/410:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/27![Volaris logo]()
$539
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/2012:46 pm
MDW
- BJX
2 stops11h 31m
Delta
Wed 8/268:02 am
BJX
- MDW
2 stops13h 34m
Delta
Deal found 6/23![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 6/27. 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.
Thu 7/305:15 am
MDW
- PVR
1 stop9h 50m
Southwest
Thu 8/61:15 pm
PVR
- MDW
1 stop8h 00m
Southwest
Deal found 6/27![Southwest logo]()
$549
This Delta deal was found by Cheapflights users on 6/26. 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 9/96:05 am
MDW
- BJX
2 stops14h 30m
Delta
Mon 9/288:12 am
BJX
- MDW
2 stops13h 33m
Delta
Deal found 6/26![Delta logo]()
$492
This CheapOair deal was found by Cheapflights users on 6/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Wed 8/198:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 6/26![Volaris logo]()
$549
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/245:30 am
MDW
- PVR
2 stops9h 45m
Southwest
Sun 8/302:45 pm
PVR
- MDW
2 stops13h 55m
Southwest
Deal found 6/23![Southwest logo]()
$574
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:35 am
MDW
- CUN
1 stop9h 35m
Delta
Thu 12/101:40 pm
CUN
- MDW
1 stop9h 30m
Delta
Deal found 6/23![Delta logo]()
$492
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Sun 7/268:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 6/27![Volaris logo]()
$559
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/239:25 pm
MDW
- PVR
2 stops14h 40m
Southwest
Thu 7/303:00 pm
PVR
- MDW
1 stop7h 05m
Southwest
Deal found 6/25![Southwest logo]()
$592
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/286:05 am
MDW
- CUN
1 stop5h 20m
Delta
Sun 10/48:05 am
CUN
- MDW
1 stop8h 11m
Delta
Deal found 6/23![Delta logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Sat 8/88:49 pm
MDW
- PVR
1 stop15h 47m
Volaris
Sat 8/1510:00 am
PVR
- MDW
1 stop8h 34m
Volaris
Deal found 6/27![Volaris logo]()
$571
This Southwest deal was found by Cheapflights users on 6/26. 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 7/255:25 am
MDW
- PVR
2 stops10h 35m
Southwest
Sun 7/2612:55 pm
PVR
- MDW
1 stop10h 25m
Southwest
Deal found 6/26![Southwest logo]()
$592
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated June 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated June 28, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Tue 7/77:00 am
MEX
- MDW
1 stop8h 51m
Volaris
Deal found 6/26![Volaris logo]()
$408
This FlightHub deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/68:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 7/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/25![Volaris logo]()
$383
This CheapOair deal was found by Cheapflights users on 6/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Fri 7/107:00 am
MEX
- MDW
1 stop9h 22m
Volaris
Deal found 6/26![Volaris logo]()
$406
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/23![Volaris logo]()
$369
This FlightHub deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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.
Thu 7/168:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 7/2010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/25![Volaris logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/168:49 pm
MDW
- MEX
1 stop11h 36m
Volaris
Sat 7/257:00 am
MEX
- MDW
1 stop9h 26m
Volaris
Deal found 6/25![Volaris logo]()
$400
This FlightHub deal was found by Cheapflights users on 6/27. 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.
Sat 7/188:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/27![Volaris logo]()
$351
This CheapOair deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Sun 7/198:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Mon 7/277:00 am
MEX
- MDW
1 stop9h 22m
Volaris
Deal found 6/23![Volaris logo]()
$405
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/208:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Mon 8/312:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/23![Volaris logo]()
$386
This CheapOair deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:49 pm
MDW
- MEX
1 stop11h 36m
Volaris
Tue 7/287:00 am
MEX
- MDW
1 stop8h 51m
Volaris
Deal found 6/24![Volaris logo]()
$407
This Trip.com deal was found by Cheapflights users on 6/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 8/611:10 am
CUN
- MDW
1 stop9h 22m
Volaris
Deal found 6/27![Volaris logo]()
$402
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Fri 8/282:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/27![Volaris logo]()
$389
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 June 28, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated June 28, 2026.
