$136+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jun 27 — Jul 41
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Riviera Maya 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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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 Riviera Maya
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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 May 28, 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 May 28, 2026.
This Super.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/88:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 6/1110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 5/27![Volaris logo]()
$342
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/118:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Wed 6/1710:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/25![Volaris logo]()
$349
This FlightHub deal was found by Cheapflights users on 5/23. 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 6/118:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 5/23![Volaris logo]()
$356
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/128:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 6/1710:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/25![Volaris logo]()
$358
This FlightHub deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 5/26![Volaris logo]()
$360
This FlightHub deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/108:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 7/1310:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/26![Volaris logo]()
$362
This FlightHub deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 6/1210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/26![Volaris logo]()
$366
This Mytrip deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:23 pm
MDW
- CZM
2 stops19h 34m
Volaris
Tue 10/64:47 pm
CZM
- MDW
2 stops26h 17m
Volaris
Deal found 5/25![Volaris logo]()
$719
This Mytrip deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 9/57:30 pm
MDW
- CZM
3 stops20h 27m
Volaris
Tue 9/84:47 pm
CZM
- MDW
2 stops26h 17m
Volaris
Deal found 5/27![Volaris logo]()
$791
This Mytrip deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:23 pm
MDW
- CZM
2 stops19h 34m
Volaris
Mon 9/74:47 pm
CZM
- MDW
3 stops25h 18m
Volaris
Deal found 5/25![Volaris logo]()
$820
This Mytrip deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:23 pm
MDW
- CZM
2 stops19h 34m
Volaris
Sat 6/64:47 pm
CZM
- MDW
3 stops25h 18m
Volaris
Deal found 5/25![Volaris logo]()
$860
This Mytrip deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 9/12:32 pm
MDW
- CZM
3 stops25h 25m
Volaris
Wed 9/164:47 pm
CZM
- MDW
3 stops25h 18m
Volaris
Deal found 5/26![Volaris logo]()
$972
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 May 28, 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 May 28, 2026.
This Delta deal was found by Cheapflights users on 5/23. 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.
Sun 7/56:00 am
MDW
- CUN
1 stop8h 39m
Delta
Tue 7/143:36 pm
CUN
- MDW
1 stop6h 39m
Delta
Deal found 5/23![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 5/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:50 am
MDW
- CUN
1 stop7h 10m
Southwest
Tue 8/2512:50 pm
CUN
- MDW
1 stop6h 20m
Southwest
Deal found 5/24![Southwest logo]()
$432
This Mytrip deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:23 pm
MDW
- CZM
2 stops19h 34m
Volaris
Tue 10/64:47 pm
CZM
- MDW
3 stops26h 17m
Volaris
Deal found 5/25![Volaris logo]()
$748
This Delta deal was found by Cheapflights users on 5/23. 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.
Thu 7/2311:05 am
MDW
- CUN
1 stop9h 18m
Delta
Tue 7/2810:55 am
CUN
- MDW
1 stop11h 20m
Delta
Deal found 5/23![Delta logo]()
$408
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/410:55 am
MDW
- CUN
1 stop9h 30m
Delta
Wed 7/812:35 pm
CUN
- MDW
1 stop9h 40m
Delta
Deal found 5/26![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/176:25 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 7/223:25 pm
CUN
- MDW
Nonstop3h 30m
Southwest
Deal found 5/27![Southwest logo]()
$524
This Delta deal was found by Cheapflights users on 5/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
MDW
- CUN
1 stop5h 25m
Delta
Tue 7/288:00 am
CUN
- MDW
2 stops10h 25m
Delta
Deal found 5/24![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/69:17 am
MDW
- CUN
2 stops11h 08m
Delta
Mon 7/278:00 am
CUN
- MDW
1 stop14h 15m
Delta
Deal found 5/27![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 5/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 am
MDW
- CUN
1 stop5h 20m
Delta
Sat 8/1510:55 am
CUN
- MDW
1 stop11h 41m
Delta
Deal found 5/24![Delta logo]()
$468
This Delta deal was found by Cheapflights users on 5/23. 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.
Thu 8/276:05 am
MDW
- CUN
1 stop8h 17m
Delta
Thu 9/33:22 pm
CUN
- MDW
1 stop7h 14m
Delta
Deal found 5/23![Delta logo]()
$503
This Mytrip deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:23 pm
MDW
- CZM
2 stops19h 34m
Volaris
Mon 9/74:47 pm
CZM
- MDW
3 stops25h 18m
Volaris
Deal found 5/25![Volaris logo]()
$820
This Delta deal was found by Cheapflights users on 5/23. 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.
Fri 7/316:00 am
MDW
- CUN
1 stop7h 05m
Delta
Tue 8/42:10 pm
CUN
- MDW
1 stop8h 26m
Delta
Deal found 5/23![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 8/56:05 am
MDW
- CUN
1 stop8h 17m
Delta
Mon 8/108:05 am
CUN
- MDW
1 stop14h 31m
Delta
Deal found 5/27![Delta logo]()
$513
This Mytrip deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 9/12:32 pm
MDW
- CZM
3 stops25h 25m
Volaris
Wed 9/164:47 pm
CZM
- MDW
3 stops25h 18m
Volaris
Deal found 5/26![Volaris logo]()
$972
This Delta deal was found by Cheapflights users on 5/23. 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.
Sun 11/226:00 am
MDW
- CZM
2 stops32h 23m
Delta
Thu 11/263:11 pm
CZM
- MDW
2 stops31h 34m
Delta
Deal found 5/23![Delta logo]()
$1,100
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 10/175:25 pm
MDW
- CZM
2 stops21h 13m
Delta
Sun 10/251:13 pm
CZM
- MDW
2 stops27h 12m
Delta
Deal found 5/27![Delta logo]()
$1,111
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 10/51:00 pm
MDW
- CZM
2 stops26h 32m
Delta
Fri 10/94:09 pm
CZM
- MDW
2 stops24h 16m
Delta
Deal found 5/25![Delta logo]()
$1,145
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 11/11:05 pm
MDW
- CZM
2 stops25h 18m
Delta
Fri 11/63:11 pm
CZM
- MDW
2 stops26h 14m
Delta
Deal found 5/27![Delta logo]()
$1,181
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 10/86:00 am
MDW
- CZM
2 stops33h 32m
Delta
Mon 10/124:09 pm
CZM
- MDW
2 stops40h 40m
Delta
Deal found 5/26![Delta logo]()
$1,181
This Delta deal was found by Cheapflights users on 5/23. 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 11/2410:35 am
MDW
- CZM
2 stops26h 40m
Delta
Thu 11/263:11 pm
CZM
- MDW
2 stops31h 34m
Delta
Deal found 5/23![Delta logo]()
$1,220
This Delta deal was found by Cheapflights users on 5/23. 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 11/241:05 pm
MDW
- CZM
2 stops24h 10m
Delta
Mon 11/304:26 pm
CZM
- MDW
2 stops30h 19m
Delta
Deal found 5/23![Delta logo]()
$1,220
This Delta deal was found by Cheapflights users on 5/23. 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.
Sun 11/226:00 am
MDW
- CZM
2 stops32h 23m
Delta
Mon 11/304:26 pm
CZM
- MDW
2 stops24h 59m
Delta
Deal found 5/23![Delta logo]()
$1,220
Last-minute flights from Midway to Riviera MayaDiscover last-minute flight deals from Midway to Riviera Maya. Data last updated May 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Riviera Maya. Data last updated May 28, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:23 pm
MDW
- CZM
2 stops19h 34m
Volaris
Sat 6/64:47 pm
CZM
- MDW
3 stops25h 18m
Volaris
Deal found 5/25![Volaris logo]()
$860
This FlightHub deal was found by Cheapflights users on 5/24. 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.
Fri 6/58:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 6/1210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/24![Volaris logo]()
$367
This Super.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/88:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 6/1110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 5/27![Volaris logo]()
$342
This FlightHub deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 6/1210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/26![Volaris logo]()
$366
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/118:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Wed 6/1710:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/25![Volaris logo]()
$349
This FlightHub deal was found by Cheapflights users on 5/23. 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 6/118:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 5/23![Volaris logo]()
$356
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/128:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 6/1710:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 5/25![Volaris logo]()
$358
This FlightHub deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 5/26![Volaris logo]()
$360
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/176:00 am
MDW
- CZM
2 stops33h 11m
Delta
Wed 6/244:02 pm
CZM
- MDW
2 stops40h 35m
Delta
Deal found 5/25![Delta logo]()
$1,312
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/176:00 am
MDW
- CZM
2 stops33h 11m
Delta
Fri 6/263:39 pm
CZM
- MDW
2 stops30h 38m
Delta
Deal found 5/25![Delta logo]()
$1,351
This Aeromexico deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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.
Thu 6/1812:50 pm
MDW
- CZM
2 stops26h 26m
Aeromexico
Thu 6/253:30 pm
CZM
- MDW
2 stops24h 46m
Aeromexico
Deal found 5/25![Aeromexico logo]()
$1,356
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/304:25 pm
MDW
- CZM
2 stops22h 15m
Delta
Thu 7/93:25 pm
CZM
- MDW
2 stops30h 50m
Delta
Deal found 5/27![Delta logo]()
$1,220
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 May 28, 2026.
Search for one-way flight options from Midway to Riviera Maya. Find affordable one-way fares based on user searches. Data last updated May 28, 2026.
This FlightHub deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/288:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 5/27![Volaris logo]()
$136
This FlightHub deal was found by Cheapflights users on 5/23. 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.
Mon 6/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 5/23![Volaris logo]()
$141
This FlightHub deal was found by Cheapflights users on 5/24. 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.
Sat 6/208:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 5/24![Volaris logo]()
$142
This Super.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 5/25![Volaris logo]()
$153
This Gotogate deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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.
Mon 8/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 5/25![Volaris logo]()
$154
This Kissandfly.com deal was found by Cheapflights users on 5/23. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 5/23![Volaris logo]()
$158
This FlightHub deal was found by Cheapflights users on 5/24. 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.
Fri 6/128:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 5/24![Volaris logo]()
$160
This Super.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/208:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 5/26![Volaris logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 5/26![Volaris logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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.
Mon 9/78:23 pm
MDW
- CUN
1 stop24h 52m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$163
This Super.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 5/25![Volaris logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 10/168:23 pm
MDW
- CZM
2 stops19h 34m
Volaris
Deal found 5/27![Volaris logo]()
$208
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 May 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $342 (Super.com) |
One-way from | $136 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $449 |
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 May 28, 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
Sun 7/5
6:00 am-2:39 pm
1 stop8h 39m
Cancun
Tue 7/14
3:36 pm-10:15 pm
1 stop6h 39m
$408
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 7/23
11:05 am-8:23 pm
1 stop9h 18m
Cancun
Tue 7/28
10:55 am-10:15 pm
1 stop11h 20m
$408
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 7/4
10:55 am-8:25 pm
1 stop9h 30m
Cancun
Wed 7/8
12:35 pm-10:15 pm
1 stop9h 40m
$408
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 8/18
7:50 am-3:00 pm
1 stop7h 10m
Cancun
Tue 8/25
12:50 pm-7:10 pm
1 stop6h 20m
$432
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 7/21
6:00 am-11:25 am
1 stop5h 25m
Cancun
Tue 7/28
8:00 am-6:25 pm
2 stops10h 25m
$443
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 7/6
9:17 am-8:25 pm
2 stops11h 08m
Cancun
Mon 7/27
8:00 am-10:15 pm
1 stop14h 15m
$443
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 8/8
6:05 am-11:25 am
1 stop5h 20m
Cancun
Sat 8/15
10:55 am-10:36 pm
1 stop11h 41m
$468
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 8/27
6:05 am-2:22 pm
1 stop8h 17m
Cancun
Thu 9/3
3:22 pm-10:36 pm
1 stop7h 14m
$503
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 7/31
6:00 am-1:05 pm
1 stop7h 05m
Cancun
Tue 8/4
2:10 pm-10:36 pm
1 stop8h 26m
$503
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 8/5
6:05 am-2:22 pm
1 stop8h 17m
Cancun
Mon 8/10
8:05 am-10:36 pm
1 stop14h 31m
$513
Showing 1-10 of 41 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 $719). 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 May 28, 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.
How far ahead should I book a flight from Chicago Midway Airport to Riviera Maya?
The price you pay for your flight from Chicago Midway Airport to Riviera Maya may vary depending on when you book. For the best chance of a lower fare, look to book 6 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 May 28, 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.
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
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 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 May 28, 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 May 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$198 | Average$515 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$300 | Average$513 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$309 | Average$452 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$377 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |