$119+ Cheap flights from Midway (MDW) to Mexico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
May 7 — May 141
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Mexico with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Midway to MexicoExplore the most affordable flight options available from Midway to Mexico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 7, 2026.
Explore the most affordable flight options available from Midway to Mexico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 7, 2026.
This Frontier deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/257:34 pm
MDW
- CUN
1 stop19h 22m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/4![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 4/3![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/5![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/251:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 4/2![Frontier logo]()
$270
This Expedia deal was found by Cheapflights users on 4/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/6![Frontier logo]()
$273
This Justfly.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Fri 4/174:07 pm
CUN
- MDW
1 stop26h 30m
Frontier
Deal found 4/2![Frontier logo]()
$274
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/251:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 4/5![Frontier logo]()
$280
This FlightHub deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/257:34 pm
MDW
- CUN
1 stop19h 22m
Frontier
Fri 5/14:07 pm
CUN
- MDW
1 stop26h 30m
Frontier
Deal found 4/3![Frontier logo]()
$282
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- CUN
1 stop23h 05m
Frontier
Mon 5/113:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/6![Frontier logo]()
$283
This Mytrip deal was found by Cheapflights users on 4/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:48 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Sun 5/312:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/7![Volaris logo]()
$295
This Mytrip deal was found by Cheapflights users on 4/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Wed 4/222:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/7![Volaris logo]()
$299
This Trip.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Thu 5/75:53 pm
MDW
- AGU
Nonstop4h 10m
Volaris
Thu 5/1411:52 am
AGU
- MDW
Nonstop3h 38m
Volaris
Deal found 4/5![Volaris logo]()
$337
Best flights from Midway to MexicoDiscover carefully curated flight deals from Midway to Mexico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 7, 2026.
Discover carefully curated flight deals from Midway to Mexico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 7, 2026.
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:00 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 5/63:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/3![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/196:00 am
MDW
- CUN
1 stop5h 30m
Delta
Tue 5/129:14 am
CUN
- MDW
2 stops11h 55m
Delta
Deal found 4/4![Delta logo]()
$338
This Jetabroad deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/32:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Sun 5/108:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/3![Volaris logo]()
$398
This CheapOair deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/272:32 pm
MDW
- MLM
Nonstop4h 09m
Multiple Airlines
Sun 5/36:53 am
MLM
- MDW
1 stop14h 22m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$462
This Frontier deal was found by Cheapflights users on 4/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/272:32 pm
MDW
- MLM
Nonstop4h 09m
Frontier
Wed 4/298:22 am
MLM
- MDW
Nonstop3h 53m
Frontier
Deal found 4/6![Frontier logo]()
$485
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:30 am
MDW
- CUN
Nonstop3h 30m
Southwest
Tue 5/123:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/5![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 4/6. 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.
Tue 4/287:25 am
MDW
- CUN
1 stop7h 55m
Southwest
Thu 5/144:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/6![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/136:00 am
MDW
- CUN
1 stop5h 30m
Delta
Fri 4/178:00 am
CUN
- MDW
1 stop14h 28m
Delta
Deal found 4/2![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/196:50 am
MDW
- CUN
1 stop6h 20m
Southwest
Tue 5/123:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/4![Southwest logo]()
$317
This Cheapflightsfares deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Sat 6/138:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/3![Volaris logo]()
$406
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:05 am
MDW
- CUN
1 stop14h 20m
Delta
Thu 7/93:36 pm
CUN
- MDW
1 stop6h 39m
Delta
Deal found 4/7![Delta logo]()
$378
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/195:05 am
MDW
- CUN
1 stop7h 45m
Southwest
Wed 4/223:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/5![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 4/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:27 am
MDW
- CUN
2 stops10h 48m
Delta
Tue 5/512:40 pm
CUN
- MDW
1 stop9h 48m
Delta
Deal found 4/6![Delta logo]()
$382
This CheapOair deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/276:20 am
MDW
- MLM
1 stop14h 49m
Multiple Airlines
Wed 5/138:22 am
MLM
- MDW
Nonstop3h 53m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$493
This Jetabroad deal was found by Cheapflights users on 4/7. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Mon 5/118:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/7![Volaris logo]()
$458
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1711:00 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 5/224:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/4![Southwest logo]()
$348
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/2712:52 pm
MDW
- MEX
1 stop9h 58m
Delta
Wed 5/208:40 am
MEX
- MDW
1 stop11h 29m
Delta
Deal found 4/2![Delta logo]()
$430
This Volaris deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/168:48 pm
MDW
- MEX
1 stop11h 37m
Volaris
Sun 5/1710:00 am
MEX
- MDW
1 stop8h 04m
Volaris
Deal found 4/5![Volaris logo]()
$475
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 4/275:35 am
MDW
- CUN
1 stop6h 45m
Southwest
Fri 5/13:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/2![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:53 pm
MDW
- MEX
1 stop7h 07m
Delta
Mon 5/1811:25 am
MEX
- MDW
1 stop8h 44m
Delta
Deal found 4/3![Delta logo]()
$430
This Mytrip deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/252:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Sat 5/1610:38 pm
MLM
- MDW
2 stops19h 26m
Volaris
Deal found 4/5![Volaris logo]()
$480
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:52 pm
MDW
- MEX
1 stop9h 58m
Delta
Tue 5/128:40 am
MEX
- MDW
1 stop11h 29m
Delta
Deal found 4/3![Delta logo]()
$430
This Mytrip deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Fri 5/88:23 pm
MDW
- MLM
2 stops26h 23m
Volaris
Thu 5/218:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 4/5![Volaris logo]()
$487
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:30 am
MDW
- CUN
1 stop7h 35m
Southwest
Sun 5/171:50 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/5![Southwest logo]()
$422
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:23 am
MDW
- MEX
1 stop6h 27m
Delta
Tue 5/197:05 am
MEX
- MDW
1 stop8h 07m
Delta
Deal found 4/7![Delta logo]()
$430
This CheapOair deal was found by Cheapflights users on 4/7. 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.
Tue 6/94:15 pm
MDW
- DGO
Nonstop3h 40m
Volaris
Tue 6/2310:16 am
DGO
- MDW
Nonstop3h 35m
Volaris
Deal found 4/7![Volaris logo]()
$495
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
MDW
- GDL
1 stop6h 37m
Delta
Tue 5/57:42 am
GDL
- MDW
2 stops13h 46m
Delta
Deal found 4/5![Delta logo]()
$436
This CheapOair deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” 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 6/122:32 pm
MDW
- MLM
Nonstop3h 59m
Volaris
Mon 6/228:14 am
MLM
- MDW
Nonstop4h 01m
Volaris
Deal found 4/2![Volaris logo]()
$502
This Delta deal was found by Cheapflights users on 4/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:53 pm
MDW
- MEX
1 stop9h 57m
Delta
Sat 5/308:40 am
MEX
- MDW
1 stop11h 29m
Delta
Deal found 4/7![Delta logo]()
$437
This Mytrip deal was found by Cheapflights users on 4/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Tue 5/1910:38 pm
MLM
- MDW
2 stops19h 26m
Volaris
Deal found 4/7![Volaris logo]()
$502
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated April 7, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated April 7, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 4/3![Frontier logo]()
$257
This Justfly.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Fri 4/174:07 pm
CUN
- MDW
1 stop26h 30m
Frontier
Deal found 4/2![Frontier logo]()
$274
This Mytrip deal was found by Cheapflights users on 4/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Wed 4/222:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/7![Volaris logo]()
$299
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/251:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 4/5![Frontier logo]()
$280
This Frontier deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/251:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 4/2![Frontier logo]()
$270
This Frontier deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/257:34 pm
MDW
- CUN
1 stop19h 22m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/4![Frontier logo]()
$251
This FlightHub deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/257:34 pm
MDW
- CUN
1 stop19h 22m
Frontier
Fri 5/14:07 pm
CUN
- MDW
1 stop26h 30m
Frontier
Deal found 4/3![Frontier logo]()
$282
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/5![Frontier logo]()
$260
This Expedia deal was found by Cheapflights users on 4/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/6![Frontier logo]()
$273
This Mytrip deal was found by Cheapflights users on 4/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:48 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Sun 5/312:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 4/7![Volaris logo]()
$295
This Trip.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Thu 5/75:53 pm
MDW
- AGU
Nonstop4h 10m
Volaris
Thu 5/1411:52 am
AGU
- MDW
Nonstop3h 38m
Volaris
Deal found 4/5![Volaris logo]()
$337
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- CUN
1 stop23h 05m
Frontier
Mon 5/113:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/6![Frontier logo]()
$283
One-way flights from Midway to MexicoSearch for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated April 7, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated April 7, 2026.
This Super.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 5/36:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/3![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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 4/306:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/3![Frontier logo]()
$120
This Trip.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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.
Tue 5/53:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$126
This Jetabroad deal was found by Cheapflights users on 4/7. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Deal found 4/7![Volaris logo]()
$128
This Super.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/186:00 am
MDW
- CUN
1 stop6h 46m
Frontier
Deal found 4/4![Frontier logo]()
$129
This Jetabroad deal was found by Cheapflights users on 4/7. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:23 pm
MDW
- MEX
1 stop12h 02m
Volaris
Deal found 4/7![Volaris logo]()
$130
This Frontier deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” 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.
Fri 4/176:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/3![Frontier logo]()
$130
This CheapOair deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/196:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/5![Frontier logo]()
$131
This Flightnetwork deal was found by Cheapflights users on 4/7. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Deal found 4/7![Volaris logo]()
$132
This Trip.com deal was found by Cheapflights users on 4/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:07 pm
MDW
- MEX
1 stop8h 38m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/93:07 pm
MDW
- GDL
1 stop24h 13m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$135
This Priceline deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:34 pm
MDW
- CUN
1 stop19h 22m
Frontier
Deal found 4/3![Frontier logo]()
$137
Find flight deals from Midway to Mexico
Keep the following information in mind while searching for Midway to Mexico flight deals. Data was last updated April 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Frontier) |
One-way from | $119 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $323 |
Good round-trip deal | $268 or less |
Good one-way deal | $103 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Mexico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 7, 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 5/3
11:00 am-2:35 pm
Nonstop3h 35m
Cancun
Wed 5/6
3:15 pm-6:55 pm
Nonstop3h 40m
$313
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 5/5
10:30 am-2:00 pm
Nonstop3h 30m
Cancun
Tue 5/12
3:15 pm-6:55 pm
Nonstop3h 40m
$313
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 4/28
7:25 am-3:20 pm
1 stop7h 55m
Cancun
Thu 5/14
4:10 pm-7:50 pm
Nonstop3h 40m
$317
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 4/19
6:50 am-1:10 pm
1 stop6h 20m
Cancun
Tue 5/12
3:15 pm-6:55 pm
Nonstop3h 40m
$317
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 4/19
5:05 am-12:50 pm
1 stop7h 45m
Cancun
Wed 4/22
3:15 pm-6:55 pm
Nonstop3h 40m
$317
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 4/19
6:00 am-11:30 am
1 stop5h 30m
Cancun
Tue 5/12
9:14 am-9:09 pm
2 stops11h 55m
$338
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 5/17
11:00 am-2:35 pm
Nonstop3h 35m
Cancun
Fri 5/22
4:10 pm-7:50 pm
Nonstop3h 40m
$348
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 4/27
5:35 am-12:20 pm
1 stop6h 45m
Cancun
Fri 5/1
3:15 pm-6:55 pm
Nonstop3h 40m
$357
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 4/13
6:00 am-11:30 am
1 stop5h 30m
Cancun
Fri 4/17
8:00 am-10:28 pm
1 stop14h 28m
$368
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 7/2
6:05 am-8:25 pm
1 stop14h 20m
Cancun
Thu 7/9
3:36 pm-10:15 pm
1 stop6h 39m
$378
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-MLM
MDW-CUN
MDW-MEX
MDW-PVR
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-MLM
MDW-CUN
MDW-MEX
MDW-PVR
What is the cheapest month to book a flight from Chicago Midway Airport to Mexico?
Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $144). Flying from Chicago Midway Airport to Mexico in November is currently the most expensive (average of $243). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to MX?
Find hourly flight availability from Midway to Mexico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 7, 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 24% on airfare.
How often are flights from Chicago to Mexico delayed?
About 16% of weekly flights between Chicago and Mexico have experienced delays in the past year, with the average delay time being 152 minutes.
What is the most punctual flight time for Chicago to Mexico flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
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, Southwest have had the lowest number of delays on this route, with just 15% of flights being delayed.
Reviews of airlines servicing Mexico
Get insights into the airlines that provide service to Mexico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Mexico. Reviews last updated April 7, 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.
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Mexico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Mexico
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Complete your trip
Complete your trip to Mexico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Mexico by cabin class
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 April 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Mexico flights
Consider these flights traveling from Midway to Mexico.
Fly to Mexico regions
Consider these flights traveling to Mexico regions.
Top 5 airlines flying from Midway to Mexico
Discover the top 5 airlines that operate flights from Midway to Mexico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$490 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$416 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$198 | Average$425 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$291 | Average$619 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$375 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |