$105+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Mar 6 — Mar 131
1 adult, Economy
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Find cheap flights from Midway to Mexico with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 February 4, 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 February 4, 2026.
This Frontier deal was found by Cheapflights users on 2/3. 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/3![Frontier logo]()
$250
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$255
This Frontier deal was found by Cheapflights users on 2/3. 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 2/286:25 am
MDW
- CUN
1 stop7h 57m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/3![Frontier logo]()
$256
This Frontier deal was found by Cheapflights users on 2/2. 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.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 54m
Frontier
Deal found 2/2![Frontier logo]()
$278
This Priceline deal was found by Cheapflights users on 2/3. 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.
Wed 3/47:15 am
MDW
- CUN
1 stop24h 36m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/3![Frontier logo]()
$279
This eDestinos deal was found by Cheapflights users on 2/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:05 am
MDW
- CUN
1 stop8h 54m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/2![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:53 pm
MDW
- CUN
1 stop12h 13m
Frontier
Mon 3/210:19 am
CUN
- MDW
1 stop10h 28m
Frontier
Deal found 2/3![Frontier logo]()
$289
This Gotogate deal was found by Cheapflights users on 2/3. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Thu 3/121:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/2![Volaris logo]()
$307
This Trip.com deal was found by Cheapflights users on 2/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:32 pm
MDW
- MLM
Nonstop4h 00m
Volaris
Sun 4/198:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/4![Volaris logo]()
$316
This Trip.com deal was found by Cheapflights users on 2/3. 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 3/102:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Sat 5/28:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/3![Volaris logo]()
$317
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Thu 3/127:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Fri 3/201:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/3![Volaris logo]()
$318
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 February 4, 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 February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/3. 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.
Mon 3/94:05 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Thu 3/128:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/3![Southwest logo]()
$293
This Trip.com deal was found by Cheapflights users on 2/3. 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 3/102:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Sat 5/28:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/3![Volaris logo]()
$317
This Delta deal was found by Cheapflights users on 2/3. 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.
Sun 3/16:00 am
MDW
- CUN
1 stop9h 45m
Delta
Thu 3/58:00 am
CUN
- MDW
1 stop10h 45m
Delta
Deal found 2/3![Delta logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/203:00 pm
MDW
- MTY
1 stop8h 59m
Multiple Airlines
Sun 3/18:20 pm
MTY
- MDW
2 stops23h 27m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$378
This Aeromexico deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:47 pm
MDW
- BJX
2 stops11h 20m
Aeromexico
Wed 4/89:20 am
BJX
- MDW
1 stop12h 11m
Aeromexico
Deal found 2/1![Aeromexico logo]()
$434
This Southwest deal was found by Cheapflights users on 2/2. 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 3/94:05 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Fri 3/138:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/2![Southwest logo]()
$293
This Priceline deal was found by Cheapflights users on 2/3. 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.
Fri 3/66:05 am
MDW
- OAX
2 stops34h 07m
Frontier
Mon 3/98:40 am
OAX
- MDW
2 stops32h 33m
Frontier
Deal found 2/3![Frontier logo]()
$592
This FlightHub deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Tue 3/108:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/1![Volaris logo]()
$319
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 3/64:05 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Mon 3/98:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/2![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2811:06 am
MDW
- CUN
1 stop9h 05m
Delta
Sat 3/78:00 am
CUN
- MDW
1 stop8h 21m
Delta
Deal found 2/1![Delta logo]()
$338
This FlightHub deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/12:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Sun 3/88:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/1![Volaris logo]()
$319
This Southwest deal was found by Cheapflights users on 2/2. 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.
Thu 3/54:05 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Mon 3/98:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/2![Southwest logo]()
$303
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Fri 3/137:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Tue 3/171:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/3![Volaris logo]()
$322
This Delta deal was found by Cheapflights users on 2/3. 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.
Mon 4/1310:43 am
MDW
- CUN
1 stop9h 31m
Delta
Wed 4/2212:40 pm
CUN
- MDW
1 stop9h 48m
Delta
Deal found 2/3![Delta logo]()
$367
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Tue 2/172:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Thu 3/59:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/3![Volaris logo]()
$322
This Aeromexico deal was found by Cheapflights users on 2/3. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/410:43 am
MDW
- BJX
2 stops23h 12m
Aeromexico
Sun 5/108:05 pm
BJX
- MDW
2 stops24h 04m
Aeromexico
Deal found 2/3![Aeromexico logo]()
$434
This Delta deal was found by Cheapflights users on 2/2. 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.
Fri 3/209:35 am
MDW
- CUN
2 stops10h 45m
Delta
Wed 3/258:00 am
CUN
- MDW
1 stop9h 22m
Delta
Deal found 2/2![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sun 3/84:35 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Wed 3/111:10 pm
CUN
- MDW
1 stop6h 30m
Southwest
Deal found 2/2![Southwest logo]()
$347
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Fri 5/82:32 pm
MDW
- MLM
Nonstop4h 00m
Volaris
Wed 5/138:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/3![Volaris logo]()
$322
This Aeromexico deal was found by Cheapflights users on 2/2. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2811:06 am
MDW
- MEX
1 stop9h 44m
Aeromexico
Wed 3/48:55 am
MEX
- MDW
2 stops13h 36m
Aeromexico
Deal found 2/2![Aeromexico logo]()
$444
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Sun 2/226:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Wed 2/251:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/3![Volaris logo]()
$327
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:05 am
MDW
- CUN
Nonstop3h 45m
Southwest
Wed 3/188:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/1![Southwest logo]()
$363
This Aeromexico deal was found by Cheapflights users on 2/3. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- BJX
2 stops18h 20m
Aeromexico
Mon 5/46:10 pm
BJX
- MDW
2 stops21h 15m
Aeromexico
Deal found 2/3![Aeromexico logo]()
$454
This Delta deal was found by Cheapflights users on 2/2. 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.
Thu 4/236:00 am
MDW
- MTY
1 stop6h 40m
Delta
Tue 4/288:00 am
MTY
- MDW
1 stop13h 28m
Delta
Deal found 2/2![Delta logo]()
$415
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Mon 3/98:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/2![Volaris logo]()
$330
This Delta deal was found by Cheapflights users on 2/3. 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.
Thu 4/910:45 am
MDW
- MTY
1 stop8h 05m
Delta
Wed 4/155:46 am
MTY
- MDW
2 stops9h 43m
Delta
Deal found 2/3![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 3/71:25 pm
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 3/118:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/2![Southwest logo]()
$378
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Mon 3/168:15 am
MLM
- MDW
Nonstop3h 49m
Volaris
Deal found 2/2![Volaris logo]()
$330
This Aeromexico deal was found by Cheapflights users on 2/3. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:00 am
MDW
- PVR
1 stop7h 17m
Aeromexico
Wed 3/46:03 am
PVR
- MDW
2 stops16h 28m
Aeromexico
Deal found 2/3![Aeromexico logo]()
$517
This Delta deal was found by Cheapflights users on 2/2. 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.
Thu 3/126:00 am
MDW
- MEX
1 stop9h 10m
Delta
Wed 3/188:40 am
MEX
- MDW
1 stop12h 51m
Delta
Deal found 2/2![Delta logo]()
$431
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated February 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:53 pm
MDW
- CUN
1 stop12h 13m
Frontier
Mon 3/210:19 am
CUN
- MDW
1 stop10h 28m
Frontier
Deal found 2/3![Frontier logo]()
$289
This Frontier deal was found by Cheapflights users on 2/3. 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 2/286:25 am
MDW
- CUN
1 stop7h 57m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/3![Frontier logo]()
$256
This Priceline deal was found by Cheapflights users on 2/3. 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.
Wed 3/47:15 am
MDW
- CUN
1 stop24h 36m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/3![Frontier logo]()
$279
This Gotogate deal was found by Cheapflights users on 2/3. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Thu 3/121:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/2![Volaris logo]()
$307
This Frontier deal was found by Cheapflights users on 2/3. 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/3![Frontier logo]()
$250
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sun 3/84:35 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Thu 3/128:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/2![Southwest logo]()
$293
This Trip.com deal was found by Cheapflights users on 2/3. 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 3/102:32 pm
MDW
- MLM
Nonstop4h 16m
Volaris
Sat 5/28:15 am
MLM
- MDW
Nonstop4h 00m
Volaris
Deal found 2/3![Volaris logo]()
$317
This eDestinos deal was found by Cheapflights users on 2/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:05 am
MDW
- CUN
1 stop8h 54m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/2![Frontier logo]()
$282
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Thu 3/127:54 pm
MDW
- GDL
Nonstop4h 30m
Volaris
Fri 3/201:39 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 2/3![Volaris logo]()
$318
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/157:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Thu 3/1910:39 am
CUN
- MDW
1 stop7h 55m
Volaris
Deal found 2/2![Volaris logo]()
$295
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 February 4, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Kissandfly.com deal was found by Cheapflights users on 2/2. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/2![Volaris logo]()
$105
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/2![Volaris logo]()
$107
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/217:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/2![Volaris logo]()
$114
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Tue 3/36:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/3![Volaris logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/223:00 pm
MDW
- GDL
1 stop22h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$117
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/2![Volaris logo]()
$123
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Thu 3/197:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/3![Volaris logo]()
$124
This Frontier deal was found by Cheapflights users on 2/3. 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Deal found 2/3![Frontier logo]()
$125
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:05 am
MDW
- CUN
1 stop8h 54m
Frontier
Deal found 2/2![Frontier logo]()
$126
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Fri 2/277:53 pm
MDW
- SJD
1 stop18h 22m
Frontier
Deal found 2/3![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:16 pm
MDW
- MEX
1 stop25h 14m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$128
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Wed 3/186:05 am
MDW
- CUN
1 stop8h 54m
Frontier
Deal found 2/3![Frontier logo]()
$128
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 February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $250 (Frontier) |
One-way from | $105 (Kissandfly.com) |
Popular in | December |
Cheapest in | April |
Average price | $305 |
Good round-trip deal | $285 or less |
Good one-way deal | $128 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 February 4, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Mexico that are best for you.
Fly from
Midway
Fly to
Mexico
Route
Depart
Return
Price
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 3/9
4:05 pm-7:45 pm
Nonstop3h 40m
Cancun
Thu 3/12
8:30 am-12:10 pm
Nonstop3h 40m
$293
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 3/9
4:05 pm-7:45 pm
Nonstop3h 40m
Cancun
Fri 3/13
8:30 am-12:10 pm
Nonstop3h 40m
$293
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 3/6
4:05 pm-8:45 pm
Nonstop3h 40m
Cancun
Mon 3/9
8:30 am-12:10 pm
Nonstop3h 40m
$303
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 3/5
4:05 pm-8:45 pm
Nonstop3h 40m
Cancun
Mon 3/9
8:30 am-12:10 pm
Nonstop3h 40m
$303
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Tue 3/10
2:32 pm-5:48 pm
Nonstop4h 16m
Morelia
Sat 5/2
8:15 am-1:15 pm
Nonstop4h 00m
$317
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Fri 3/6
2:32 pm-6:48 pm
Nonstop4h 16m
Morelia
Tue 3/10
8:15 am-1:04 pm
Nonstop3h 49m
$319
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Sun 3/1
2:32 pm-6:48 pm
Nonstop4h 16m
Morelia
Sun 3/8
8:15 am-1:04 pm
Nonstop3h 49m
$319
ChicagoGuadalajara
MDW - GDL
MDWGDL
Chicago Midway
Fri 3/13
7:54 pm-11:24 pm
Nonstop4h 30m
Guadalajara Miguel Hidal
Tue 3/17
1:39 pm-6:34 pm
Nonstop3h 55m
$322
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Tue 2/17
2:32 pm-6:48 pm
Nonstop4h 16m
Morelia
Thu 3/5
9:15 am-1:04 pm
Nonstop3h 49m
$322
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Fri 5/8
2:32 pm-5:32 pm
Nonstop4h 00m
Morelia
Wed 5/13
8:15 am-1:15 pm
Nonstop4h 00m
$322
Showing 1-10 of 60 results
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-SJD
MDW-MEX
MDW-MLM
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-SJD
MDW-MEX
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 $103). 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 February 4, 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 27% 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 146 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?
Friday tends to have the lowest number of delays on this route, whereas Monday 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 12% 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 February 4, 2026.
See what other customers who have flown with Southwest, Delta, and Aeromexico 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.
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 February 4, 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 6 airlines flying from Midway to Mexico
Discover the top 6 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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$410 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$190 | Average$339 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$200 | Average$398 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$295 | Average$623 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$358 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |