$98+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Apr 12 — Apr 191
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 66 days in advance, depart on a Monday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Playa del Carmen
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Last-minute
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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 March 13, 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 March 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:05 am
ORD
- CUN
Nonstop3h 49m
Spirit Airlines
Wed 3/1811:06 am
CUN
- ORD
Nonstop4h 00m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$250
This FlightHub deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:05 am
ORD
- CUN
Nonstop3h 46m
Spirit Airlines
Tue 3/1711:06 am
CUN
- ORD
Nonstop4h 00m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$251
This FlightHub deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:59 am
ORD
- CUN
1 stop13h 34m
Volaris
Thu 9/310:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 3/9![Volaris logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Wed 4/2210:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 3/8![Volaris logo]()
$253
This FlightHub deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/151:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Tue 6/239:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 3/9![Volaris logo]()
$254
This Frontier deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Sat 4/2510:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/10![Frontier logo]()
$255
This Frontier deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:00 am
ORD
- CUN
Nonstop4h 04m
Frontier
Thu 3/1910:40 am
CUN
- ORD
Nonstop4h 08m
Frontier
Deal found 3/10![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 am
ORD
- CUN
Nonstop3h 46m
Spirit Airlines
Wed 3/1811:06 am
CUN
- ORD
Nonstop4h 00m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$257
This FlightHub deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/102:19 am
ORD
- CUN
1 stop13h 09m
Volaris
Sun 6/1411:16 am
CUN
- ORD
1 stop12h 50m
Volaris
Deal found 3/9![Volaris logo]()
$258
This Frontier deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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.
Fri 4/246:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Tue 4/2810:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/13![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Sat 4/2510:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/12![Frontier logo]()
$260
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Tue 9/810:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 3/10![Volaris logo]()
$261
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 March 13, 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 March 13, 2026.
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
MDW
- CUN
1 stop5h 30m
Delta
Wed 5/68:00 am
CUN
- MDW
1 stop8h 26m
Delta
Deal found 3/8![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:00 am
MDW
- CUN
2 stops8h 40m
Southwest
Thu 7/21:20 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 3/8![Southwest logo]()
$419
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:17 am
ORD
- CUN
Nonstop3h 53m
United Airlines
Mon 8/1012:55 pm
CUN
- ORD
Nonstop4h 05m
United Airlines
Deal found 3/9![United Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:10 am
ORD
- CUN
1 stop13h 05m
Delta
Tue 4/288:06 am
CUN
- ORD
2 stops12h 10m
Delta
Deal found 3/9![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:24 am
ORD
- CUN
2 stops12h 11m
Delta
Wed 5/208:00 am
CUN
- ORD
2 stops10h 05m
Delta
Deal found 3/12![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:15 am
ORD
- CUN
1 stop7h 25m
Delta
Wed 5/68:00 am
CUN
- ORD
2 stops12h 40m
Delta
Deal found 3/12![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:40 am
MDW
- CUN
Nonstop3h 30m
Southwest
Tue 4/213:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/12![Southwest logo]()
$428
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
MDW
- CUN
1 stop8h 01m
Delta
Tue 4/211:50 pm
CUN
- MDW
1 stop8h 38m
Delta
Deal found 3/12![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:40 am
MDW
- CUN
Nonstop3h 30m
Southwest
Fri 5/152:15 pm
CUN
- MDW
2 stops9h 40m
Southwest
Deal found 3/11![Southwest logo]()
$442
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- CUN
1 stop6h 40m
Delta
Fri 4/243:15 pm
CUN
- MDW
1 stop7h 13m
Delta
Deal found 3/9![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:10 am
MDW
- CUN
Nonstop3h 35m
Southwest
Sat 4/189:55 am
CUN
- MDW
1 stop7h 10m
Southwest
Deal found 3/9![Southwest logo]()
$454
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:51 pm
MDW
- CUN
1 stop7h 25m
Delta
Thu 6/411:10 am
CUN
- MDW
1 stop9h 59m
Delta
Deal found 3/10![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:25 am
ORD
- CUN
2 stops12h 10m
Delta
Tue 4/2812:40 pm
CUN
- ORD
1 stop7h 36m
Delta
Deal found 3/10![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:45 am
MDW
- CUN
2 stops7h 35m
Southwest
Sat 6/610:05 am
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 3/8![Southwest logo]()
$481
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:00 am
ORD
- CUN
1 stop14h 23m
Delta
Mon 6/228:00 am
CUN
- ORD
1 stop13h 16m
Delta
Deal found 3/12![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/32:20 pm
MDW
- CUN
1 stop5h 55m
Southwest
Tue 4/73:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/12![Southwest logo]()
$501
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:10 am
ORD
- CUN
1 stop5h 56m
Delta
Tue 3/242:10 pm
CUN
- ORD
1 stop7h 00m
Delta
Deal found 3/8![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:10 am
ORD
- CUN
2 stops13h 13m
Delta
Thu 6/1112:35 pm
CUN
- ORD
1 stop7h 49m
Delta
Deal found 3/9![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:10 am
ORD
- CUN
1 stop5h 37m
Delta
Wed 7/298:00 am
CUN
- ORD
2 stops12h 24m
Delta
Deal found 3/12![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/79:50 am
ORD
- CUN
2 stops10h 24m
Delta
Tue 4/144:32 pm
CUN
- ORD
1 stop7h 43m
Delta
Deal found 3/9![Delta logo]()
$408
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:41 am
MDW
- CUN
1 stop9h 34m
Delta
Tue 5/511:00 am
CUN
- MDW
1 stop11h 28m
Delta
Deal found 3/8![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:00 am
MDW
- CUN
1 stop14h 23m
Delta
Sun 6/218:00 am
CUN
- MDW
1 stop8h 25m
Delta
Deal found 3/12![Delta logo]()
$462
Last-minute flights from Chicago to Playa del CarmenDiscover last-minute flight deals from Chicago to Playa del Carmen. Data last updated March 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Playa del Carmen. Data last updated March 13, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:05 am
ORD
- CUN
Nonstop3h 46m
Spirit Airlines
Mon 3/1611:06 am
CUN
- ORD
Nonstop4h 00m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$250
This FlightHub deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:05 am
ORD
- CUN
Nonstop3h 46m
Spirit Airlines
Tue 3/1711:06 am
CUN
- ORD
Nonstop4h 00m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 am
ORD
- CUN
Nonstop3h 46m
Spirit Airlines
Wed 3/1811:06 am
CUN
- ORD
Nonstop4h 00m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$257
This Frontier deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:00 am
ORD
- CUN
Nonstop4h 04m
Frontier
Thu 3/1910:40 am
CUN
- ORD
Nonstop4h 08m
Frontier
Deal found 3/10![Frontier logo]()
$256
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/151:00 am
ORD
- CUN
1 stop13h 00m
Multiple Airlines
Thu 3/1911:06 am
CUN
- ORD
Nonstop4h 00m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$254
This Super.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Tue 4/1410:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/10![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Wed 4/2210:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 3/8![Volaris logo]()
$253
This Super.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Mon 4/2010:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/11![Frontier logo]()
$261
This Frontier deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Sat 4/2510:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/10![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/191:40 am
ORD
- CUN
2 stops19h 55m
Multiple Airlines
Fri 4/2410:40 am
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Sat 4/2510:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/12![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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.
