$96+ Cheap flights from Chicago (CHI) 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Chicago 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 Chicago to Riviera Maya
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Cheapest flights from Chicago to Riviera MayaExplore the most affordable flight options available from Chicago to Riviera Maya. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Chicago to Riviera Maya. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Gotogate deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/236:23 am
ORD
- CUN
1 stop14h 03m
Multiple Airlines
Wed 3/47:19 pm
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/2411:59 pm
ORD
- CUN
1 stop14h 29m
Multiple Airlines
Thu 2/261:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/2411:59 pm
ORD
- CUN
1 stop8h 49m
Multiple Airlines
Fri 2/271:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$239
This Flightnetwork deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/57:35 am
ORD
- CUN
1 stop13h 28m
Multiple Airlines
Tue 4/1410:40 am
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:59 pm
ORD
- CUN
1 stop14h 29m
Multiple Airlines
Fri 2/271:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Wed 2/256:23 am
ORD
- CUN
1 stop14h 03m
Multiple Airlines
Fri 3/611:40 am
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$242
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:15 am
ORD
- CUN
1 stop6h 05m
Spirit Airlines
Wed 3/41:25 pm
CUN
- ORD
1 stop6h 46m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/236:10 am
ORD
- CUN
Nonstop4h 04m
Frontier
Wed 2/257:19 pm
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 2/11![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
- CUN
1 stop15h 04m
Multiple Airlines
Wed 3/47:19 pm
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$245
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/10![Frontier logo]()
$246
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/236:10 am
ORD
- CUN
Nonstop4h 04m
Frontier
Thu 2/266:27 pm
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 2/11![Frontier logo]()
$246
This Frontier deal was found by Cheapflights users on 2/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:10 am
ORD
- CUN
Nonstop4h 04m
Frontier
Fri 3/611:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 2/12![Frontier logo]()
$247
Best flights from Chicago to Riviera MayaDiscover carefully curated flight deals from Chicago to Riviera Maya that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Chicago to Riviera Maya that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/71:25 pm
MDW
- CUN
Nonstop3h 35m
Southwest
Tue 3/108:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/9![Southwest logo]()
$298
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:34 am
ORD
- CUN
Nonstop3h 56m
United Airlines
Wed 3/113:45 pm
CUN
- ORD
Nonstop4h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/2510:35 am
ORD
- CUN
2 stops9h 36m
Delta
Thu 3/56:01 am
CUN
- ORD
1 stop7h 54m
Delta
Deal found 2/11![Delta logo]()
$332
This Aeromexico deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:00 am
MDW
- CZM
1 stop7h 55m
Aeromexico
Wed 3/112:00 pm
CZM
- MDW
1 stop7h 31m
Aeromexico
Deal found 2/9![Aeromexico logo]()
$562
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:00 am
ORD
- CUN
1 stop7h 50m
United Airlines
Thu 3/122:18 pm
CUN
- ORD
Nonstop3h 51m
United Airlines
Deal found 2/9![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/310:49 am
MDW
- CUN
1 stop9h 22m
Delta
Thu 3/58:00 am
CUN
- MDW
1 stop10h 45m
Delta
Deal found 2/8![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/1012:25 pm
MDW
- CUN
1 stop7h 35m
Southwest
Fri 3/138:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/10![Southwest logo]()
$341
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:33 am
ORD
- CUN
Nonstop4h 00m
United Airlines
Tue 3/173:45 pm
CUN
- ORD
Nonstop4h 00m
United Airlines
Deal found 2/10![United Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/166:34 pm
MDW
- CUN
1 stop15h 16m
Delta
Thu 3/2610:00 am
CUN
- MDW
1 stop12h 31m
Delta
Deal found 2/8![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/165:45 am
ORD
- CUN
1 stop6h 09m
United Airlines
Wed 2/185:55 pm
CUN
- ORD
1 stop7h 31m
United Airlines
Deal found 2/9![United Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/2612:45 pm
MDW
- CUN
1 stop7h 26m
Delta
Thu 3/511:00 am
CUN
- MDW
1 stop7h 45m
Delta
Deal found 2/11![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:35 am
ORD
- CUN
1 stop6h 15m
United Airlines
Tue 2/245:55 pm
CUN
- ORD
1 stop7h 31m
United Airlines
Deal found 2/11![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/246:00 am
MDW
- CUN
1 stop7h 03m
Delta
Tue 3/31:40 pm
CUN
- MDW
1 stop9h 53m
Delta
Deal found 2/11![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/45:25 am
ORD
- CUN
2 stops12h 22m
Delta
Sun 3/84:45 pm
CUN
- ORD
1 stop7h 09m
Delta
Deal found 2/9![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/246:45 am
ORD
- CUN
1 stop7h 50m
Delta
Wed 3/412:25 pm
CUN
- ORD
1 stop9h 19m
Delta
Deal found 2/9![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/217:10 am
ORD
- CUN
1 stop13h 10m
Delta
Wed 3/2510:50 am
CUN
- ORD
1 stop7h 44m
Delta
Deal found 2/11![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/217:10 am
ORD
- CUN
1 stop13h 10m
Delta
Thu 3/2610:00 am
CUN
- ORD
1 stop6h 49m
Delta
Deal found 2/11![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/235:25 am
ORD
- CUN
1 stop10h 20m
Delta
Wed 3/43:00 pm
CUN
- ORD
1 stop6h 44m
Delta
Deal found 2/9![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/265:25 am
ORD
- CUN
1 stop14h 46m
Delta
Sun 3/84:45 pm
CUN
- ORD
1 stop7h 09m
Delta
Deal found 2/9![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/169:35 am
MDW
- CUN
2 stops23h 25m
Delta
Wed 3/2510:00 am
CUN
- MDW
2 stops22h 53m
Delta
Deal found 2/8![Delta logo]()
$342
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/412:45 pm
MDW
- CUN
1 stop7h 26m
Delta
Tue 3/1011:15 am
CUN
- MDW
1 stop6h 07m
Delta
Deal found 2/9![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/312:45 pm
MDW
- CUN
1 stop7h 26m
Delta
Fri 3/68:00 am
CUN
- MDW
1 stop10h 45m
Delta
Deal found 2/9![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/171:10 pm
MDW
- CUN
2 stops7h 10m
Delta
Wed 3/258:00 am
CUN
- MDW
2 stops9h 54m
Delta
Deal found 2/11![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:49 am
MDW
- CUN
1 stop9h 22m
Delta
Tue 3/1011:15 am
CUN
- MDW
1 stop6h 07m
Delta
Deal found 2/9![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/226:00 am
MDW
- CUN
1 stop14h 20m
Delta
Tue 3/3110:00 am
CUN
- MDW
1 stop12h 31m
Delta
Deal found 2/11![Delta logo]()
$383
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/245:37 pm
ORD
- CZM
2 stops20h 18m
Delta
Fri 2/273:10 pm
CZM
- ORD
2 stops18h 31m
Delta
Deal found 2/9![Delta logo]()
$548
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/246:20 pm
MDW
- CZM
2 stops20h 37m
Delta
Thu 2/263:10 pm
CZM
- MDW
1 stop7h 21m
Delta
Deal found 2/10![Delta logo]()
$558
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/26:45 am
ORD
- CZM
1 stop7h 10m
Delta
Wed 3/112:00 pm
CZM
- ORD
1 stop8h 54m
Delta
Deal found 2/9![Delta logo]()
$562
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/176:00 am
MDW
- CZM
1 stop7h 45m
Delta
Wed 3/253:15 pm
CZM
- MDW
1 stop16h 35m
Delta
Deal found 2/8![Delta logo]()
$562
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/35:37 pm
ORD
- CZM
2 stops20h 18m
Delta
Tue 3/102:00 pm
CZM
- ORD
1 stop8h 54m
Delta
Deal found 2/9![Delta logo]()
$566
Last-minute flights from Chicago to Riviera MayaDiscover last-minute flight deals from Chicago to Riviera Maya. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Riviera Maya. Data last updated February 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:59 pm
ORD
- CUN
1 stop14h 29m
Multiple Airlines
Wed 3/41:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$241
This Gotogate deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/236:23 am
ORD
- CUN
1 stop14h 03m
Multiple Airlines
Wed 3/47:19 pm
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/236:10 am
ORD
- CUN
Nonstop4h 04m
Frontier
Wed 2/257:19 pm
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 2/11![Frontier logo]()
$244
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/236:10 am
ORD
- CUN
Nonstop4h 04m
Frontier
Thu 2/266:27 pm
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 2/11![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/2411:59 pm
ORD
- CUN
1 stop14h 29m
Multiple Airlines
Thu 2/261:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/2411:59 pm
ORD
- CUN
1 stop8h 49m
Multiple Airlines
Fri 2/271:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/2411:59 pm
ORD
- CUN
1 stop8h 49m
Multiple Airlines
Thu 3/51:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Wed 2/256:23 am
ORD
- CUN
1 stop14h 03m
Multiple Airlines
Fri 3/611:40 am
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
- CUN
1 stop15h 04m
Multiple Airlines
Wed 3/47:19 pm
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$245
This Frontier deal was found by Cheapflights users on 2/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:10 am
ORD
- CUN
Nonstop4h 04m
Frontier
Fri 3/611:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 2/12![Frontier logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:15 am
ORD
- CUN
1 stop6h 05m
Spirit Airlines
Wed 3/41:25 pm
CUN
- ORD
1 stop6h 46m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$243
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/10![Frontier logo]()
$246
One-way flights from Chicago to Riviera MayaSearch for one-way flight options from Chicago to Riviera Maya. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Chicago to Riviera Maya. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This FlightHub deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/212:19 am
ORD
- CUN
1 stop9h 49m
Volaris
Deal found 2/9![Volaris logo]()
$96
This FlightHub deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:00 am
ORD
- CUN
1 stop10h 21m
Volaris
Deal found 2/9![Volaris logo]()
$97
This FlightHub deal was found by Cheapflights users on 2/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/231:00 am
ORD
- CUN
1 stop13h 00m
Volaris
Deal found 2/12![Volaris logo]()
$98
This FlightHub deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/131:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 2/10![Volaris logo]()
$99
This FlightHub deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/46:23 am
ORD
- CUN
1 stop14h 03m
Volaris
Deal found 2/10![Volaris logo]()
$100
This Mytrip deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/2811:59 pm
ORD
- CUN
1 stop14h 29m
Volaris
Deal found 2/11![Volaris logo]()
$101
This FlightHub deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/10![Volaris logo]()
$102
This FlightHub deal was found by Cheapflights users on 2/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:19 am
ORD
- CUN
1 stop13h 09m
Volaris
Deal found 2/12![Volaris logo]()
$102
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/177:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 2/10![Volaris logo]()
$103
This FlightHub deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:59 pm
ORD
- CUN
1 stop14h 29m
Volaris
Deal found 2/10![Volaris logo]()
$104
This FlightHub deal was found by Cheapflights users on 2/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:59 am
ORD
- CUN
1 stop12h 07m
Volaris
Deal found 2/12![Volaris logo]()
$107
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Deal found 2/11![Frontier logo]()
$108
Find flight deals from Chicago to Riviera Maya
Keep the following information in mind while searching for Chicago to Riviera Maya flight deals. Data was last updated February 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Gotogate) |
One-way from | $96 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $427 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 February 12, 2026.
Use the filters below to find and compare flights from Chicago to Riviera Maya that are best for you.
Fly from
Chicago
Fly to
Riviera Maya
Route
Depart
Return
Price
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 3/7
1:25 pm-6:00 pm
Nonstop3h 35m
Cancun
Tue 3/10
8:30 am-12:10 pm
Nonstop3h 40m
$298
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Mon 3/2
7:34 am-12:30 pm
Nonstop3h 56m
Cancun
Wed 3/11
3:45 pm-7:45 pm
Nonstop4h 00m
$303
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 3/7
7:00 am-3:50 pm
1 stop7h 50m
Cancun
Thu 3/12
2:18 pm-6:09 pm
Nonstop3h 51m
$307
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 3/10
10:33 am-2:33 pm
Nonstop4h 00m
Cancun
Tue 3/17
3:45 pm-7:45 pm
Nonstop4h 00m
$313
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Mon 2/16
5:45 am-12:54 pm
1 stop6h 09m
Cancun
Wed 2/18
5:55 pm-12:26 am
1 stop7h 31m
$318
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 2/18
10:35 am-5:50 pm
1 stop6h 15m
Cancun
Tue 2/24
5:55 pm-12:26 am
1 stop7h 31m
$328
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 2/25
10:35 am-9:11 pm
2 stops9h 36m
Cancun
Thu 3/5
6:01 am-12:55 pm
1 stop7h 54m
$332
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 3/3
10:49 am-9:11 pm
1 stop9h 22m
Cancun
Thu 3/5
8:00 am-5:45 pm
1 stop10h 45m
$338
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 3/16
6:34 pm-9:50 am
1 stop15h 16m
Cancun
Thu 3/26
10:00 am-10:31 pm
1 stop12h 31m
$338
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 2/26
12:45 pm-9:11 pm
1 stop7h 26m
Cancun
Thu 3/5
11:00 am-5:45 pm
1 stop7h 45m
$338
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Riviera Maya
Have a flexible travel schedule? Discover the best time to fly to Riviera Maya from Chicago with our price prediction graph.
ORD-CUN
MDW-CUN
ORD-CZM
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 to Riviera Maya
CHI-zzETW
ORD-CUN
MDW-CUN
ORD-CZM
MDW-CZM
What is the cheapest month to book a flight from Chicago to Riviera Maya?
Currently, April is the cheapest month in which you can book a flight from Chicago to Riviera Maya (average of $156). Flying from Chicago to Riviera Maya in August is currently the most expensive (average of $215). 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 CHI to ETW?
Find hourly flight availability from Chicago 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 February 12, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Riviera Maya in the afternoon. If you’re flexible enough to do this you can expect to save up to 28% on your trip compared to booking a flight at noon.
Weekly flight availability from Chicago to Riviera Maya
Explore weekly flight availability from Chicago to Riviera Maya. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 12, 2026.
The most flights from CHI to zzETW are scheduled on a Wednesday (12 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (5 on average).
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 February 12, 2026.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Chicago 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
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 Chicago to Riviera Maya
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Riviera Maya by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Riviera Maya by cabin class
Find flights from Chicago to Riviera Maya, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Riviera Maya flights
Browse other Chicago and Riviera Maya flight options. Last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Riviera Maya
Discover the top 10 airlines that operate flights from Chicago 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 February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$399 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$133 | Average$338 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$140 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$166 | Average$1,488 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$399 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$193 | Average$365 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$272 | Average$561 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$279 | Average$387 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$291 | Average$520 | FlexibilityNo cancel fee | On-time63% |