This iWofly deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Fri 8/288:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/23![Volaris logo]()
$124
This Super.com deal was found by Cheapflights users on 6/26. 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 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
Deal found 6/26![Volaris logo]()
$125
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/158:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 6/23![Volaris logo]()
$135
This Super.com deal was found by Cheapflights users on 6/26. 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 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
Deal found 6/26![Volaris logo]()
$137
This FlightHub deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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
Deal found 6/25![Volaris logo]()
$139
This FlightHub deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/58:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/23![Volaris logo]()
$142
This Super.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
- CUN
1 stop14h 32m
Volaris
Deal found 6/24![Volaris logo]()
$143
This CheapOair deal was found by Cheapflights users on 6/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:49 pm
MDW
- MEX
1 stop11h 36m
Volaris
Deal found 6/28![Volaris logo]()
$147
This CheapOair deal was found by Cheapflights users on 6/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 6/27![Volaris logo]()
$148
This Trip.com deal was found by Cheapflights users on 6/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/27![Volaris logo]()
$148
This Super.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/108:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/25![Volaris logo]()
$154
This CheapOair deal was found by Cheapflights users on 6/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 6/26![Volaris logo]()
$155
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 June 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $351 (FlightHub) |
One-way from | $124 (iWofly) |
Popular in | December |
Cheapest in | January |
Average price | $400 |
Good round-trip deal | $341 or less |
Good one-way deal | $124 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 June 28, 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
8:25 am-12:00 pm
Nonstop3h 35m
Cancun
Wed 8/26
1:10 pm-8:45 pm
1 stop7h 35m
$369
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Mon 9/14
6:05 am-11:55 am
1 stop6h 50m
Mexico City Benito Juarez
Tue 9/29
7:05 am-4:16 pm
1 stop8h 11m
$486
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Wed 9/2
10:54 am-7:05 pm
1 stop9h 11m
Mexico City Benito Juarez
Tue 9/22
7:05 am-4:16 pm
1 stop8h 11m
$486
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Sat 8/22
6:11 am-11:55 am
1 stop6h 44m
Mexico City Benito Juarez
Wed 8/26
1:20 pm-10:36 pm
1 stop8h 16m
$486
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Sun 9/13
6:05 am-1:55 pm
1 stop8h 50m
Mexico City Benito Juarez
Tue 9/22
7:05 am-10:45 pm
1 stop14h 40m
$486
ChicagoMonterrey
MDW - MTY
MDWMTY
Chicago Midway
Thu 9/10
6:05 am-4:32 pm
1 stop11h 27m
Monterrey Gen Mariano Escobedo
Wed 9/16
8:42 am-10:45 pm
2 stops13h 03m
$486
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 11/9
12:25 pm-7:45 pm
1 stop6h 20m
Cancun
Sun 11/15
8:20 am-5:00 pm
2 stops9h 40m
$488
ChicagoLeón
MDW - BJX
MDWBJX
Chicago Midway
Thu 8/20
12:46 pm-11:17 pm
2 stops11h 31m
León Del Bajio
Wed 8/26
8:02 am-10:36 pm
2 stops13h 34m
$492
ChicagoLeón
MDW - BJX
MDWBJX
Chicago Midway
Wed 9/9
6:05 am-7:35 pm
2 stops14h 30m
León Del Bajio
Mon 9/28
8:12 am-10:45 pm
2 stops13h 33m
$492
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 12/3
10:35 am-9:10 pm
1 stop9h 35m
Cancun
Thu 12/10
1:40 pm-10:10 pm
1 stop9h 30m
$492
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-GDL
MDW-MEX
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-GDL
MDW-MEX
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 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 June 28, 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 150 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 16% 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 June 28, 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.
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
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 June 28, 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 June 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$193 | Average$464 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$194 | Average$425 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$468 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$231 | Average$420 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$301 | Average$629 | FlexibilityNo cancel fee | On-time63% |