Fri 4/246:30 am
ORD
- CUN
Nonstop4h 08m
Frontier
Tue 4/2810:40 am
CUN
- ORD
Nonstop4h 09m
Frontier
Deal found 3/13![Frontier logo]()
$259
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 March 13, 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 March 13, 2026.
This FlightHub deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 3/8![Volaris logo]()
$98
This FlightHub deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 3/9![Volaris logo]()
$99
This Mytrip deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 3/12![Volaris logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2312:58 am
ORD
- CUN
1 stop8h 58m
Volaris
Deal found 3/10![Volaris logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:23 am
ORD
- CUN
1 stop14h 03m
Volaris
Deal found 3/10![Volaris logo]()
$101
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/62:35 am
ORD
- CUN
1 stop9h 19m
Volaris
Deal found 3/12![Volaris logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 3/9![Volaris logo]()
$103
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 3/10![Volaris logo]()
$104
This FlightHub deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2111:59 pm
ORD
- CUN
1 stop9h 49m
Volaris
Deal found 3/11![Volaris logo]()
$105
This FlightHub deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:40 am
ORD
- CUN
1 stop12h 48m
Volaris
Deal found 3/9![Volaris logo]()
$106
This Mytrip deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 3/12![Volaris logo]()
$107
This Super.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Deal found 3/12![Frontier logo]()
$108
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 March 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $252 (FlightHub) |
One-way from | $98 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $526 |
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 March 13, 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 4/29
6:00 am-11:30 am
1 stop5h 30m
Cancun
Wed 5/6
8:00 am-4:26 pm
1 stop8h 26m
$339
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Thu 4/23
7:10 am-8:15 pm
1 stop13h 05m
Cancun
Tue 4/28
8:06 am-8:16 pm
2 stops12h 10m
$339
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 5/17
6:24 am-6:35 pm
2 stops12h 11m
Cancun
Wed 5/20
8:00 am-6:05 pm
2 stops10h 05m
$344
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 5/3
5:15 am-12:40 pm
1 stop7h 25m
Cancun
Wed 5/6
8:00 am-8:40 pm
2 stops12h 40m
$344
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 4/18
6:00 am-2:01 pm
1 stop8h 01m
Cancun
Tue 4/21
1:50 pm-10:28 pm
1 stop8h 38m
$349
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 4/20
6:00 am-12:40 pm
1 stop6h 40m
Cancun
Fri 4/24
3:15 pm-10:28 pm
1 stop7h 13m
$359
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/29
12:51 pm-8:16 pm
1 stop7h 25m
Cancun
Thu 6/4
11:10 am-9:09 pm
1 stop9h 59m
$359
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 4/25
6:25 am-6:35 pm
2 stops12h 10m
Cancun
Tue 4/28
12:40 pm-8:16 pm
1 stop7h 36m
$359
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 6/13
6:00 am-8:23 pm
1 stop14h 23m
Cancun
Mon 6/22
8:00 am-9:16 pm
1 stop13h 16m
$359
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Mon 3/23
7:10 am-1:06 pm
1 stop5h 56m
Cancun
Tue 3/24
2:10 pm-9:10 pm
1 stop7h 00m
$359
Showing 1-10 of 43 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
How far ahead should I book a flight from Chicago to Playa del Carmen?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Playa del Carmen. Price data was last updated on March 6, 2026.
To ensure you get the cheapest price possible for a flight from Chicago to Playa del Carmen, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago to Playa del Carmen?
Currently, April is the cheapest month in which you can book a flight from Chicago to Playa del Carmen (average of $167). Flying from Chicago to Playa del Carmen in March is currently the most expensive (average of $226). 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 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 March 13, 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 29% 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 March 13, 2026.
The most flights from CHI to PL9 are scheduled on a Monday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 March 13, 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.
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next 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 March 13, 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 March 13, 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 March 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$390 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$139 | Average$341 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$140 | Average$341 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$1,219 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$426 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$250 | Average$465 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$261 | Average$345 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$279 | Average$387 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$283 | Average$534 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$291 | Average$520 | FlexibilityNo cancel fee | On-time63% |