$106+ 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 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Apr 23 — Apr 301
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Mexico
Cheapest
Best
Last-minute
One-way
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 March 24, 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 March 24, 2026.
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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
Thu 4/1612:04 pm
CUN
- MDW
1 stop10h 18m
Frontier
Deal found 3/22![Frontier logo]()
$251
This Trip.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/21![Frontier logo]()
$254
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Tue 4/71:31 pm
CUN
- MDW
1 stop8h 48m
Frontier
Deal found 3/20![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/115:17 pm
CUN
- MDW
1 stop7h 20m
Frontier
Deal found 3/23![Frontier logo]()
$258
This Expedia deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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
Wed 4/154:07 pm
CUN
- MDW
1 stop27h 24m
Frontier
Deal found 3/23![Frontier logo]()
$260
This Travelocity deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 3/23![Frontier logo]()
$261
This Trip.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- CUN
1 stop9h 05m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/20![Frontier logo]()
$265
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Mon 5/113:39 pm
CUN
- MDW
2 stops19h 33m
Frontier
Deal found 3/20![Frontier logo]()
$266
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/23![Frontier logo]()
$271
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Wed 5/136:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Mon 5/183:22 pm
CUN
- MDW
1 stop19h 50m
Frontier
Deal found 3/20![Frontier logo]()
$274
This FlightHub deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Wed 5/62:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 3/24![Volaris logo]()
$287
This FlightHub deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:48 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Mon 5/112:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 3/23![Volaris logo]()
$288
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 March 24, 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 March 24, 2026.
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/216:00 am
MDW
- CUN
1 stop8h 01m
Delta
Fri 4/243:15 pm
CUN
- MDW
1 stop7h 13m
Delta
Deal found 3/19![Delta logo]()
$339
This CheapOair deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/22:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Sat 5/98:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 3/21![Volaris logo]()
$343
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/96:10 am
MDW
- CUN
Nonstop3h 35m
Southwest
Tue 5/123:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/19![Southwest logo]()
$344
This CheapOair deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/112:32 pm
MDW
- MLM
Nonstop4h 09m
Multiple Airlines
Sun 4/196:53 am
MLM
- MDW
1 stop14h 25m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$429
This FlightHub deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/252:32 pm
MDW
- MLM
Nonstop4h 09m
Frontier
Tue 4/288:07 pm
MLM
- MDW
2 stops46h 24m
Frontier
Deal found 3/19![Frontier logo]()
$605
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/76:23 am
MDW
- CUN
1 stop13h 53m
Delta
Thu 5/143:02 pm
CUN
- MDW
1 stop6h 07m
Delta
Deal found 3/22![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/2510:40 am
MDW
- CUN
Nonstop3h 30m
Southwest
Sat 5/24:00 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/19![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/166:23 am
MDW
- CUN
1 stop6h 17m
Delta
Tue 5/198:00 am
CUN
- MDW
1 stop8h 12m
Delta
Deal found 3/19![Delta logo]()
$359
This CheapOair deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:15 pm
MDW
- DGO
Nonstop3h 59m
Volaris
Tue 5/1910:26 am
DGO
- MDW
Nonstop3h 25m
Volaris
Deal found 3/23![Volaris logo]()
$396
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Thu 4/234:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/23![Southwest logo]()
$422
This Volaris deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/28:48 pm
MDW
- MEX
1 stop11h 37m
Volaris
Tue 5/58:10 am
MEX
- MDW
1 stop10h 10m
Volaris
Deal found 3/19![Volaris logo]()
$443
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/126:00 am
MDW
- CUN
1 stop8h 08m
Delta
Wed 4/151:50 pm
CUN
- MDW
1 stop8h 38m
Delta
Deal found 3/19![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/47:50 am
MDW
- CUN
1 stop6h 20m
Southwest
Mon 5/114:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/21![Southwest logo]()
$432
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/126:00 am
MDW
- CUN
1 stop8h 08m
Delta
Mon 4/208:00 am
CUN
- MDW
1 stop14h 28m
Delta
Deal found 3/22![Delta logo]()
$422
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/1810:40 am
MDW
- CUN
Nonstop3h 30m
Southwest
Tue 4/211:20 pm
CUN
- MDW
1 stop8h 05m
Southwest
Deal found 3/22![Southwest logo]()
$450
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:32 pm
MDW
- MLM
Nonstop4h 09m
Frontier
Fri 4/248:22 am
MLM
- MDW
Nonstop3h 53m
Frontier
Deal found 3/23![Frontier logo]()
$609
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
MDW
- MEX
1 stop6h 50m
Delta
Tue 4/287:05 am
MEX
- MDW
1 stop8h 21m
Delta
Deal found 3/23![Delta logo]()
$428
This CheapOair deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/102:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Mon 4/208:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 3/20![Volaris logo]()
$538
This FlightHub deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/142:32 pm
MDW
- MLM
Nonstop4h 09m
Frontier
Tue 4/218:04 am
MLM
- MDW
2 stops37h 10m
Frontier
Deal found 3/21![Frontier logo]()
$611
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/1510:41 am
MDW
- MEX
1 stop12h 09m
Delta
Wed 4/2211:30 am
MEX
- MDW
1 stop9h 58m
Delta
Deal found 3/19![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/146:10 am
MDW
- PVR
1 stop8h 10m
Southwest
Tue 4/211:20 pm
PVR
- MDW
1 stop6h 15m
Southwest
Deal found 3/19![Southwest logo]()
$484
This Mytrip deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/183:04 pm
MDW
- DGO
2 stops19h 15m
Volaris
Tue 4/2810:26 am
DGO
- MDW
Nonstop3h 25m
Volaris
Deal found 3/20![Volaris logo]()
$561
This FlightHub deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 am
MDW
- MLM
2 stops33h 10m
Frontier
Sat 6/68:14 am
MLM
- MDW
Nonstop4h 01m
Frontier
Deal found 3/23![Frontier logo]()
$618
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/510:41 am
MDW
- MEX
1 stop12h 09m
Delta
Tue 5/197:05 am
MEX
- MDW
1 stop8h 07m
Delta
Deal found 3/22![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/45:25 am
MDW
- SJD
1 stop7h 20m
Southwest
Sat 5/912:40 pm
SJD
- MDW
1 stop13h 55m
Southwest
Deal found 3/20![Southwest logo]()
$499
This Mytrip deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/163:04 pm
MDW
- MLM
2 stops23h 54m
Volaris
Thu 4/238:22 am
MLM
- MDW
Nonstop3h 53m
Volaris
Deal found 3/19![Volaris logo]()
$563
This Frontier deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/182:32 pm
MDW
- MLM
Nonstop4h 09m
Frontier
Mon 5/48:07 pm
MLM
- MDW
2 stops17h 05m
Frontier
Deal found 3/19![Frontier logo]()
$623
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/239:22 am
MDW
- CUN
2 stops10h 54m
Delta
Sat 5/308:00 am
CUN
- MDW
2 stops10h 33m
Delta
Deal found 3/21![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/1310:59 am
MDW
- MEX
1 stop11h 51m
Delta
Sat 5/231:20 pm
MEX
- MDW
1 stop6h 49m
Delta
Deal found 3/20![Delta logo]()
$437
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/15:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Fri 5/13:05 pm
SJD
- MDW
1 stop11h 55m
Southwest
Deal found 3/19![Southwest logo]()
$539
Last-minute flights from Midway to MexicoDiscover last-minute flight deals from Midway to Mexico. Data last updated March 24, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Mexico. Data last updated March 24, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Tue 4/71:31 pm
CUN
- MDW
1 stop8h 48m
Frontier
Deal found 3/20![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/115:17 pm
CUN
- MDW
1 stop7h 20m
Frontier
Deal found 3/23![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/23![Frontier logo]()
$271
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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
Thu 4/1612:04 pm
CUN
- MDW
1 stop10h 18m
Frontier
Deal found 3/22![Frontier logo]()
$251
This Trip.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/21![Frontier logo]()
$254
This Expedia deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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
Wed 4/154:07 pm
CUN
- MDW
1 stop27h 24m
Frontier
Deal found 3/23![Frontier logo]()
$260
This Trip.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- CUN
1 stop9h 05m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/20![Frontier logo]()
$265
This Booking.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Tue 5/122:25 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 3/20![Volaris logo]()
$298
This Expedia deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Tue 4/284:07 pm
CUN
- MDW
1 stop27h 24m
Frontier
Deal found 3/23![Frontier logo]()
$274
This Trip.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/226:15 am
MDW
- CUN
1 stop8h 41m
Frontier
Sat 4/251:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/21![Frontier logo]()
$266
This Travelocity deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 3/23![Frontier logo]()
$261
This FlightHub deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Wed 5/62:09 pm
GDL
- MDW
Nonstop3h 55m
Volaris
Deal found 3/24![Volaris logo]()
$287
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 March 24, 2026.
Search for one-way flight options from Midway to Mexico. Find affordable one-way fares based on user searches. Data last updated March 24, 2026.
This Super.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Deal found 3/23![Frontier logo]()
$106
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Deal found 3/20![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Deal found 3/23![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 3/23![Frontier logo]()
$119
This Mytrip deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Mon 4/208:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Deal found 3/22![Volaris logo]()
$120
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- CUN
1 stop9h 05m
Frontier
Deal found 3/23![Frontier logo]()
$121
This FlightHub deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/18:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Deal found 3/23![Volaris logo]()
$122
This FlightHub deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/52:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Deal found 3/23![Volaris logo]()
$122
This Jetabroad deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Tue 4/142:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Deal found 3/20![Volaris logo]()
$123
This Mytrip deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Sun 4/192:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Deal found 3/20![Volaris logo]()
$124
This Mytrip deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/72:32 pm
MDW
- MLM
Nonstop4h 09m
Volaris
Deal found 3/20![Volaris logo]()
$125
This Mytrip deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Sun 5/178:23 pm
MDW
- GDL
Nonstop4h 24m
Volaris
Deal found 3/20![Volaris logo]()
$126
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 March 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Frontier) |
One-way from | $106 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $353 |
Good round-trip deal | $254 or less |
Good one-way deal | $91 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 March 24, 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
Tue 4/21
6:00 am-2:01 pm
1 stop8h 01m
Cancun
Fri 4/24
3:15 pm-10:28 pm
1 stop7h 13m
$339
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Sat 5/2
2:32 pm-5:41 pm
Nonstop4h 09m
Morelia
Sat 5/9
8:22 am-1:15 pm
Nonstop3h 53m
$343
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/9
6:10 am-9:45 am
Nonstop3h 35m
Cancun
Tue 5/12
3:15 pm-6:55 pm
Nonstop3h 40m
$344
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 5/7
6:23 am-8:16 pm
1 stop13h 53m
Cancun
Thu 5/14
3:02 pm-9:09 pm
1 stop6h 07m
$359
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/16
6:23 am-12:40 pm
1 stop6h 17m
Cancun
Tue 5/19
8:00 am-4:12 pm
1 stop8h 12m
$359
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 4/25
10:40 am-2:10 pm
Nonstop3h 30m
Cancun
Sat 5/2
4:00 pm-7:40 pm
Nonstop3h 40m
$365
ChicagoDurango
MDW - DGO
MDWDGO
Chicago Midway
Sat 5/9
4:15 pm-7:14 pm
Nonstop3h 59m
Durango Guadalupe Victoria
Tue 5/19
10:26 am-2:51 pm
Nonstop3h 25m
$396
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 4/12
6:00 am-2:08 pm
1 stop8h 08m
Cancun
Wed 4/15
1:50 pm-10:28 pm
1 stop8h 38m
$404
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 4/16
9:35 am-1:10 pm
Nonstop3h 35m
Cancun
Thu 4/23
4:10 pm-7:50 pm
Nonstop3h 40m
$422
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 4/12
6:00 am-2:08 pm
1 stop8h 08m
Cancun
Mon 4/20
8:00 am-10:28 pm
1 stop14h 28m
$422
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-GDL
MDW-PVR
MDW-CUN
MDW-MTY
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-GDL
MDW-PVR
MDW-CUN
MDW-MTY
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 $101). 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 March 24, 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 at noon 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 149 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 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 13% 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 March 24, 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.
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Top regions
Alternative routes for Midway to Mexico
See prices for flight routes from nearby airports that may be better suited for you.
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 March 24, 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 March 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$417 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$198 | Average$420 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$292 | Average$606 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$358 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |