$136+ 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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Jul 11 — Jul 181
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 11, 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 11, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 8/267:50 am
MDW
- CUN
1 stop7h 10m
Southwest
Wed 9/212:40 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/10![Southwest logo]()
$341
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/88:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 6/1110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/7![Volaris logo]()
$356
This Super.com deal was found by Cheapflights users on 6/9. 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.
Sat 6/138:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 6/2210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/9![Volaris logo]()
$361
This FlightHub deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/158:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/8![Volaris logo]()
$362
This Southwest deal was found by Cheapflights users on 6/10. 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 9/217:30 am
MDW
- CUN
1 stop6h 40m
Southwest
Thu 9/241:05 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/10![Southwest logo]()
$369
This FlightHub deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/138:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Sat 6/2010:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/8![Volaris logo]()
$372
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/208:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 6/2910:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/7![Volaris logo]()
$375
This FlightHub deal was found by Cheapflights users on 6/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 6/2410:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/9![Volaris logo]()
$376
This CheapOair deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 6/188:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Thu 6/2510:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/6![Volaris logo]()
$377
This Super.com deal was found by Cheapflights users on 6/10. 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.
Sat 6/208:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 6/2210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/10![Volaris logo]()
$378
This CheapOair deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 10/98:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Fri 10/162:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/8![Volaris logo]()
$381
This Super.com deal was found by Cheapflights users on 6/9. 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.
Fri 10/238:23 pm
MDW
- GDL
Nonstop4h 07m
Volaris
Sun 10/252:01 pm
GDL
- MDW
Nonstop4h 03m
Volaris
Deal found 6/9![Volaris logo]()
$391
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 11, 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 11, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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 8/98:40 am
MDW
- CUN
Nonstop3h 35m
Southwest
Thu 8/1311:35 am
CUN
- MDW
1 stop8h 35m
Southwest
Deal found 6/9![Southwest logo]()
$431
This Delta deal was found by Cheapflights users on 6/10. 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.
Sat 10/101:05 pm
MDW
- CUN
1 stop7h 10m
Delta
Wed 10/148:00 am
CUN
- MDW
1 stop8h 25m
Delta
Deal found 6/10![Delta logo]()
$468
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 9/48:23 pm
MDW
- ZCL
1 stop20h 37m
Volaris
Sun 9/138:01 am
ZCL
- MDW
Nonstop3h 45m
Volaris
Deal found 6/11![Volaris logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/82:32 pm
MDW
- MLM
Nonstop3h 59m
Multiple Airlines
Fri 8/217:07 pm
MLM
- MDW
3 stops26h 04m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$614
This Frontier deal was found by Cheapflights users on 6/10. 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.
Sat 10/317:25 am
MDW
- MLM
2 stops13h 58m
Frontier
Sun 11/89:00 am
MLM
- MDW
2 stops12h 53m
Frontier
Deal found 6/10![Frontier logo]()
$635
This Southwest deal was found by Cheapflights users on 6/10. 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.
Thu 11/127:50 am
MDW
- CUN
2 stops9h 05m
Southwest
Wed 11/181:45 pm
CUN
- MDW
1 stop10h 20m
Southwest
Deal found 6/10![Southwest logo]()
$444
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 9/156:05 am
MDW
- SJD
1 stop7h 05m
Delta
Tue 9/2212:15 pm
SJD
- MDW
1 stop8h 10m
Delta
Deal found 6/10![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 6/10. 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 7/65:05 am
MDW
- CUN
1 stop5h 50m
Southwest
Fri 7/1012:00 pm
CUN
- MDW
2 stops9h 20m
Southwest
Deal found 6/10![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 6/9. 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.
Mon 9/146:05 am
MDW
- SJD
1 stop7h 05m
Delta
Fri 9/1812:15 pm
SJD
- MDW
1 stop8h 10m
Delta
Deal found 6/9![Delta logo]()
$480
This Mytrip deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/152:03 pm
MDW
- ZCL
Nonstop3h 45m
Volaris
Sun 8/308:01 am
ZCL
- MDW
Nonstop3h 45m
Volaris
Deal found 6/6![Volaris logo]()
$529
This Southwest deal was found by Cheapflights users on 6/9. 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 9/215:55 am
MDW
- CUN
2 stops9h 05m
Southwest
Fri 9/2511:35 am
CUN
- MDW
2 stops8h 45m
Southwest
Deal found 6/9![Southwest logo]()
$462
This Delta deal was found by Cheapflights users on 6/9. 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 9/412:46 pm
MDW
- MEX
1 stop10h 04m
Delta
Wed 9/301:10 pm
MEX
- MDW
1 stop8h 15m
Delta
Deal found 6/9![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 6/206:00 am
MDW
- MEX
1 stop6h 55m
Delta
Fri 8/1411:10 am
MEX
- MDW
1 stop10h 26m
Delta
Deal found 6/9![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 7/228:20 am
MDW
- CUN
1 stop5h 40m
Southwest
Sat 7/2510:45 am
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/10![Southwest logo]()
$487
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 9/910:35 am
MDW
- MEX
1 stop9h 25m
Delta
Sat 9/267:05 am
MEX
- MDW
1 stop7h 30m
Delta
Deal found 6/10![Delta logo]()
$486
This Super.com deal was found by Cheapflights users on 6/9. 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.
Tue 7/72:03 pm
MDW
- ZCL
Nonstop3h 45m
Volaris
Tue 7/148:01 am
ZCL
- MDW
Nonstop3h 45m
Volaris
Deal found 6/9![Volaris logo]()
$652
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Sun 8/92:03 pm
MDW
- ZCL
Nonstop3h 45m
Multiple Airlines
Mon 8/178:54 pm
ZCL
- MDW
2 stops37h 15m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$740
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/287:30 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 7/311:45 am
CUN
- MDW
1 stop8h 40m
Southwest
Deal found 6/8![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/296:58 pm
MDW
- MEX
1 stop17h 32m
Delta
Thu 7/91:55 pm
MEX
- MDW
1 stop17h 42m
Delta
Deal found 6/8![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/88:40 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 8/281:05 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/6![Southwest logo]()
$514
This Volaris deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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.
Sat 7/258:49 pm
MDW
- MTY
1 stop11h 42m
Volaris
Sat 8/18:09 am
MTY
- MDW
1 stop10h 25m
Volaris
Deal found 6/6![Volaris logo]()
$689
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/36:00 am
MDW
- MLM
2 stops23h 55m
Frontier
Tue 7/77:58 am
MLM
- MDW
2 stops37h 05m
Frontier
Deal found 6/7![Frontier logo]()
$849
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/178:23 pm
MDW
- OAX
1 stop25h 46m
Multiple Airlines
Fri 7/318:56 am
OAX
- MDW
2 stops12h 07m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$773
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/276:00 am
MDW
- MEX
2 stops14h 05m
Delta
Fri 7/103:30 pm
MEX
- MDW
2 stops16h 43m
Delta
Deal found 6/8![Delta logo]()
$490
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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
Sat 8/2910:45 am
CUN
- MDW
1 stop9h 45m
Southwest
Deal found 6/6![Southwest logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 9/122:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Mon 9/218:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 6/6![Volaris logo]()
$697
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/38:23 pm
MDW
- MLM
2 stops19h 42m
Multiple Airlines
Sun 7/128:14 am
MLM
- MDW
Nonstop4h 01m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$778
This Delta deal was found by Cheapflights users on 6/9. 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 7/296:00 am
MDW
- MTY
2 stops12h 58m
Delta
Mon 8/37:49 am
MTY
- MDW
1 stop13h 47m
Delta
Deal found 6/9![Delta logo]()
$491
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:32 pm
MDW
- MLM
Nonstop3h 59m
Frontier
Tue 7/147:58 am
MLM
- MDW
2 stops37h 05m
Frontier
Deal found 6/10![Frontier logo]()
$903
This Southwest deal was found by Cheapflights users on 6/10. 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.
Sun 10/115:10 am
MDW
- CUN
1 stop8h 30m
Southwest
Sat 10/172:05 pm
CUN
- MDW
2 stops17h 20m
Southwest
Deal found 6/10![Southwest logo]()
$526
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated June 11, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/9. 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.
Sat 6/138:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 6/2210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/9![Volaris logo]()
$361
This FlightHub deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/138:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Sat 6/2010:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/8![Volaris logo]()
$372
This Super.com deal was found by Cheapflights users on 6/9. 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.
Sat 6/138:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 6/1510:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/9![Volaris logo]()
$379
This CheapOair deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/138:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Sun 6/2110:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/8![Volaris logo]()
$384
This FlightHub deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/158:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/8![Volaris logo]()
$362
This CheapOair deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 6/188:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Thu 6/2510:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/6![Volaris logo]()
$377
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/208:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 6/2910:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/7![Volaris logo]()
$375
This Super.com deal was found by Cheapflights users on 6/10. 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.
Sat 6/208:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 6/2210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/10![Volaris logo]()
$378
This FlightHub deal was found by Cheapflights users on 6/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 6/2410:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/9![Volaris logo]()
$376
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/18:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 7/911:10 am
CUN
- MDW
1 stop9h 22m
Volaris
Deal found 6/7![Volaris logo]()
$383
This CheapOair deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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
- CUN
1 stop13h 32m
Volaris
Fri 7/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/8![Volaris logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/218:49 pm
MDW
- MEX
1 stop11h 36m
Volaris
Thu 7/307:00 am
MEX
- MDW
1 stop12h 32m
Volaris
Deal found 6/7![Volaris logo]()
$406
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 11, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Super.com deal was found by Cheapflights users on 6/9. 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.
Sat 6/208:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 6/9![Volaris logo]()
$136
This FlightHub deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/8![Volaris logo]()
$142
This FlightHub deal was found by Cheapflights users on 6/10. 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.
Sun 7/58:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/10![Volaris logo]()
$146
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/178:58 pm
MDW
- CUN
1 stop12h 57m
Volaris
Deal found 6/7![Volaris logo]()
$152
This Super.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 6/188:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 6/6![Volaris logo]()
$153
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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
- CUN
1 stop13h 32m
Volaris
Deal found 6/7![Volaris logo]()
$154
This Super.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/148:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 6/8![Volaris logo]()
$155
This Super.com deal was found by Cheapflights users on 6/9. 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.
Fri 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/9![Volaris logo]()
$155
This CheapOair deal was found by Cheapflights users on 6/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/11![Volaris logo]()
$158
This CheapOair deal was found by Cheapflights users on 6/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/288:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/9![Volaris logo]()
$159
This CheapOair deal was found by Cheapflights users on 6/10. 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 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
Deal found 6/10![Volaris logo]()
$160
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:23 pm
MDW
- MTY
1 stop12h 08m
Volaris
Deal found 6/10![Volaris logo]()
$160
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 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $341 (Southwest) |
One-way from | $136 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $400 |
Good round-trip deal | $351 or less |
Good one-way deal | $178 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 11, 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
Sun 8/9
8:40 am-12:15 pm
Nonstop3h 35m
Cancun
Thu 8/13
11:35 am-8:10 pm
1 stop8h 35m
$431
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 11/12
7:50 am-5:55 pm
2 stops9h 05m
Cancun
Wed 11/18
1:45 pm-11:05 pm
1 stop10h 20m
$444
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 7/6
5:05 am-10:55 am
1 stop5h 50m
Cancun
Fri 7/10
12:00 pm-9:20 pm
2 stops9h 20m
$447
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 9/21
5:55 am-3:00 pm
2 stops9h 05m
Cancun
Fri 9/25
11:35 am-8:20 pm
2 stops8h 45m
$462
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 10/10
1:05 pm-8:15 pm
1 stop7h 10m
Cancun
Wed 10/14
8:00 am-4:25 pm
1 stop8h 25m
$468
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Tue 9/15
6:05 am-11:10 am
1 stop7h 05m
San José del Cabo Los Cabos
Tue 9/22
12:15 pm-10:25 pm
1 stop8h 10m
$480
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 9/14
6:05 am-11:10 am
1 stop7h 05m
San José del Cabo Los Cabos
Fri 9/18
12:15 pm-10:25 pm
1 stop8h 10m
$480
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Fri 9/4
12:46 pm-9:50 pm
1 stop10h 04m
Mexico City Benito Juarez
Wed 9/30
1:10 pm-10:25 pm
1 stop8h 15m
$486
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Sat 6/20
6:00 am-11:55 am
1 stop6h 55m
Mexico City Benito Juarez
Fri 8/14
11:10 am-10:36 pm
1 stop10h 26m
$486
ChicagoMexico City
MDW - MEX
MDWMEX
Chicago Midway
Wed 9/9
10:35 am-7:00 pm
1 stop9h 25m
Mexico City Benito Juarez
Sat 9/26
7:05 am-3:35 pm
1 stop7h 30m
$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-MEX
MDW-ZCL
MDW-MLM
MDW-SJD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Mexico
MDW-MX0
MDW-CUN
MDW-MEX
MDW-ZCL
MDW-MLM
What is the cheapest month to book a flight from Chicago Midway Airport to Mexico?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $101). Flying from Chicago Midway Airport to Mexico in June is currently the most expensive (average of $643). 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 11, 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 14% on airfare.
How often are flights from Chicago to Mexico delayed?
About 19% 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 11, 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
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 11, 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 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$170 | Average$415 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$194 | Average$610 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$468 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$280 | Average$627 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$377 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |