$139+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Sep 23 — Sep 301
Round-trip
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 August 24, 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 August 24, 2026.
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:35 am -
1 stop13h 28m
Fri 9/1111:16 am -
1 stop12h 50m
Deal found 8/19![Volaris logo]()
$332
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:35 am -
1 stop13h 28m
Sun 9/2711:16 am -
1 stop12h 50m
Deal found 8/19![Volaris logo]()
$333
This Viva deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:35 am -
1 stop20h 10m
Sun 11/1510:25 am -
1 stop13h 30m
Deal found 8/21![Viva logo]()
$334
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:35 am -
1 stop13h 28m
Fri 10/99:50 pm -
1 stop8h 02m
Deal found 8/21![Volaris logo]()
$335
This FlightHub deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:24 am -
1 stop13h 07m
Sat 11/149:55 pm -
1 stop7h 48m
Deal found 8/21![Volaris logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:40 am -
1 stop8h 23m
Sat 10/109:50 pm -
1 stop8h 02m
Deal found 8/22![Volaris logo]()
$337
This Super.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:04 am -
1 stop13h 13m
Sat 11/149:55 pm -
1 stop7h 48m
Deal found 8/22![Volaris logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:35 am -
1 stop13h 28m
Tue 10/139:50 pm -
1 stop8h 02m
Deal found 8/22![Volaris logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:35 am -
1 stop13h 28m
Tue 10/69:50 pm -
1 stop8h 02m
Deal found 8/24![Volaris logo]()
$340
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:35 am -
1 stop13h 28m
Sun 10/411:16 am -
1 stop12h 50m
Deal found 8/19![Volaris logo]()
$341
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:35 am -
1 stop13h 28m
Wed 10/1410:50 am -
1 stop12h 57m
Deal found 8/21![Volaris logo]()
$342
This Justfly.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/191:40 am -
1 stop8h 23m
Tue 10/276:30 pm -
1 stop11h 13m
Deal found 8/19![Volaris logo]()
$343
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 August 24, 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 August 24, 2026.
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:10 am -
1 stop6h 40m
Thu 10/11:05 pm -
Nonstop3h 40m
Deal found 8/19![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:30 am -
1 stop11h 11m
Fri 11/131:37 pm -
2 stops11h 22m
Deal found 8/20![Delta logo]()
$462
This United Airlines deal was found by Cheapflights users on 8/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:30 am -
1 stop7h 12m
Wed 10/73:52 pm -
1 stop7h 35m
Deal found 8/23![United Airlines logo]()
$841
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:00 am -
1 stop10h 00m
Wed 10/213:20 pm -
Nonstop3h 35m
Deal found 8/19![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:05 am -
1 stop11h 50m
Tue 11/38:00 am -
2 stops13h 30m
Deal found 8/20![Delta logo]()
$471
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:40 am -
1 stop7h 50m
Tue 11/176:00 pm -
Nonstop3h 35m
Deal found 8/19![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 8/23. 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 11/177:05 am -
2 stops12h 50m
Sun 11/226:04 am -
1 stop8h 08m
Deal found 8/23![Delta logo]()
$477
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/18:20 am -
Nonstop3h 45m
Fri 1/89:40 am -
1 stop12h 20m
Deal found 8/20![Southwest logo]()
$478
This Delta deal was found by Cheapflights users on 8/23. 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.
Sat 11/71:30 am -
1 stop9h 59m
Sat 11/141:37 pm -
2 stops11h 17m
Deal found 8/23![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:55 am -
2 stops10h 55m
Thu 9/172:00 pm -
1 stop9h 59m
Deal found 8/20![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:20 am -
1 stop9h 40m
Mon 11/2311:20 am -
2 stops9h 45m
Deal found 8/22![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:28 am -
1 stop8h 42m
Sat 12/126:04 am -
2 stops10h 15m
Deal found 8/19![Delta logo]()
$498
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:50 am -
2 stops9h 05m
Wed 12/161:45 pm -
2 stops8h 45m
Deal found 8/22![Southwest logo]()
$516
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:29 am -
2 stops10h 26m
Sat 10/248:00 am -
2 stops10h 00m
Deal found 8/20![Delta logo]()
$503
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:30 am -
1 stop9h 12m
Tue 11/104:50 pm -
1 stop16h 01m
Deal found 8/19![United Airlines logo]()
$841
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/157:15 am -
1 stop6h 20m
Thu 2/182:55 pm -
1 stop8h 50m
Deal found 8/20![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:29 am -
2 stops11h 26m
Sat 10/2412:55 pm -
1 stop8h 48m
Deal found 8/20![Delta logo]()
$503
This United Airlines deal was found by Cheapflights users on 8/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:38 pm -
1 stop17h 04m
Fri 10/163:52 pm -
1 stop7h 35m
Deal found 8/23![United Airlines logo]()
$841
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:40 am -
2 stops9h 05m
Tue 11/242:10 pm -
1 stop11h 05m
Deal found 8/23![Southwest logo]()
$549
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:10 pm -
2 stops18h 05m
Tue 10/66:04 am -
2 stops17h 53m
Deal found 8/22![Delta logo]()
$507
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:15 pm -
1 stop16h 27m
Sat 10/311:05 pm -
Nonstop4h 00m
Deal found 8/21![United Airlines logo]()
$856
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Sat 1/237:55 am -
2 stops10h 50m
Mon 2/19:40 am -
1 stop12h 20m
Deal found 8/23![Southwest logo]()
$556
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 am -
2 stops12h 55m
Thu 10/228:00 am -
2 stops12h 38m
Deal found 8/21![Delta logo]()
$532
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:55 am -
1 stop7h 47m
Fri 11/134:50 pm -
1 stop17h 21m
Deal found 8/19![United Airlines logo]()
$866
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:55 am -
2 stops10h 55m
Wed 9/3011:30 am -
2 stops12h 29m
Deal found 8/22![Delta logo]()
$532
This United Airlines deal was found by Cheapflights users on 8/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:38 pm -
1 stop17h 04m
Sat 10/173:52 pm -
1 stop7h 35m
Deal found 8/23![United Airlines logo]()
$866
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:55 am -
1 stop7h 47m
Sun 11/154:50 pm -
1 stop8h 55m
Deal found 8/19![United Airlines logo]()
$866
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3011:27 am -
1 stop8h 28m
Sun 12/68:15 am -
1 stop9h 02m
Deal found 8/22![Delta logo]()
$541
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:38 pm -
1 stop17h 04m
Sat 10/33:52 pm -
1 stop7h 35m
Deal found 8/21![United Airlines logo]()
$866
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:59 am -
2 stops13h 06m
Wed 9/911:30 am -
2 stops12h 29m
Deal found 8/22![Delta logo]()
$566
Last-minute flights from Chicago to Riviera MayaDiscover last-minute flight deals from Chicago to Riviera Maya. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Riviera Maya. Data last updated August 24, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:53 am -
1 stop9h 11m
Wed 9/29:50 pm -
1 stop8h 02m
Deal found 8/20![Volaris logo]()
$342
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:35 am -
1 stop13h 28m
Wed 9/2310:50 am -
1 stop12h 57m
Deal found 8/20![Volaris logo]()
$341
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:35 am -
1 stop13h 28m
Fri 9/1111:16 am -
1 stop12h 50m
Deal found 8/19![Volaris logo]()
$332
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:40 am -
1 stop8h 23m
Sun 9/1311:16 am -
1 stop12h 50m
Deal found 8/20![Volaris logo]()
$339
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:35 am -
1 stop13h 28m
Mon 9/149:50 pm -
1 stop8h 02m
Deal found 8/21![Volaris logo]()
$343
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:35 am -
1 stop13h 28m
Thu 9/175:40 pm -
1 stop11h 14m
Deal found 8/19![Volaris logo]()
$338
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:35 am -
1 stop13h 28m
Sun 9/2711:16 am -
1 stop12h 50m
Deal found 8/19![Volaris logo]()
$333
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:35 am -
1 stop13h 28m
Wed 10/73:20 pm -
1 stop8h 27m
Deal found 8/21![Volaris logo]()
$336
This Kissandfly.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:40 am -
1 stop8h 23m
Fri 10/29:50 pm -
1 stop8h 02m
Deal found 8/21![Volaris logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:35 am -
1 stop13h 28m
Tue 10/69:50 pm -
1 stop8h 02m
Deal found 8/24![Volaris logo]()
$340
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:35 am -
1 stop13h 28m
Sat 10/310:50 am -
1 stop12h 57m
Deal found 8/23![Volaris logo]()
$334
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:35 am -
1 stop13h 28m
Fri 10/99:50 pm -
1 stop8h 02m
Deal found 8/21![Volaris logo]()
$335
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 August 24, 2026.
Search for one-way flight options from Chicago to Riviera Maya. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/71:40 am -
1 stop12h 48m
Deal found 8/20![Volaris logo]()
$139
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:35 am -
1 stop13h 28m
Deal found 8/19![Volaris logo]()
$140
This Kissandfly.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:29 am -
1 stop13h 28m
Deal found 8/21![Volaris logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:35 am -
1 stop13h 28m
Deal found 8/20![Volaris logo]()
$142
This Super.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:35 am -
1 stop13h 28m
Deal found 8/23![Volaris logo]()
$143
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:35 am -
1 stop13h 28m
Deal found 8/19![Volaris logo]()
$144
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:35 am -
1 stop13h 28m
Deal found 8/19![Volaris logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:35 am -
1 stop13h 28m
Deal found 8/22![Volaris logo]()
$147
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:53 am -
1 stop9h 11m
Deal found 8/19![Volaris logo]()
$149
This Viva deal was found by Cheapflights users on 8/23. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:20 pm -
1 stop26h 26m
Deal found 8/23![Viva logo]()
$159
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:15 am -
1 stop6h 26m
Deal found 8/19![Frontier logo]()
$171
This FlightHub deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:23 pm -
1 stop13h 32m
Deal found 8/19![Volaris logo]()
$172
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 August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (Super.com) |
One-way from | $139 (CheapOair) |
Popular in | December |
Cheapest in | January |
Average price | $518 |
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 7,457,451 searches. Data last updated August 24, 2026.
Use the filters below to find and compare flights from Chicago to Riviera Maya that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sun 9/27
7:10 am-1:50 pm
1 stop6h 40m
Cancun
Thu 10/1
1:05 pm-4:45 pm
Nonstop3h 40m
$456
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 10/12
5:00 am-3:00 pm
1 stop10h 00m
Cancun
Wed 10/21
3:20 pm-6:55 pm
Nonstop3h 35m
$456
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Tue 11/10
6:40 am-3:30 pm
1 stop7h 50m
Cancun
Tue 11/17
6:00 pm-8:35 pm
Nonstop3h 35m
$456
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Tue 11/3
1:30 am-1:41 pm
1 stop11h 11m
Cancun
Fri 11/13
1:37 pm-11:59 pm
2 stops11h 22m
$462
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Tue 10/27
8:05 am-7:55 pm
1 stop11h 50m
Cancun
Tue 11/3
8:00 am-8:30 pm
2 stops13h 30m
$471
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Tue 11/17
7:05 am-8:55 pm
2 stops12h 50m
Cancun
Sun 11/22
6:04 am-1:12 pm
1 stop8h 08m
$477
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Fri 1/1
8:20 am-1:05 pm
Nonstop3h 45m
Cancun
Fri 1/8
9:40 am-9:00 pm
1 stop12h 20m
$478
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Sat 11/7
1:30 am-12:29 pm
1 stop9h 59m
Cancun
Sat 11/14
1:37 pm-11:54 pm
2 stops11h 17m
$478
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Sat 9/12
8:55 am-7:50 pm
2 stops10h 55m
Cancun
Thu 9/17
2:00 pm-11:59 pm
1 stop9h 59m
$487
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 12/5
11:28 am-9:10 pm
1 stop8h 42m
Cancun
Sat 12/12
6:04 am-3:19 pm
2 stops10h 15m
$498
Showing 1-10 of 60 resultsSorted by cheapest first
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.
MDW-CUN
ORD-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
MDW-CUN
ORD-CUN
ORD-CZM
MDW-CZM
What is the cheapest month to book a flight from Chicago to Riviera Maya?
Currently, January is the cheapest month in which you can book a flight from Chicago to Riviera Maya (average of $375). Flying from Chicago to Riviera Maya in December is currently the most expensive (average of $552). 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 August 24, 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 18% 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 August 24, 2026.
The most flights from CHI to zzETW are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
How far ahead should I book a flight from Chicago to Riviera Maya?
The price you pay for your flight from Chicago to Riviera Maya may vary depending on when you book. For the best chance of a lower fare, look to book 77 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 August 24, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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.
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
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Complete your trip
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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 August 24, 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 7,457,451 searches. Data last updated August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$129 | Average$411 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$158 | Average$449 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$192 | Average$431 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$484 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$292 | Average$618 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$493 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$322 | Average$579 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$492 | FlexibilityNo cancel fee | On-time67% |