$157+ Cheap flights from Chicago (CHI) to Quintana Roo
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Oct 20 — Oct 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
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Quintana Roo
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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 September 20, 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 September 20, 2026.
This CheapOair deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Sat 11/76:29 am -
1 stop13h 28m
Wed 11/1111:44 am -
Nonstop4h 01m
Deal found 9/14![Multiple Airlines logo]()
$385
This Gotogate deal was found by Cheapflights users on 9/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:40 am -
1 stop14h 17m
Sun 10/2511:50 am -
1 stop29h 53m
Deal found 9/18![Multiple Airlines logo]()
$386
This Air Canada deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:15 am -
1 stop12h 15m
Sun 11/111:35 am -
1 stop9h 23m
Deal found 9/14![Air Canada logo]()
$386
This CheapOair deal was found by Cheapflights users on 9/16. 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 10/67:35 am -
1 stop13h 28m
Tue 10/139:50 pm -
1 stop8h 02m
Deal found 9/16![Volaris logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/92:41 am -
1 stop15h 24m
Thu 10/229:50 pm -
1 stop8h 02m
Deal found 9/16![Multiple Airlines logo]()
$388
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop25h 50m
Sat 10/317:00 am -
2 stops12h 52m
Deal found 9/17![Air Canada logo]()
$389
This Trip.com deal was found by Cheapflights users on 9/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:40 pm -
1 stop25h 50m
Sun 11/89:30 pm -
1 stop19h 08m
Deal found 9/17![Air Canada logo]()
$390
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:40 am -
1 stop8h 23m
Fri 10/99:05 pm -
1 stop11h 55m
Deal found 9/17![Multiple Airlines logo]()
$391
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Thu 12/38:45 am -
2 stops13h 00m
Sun 12/66:55 pm -
2 stops21h 43m
Deal found 9/16![Air Canada logo]()
$392
This Air Canada deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:20 pm -
1 stop13h 25m
Mon 11/22:55 pm -
2 stops28h 35m
Deal found 9/14![Air Canada logo]()
$393
This FlightHub deal was found by Cheapflights users on 9/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:50 pm -
1 stop16h 51m
Tue 11/103:00 pm -
1 stop18h 00m
Deal found 9/17![Multiple Airlines logo]()
$393
This Gotogate deal was found by Cheapflights users on 9/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 am -
1 stop8h 22m
Mon 10/261:55 pm -
2 stops23h 18m
Deal found 9/16![Multiple Airlines logo]()
$394
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 September 20, 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 September 20, 2026.
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/308:05 am -
Nonstop3h 45m
Fri 12/46:00 pm -
Nonstop3h 35m
Deal found 9/15![Southwest logo]()
$427
This Booking.com deal was found by Cheapflights users on 9/16. 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.
Sun 10/181:30 am -
1 stop12h 00m
Thu 10/292:14 pm -
1 stop20h 46m
Deal found 9/16![Viva logo]()
$446
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 12/111:28 am -
1 stop8h 40m
Tue 12/88:15 am -
1 stop9h 02m
Deal found 9/16![Delta logo]()
$480
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/258:40 am -
Nonstop4h 03m
Fri 10/301:55 pm -
Nonstop4h 04m
Deal found 9/15![United Airlines logo]()
$481
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:55 pm -
3 stops17h 32m
Thu 10/292:14 pm -
1 stop20h 46m
Deal found 9/16![Multiple Airlines logo]()
$600
This Aeromexico deal was found by Cheapflights users on 9/17. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/301:04 pm -
2 stops22h 30m
Wed 2/31:42 pm -
1 stop10h 18m
Deal found 9/17![Aeromexico logo]()
$707
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:50 am -
1 stop5h 25m
Wed 10/283:20 pm -
Nonstop3h 35m
Deal found 9/16![Southwest logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Thu 11/268:40 am -
Nonstop4h 03m
Thu 12/33:11 pm -
Nonstop4h 02m
Deal found 9/15![United Airlines logo]()
$505
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/27:05 am -
2 stops13h 03m
Mon 12/76:04 am -
1 stop8h 08m
Deal found 9/15![Delta logo]()
$508
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/246:35 am -
2 stops9h 30m
Fri 10/301:45 pm -
2 stops10h 10m
Deal found 9/15![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 12/211:28 am -
1 stop8h 40m
Tue 12/88:15 am -
1 stop9h 02m
Deal found 9/17![Delta logo]()
$543
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/510:46 am -
Nonstop3h 40m
Thu 10/83:38 pm -
Nonstop3h 57m
Deal found 9/14![United Airlines logo]()
$593
This Delta deal was found by Cheapflights users on 9/19. 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 12/97:05 am -
2 stops13h 03m
Sun 12/1312:31 pm -
2 stops12h 21m
Deal found 9/19![Delta logo]()
$578
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/69:29 am -
Nonstop3h 41m
Thu 10/812:11 pm -
Nonstop3h 53m
Deal found 9/14![United Airlines logo]()
$593
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/168:50 am -
1 stop7h 10m
Thu 12/1711:20 am -
2 stops9h 45m
Deal found 9/15![Southwest logo]()
$601
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/76:30 am -
2 stops13h 10m
Wed 11/111:32 pm -
2 stops11h 22m
Deal found 9/14![Delta logo]()
$601
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:40 am -
2 stops9h 05m
Mon 12/78:20 am -
2 stops9h 45m
Deal found 9/16![Southwest logo]()
$625
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/37:00 am -
2 stops12h 55m
Sat 11/76:04 am -
1 stop8h 08m
Deal found 9/15![Delta logo]()
$612
This Southwest deal was found by Cheapflights users on 9/18. 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.
