$123+ Cheap flights from Chicago (CHI) to Playa del Carmen, Mexico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Jul 20 — Jul 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Playa del Carmen 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.Cheapflights Tip: The best prices from Chicago to Playa del Carmen are usually found in September or January, booked 61 days in advance, depart on a Sunday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Playa del Carmen
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Best
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Cheapest flights from Chicago to Playa del CarmenExplore the most affordable flight options available from Chicago to Playa del Carmen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
Explore the most affordable flight options available from Chicago to Playa del Carmen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Fri 9/43:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/15![Volaris logo]()
$299
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Tue 9/13:20 pm
CUN
- ORD
1 stop14h 32m
Volaris
Deal found 6/16![Volaris logo]()
$301
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Sat 9/510:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 6/16![Volaris logo]()
$303
This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Tue 7/73:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/15![Volaris logo]()
$304
This FlightHub deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:40 am
ORD
- CUN
1 stop12h 48m
Volaris
Wed 9/309:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/16![Volaris logo]()
$305
This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Wed 7/13:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/15![Volaris logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Fri 9/113:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/16![Volaris logo]()
$307
This CheapOair deal was found by Cheapflights users on 6/19. 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.
Tue 7/71:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Fri 7/104:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Wed 7/83:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/15![Volaris logo]()
$309
This Justfly.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 6/291:40 am
ORD
- CUN
1 stop12h 48m
Volaris
Sat 7/44:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Deal found 6/18![Volaris logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Sat 7/184:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/71:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Fri 9/113:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/16![Volaris logo]()
$312
Best flights from Chicago to Playa del CarmenDiscover carefully curated flight deals from Chicago to Playa del Carmen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
Discover carefully curated flight deals from Chicago to Playa del Carmen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Sun 8/2310:46 am
ORD
- CUN
Nonstop3h 40m
United Airlines
Wed 8/2612:11 pm
CUN
- ORD
Nonstop3h 53m
United Airlines
Deal found 6/19![United Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 6/19. 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 8/188:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 8/2111:35 am
CUN
- MDW
1 stop6h 40m
Southwest
Deal found 6/19![Southwest logo]()
$443
This Volaris deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Sun 8/164:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$443
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 11/311:30 am
ORD
- CUN
2 stops8h 45m
Delta
Wed 11/1112:27 pm
CUN
- ORD
1 stop11h 33m
Delta
Deal found 6/18![Delta logo]()
$451
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:46 am
ORD
- CUN
Nonstop3h 40m
United Airlines
Tue 9/2912:11 pm
CUN
- ORD
Nonstop3h 53m
United Airlines
Deal found 6/14![United Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:30 am
ORD
- CUN
1 stop6h 30m
Delta
Wed 7/298:00 am
CUN
- ORD
2 stops10h 29m
Delta
Deal found 6/16![Delta logo]()
$478
This Volaris deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Sun 8/94:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/16![Volaris logo]()
$483
This Southwest deal was found by Cheapflights users on 6/19. 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.
Thu 9/107:30 am
MDW
- CUN
1 stop6h 40m
Southwest
Fri 9/111:05 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/19![Southwest logo]()
$487
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/67:04 am
ORD
- CUN
1 stop13h 21m
Delta
Thu 8/138:05 am
CUN
- ORD
2 stops26h 37m
Delta
Deal found 6/18![Delta logo]()
$483
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:29 am
ORD
- CUN
Nonstop3h 41m
United Airlines
Tue 8/2512:11 pm
CUN
- ORD
Nonstop3h 53m
United Airlines
Deal found 6/15![United Airlines logo]()
$490
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:50 am
MDW
- CUN
1 stop6h 10m
Southwest
Wed 7/153:25 pm
CUN
- MDW
Nonstop3h 30m
Southwest
Deal found 6/16![Southwest logo]()
$492
This Volaris deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Mon 8/1711:00 am
CUN
- ORD
Nonstop4h 09m
Volaris
Deal found 6/19![Volaris logo]()
$499
This Delta deal was found by Cheapflights users on 6/19. 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.
Thu 9/106:05 am
MDW
- CUN
1 stop6h 55m
Delta
Fri 9/183:20 pm
CUN
- MDW
1 stop7h 05m
Delta
Deal found 6/19![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:50 am
MDW
- CUN
1 stop6h 10m
Southwest
Thu 7/1612:00 pm
CUN
- MDW
2 stops9h 20m
Southwest
Deal found 6/15![Southwest logo]()
$492
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/197:50 am
MDW
- CUN
1 stop7h 10m
Southwest
Mon 8/2411:35 am
CUN
- MDW
2 stops8h 45m
Southwest
Deal found 6/18![Southwest logo]()
$507
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:05 am
ORD
- CUN
2 stops12h 20m
Delta
Sun 10/46:59 am
CUN
- ORD
2 stops13h 56m
Delta
Deal found 6/19![Delta logo]()
$517
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:05 am
MDW
- CUN
Nonstop3h 35m
Southwest
Tue 8/41:10 pm
CUN
- MDW
1 stop7h 35m
Southwest
Deal found 6/15![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 6/19. 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 9/198:05 am
ORD
- CUN
2 stops10h 34m
Delta
Sat 9/266:04 am
CUN
- ORD
1 stop8h 12m
Delta
Deal found 6/19![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 6/19. 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 9/510:56 am
MDW
- CUN
1 stop9h 09m
Delta
Sat 9/122:00 pm
CUN
- MDW
1 stop8h 45m
Delta
Deal found 6/19![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am
ORD
- CUN
1 stop7h 00m
Delta
Sat 10/316:06 am
CUN
- ORD
2 stops10h 31m
Delta
Deal found 6/16![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MDW
- CUN
1 stop8h 36m
Delta
Sat 8/88:05 am
CUN
- MDW
1 stop7h 33m
Delta
Deal found 6/15![Delta logo]()
$551
Last-minute flights from Chicago to Playa del CarmenDiscover last-minute flight deals from Chicago to Playa del Carmen. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Playa del Carmen. Data last updated June 20, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/201:40 am
ORD
- CUN
1 stop12h 48m
Volaris
Wed 6/244:32 pm
CUN
- ORD
1 stop9h 49m
Volaris
Deal found 6/16![Volaris logo]()
$312
This CheapOair deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 6/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 6/2610:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/18![Volaris logo]()
$357
This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Wed 7/13:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/15![Volaris logo]()
$306
This Justfly.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 6/291:40 am
ORD
- CUN
1 stop12h 48m
Volaris
Sat 7/44:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Deal found 6/18![Volaris logo]()
$310
This Super.com deal was found by Cheapflights users on 6/19. 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 6/292:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Thu 7/24:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Deal found 6/19![Volaris logo]()
$315
This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Tue 7/73:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/15![Volaris logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Wed 7/83:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 6/15![Volaris logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/42:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Tue 7/1412:49 pm
CUN
- ORD
1 stop12h 06m
Volaris
Deal found 6/19![Volaris logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Sat 7/184:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Sat 7/114:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Sun 7/56:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Wed 7/159:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/18![Volaris logo]()
$316
This CheapOair deal was found by Cheapflights users on 6/19. 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.
Tue 7/71:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Fri 7/104:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$308
One-way flights from Chicago to Playa del CarmenSearch for one-way flight options from Chicago to Playa del Carmen. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
Search for one-way flight options from Chicago to Playa del Carmen. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/16![Volaris logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Deal found 6/15![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/15![Volaris logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/14![Volaris logo]()
$126
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/292:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Deal found 6/16![Volaris logo]()
$127
This Gotogate deal was found by Cheapflights users on 6/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 6/19![Volaris logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/17![Volaris logo]()
$129
This CheapOair deal was found by Cheapflights users on 6/19. 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 6/271:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/19![Volaris logo]()
$133
This Super.com deal was found by Cheapflights users on 6/19. 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.
Fri 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/19![Volaris logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/17![Volaris logo]()
$134
This Super.com deal was found by Cheapflights users on 6/19. 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 7/168:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 6/19![Volaris logo]()
$135
Find flight deals from Chicago to Playa del Carmen
Keep the following information in mind while searching for Chicago to Playa del Carmen flight deals. Data was last updated June 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Kiwi.com) |
One-way from | $123 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $473 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Playa del Carmen 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 June 20, 2026.
Use the filters below to find and compare flights from Chicago to Playa del Carmen that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 8/23
10:46 am-2:26 pm
Nonstop3h 40m
Cancun
Wed 8/26
12:11 pm-4:04 pm
Nonstop3h 53m
$442
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 8/18
8:35 am-12:10 pm
Nonstop3h 35m
Cancun
Fri 8/21
11:35 am-6:15 pm
1 stop6h 40m
$443
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 8/11
1:40 am-10:03 am
1 stop8h 23m
Cancun
Sun 8/16
4:32 pm-12:55 am
1 stop8h 23m
$443
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 11/3
11:30 am-9:15 pm
2 stops8h 45m
Cancun
Wed 11/11
12:27 pm-11:00 pm
1 stop11h 33m
$451
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Thu 9/24
10:46 am-2:26 pm
Nonstop3h 40m
Cancun
Tue 9/29
12:11 pm-4:04 pm
Nonstop3h 53m
$477
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 7/21
6:30 am-1:00 pm
1 stop6h 30m
Cancun
Wed 7/29
8:00 am-6:29 pm
2 stops10h 29m
$478
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 7/31
6:21 am-3:28 pm
1 stop9h 07m
Cancun
Sun 8/9
4:32 pm-12:55 am
1 stop8h 23m
$483
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Thu 8/6
7:04 am-8:25 pm
1 stop13h 21m
Cancun
Thu 8/13
8:05 am-10:42 am
2 stops26h 37m
$483
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 9/10
7:30 am-2:10 pm
1 stop6h 40m
Cancun
Fri 9/11
1:05 pm-4:40 pm
Nonstop3h 35m
$487
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Thu 8/20
9:29 am-1:10 pm
Nonstop3h 41m
Cancun
Tue 8/25
12:11 pm-4:04 pm
Nonstop3h 53m
$490
Showing 1-10 of 44 resultsSorted by cheapest first
Best time to book a flight from Chicago to Playa del Carmen
Have a flexible travel schedule? Discover the best time to fly to Playa del Carmen from Chicago with our price prediction graph.
ORD-CUN
MDW-CUN
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 Playa del Carmen
CHI-PL9
ORD-CUN
MDW-CUN
What is the cheapest time of day to fly from CHI to PL9?
Find hourly flight availability from Chicago to Playa del Carmen. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 20, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Playa del Carmen in the afternoon. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight at noon.
Weekly flight availability from Chicago to Playa del Carmen
Explore weekly flight availability from Chicago to Playa del Carmen. 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 June 20, 2026.
The most flights from CHI to PL9 are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Chicago to Playa del Carmen?
Reviews of airlines servicing Playa del Carmen
Get insights into the airlines that provide service to Playa del Carmen. 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 Playa del Carmen. Reviews last updated June 20, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Playa del Carmen have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Chicago to Playa del Carmen. 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip
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Alternative routes for Chicago to Playa del Carmen
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Playa del Carmen by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Playa del Carmen by cabin class
Find flights from Chicago to Playa del Carmen, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Playa del Carmen flights
Browse other Chicago and Playa del Carmen flight options. Last updated on June 20, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Playa del Carmen flights
Consider these flights traveling from Chicago to Playa del Carmen.
Top 10 airlines flying from Chicago to Playa del Carmen
Discover the top 10 airlines that operate flights from Chicago to Playa del Carmen. 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 June 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$326 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$158 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$192 | Average$426 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$556 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$301 | Average$506 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$319 | Average$533 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$425 | FlexibilityNo cancel fee | On-time67% |