$111+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Jun 2 — Jun 91
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 July, booked 87 days in advance, depart on a Tuesday or Monday and return on a Thursday
Cheap flight deals from Chicago to Playa del Carmen
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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 May 3, 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 May 3, 2026.
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/36:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Tue 5/510:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$243
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/166:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Wed 5/2010:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$244
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Thu 5/710:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/30![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Wed 5/610:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/28![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/36:21 am
ORD
- CUN
1 stop9h 07m
Multiple Airlines
Thu 7/911:00 am
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$247
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Sun 5/1710:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/286:00 am
ORD
- CUN
Nonstop4h 01m
Frontier
Wed 7/111:00 am
CUN
- ORD
Nonstop4h 17m
Frontier
Deal found 4/29![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Tue 5/56:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Sat 5/910:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$250
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/297:35 am
ORD
- CUN
1 stop13h 28m
Multiple Airlines
Thu 6/410:25 am
CUN
- ORD
Nonstop4h 10m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$251
This Justfly.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Sat 6/131:40 am
ORD
- CUN
1 stop12h 48m
Multiple Airlines
Thu 6/1811:00 am
CUN
- ORD
Nonstop4h 17m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$252
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
Tue 7/76:00 am
ORD
- CUN
Nonstop3h 49m
Frontier
Sat 7/1111:00 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 4/30![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Tue 5/1210:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/30![Frontier logo]()
$254
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 May 3, 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 May 3, 2026.
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/1310:59 am
MDW
- CUN
1 stop9h 17m
Delta
Wed 5/2012:45 pm
CUN
- MDW
1 stop8h 24m
Delta
Deal found 4/29![Delta logo]()
$348
This Viva deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 10/251:30 am
ORD
- CUN
1 stop19h 55m
Viva
Thu 10/297:00 am
CUN
- ORD
1 stop16h 45m
Viva
Deal found 4/28![Viva logo]()
$360
This Volaris deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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
Thu 8/209:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 5/2![Volaris logo]()
$408
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/117:30 am
MDW
- CUN
Nonstop3h 35m
Southwest
Sat 7/1812:10 pm
CUN
- MDW
1 stop7h 10m
Southwest
Deal found 4/28![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:30 am
ORD
- CUN
2 stops8h 55m
Delta
Wed 7/811:19 am
CUN
- ORD
1 stop12h 49m
Delta
Deal found 5/1![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:41 pm
MDW
- CUN
1 stop7h 34m
Delta
Wed 7/228:00 am
CUN
- MDW
1 stop8h 15m
Delta
Deal found 4/30![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/146:00 am
MDW
- CUN
1 stop5h 20m
Delta
Wed 7/152:10 pm
CUN
- MDW
1 stop8h 05m
Delta
Deal found 5/2![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/148:05 am
MDW
- CUN
1 stop5h 55m
Southwest
Wed 6/171:00 pm
CUN
- MDW
1 stop7h 15m
Southwest
Deal found 5/1![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/286:35 am
ORD
- CUN
2 stops11h 54m
Delta
Mon 8/312:30 pm
CUN
- ORD
1 stop9h 38m
Delta
Deal found 5/1![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:30 am
ORD
- CUN
1 stop14h 45m
Delta
Mon 8/38:05 am
CUN
- ORD
1 stop12h 41m
Delta
Deal found 5/2![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/2010:30 am
MDW
- CUN
Nonstop3h 30m
Southwest
Sun 5/243:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 4/29![Southwest logo]()
$563
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:45 am
MDW
- CUN
1 stop9h 31m
Delta
Tue 6/28:00 am
CUN
- MDW
2 stops10h 33m
Delta
Deal found 4/28![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/166:50 am
MDW
- CUN
1 stop8h 35m
Southwest
Mon 7/201:20 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 5/2![Southwest logo]()
$578
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/146:35 am
ORD
- CUN
1 stop8h 01m
Delta
Tue 7/218:00 am
CUN
- ORD
2 stops12h 31m
Delta
Deal found 4/29![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/85:05 am
MDW
- CUN
1 stop5h 50m
Southwest
Sat 6/1310:05 am
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 4/30![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3111:30 am
ORD
- CUN
2 stops8h 45m
Delta
Tue 8/410:55 am
CUN
- ORD
2 stops9h 36m
Delta
Deal found 4/30![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/87:05 am
ORD
- CUN
1 stop5h 56m
Delta
Wed 7/158:00 am
CUN
- ORD
2 stops12h 31m
Delta
Deal found 4/28![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:05 am
MDW
- CUN
1 stop9h 10m
Delta
Thu 8/68:00 am
CUN
- MDW
2 stops10h 25m
Delta
Deal found 5/1![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:17 am
MDW
- CUN
2 stops11h 08m
Delta
Tue 7/78:00 am
CUN
- MDW
1 stop14h 15m
Delta
Deal found 5/1![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/271:49 pm
ORD
- CUN
1 stop6h 36m
Delta
Wed 7/18:00 am
CUN
- ORD
2 stops12h 31m
Delta
Deal found 5/2![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/217:05 am
ORD
- CUN
2 stops7h 31m
Delta
Tue 7/288:00 am
CUN
- ORD
2 stops10h 29m
Delta
Deal found 5/1![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:19 am
MDW
- CUN
2 stops10h 56m
Delta
Fri 7/248:00 am
CUN
- MDW
1 stop8h 15m
Delta
Deal found 4/28![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:10 am
ORD
- CUN
2 stops11h 25m
Delta
Tue 6/91:30 pm
CUN
- ORD
1 stop9h 12m
Delta
Deal found 5/1![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/289:49 am
ORD
- CUN
1 stop10h 27m
Delta
Mon 6/112:39 pm
CUN
- ORD
2 stops11h 20m
Delta
Deal found 5/1![Delta logo]()
$508
Last-minute flights from Chicago to Playa del CarmenDiscover last-minute flight deals from Chicago to Playa del Carmen. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Playa del Carmen. Data last updated May 3, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/36:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Tue 5/510:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$243
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Wed 5/610:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/28![Frontier logo]()
$246
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Tue 5/1210:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/30![Frontier logo]()
$254
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Thu 5/710:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/30![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Tue 5/56:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Sat 5/910:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Thu 5/76:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Mon 5/1110:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/28![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Sun 5/1710:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$248
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/91:40 am
ORD
- CUN
1 stop8h 23m
Multiple Airlines
Fri 5/1510:25 am
CUN
- ORD
Nonstop4h 10m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$257
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/126:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Sat 5/1610:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$247
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/166:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Wed 5/2010:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Fri 6/510:25 am
CUN
- ORD
Nonstop4h 10m
Frontier
Deal found 4/29![Frontier logo]()
$256
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/297:35 am
ORD
- CUN
1 stop13h 28m
Multiple Airlines
Thu 6/410:25 am
CUN
- ORD
Nonstop4h 10m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$251
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 May 3, 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 May 3, 2026.
This eDestinos deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Deal found 4/30![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/121:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Deal found 4/29![Volaris logo]()
$115
This eDestinos deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
ORD
- CUN
Nonstop4h 03m
Frontier
Deal found 4/29![Frontier logo]()
$116
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/266:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/29![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/286:00 am
ORD
- CUN
Nonstop3h 49m
Frontier
Deal found 4/29![Frontier logo]()
$119
This Super.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 4/30![Volaris logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/157:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 4/30![Volaris logo]()
$122
This Justfly.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Sun 5/249:37 pm
ORD
- CUN
1 stop14h 27m
Frontier
Deal found 5/1![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/30![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:55 am
ORD
- CUN
1 stop7h 12m
Frontier
Deal found 4/30![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Mon 5/186:00 am
MDW
- CUN
1 stop8h 07m
Frontier
Deal found 4/28![Frontier logo]()
$126
This FlightHub deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 4/30![Volaris logo]()
$140
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 May 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $243 (Orbitz) |
One-way from | $111 (eDestinos) |
Popular in | December |
Cheapest in | September |
Average price | $420 |
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 May 3, 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
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 5/13
10:59 am-8:16 pm
1 stop9h 17m
Cancun
Wed 5/20
12:45 pm-9:09 pm
1 stop8h 24m
$348
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 10/25
1:30 am-9:25 pm
1 stop19h 55m
Cancun
Thu 10/29
7:00 am-11:45 pm
1 stop16h 45m
$360
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 7/3
11:30 am-8:25 pm
2 stops8h 55m
Cancun
Wed 7/8
11:19 am-12:08 am
1 stop12h 49m
$393
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 7/17
12:41 pm-8:15 pm
1 stop7h 34m
Cancun
Wed 7/22
8:00 am-4:15 pm
1 stop8h 15m
$398
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 7/14
6:00 am-11:20 am
1 stop5h 20m
Cancun
Wed 7/15
2:10 pm-10:15 pm
1 stop8h 05m
$398
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 7/28
6:35 am-6:29 pm
2 stops11h 54m
Cancun
Mon 8/3
12:30 pm-10:08 pm
1 stop9h 38m
$398
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 7/26
5:30 am-8:15 pm
1 stop14h 45m
Cancun
Mon 8/3
8:05 am-8:46 pm
1 stop12h 41m
$398
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/30
10:45 am-8:16 pm
1 stop9h 31m
Cancun
Tue 6/2
8:00 am-6:33 pm
2 stops10h 33m
$402
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 7/14
6:35 am-2:36 pm
1 stop8h 01m
Cancun
Tue 7/21
8:00 am-8:31 pm
2 stops12h 31m
$402
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 7/31
11:30 am-8:15 pm
2 stops8h 45m
Cancun
Tue 8/4
10:55 am-8:31 pm
2 stops9h 36m
$402
Showing 1-10 of 45 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.
MDW-CUN
ORD-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
MDW-CUN
ORD-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 May 3, 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 25% 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 May 3, 2026.
The most flights from CHI to PL9 are scheduled on a Saturday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 May 3, 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.
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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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 May 3, 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 May 3, 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 May 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$314 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$147 | Average$348 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$156 | Average$390 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$1,482 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$431 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$193 | Average$516 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$546 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$291 | Average$495 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$313 | Average$511 | FlexibilityNo cancel fee | On-time71% |