$124+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Sep 11 — Sep 181
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 January or February, booked 61 days in advance, depart on a Sunday 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 August 12, 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 August 12, 2026.
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:35 am -
1 stop13h 28m
Fri 9/410:50 am -
1 stop12h 57m
Deal found 8/7![Volaris logo]()
$325
This FlightHub deal was found by Cheapflights users on 8/8. 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.
Mon 8/312:53 am -
1 stop9h 11m
Tue 9/2210:50 am -
1 stop12h 57m
Deal found 8/8![Volaris logo]()
$326
This Viva deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Wed 11/1112:35 am -
1 stop18h 50m
Sun 11/1511:00 am -
1 stop12h 55m
Deal found 8/7![Viva logo]()
$328
This Super.com deal was found by Cheapflights users on 8/10. 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 9/82:53 am -
1 stop12h 35m
Fri 9/119:50 pm -
1 stop8h 02m
Deal found 8/10![Volaris logo]()
$329
This CheapOair deal was found by Cheapflights users on 8/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:53 am -
1 stop9h 11m
Tue 9/153:20 pm -
1 stop8h 27m
Deal found 8/11![Volaris logo]()
$330
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:35 am -
1 stop13h 28m
Sat 10/1710:50 am -
1 stop12h 57m
Deal found 8/11![Volaris logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/77:35 am -
1 stop13h 28m
Mon 9/1410:40 am -
1 stop14h 15m
Deal found 8/10![Volaris logo]()
$332
This FlightHub deal was found by Cheapflights users on 8/11. 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.
Tue 8/252:53 am -
1 stop9h 11m
Wed 9/210:50 am -
1 stop12h 57m
Deal found 8/11![Volaris logo]()
$333
This Super.com deal was found by Cheapflights users on 8/11. 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.
Thu 9/247:35 am -
1 stop13h 28m
Sun 9/2710:50 am -
1 stop12h 57m
Deal found 8/11![Volaris logo]()
$334
This Viva deal was found by Cheapflights users on 8/11. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2712:35 am -
1 stop20h 10m
Thu 12/310:35 pm -
1 stop25h 25m
Deal found 8/11![Viva logo]()
$335
This FlightHub deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:53 am -
1 stop12h 35m
Thu 9/39:50 pm -
1 stop8h 02m
Deal found 8/9![Volaris logo]()
$336
This Justfly.com deal was found by Cheapflights users on 8/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:23 pm -
1 stop13h 32m
Sun 9/1310:40 am -
1 stop8h 24m
Deal found 8/12![Volaris logo]()
$341
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 August 12, 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 August 12, 2026.
This Viva deal was found by Cheapflights users on 8/11. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:35 am -
1 stop22h 20m
Sun 11/811:00 am -
1 stop12h 55m
Deal found 8/11![Viva logo]()
$339
This Southwest deal was found by Cheapflights users on 8/8. 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 9/75:30 am -
1 stop6h 40m
Wed 9/1612:40 pm -
Nonstop3h 40m
Deal found 8/8![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 8/8. 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 11/306:00 am -
1 stop5h 30m
Tue 12/88:00 am -
1 stop9h 14m
Deal found 8/8![Delta logo]()
$466
This United Airlines deal was found by Cheapflights users on 8/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:29 am -
Nonstop3h 41m
Sun 10/2512:16 pm -
Nonstop4h 02m
Deal found 8/8![United Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 8/8. 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.
Sun 9/66:00 am -
2 stops12h 49m
Wed 9/911:30 am -
2 stops12h 29m
Deal found 8/8![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 11/276:30 am -
1 stop5h 35m
Wed 12/26:00 pm -
Nonstop3h 35m
Deal found 8/11![Southwest logo]()
$496
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/96:10 am -
2 stops12h 39m
Tue 9/1512:41 pm -
2 stops11h 18m
Deal found 8/7![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 11/710:20 am -
1 stop8h 25m
Wed 11/1112:35 pm -
1 stop9h 50m
Deal found 8/7![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 8/8. 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.
Fri 10/26:40 am -
1 stop13h 10m
Tue 10/612:40 pm -
2 stops11h 12m
Deal found 8/8![Delta logo]()
$482
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 11/277:20 am -
2 stops11h 25m
Thu 12/32:25 pm -
1 stop8h 05m
Deal found 8/11![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 8/10. 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 11/79:29 am -
2 stops10h 26m
Wed 11/118:00 am -
2 stops11h 04m
Deal found 8/10![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 8/8. 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.
Sat 10/318:00 am -
Nonstop3h 45m
Thu 11/52:10 pm -
Nonstop3h 40m
Deal found 8/8![Southwest logo]()
$513
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:35 am -
1 stop9h 20m
Wed 11/48:00 am -
2 stops13h 30m
Deal found 8/11![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 8/9. 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.
Mon 11/28:55 am -
Nonstop3h 45m
Mon 11/96:55 pm -
1 stop7h 10m
Deal found 8/9![Southwest logo]()
$524
This Delta deal was found by Cheapflights users on 8/8. 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.
Sat 10/3110:55 am -
2 stops9h 00m
Sat 11/76:04 am -
1 stop8h 08m
Deal found 8/8![Delta logo]()
$493
This Southwest deal was found by Cheapflights users on 8/9. 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.
Tue 9/87:50 am -
1 stop7h 10m
Thu 9/1011:35 am -
1 stop10h 45m
Deal found 8/9![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 8/10. 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.
Thu 10/16:40 am -
1 stop13h 10m
Mon 10/512:40 pm -
2 stops11h 19m
Deal found 8/10![Delta logo]()
$498
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 1/187:50 am -
2 stops8h 35m
Sun 1/242:10 pm -
1 stop7h 50m
Deal found 8/7![Southwest logo]()
$544
This Delta deal was found by Cheapflights users on 8/10. 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.
Wed 8/266:00 am -
2 stops12h 44m
Thu 9/31:30 pm -
1 stop9h 14m
Deal found 8/10![Delta logo]()
$525
This Southwest deal was found by Cheapflights users on 8/11. 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.
Thu 10/17:25 am -
1 stop7h 35m
Mon 10/52:10 pm -
2 stops10h 05m
Deal found 8/11![Southwest logo]()
$561
This Delta deal was found by Cheapflights users on 8/8. 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.
Sun 11/86:30 am -
2 stops11h 12m
Fri 11/131:37 pm -
2 stops11h 22m
Deal found 8/8![Delta logo]()
$525
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:30 am -
1 stop6h 40m
Thu 8/271:05 pm -
Nonstop3h 35m
Deal found 8/10![Southwest logo]()
$574
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:29 am -
2 stops11h 26m
Thu 11/512:16 pm -
2 stops12h 36m
Deal found 8/11![Delta logo]()
$530
Last-minute flights from Chicago to Playa del CarmenDiscover last-minute flight deals from Chicago to Playa del Carmen. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Playa del Carmen. Data last updated August 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:59 am -
1 stop14h 07m
Fri 9/410:50 am -
1 stop12h 57m
Deal found 8/11![Volaris logo]()
$331
This FlightHub deal was found by Cheapflights users on 8/11. 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.
Tue 8/252:53 am -
1 stop9h 11m
Wed 9/210:50 am -
1 stop12h 57m
Deal found 8/11![Volaris logo]()
$333
This FlightHub deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:53 am -
1 stop12h 35m
Thu 9/39:50 pm -
1 stop8h 02m
Deal found 8/9![Volaris logo]()
$336
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 8/277:35 am -
1 stop13h 28m
Tue 9/13:20 pm -
1 stop14h 32m
Deal found 8/7![Volaris logo]()
$328
This FlightHub deal was found by Cheapflights users on 8/8. 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.
Mon 8/312:53 am -
1 stop9h 11m
Tue 9/2210:50 am -
1 stop12h 57m
Deal found 8/8![Volaris logo]()
$326
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:35 am -
1 stop13h 28m
Fri 9/410:50 am -
1 stop12h 57m
Deal found 8/7![Volaris logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Wed 9/27:35 am -
1 stop13h 28m
Tue 9/89:50 pm -
1 stop8h 02m
Deal found 8/10![Volaris logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/77:35 am -
1 stop13h 28m
Mon 9/1410:40 am -
1 stop14h 15m
Deal found 8/10![Volaris logo]()
$332
This Super.com deal was found by Cheapflights users on 8/10. 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 9/82:53 am -
1 stop12h 35m
Fri 9/119:50 pm -
1 stop8h 02m
Deal found 8/10![Volaris logo]()
$329
This CheapOair deal was found by Cheapflights users on 8/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:53 am -
1 stop9h 11m
Tue 9/153:20 pm -
1 stop8h 27m
Deal found 8/11![Volaris logo]()
$330
This Justfly.com deal was found by Cheapflights users on 8/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:23 pm -
1 stop13h 32m
Sun 9/1310:40 am -
1 stop8h 24m
Deal found 8/12![Volaris logo]()
$341
This Super.com deal was found by Cheapflights users on 8/11. 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.
Thu 9/247:35 am -
1 stop13h 28m
Sun 9/2710:50 am -
1 stop12h 57m
Deal found 8/11![Volaris logo]()
$334
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 August 12, 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 August 12, 2026.
This Jetabroad deal was found by Cheapflights users on 8/11. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:35 am -
1 stop13h 28m
Deal found 8/11![Volaris logo]()
$124
This Booking.com deal was found by Cheapflights users on 8/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:35 am -
1 stop22h 20m
Deal found 8/11![Viva logo]()
$128
This Booking.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/74:20 pm -
1 stop7h 30m
Deal found 8/7![Viva logo]()
$130
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/311:04 am -
1 stop13h 13m
Deal found 8/7![Volaris logo]()
$131
This Super.com deal was found by Cheapflights users on 8/11. 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 9/27:35 am -
1 stop13h 28m
Deal found 8/11![Volaris logo]()
$132
This Super.com deal was found by Cheapflights users on 8/11. 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.
Tue 9/17:35 am -
1 stop13h 28m
Deal found 8/11![Volaris logo]()
$133
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/97:35 am -
1 stop13h 28m
Deal found 8/7![Volaris logo]()
$135
This Super.com deal was found by Cheapflights users on 8/11. 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.
Thu 8/271:40 am -
1 stop12h 48m
Deal found 8/11![Volaris logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:21 am -
1 stop9h 07m
Deal found 8/11![Volaris logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/71:40 am -
1 stop8h 23m
Deal found 8/10![Volaris logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:35 am -
1 stop13h 28m
Deal found 8/9![Volaris logo]()
$139
This Super.com deal was found by Cheapflights users on 8/11. 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 8/268:23 pm -
1 stop13h 32m
Deal found 8/11![Volaris logo]()
$162
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 August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $325 (Super.com) |
One-way from | $124 (Jetabroad) |
Popular in | March |
Cheapest in | January |
Average price | $503 |
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 August 12, 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
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Wed 11/4
12:35 am-11:55 pm
1 stop22h 20m
Cancun
Sun 11/8
11:00 am-10:55 pm
1 stop12h 55m
$339
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 9/7
5:30 am-12:10 pm
1 stop6h 40m
Cancun
Wed 9/16
12:40 pm-4:20 pm
Nonstop3h 40m
$456
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/30
6:00 am-12:30 pm
1 stop5h 30m
Cancun
Tue 12/8
8:00 am-4:14 pm
1 stop9h 14m
$466
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Sun 9/6
6:00 am-6:49 pm
2 stops12h 49m
Cancun
Wed 9/9
11:30 am-11:59 pm
2 stops12h 29m
$466
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Wed 9/9
6:10 am-6:49 pm
2 stops12h 39m
Cancun
Tue 9/15
12:41 pm-11:59 pm
2 stops11h 18m
$466
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Fri 10/2
6:40 am-7:50 pm
1 stop13h 10m
Cancun
Tue 10/6
12:40 pm-11:52 pm
2 stops11h 12m
$482
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 11/7
9:29 am-8:55 pm
2 stops10h 26m
Cancun
Wed 11/11
8:00 am-6:04 pm
2 stops11h 04m
$487
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Sat 10/31
10:35 am-7:55 pm
1 stop9h 20m
Cancun
Wed 11/4
8:00 am-8:30 pm
2 stops13h 30m
$487
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Sat 10/31
10:55 am-7:55 pm
2 stops9h 00m
Cancun
Sat 11/7
6:04 am-1:12 pm
1 stop8h 08m
$493
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Fri 11/27
6:30 am-1:05 pm
1 stop5h 35m
Cancun
Wed 12/2
6:00 pm-8:35 pm
Nonstop3h 35m
$496
Showing 1-10 of 47 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 August 12, 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 18% 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 August 12, 2026.
The most flights from CHI to PL9 are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Chicago to Playa del Carmen?
Airfare is below average for this route at the moment.
Chicago to Playa del Carmen flights typically cost between $413 and $596 in September.The cheapest round-trip price found within the last 5 days was $325 on Volaris (Sep 1-Sep 4).
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 August 12, 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
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to 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
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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 August 12, 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 August 12, 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 August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$120 | Average$408 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$158 | Average$441 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$191 | Average$429 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$484 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$292 | Average$563 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$313 | Average$504 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$320 | Average$556 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$524 | FlexibilityNo cancel fee | On-time67% |