$116+ Cheap flights from Midway (MDW) to Riviera Maya
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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
May 17 — May 241
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Riviera Maya with Cheapflights
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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 Riviera MayaExplore the most affordable flight options available from Midway to Riviera Maya. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
Explore the most affordable flight options available from Midway to Riviera Maya. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Mon 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Mon 5/113:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/13![Frontier logo]()
$272
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Thu 4/306:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/14![Frontier logo]()
$280
This FlightHub deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/1611:59 am
MDW
- CUN
1 stop26h 08m
Frontier
Mon 5/183:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/14![Frontier logo]()
$282
This FlightHub deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/266:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/13![Frontier logo]()
$284
This FlightHub deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/302:15 pm
MDW
- CUN
1 stop24h 41m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/13![Frontier logo]()
$292
This Frontier deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/292:15 pm
MDW
- CUN
2 stops19h 09m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/15![Frontier logo]()
$300
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/292:15 pm
MDW
- CUN
1 stop24h 41m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/14![Frontier logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Fri 4/244:07 pm
CUN
- MDW
1 stop26h 30m
Frontier
Deal found 4/13![Frontier logo]()
$307
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/96:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/14![Frontier logo]()
$311
This Mytrip deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 6/68:49 pm
MDW
- CZM
2 stops20h 08m
Volaris
Sat 6/134:47 pm
CZM
- MDW
2 stops25h 17m
Volaris
Deal found 4/12![Volaris logo]()
$790
This Mytrip deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/318:23 pm
MDW
- CZM
2 stops20h 34m
Volaris
Sat 6/64:47 pm
CZM
- MDW
2 stops25h 17m
Volaris
Deal found 4/16![Volaris logo]()
$809
This Aeromexico deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/186:00 am
MDW
- CZM
1 stop7h 57m
Aeromexico
Sat 4/252:14 pm
CZM
- MDW
1 stop7h 14m
Aeromexico
Deal found 4/13![Aeromexico logo]()
$898
Best flights from Midway to Riviera MayaDiscover carefully curated flight deals from Midway to Riviera Maya that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals from Midway to Riviera Maya that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 7/46:05 am
MDW
- CUN
1 stop8h 34m
Delta
Mon 7/138:00 am
CUN
- MDW
1 stop14h 15m
Delta
Deal found 4/14![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/49:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Thu 5/214:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/14![Southwest logo]()
$423
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/412:53 pm
MDW
- CUN
1 stop7h 23m
Delta
Wed 6/103:39 pm
CUN
- MDW
1 stop6h 38m
Delta
Deal found 4/13![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/210:59 am
MDW
- CUN
1 stop9h 17m
Delta
Thu 6/113:39 pm
CUN
- MDW
1 stop6h 38m
Delta
Deal found 4/13![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 7/55:05 am
MDW
- CUN
1 stop8h 05m
Southwest
Mon 7/134:10 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 4/15![Southwest logo]()
$452
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 6/269:17 am
MDW
- CUN
2 stops11h 08m
Delta
Fri 7/310:55 am
CUN
- MDW
1 stop11h 22m
Delta
Deal found 4/12![Delta logo]()
$402
This Mytrip deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/306:36 pm
MDW
- CZM
2 stops18h 54m
Multiple Airlines
Sat 6/64:47 pm
CZM
- MDW
2 stops25h 17m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$990
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 6/309:17 am
MDW
- CUN
2 stops11h 08m
Delta
Sat 7/412:35 pm
CUN
- MDW
1 stop9h 42m
Delta
Deal found 4/14![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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
- CUN
2 stops10h 38m
Delta
Wed 5/61:50 pm
CUN
- MDW
1 stop8h 38m
Delta
Deal found 4/16![Delta logo]()
$408
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/16:00 am
MDW
- CUN
1 stop5h 30m
Delta
Sat 5/98:00 am
CUN
- MDW
1 stop13h 09m
Delta
Deal found 4/17![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 7/309:20 am
MDW
- CUN
2 stops10h 55m
Delta
Mon 8/312:30 pm
CUN
- MDW
1 stop9h 45m
Delta
Deal found 4/15![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/316:23 am
MDW
- CUN
1 stop7h 39m
Delta
Sat 6/68:00 am
CUN
- MDW
2 stops10h 33m
Delta
Deal found 4/17![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 8/166:00 am
MDW
- CUN
1 stop14h 08m
Delta
Wed 8/193:20 pm
CUN
- MDW
1 stop6h 26m
Delta
Deal found 4/17![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/310:35 am
MDW
- CZM
2 stops26h 36m
Delta
Mon 10/124:18 pm
CZM
- MDW
2 stops23h 07m
Delta
Deal found 4/14![Delta logo]()
$930
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:35 am
MDW
- CZM
2 stops26h 36m
Delta
Thu 8/274:18 pm
CZM
- MDW
2 stops28h 28m
Delta
Deal found 4/17![Delta logo]()
$1,050
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:35 am
MDW
- CZM
2 stops26h 36m
Delta
Sun 8/301:13 pm
CZM
- MDW
2 stops26h 14m
Delta
Deal found 4/17![Delta logo]()
$1,090
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:35 am
MDW
- CZM
2 stops26h 36m
Delta
Mon 8/314:18 pm
CZM
- MDW
2 stops28h 28m
Delta
Deal found 4/17![Delta logo]()
$1,126
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 10/26:00 am
MDW
- CZM
2 stops32h 11m
Delta
Wed 10/74:18 pm
CZM
- MDW
2 stops39h 31m
Delta
Deal found 4/14![Delta logo]()
$1,130
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 10/21:05 pm
MDW
- CZM
2 stops25h 06m
Delta
Mon 10/124:18 pm
CZM
- MDW
2 stops39h 31m
Delta
Deal found 4/14![Delta logo]()
$1,130
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 10/11:05 pm
MDW
- CZM
2 stops26h 06m
Delta
Tue 10/64:18 pm
CZM
- MDW
2 stops39h 31m
Delta
Deal found 4/14![Delta logo]()
$1,130
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 10/110:35 am
MDW
- CZM
2 stops28h 36m
Delta
Thu 10/84:18 pm
CZM
- MDW
2 stops23h 07m
Delta
Deal found 4/14![Delta logo]()
$1,130
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 10/11:05 pm
MDW
- CZM
2 stops26h 06m
Delta
Wed 10/74:18 pm
CZM
- MDW
2 stops28h 27m
Delta
Deal found 4/14![Delta logo]()
$1,130
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 8/176:00 am
MDW
- CZM
2 stops33h 11m
Delta
Wed 8/194:18 pm
CZM
- MDW
2 stops28h 28m
Delta
Deal found 4/16![Delta logo]()
$1,210
Last-minute flights from Midway to Riviera MayaDiscover last-minute flight deals from Midway to Riviera Maya. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Riviera Maya. Data last updated April 17, 2026 and is based on user searches.
This Aeromexico deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/186:00 am
MDW
- CZM
1 stop7h 57m
Aeromexico
Sat 4/252:14 pm
CZM
- MDW
1 stop7h 14m
Aeromexico
Deal found 4/13![Aeromexico logo]()
$898
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Fri 4/244:07 pm
CUN
- MDW
1 stop26h 30m
Frontier
Deal found 4/13![Frontier logo]()
$307
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 4/256:00 am
MDW
- CZM
1 stop7h 57m
Delta
Sat 5/22:14 pm
CZM
- MDW
1 stop7h 14m
Delta
Deal found 4/16![Delta logo]()
$934
This FlightHub deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/266:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/13![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/292:15 pm
MDW
- CUN
2 stops19h 09m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/15![Frontier logo]()
$300
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/292:15 pm
MDW
- CUN
1 stop24h 41m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/14![Frontier logo]()
$303
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Thu 4/306:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 4/14![Frontier logo]()
$280
This FlightHub deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/302:15 pm
MDW
- CUN
1 stop24h 41m
Frontier
Mon 5/44:07 pm
CUN
- MDW
1 stop19h 02m
Frontier
Deal found 4/13![Frontier logo]()
$292
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Mon 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Mon 5/113:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/13![Frontier logo]()
$272
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/96:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Fri 5/153:22 pm
CUN
- MDW
1 stop19h 42m
Frontier
Deal found 4/14![Frontier logo]()
$311
This FlightHub deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/1611:59 am
MDW
- CUN
1 stop26h 08m
Frontier
Mon 5/183:22 pm
CUN
- MDW
1 stop19h 47m
Frontier
Deal found 4/14![Frontier logo]()
$282
This Mytrip deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/318:23 pm
MDW
- CZM
2 stops20h 34m
Volaris
Sat 6/64:47 pm
CZM
- MDW
2 stops25h 17m
Volaris
Deal found 4/16![Volaris logo]()
$809
One-way flights from Midway to Riviera MayaSearch for one-way flight options from Midway to Riviera Maya. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from Midway to Riviera Maya. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Frontier deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/96:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/13![Frontier logo]()
$116
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/76:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/16![Frontier logo]()
$125
This FlightHub deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/612:04 pm
MDW
- CUN
1 stop26h 03m
Frontier
Deal found 4/15![Frontier logo]()
$127
This Super.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/17![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- CUN
1 stop23h 05m
Frontier
Deal found 4/14![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/36:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/16![Frontier logo]()
$130
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/13![Frontier logo]()
$131
This Trip.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/306:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 4/15![Frontier logo]()
$132
This Priceline deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Thu 5/1412:19 pm
MDW
- CUN
1 stop25h 48m
Frontier
Deal found 4/16![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:07 pm
MDW
- CZM
2 stops25h 50m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1010:35 am
MDW
- CZM
2 stops26h 36m
Delta
Deal found 4/13![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/95:29 pm
MDW
- CZM
2 stops22h 51m
Delta
Deal found 4/12![Delta logo]()
$368
Find flight deals from Midway to Riviera Maya
Keep the following information in mind while searching for Midway to Riviera Maya flight deals. Data was last updated April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $272 (Expedia) |
One-way from | $116 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $470 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Riviera Maya 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 17, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Riviera Maya that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 7/4
6:05 am-2:39 pm
1 stop8h 34m
Cancun
Mon 7/13
8:00 am-10:15 pm
1 stop14h 15m
$398
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 6/4
12:53 pm-8:16 pm
1 stop7h 23m
Cancun
Wed 6/10
3:39 pm-10:17 pm
1 stop6h 38m
$398
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 6/2
10:59 am-8:16 pm
1 stop9h 17m
Cancun
Thu 6/11
3:39 pm-10:17 pm
1 stop6h 38m
$398
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 6/26
9:17 am-8:25 pm
2 stops11h 08m
Cancun
Fri 7/3
10:55 am-10:17 pm
1 stop11h 22m
$402
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 6/30
9:17 am-8:25 pm
2 stops11h 08m
Cancun
Sat 7/4
12:35 pm-10:17 pm
1 stop9h 42m
$402
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 4/29
6:00 am-4:38 pm
2 stops10h 38m
Cancun
Wed 5/6
1:50 pm-10:28 pm
1 stop8h 38m
$408
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/1
6:00 am-11:30 am
1 stop5h 30m
Cancun
Sat 5/9
8:00 am-9:09 pm
1 stop13h 09m
$418
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 5/4
9:35 am-1:10 pm
Nonstop3h 35m
Cancun
Thu 5/21
4:10 pm-7:50 pm
Nonstop3h 40m
$423
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 7/30
9:20 am-8:15 pm
2 stops10h 55m
Cancun
Mon 8/3
12:30 pm-10:15 pm
1 stop9h 45m
$447
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 5/31
6:23 am-2:02 pm
1 stop7h 39m
Cancun
Sat 6/6
8:00 am-6:33 pm
2 stops10h 33m
$447
Showing 1-10 of 44 resultsSorted by cheapest first
Best time to book a flight from Midway to Riviera Maya
Have a flexible travel schedule? Discover the best time to fly to Riviera Maya from Midway with our price prediction graph.
MDW-CUN
MDW-CZM
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 Riviera Maya
MDW-zzETW
MDW-CUN
MDW-CZM
What is the cheapest month to book a flight from Chicago Midway Airport to Riviera Maya?
Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Riviera Maya (average of $198). Flying from Chicago Midway Airport to Riviera Maya in June is currently the most expensive (average of $774). 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 ETW?
Find hourly flight availability from Midway to Riviera Maya. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.
When flying from Chicago Midway Airport to Riviera Maya, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Riviera Maya
Get insights into the airlines that provide service to Riviera Maya. 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 Riviera Maya. Reviews last updated April 17, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAeromexico from Chicago Midway Airport to Riviera Maya by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
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 Riviera Maya. 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 Riviera Maya
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Complete your trip
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Search flights from Midway to Riviera Maya by cabin class
Find flights from Midway to Riviera Maya, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Riviera Maya flights
Browse other Midway and Riviera Maya flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Midway to Riviera Maya
Discover the top 4 airlines that operate flights from Midway to Riviera Maya. 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$198 | Average$515 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$290 | Average$508 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$309 | Average$401 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$375 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |