$121+ Cheap flights from Chicago (CHI) to Quintana Roo
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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Aug 20 — Aug 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Quintana Roo 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
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Cheapest flights from Chicago to Quintana RooExplore the most affordable flight options available from Chicago to Quintana Roo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 21, 2026.
Explore the most affordable flight options available from Chicago to Quintana Roo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 21, 2026.
This Viva deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:40 pm
ORD
- CUN
1 stop28h 05m
Viva
Mon 10/127:00 am
CUN
- ORD
1 stop8h 50m
Viva
Deal found 7/20![Viva logo]()
$314
This Viva deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:35 am
ORD
- CUN
1 stop20h 10m
Viva
Tue 11/1710:35 pm
CUN
- ORD
1 stop25h 20m
Viva
Deal found 7/17![Viva logo]()
$315
This Viva deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:30 am
ORD
- CUN
1 stop17h 20m
Viva
Sun 12/611:25 am
CUN
- ORD
1 stop12h 25m
Viva
Deal found 7/19![Viva logo]()
$316
This Super.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:23 am
ORD
- CUN
1 stop13h 38m
Volaris
Wed 11/189:53 pm
CUN
- ORD
1 stop7h 43m
Volaris
Deal found 7/16![Volaris logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Thu 8/2710:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/19![Volaris logo]()
$318
This Viva deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:22 pm
ORD
- CUN
1 stop7h 28m
Viva
Wed 9/306:15 am
CUN
- ORD
1 stop28h 45m
Viva
Deal found 7/16![Viva logo]()
$319
This Mytrip deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:20 pm
ORD
- CUN
1 stop7h 30m
Multiple Airlines
Tue 9/110:50 am
CUN
- ORD
1 stop12h 57m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$320
This Super.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Mon 9/1410:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/16![Volaris logo]()
$321
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Sat 9/53:20 pm
CUN
- ORD
1 stop14h 32m
Volaris
Deal found 7/19![Volaris logo]()
$322
This Super.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:40 am
ORD
- CUN
1 stop12h 48m
Volaris
Wed 9/910:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/16![Volaris logo]()
$323
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:21 am
ORD
- CUN
1 stop11h 53m
Volaris
Mon 8/3112:49 pm
CUN
- ORD
1 stop12h 06m
Volaris
Deal found 7/19![Volaris logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Sun 8/2310:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Deal found 7/16![Volaris logo]()
$325
Best flights from Chicago to Quintana RooDiscover carefully curated flight deals from Chicago to Quintana Roo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 21, 2026.
Discover carefully curated flight deals from Chicago to Quintana Roo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 21, 2026.
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:25 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 8/2612:40 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/18![Southwest logo]()
$442
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:50 am
ORD
- CUN
1 stop18h 35m
Delta
Tue 10/136:04 am
CUN
- ORD
2 stops17h 47m
Delta
Deal found 7/19![Delta logo]()
$473
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:30 am
ORD
- CUN
1 stop7h 03m
United Airlines
Mon 9/283:38 pm
CUN
- ORD
Nonstop3h 57m
United Airlines
Deal found 7/20![United Airlines logo]()
$492
This Volaris deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:26 pm
MDW
- CUN
1 stop12h 34m
Volaris
Mon 8/2410:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/16![Volaris logo]()
$526
This Viva deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/301:05 am
ORD
- CTM
1 stop11h 23m
Viva
Fri 1/12:10 pm
CTM
- ORD
1 stop10h 25m
Viva
Deal found 7/19![Viva logo]()
$643
This Aeromexico deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/41:50 am
ORD
- CTM
1 stop14h 40m
Aeromexico
Fri 10/95:09 pm
CTM
- ORD
2 stops27h 51m
Aeromexico
Deal found 7/16![Aeromexico logo]()
$914
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Tue 9/291:10 pm
CUN
- MDW
1 stop7h 35m
Southwest
Deal found 7/19![Southwest logo]()
$472
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:19 am
ORD
- CUN
2 stops8h 56m
Delta
Fri 10/236:59 am
CUN
- ORD
1 stop16h 54m
Delta
Deal found 7/17![Delta logo]()
$477
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:46 am
ORD
- CUN
Nonstop3h 40m
United Airlines
Sun 8/303:38 pm
CUN
- ORD
Nonstop3h 57m
United Airlines
Deal found 7/16![United Airlines logo]()
$497
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:45 am
ORD
- CUN
2 stops11h 54m
Delta
Sat 10/1012:38 pm
CUN
- ORD
2 stops11h 13m
Delta
Deal found 7/20![Delta logo]()
$478
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:10 am
MDW
- CUN
1 stop8h 30m
Southwest
Tue 10/131:45 pm
CUN
- MDW
1 stop8h 10m
Southwest
Deal found 7/17![Southwest logo]()
$498
This Volaris deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:40 am
ORD
- CZM
1 stop14h 17m
Volaris
Tue 9/2211:52 am
CZM
- ORD
1 stop11h 55m
Volaris
Deal found 7/21![Volaris logo]()
$571
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:33 am
ORD
- CUN
Nonstop3h 53m
United Airlines
Sat 8/13:38 pm
CUN
- ORD
Nonstop4h 07m
United Airlines
Deal found 7/19![United Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:40 am
ORD
- CUN
2 stops13h 45m
Delta
Wed 9/3011:16 am
CUN
- ORD
2 stops12h 43m
Delta
Deal found 7/19![Delta logo]()
$478
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:55 am
MDW
- CUN
1 stop7h 45m
Southwest
Fri 8/213:10 pm
CUN
- MDW
2 stops8h 10m
Southwest
Deal found 7/20![Southwest logo]()
$502
This Volaris deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Mon 8/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/18![Volaris logo]()
$578
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:29 am
ORD
- CUN
Nonstop3h 41m
United Airlines
Sat 10/1712:11 pm
CUN
- ORD
Nonstop3h 53m
United Airlines
Deal found 7/20![United Airlines logo]()
$526
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:10 am
ORD
- CUN
2 stops13h 05m
Delta
Tue 10/136:59 am
CUN
- ORD
2 stops16h 52m
Delta
Deal found 7/18![Delta logo]()
$482
This Volaris deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/308:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Sun 8/210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/18![Volaris logo]()
$588
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:48 am
MDW
- CUN
1 stop9h 02m
Delta
Sat 9/198:05 am
CUN
- MDW
2 stops10h 15m
Delta
Deal found 7/16![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:40 am
MDW
- CUN
Nonstop3h 35m
Southwest
Tue 9/112:40 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/20![Southwest logo]()
$546
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:55 am
ORD
- CUN
2 stops10h 55m
Delta
Thu 9/248:05 am
CUN
- ORD
2 stops12h 25m
Delta
Deal found 7/17![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:25 am
MDW
- CUN
1 stop9h 35m
Southwest
Mon 9/2112:50 pm
CUN
- MDW
2 stops9h 30m
Southwest
Deal found 7/19![Southwest logo]()
$551
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:05 am
MDW
- CUN
1 stop5h 20m
Delta
Wed 9/309:11 am
CUN
- MDW
2 stops13h 34m
Delta
Deal found 7/16![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:24 am
MDW
- CUN
2 stops10h 41m
Delta
Thu 9/38:05 am
CUN
- MDW
2 stops10h 28m
Delta
Deal found 7/18![Delta logo]()
$546
This Mytrip deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:49 pm
MDW
- CZM
2 stops19h 08m
Volaris
Mon 8/104:47 pm
CZM
- MDW
2 stops26h 47m
Volaris
Deal found 7/17![Volaris logo]()
$833
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:35 pm
ORD
- CZM
1 stop17h 07m
United Airlines
Thu 9/243:52 pm
CZM
- ORD
1 stop7h 35m
United Airlines
Deal found 7/17![United Airlines logo]()
$841
This Aeromexico deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:55 am
ORD
- CTM
1 stop14h 21m
Aeromexico
Sat 8/295:49 pm
CTM
- ORD
1 stop20h 22m
Aeromexico
Deal found 7/19![Aeromexico logo]()
$1,166
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:59 am
ORD
- CUN
2 stops13h 06m
Delta
Sat 8/158:05 am
CUN
- ORD
2 stops12h 25m
Delta
Deal found 7/17![Delta logo]()
$548
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:30 am
ORD
- CZM
1 stop7h 12m
United Airlines
Tue 9/13:52 pm
CZM
- ORD
1 stop7h 34m
United Airlines
Deal found 7/17![United Airlines logo]()
$841
Last-minute flights from Chicago to Quintana RooDiscover last-minute flight deals from Chicago to Quintana Roo. Data last updated July 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Quintana Roo. Data last updated July 21, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/161:30 am
ORD
- CUN
1 stop21h 40m
Viva
Wed 8/2610:05 pm
CUN
- ORD
1 stop25h 50m
Viva
Deal found 7/17![Viva logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Sun 8/2310:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Deal found 7/16![Volaris logo]()
$325
This iWofly deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:21 am
ORD
- CUN
1 stop11h 53m
Volaris
Wed 8/2610:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Deal found 7/21![Volaris logo]()
$332
This Mytrip deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:20 pm
ORD
- CUN
1 stop7h 30m
Multiple Airlines
Tue 9/110:50 am
CUN
- ORD
1 stop12h 57m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Thu 8/2710:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/19![Volaris logo]()
$318
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Tue 9/110:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Deal found 7/21![Volaris logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Mon 8/3110:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/19![Volaris logo]()
$326
This CheapOair deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Thu 9/34:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 7/16![Volaris logo]()
$333
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Sat 8/2912:49 pm
CUN
- ORD
1 stop12h 06m
Volaris
Deal found 7/19![Volaris logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Fri 9/410:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/16![Volaris logo]()
$328
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:21 am
ORD
- CUN
1 stop11h 53m
Volaris
Mon 8/3112:49 pm
CUN
- ORD
1 stop12h 06m
Volaris
Deal found 7/19![Volaris logo]()
$324
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Tue 9/110:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/20![Volaris logo]()
$329
One-way flights from Chicago to Quintana RooSearch for one-way flight options from Chicago to Quintana Roo. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
Search for one-way flight options from Chicago to Quintana Roo. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 7/20![Volaris logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 7/16![Volaris logo]()
$122
This Booking.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:35 am
ORD
- CUN
1 stop20h 10m
Viva
Deal found 7/16![Viva logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 7/16![Volaris logo]()
$128
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 7/20![Volaris logo]()
$130
This Viva deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:22 pm
ORD
- CUN
1 stop7h 28m
Viva
Deal found 7/17![Viva logo]()
$132
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:19 am
ORD
- CUN
1 stop14h 09m
Volaris
Deal found 7/20![Volaris logo]()
$133
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Deal found 7/19![Volaris logo]()
$134
This Viva deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:20 pm
ORD
- CZM
1 stop27h 22m
Viva
Deal found 7/20![Viva logo]()
$135
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 7/20![Volaris logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 7/16![Volaris logo]()
$136
This Viva deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:40 pm
ORD
- CZM
1 stop29h 06m
Viva
Deal found 7/20![Viva logo]()
$140
Find flight deals from Chicago to Quintana Roo
Keep the following information in mind while searching for Chicago to Quintana Roo flight deals. Data was last updated July 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $314 (Viva) |
One-way from | $121 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $443 |
Good round-trip deal | $498 or less |
Good one-way deal | $224 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Quintana Roo 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 July 21, 2026.
Use the filters below to find and compare flights from Chicago to Quintana Roo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 8/17
8:25 am-12:00 pm
Nonstop3h 35m
Cancun
Wed 8/26
12:40 pm-4:15 pm
Nonstop3h 35m
$442
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 9/22
8:35 am-12:10 pm
Nonstop3h 35m
Cancun
Tue 9/29
1:10 pm-8:45 pm
1 stop7h 35m
$472
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Thu 10/8
1:50 am-8:25 pm
1 stop18h 35m
Cancun
Tue 10/13
6:04 am-11:51 pm
2 stops17h 47m
$473
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 10/16
11:19 am-8:15 pm
2 stops8h 56m
Cancun
Fri 10/23
6:59 am-11:53 pm
1 stop16h 54m
$477
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 10/6
6:45 am-6:39 pm
2 stops11h 54m
Cancun
Sat 10/10
12:38 pm-11:51 pm
2 stops11h 13m
$478
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 9/25
6:40 am-8:25 pm
2 stops13h 45m
Cancun
Wed 9/30
11:16 am-11:59 pm
2 stops12h 43m
$478
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 10/10
7:10 am-8:15 pm
2 stops13h 05m
Cancun
Tue 10/13
6:59 am-11:51 pm
2 stops16h 52m
$482
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 9/16
10:48 am-7:50 pm
1 stop9h 02m
Cancun
Sat 9/19
8:05 am-6:20 pm
2 stops10h 15m
$487
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 9/19
8:55 am-7:50 pm
2 stops10h 55m
Cancun
Thu 9/24
8:05 am-8:30 pm
2 stops12h 25m
$487
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 9/23
5:30 am-12:33 pm
1 stop7h 03m
Cancun
Mon 9/28
3:38 pm-7:35 pm
Nonstop3h 57m
$492
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Quintana Roo
Have a flexible travel schedule? Discover the best time to fly to Quintana Roo from Chicago with our price prediction graph.
ORD-CUN
ORD-CZM
MDW-CUN
ORD-CTM
MDW-CZM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Quintana Roo
CHI-MXQR
ORD-CUN
ORD-CZM
MDW-CUN
ORD-CTM
What is the cheapest month to book a flight from Chicago to Quintana Roo?
Currently, January is the cheapest month in which you can book a flight from Chicago to Quintana Roo (average of $379). Flying from Chicago to Quintana Roo in March is currently the most expensive (average of $551). 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 QR?
Find hourly flight availability from Chicago to Quintana Roo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 21, 2026.
When flying from Chicago to Quintana Roo, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 21% versus a flight at noon.
Weekly flight availability from Chicago to Quintana Roo
Explore weekly flight availability from Chicago to Quintana Roo. 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 July 21, 2026.
The most flights from CHI to MXQR 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 (8 on average).
How much does it cost to fly round-trip from Chicago to Quintana Roo?
How far ahead should I book a flight from Chicago to Quintana Roo?
The best time to book flights from Chicago to Quintana Roo is 16 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Quintana Roo
Get insights into the airlines that provide service to Quintana Roo. 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 Quintana Roo. Reviews last updated July 21, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Quintana Roo to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
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 Quintana Roo. 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 Quintana Roo
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Quintana Roo by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Quintana Roo by cabin class
Find flights from Chicago to Quintana Roo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Quintana Roo flights
Browse other Chicago and Quintana Roo flight options. Last updated on July 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Quintana Roo
Discover the top 10 airlines that operate flights from Chicago to Quintana Roo. 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 July 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$406 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$158 | Average$441 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$192 | Average$427 | 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$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$563 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$512 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$320 | Average$538 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$431 | FlexibilityNo cancel fee | On-time67% |