$116+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Jul 24 — Jul 311
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
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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 June 24, 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 June 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Wed 7/84:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/21![Volaris logo]()
$308
This CheapOair deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Mon 7/139:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/19![Volaris logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/217:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Sat 8/294:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/24![Volaris logo]()
$311
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/62:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Fri 7/174:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/23![Volaris logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/112:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Mon 7/139:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/23![Volaris logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/87:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Thu 7/97:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Deal found 6/23![Volaris logo]()
$314
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Mon 7/63:20 pm
CUN
- ORD
1 stop14h 32m
Volaris
Deal found 6/23![Volaris logo]()
$315
This FlightHub deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Mon 10/1211:16 am
CUN
- ORD
1 stop12h 50m
Volaris
Deal found 6/24![Volaris logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Tue 8/252:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Tue 9/14:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/20![Volaris logo]()
$317
This Super.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 6/307:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Sat 7/44:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/24![Volaris logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Fri 7/1712:49 pm
CUN
- ORD
1 stop12h 06m
Volaris
Deal found 6/23![Volaris logo]()
$319
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/22![Southwest logo]()
$358
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 June 24, 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 June 24, 2026.
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/261:10 pm
CUN
- MDW
1 stop7h 35m
Southwest
Deal found 6/24![Southwest logo]()
$369
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/219:17 am
ORD
- CUN
Nonstop3h 53m
United Airlines
Tue 7/2812:11 pm
CUN
- ORD
Nonstop4h 05m
United Airlines
Deal found 6/23![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/258:05 am
ORD
- CUN
2 stops10h 39m
Delta
Tue 9/19:11 am
CUN
- ORD
1 stop14h 42m
Delta
Deal found 6/23![Delta logo]()
$437
This Volaris deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/22![Volaris logo]()
$521
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/202:53 am
ORD
- CTM
2 stops31h 57m
Multiple Airlines
Tue 7/282:10 pm
CTM
- ORD
1 stop20h 45m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$581
This Aeromexico deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/211:50 am
ORD
- CTM
1 stop14h 40m
Aeromexico
Sat 9/265:24 pm
CTM
- ORD
1 stop20h 52m
Aeromexico
Deal found 6/24![Aeromexico logo]()
$856
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/97:30 pm
ORD
- CUN
2 stops15h 55m
Delta
Thu 8/137:04 am
CUN
- ORD
2 stops16h 53m
Delta
Deal found 6/23![Delta logo]()
$474
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
MDW
- CUN
2 stops9h 00m
Southwest
Thu 8/203:10 pm
CUN
- MDW
2 stops8h 10m
Southwest
Deal found 6/22![Southwest logo]()
$481
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Mon 8/2410:46 am
ORD
- CUN
Nonstop3h 40m
United Airlines
Sat 8/292:49 pm
CUN
- ORD
1 stop8h 37m
United Airlines
Deal found 6/22![United Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 6/20. 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.
Tue 8/256:00 am
MDW
- CUN
2 stops9h 00m
Southwest
Wed 9/212:50 pm
CUN
- MDW
2 stops9h 00m
Southwest
Deal found 6/20![Southwest logo]()
$481
This Volaris deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/238:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Tue 7/2810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/23![Volaris logo]()
$538
This Delta deal was found by Cheapflights users on 6/20. 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.
Thu 8/2012:46 pm
MDW
- CUN
1 stop7h 19m
Delta
Tue 8/258:01 am
CUN
- MDW
2 stops14h 35m
Delta
Deal found 6/20![Delta logo]()
$492
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3110:33 am
ORD
- CUN
Nonstop3h 53m
United Airlines
Mon 8/312:55 pm
CUN
- ORD
Nonstop4h 05m
United Airlines
Deal found 6/21![United Airlines logo]()
$495
This Volaris deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/138:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/22![Volaris logo]()
$541
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/276:05 am
MDW
- CUN
2 stops12h 39m
Delta
Thu 9/38:05 am
CUN
- MDW
2 stops10h 28m
Delta
Deal found 6/22![Delta logo]()
$497
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2510:33 am
ORD
- CUN
Nonstop3h 53m
United Airlines
Sat 8/112:55 pm
CUN
- ORD
Nonstop4h 05m
United Airlines
Deal found 6/19![United Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 6/20. 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.
Sun 7/195:05 am
MDW
- CUN
1 stop8h 05m
Southwest
Mon 7/204:10 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/20![Southwest logo]()
$515
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:03 am
ORD
- CUN
1 stop12h 20m
Delta
Wed 7/158:00 am
CUN
- ORD
2 stops10h 29m
Delta
Deal found 6/22![Delta logo]()
$498
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/309:17 am
ORD
- CUN
Nonstop3h 53m
United Airlines
Tue 7/73:38 pm
CUN
- ORD
Nonstop4h 07m
United Airlines
Deal found 6/22![United Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 6/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:55 am
MDW
- CUN
1 stop5h 35m
Southwest
Mon 8/1712:50 pm
CUN
- MDW
2 stops9h 30m
Southwest
Deal found 6/21![Southwest logo]()
$542
This Delta deal was found by Cheapflights users on 6/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:46 pm
MDW
- CUN
1 stop7h 19m
Delta
Mon 8/178:05 am
CUN
- MDW
1 stop14h 31m
Delta
Deal found 6/21![Delta logo]()
$499
This Southwest deal was found by Cheapflights users on 6/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/58:30 am
MDW
- CUN
1 stop8h 30m
Southwest
Thu 7/91:20 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 6/21![Southwest logo]()
$542
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:44 pm
ORD
- CUN
1 stop6h 39m
Delta
Thu 7/1610:55 am
CUN
- ORD
2 stops21h 04m
Delta
Deal found 6/19![Delta logo]()
$503
This Volaris deal was found by Cheapflights users on 6/20. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:40 am
ORD
- CZM
1 stop14h 17m
Volaris
Sun 8/94:47 pm
CZM
- ORD
1 stop13h 05m
Volaris
Deal found 6/20![Volaris logo]()
$702
This Aeromexico deal was found by Cheapflights users on 6/21. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:50 am
ORD
- CTM
1 stop14h 40m
Aeromexico
Thu 10/15:09 pm
CTM
- ORD
1 stop21h 07m
Aeromexico
Deal found 6/21![Aeromexico logo]()
$856
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:30 am
ORD
- CUN
1 stop14h 55m
Delta
Mon 7/138:00 am
CUN
- ORD
2 stops23h 59m
Delta
Deal found 6/19![Delta logo]()
$524
This Delta deal was found by Cheapflights users on 6/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:40 am
ORD
- CUN
1 stop13h 25m
Delta
Sun 8/306:05 am
CUN
- ORD
2 stops12h 44m
Delta
Deal found 6/21![Delta logo]()
$537
This Mytrip deal was found by Cheapflights users on 6/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:49 pm
MDW
- CZM
2 stops19h 08m
Volaris
Tue 8/114:47 pm
CZM
- MDW
3 stops26h 17m
Volaris
Deal found 6/21![Volaris logo]()
$791
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:30 am
ORD
- CUN
2 stops13h 09m
Delta
Sat 9/2612:38 pm
CUN
- ORD
2 stops11h 21m
Delta
Deal found 6/19![Delta logo]()
$537
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/267:30 am
ORD
- CZM
1 stop7h 12m
United Airlines
Wed 9/23:52 pm
CZM
- ORD
1 stop7h 34m
United Airlines
Deal found 6/23![United Airlines logo]()
$832
Last-minute flights from Chicago to Quintana RooDiscover last-minute flight deals from Chicago to Quintana Roo. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Quintana Roo. Data last updated June 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Thu 7/27:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Deal found 6/24![Volaris logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Mon 6/291:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Sat 7/47:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Deal found 6/20![Volaris logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/302:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Sat 7/47:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Deal found 6/22![Volaris logo]()
$312
This Super.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/302:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Thu 7/27:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Deal found 6/22![Volaris logo]()
$314
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 6/307:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Tue 7/710:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Deal found 6/23![Volaris logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/11:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Tue 7/74:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/23![Volaris logo]()
$324
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Tue 7/79:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/23![Volaris logo]()
$320
This Justfly.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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.
Fri 7/32:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Tue 7/79:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/24![Volaris logo]()
$321
This FlightHub deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Sat 7/119:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/24![Volaris logo]()
$323
This Super.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 7/810:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/22![Volaris logo]()
$367
This Super.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/47:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Mon 7/69:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 6/24![Volaris logo]()
$313
This FlightHub deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/188:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/23![Volaris logo]()
$360
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 June 24, 2026.
Search for one-way flight options from Chicago to Quintana Roo. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This FlightHub deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/201:59 am
ORD
- CUN
1 stop14h 07m
Volaris
Deal found 6/22![Volaris logo]()
$116
This FlightHub deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:21 am
ORD
- CUN
1 stop11h 53m
Volaris
Deal found 6/22![Volaris logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 6/24![Volaris logo]()
$118
This FlightHub deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/307:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/23![Volaris logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/62:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Deal found 6/22![Volaris logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/187:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/24![Volaris logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/171:59 am
ORD
- CUN
1 stop12h 07m
Volaris
Deal found 6/22![Volaris logo]()
$123
This iWofly deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/288:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/23![Volaris logo]()
$124
This FlightHub deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/37:09 am
ORD
- CUN
1 stop10h 21m
Volaris
Deal found 6/23![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/217:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/22![Volaris logo]()
$125
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Deal found 6/23![Volaris logo]()
$127
This Gotogate deal was found by Cheapflights users on 6/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:21 am
ORD
- CUN
1 stop11h 53m
Volaris
Deal found 6/21![Volaris logo]()
$128
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 June 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $308 (Kiwi.com) |
One-way from | $116 (FlightHub) |
Popular in | March |
Cheapest in | January |
Average price | $480 |
Good round-trip deal | $463 or less |
Good one-way deal | $203 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 June 24, 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
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 8/17
8:25 am-12:00 pm
Nonstop3h 35m
Cancun
Wed 8/26
1:10 pm-8:45 pm
1 stop7h 35m
$369
Quickest round-trip
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 7/21
9:17 am-1:10 pm
Nonstop3h 53m
Cancun
Tue 7/28
12:11 pm-4:16 pm
Nonstop4h 05m
$432
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 8/25
8:05 am-6:44 pm
2 stops10h 39m
Cancun
Tue 9/1
9:11 am-11:53 pm
1 stop14h 42m
$437
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 8/9
7:30 pm-11:25 am
2 stops15h 55m
Cancun
Thu 8/13
7:04 am-11:57 pm
2 stops16h 53m
$474
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 8/18
6:00 am-3:00 pm
2 stops9h 00m
Cancun
Thu 8/20
3:10 pm-11:20 pm
2 stops8h 10m
$481
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 8/25
6:00 am-3:00 pm
2 stops9h 00m
Cancun
Wed 9/2
12:50 pm-9:50 pm
2 stops9h 00m
$481
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Mon 8/24
10:46 am-2:26 pm
Nonstop3h 40m
Cancun
Sat 8/29
2:49 pm-11:26 pm
1 stop8h 37m
$488
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 8/20
12:46 pm-8:05 pm
1 stop7h 19m
Cancun
Tue 8/25
8:01 am-10:36 pm
2 stops14h 35m
$492
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 7/31
10:33 am-2:26 pm
Nonstop3h 53m
Cancun
Mon 8/3
12:55 pm-5:00 pm
Nonstop4h 05m
$495
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 8/27
6:05 am-6:44 pm
2 stops12h 39m
Cancun
Thu 9/3
8:05 am-6:33 pm
2 stops10h 28m
$497
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
MDW-CUN
ORD-CTM
ORD-CZM
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
MDW-CUN
ORD-CTM
ORD-CZM
What is the cheapest month to book a flight from Chicago to Quintana Roo?
Currently, October is the cheapest month in which you can book a flight from Chicago to Quintana Roo (average of $389). Flying from Chicago to Quintana Roo in March is currently the most expensive (average of $580). 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 June 24, 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 23% 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 June 24, 2026.
The most flights from CHI to MXQR are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Chicago to 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 June 24, 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.
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 June 24, 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 June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$324 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$158 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$192 | Average$427 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$556 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$301 | Average$508 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$319 | Average$534 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$425 | FlexibilityNo cancel fee | On-time67% |