Tue 10/139:05 am -
Nonstop3h 35m
Fri 10/161:05 pm -
1 stop8h 55m
Deal found 9/18![Southwest logo]()
$668
This Delta deal was found by Cheapflights users on 9/18. 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.
Sun 9/278:05 am -
2 stops12h 31m
Sat 10/38:05 am -
2 stops12h 25m
Deal found 9/18![Delta logo]()
$652
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/129:05 am -
Nonstop3h 35m
Mon 10/191:00 pm -
1 stop9h 00m
Deal found 9/14![Southwest logo]()
$684
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/259:35 pm -
1 stop17h 07m
Wed 12/24:50 pm -
1 stop7h 06m
Deal found 9/15![United Airlines logo]()
$862
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 11/28:29 am -
2 stops11h 26m
Mon 11/166:04 am -
1 stop8h 08m
Deal found 9/16![Delta logo]()
$693
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:20 am -
Nonstop3h 45m
Sun 12/136:55 pm -
1 stop7h 10m
Deal found 9/16![Southwest logo]()
$720
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/319:35 pm -
1 stop18h 07m
Sat 11/72:05 pm -
Nonstop4h 00m
Deal found 9/14![United Airlines logo]()
$872
This United Airlines deal was found by Cheapflights users on 9/19. 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 10/319:35 pm -
1 stop18h 07m
Tue 11/34:50 pm -
1 stop7h 35m
Deal found 9/19![United Airlines logo]()
$872
This Southwest deal was found by Cheapflights users on 9/18. 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.
Fri 10/27:25 am -
1 stop7h 35m
Mon 10/51:05 pm -
Nonstop3h 40m
Deal found 9/18![Southwest logo]()
$726
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/146:20 am -
2 stops12h 28m
Wed 10/2112:40 pm -
2 stops11h 17m
Deal found 9/17![Delta logo]()
$738
This United Airlines deal was found by Cheapflights users on 9/19. 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 11/79:35 pm -
1 stop17h 07m
Tue 11/104:50 pm -
1 stop7h 35m
Deal found 9/19![United Airlines logo]()
$872
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 1/56:00 am -
1 stop6h 50m
Mon 1/114:27 pm -
1 stop17h 22m
Deal found 9/15![Delta logo]()
$762
Last-minute flights from Chicago to Quintana RooDiscover last-minute flight deals from Chicago to Quintana Roo. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Quintana Roo. Data last updated September 20, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:59 pm -
1 stop7h 11m
Mon 10/511:16 am -
1 stop12h 50m
Deal found 9/18![Multiple Airlines logo]()
$395
This CheapOair deal was found by Cheapflights users on 9/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:09 am -
1 stop13h 01m
Sun 10/411:16 am -
1 stop12h 50m
Deal found 9/18![Multiple Airlines logo]()
$396
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:40 am -
1 stop8h 23m
Fri 10/99:05 pm -
1 stop11h 55m
Deal found 9/17![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:35 am -
1 stop13h 28m
Mon 10/511:15 pm -
1 stop11h 45m
Deal found 9/17![Multiple Airlines logo]()
$393
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/47:35 am -
1 stop13h 28m
Sat 10/106:06 pm -
1 stop11h 32m
Deal found 9/15![Volaris logo]()
$392
This CheapOair deal was found by Cheapflights users on 9/16. 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 10/67:35 am -
1 stop13h 28m
Tue 10/139:50 pm -
1 stop8h 02m
Deal found 9/16![Volaris logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/92:41 am -
1 stop15h 24m
Thu 10/229:50 pm -
1 stop8h 02m
Deal found 9/16![Multiple Airlines logo]()
$388
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/112:53 am -
1 stop9h 11m
Tue 10/2010:00 am -
1 stop10h 12m
Deal found 9/17![Multiple Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/122:41 am -
1 stop15h 04m
Sat 10/179:50 pm -
1 stop8h 02m
Deal found 9/17![Multiple Airlines logo]()
$394
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop25h 50m
Sat 10/317:00 am -
2 stops12h 52m
Deal found 9/17![Air Canada logo]()
$389
This Air Canada deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:15 am -
1 stop12h 15m
Sun 11/111:35 am -
1 stop9h 23m
Deal found 9/14![Air Canada logo]()
$386
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Fri 10/302:41 am -
1 stop14h 20m
Sat 11/79:30 pm -
1 stop23h 28m
Deal found 9/17![Multiple Airlines logo]()
$390
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 September 20, 2026.
Search for one-way flight options from Chicago to Quintana Roo. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/122:41 am -
2 stops17h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$157
This Super.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/246:29 am -
1 stop13h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Volaris logo]()
$173
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/69:05 am -
Nonstop3h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$174
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 1/2510:30 am -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/142:41 am -
1 stop15h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$175
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:00 am -
1 stop8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![JetBlue logo]()
$176
This Air Canada deal was found by Cheapflights users on 9/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:05 am -
1 stop14h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$177
This FlightHub deal was found by Cheapflights users on 9/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:35 am -
1 stop13h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Volaris logo]()
$178
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:09 am -
1 stop10h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Volaris logo]()
$179
This FlightHub deal was found by Cheapflights users on 9/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:35 am -
1 stop13h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Volaris logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:40 am -
1 stop12h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Volaris logo]()
$181
This Air Canada deal was found by Cheapflights users on 9/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:20 am -
2 stops53h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$182
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 September 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $385 (CheapOair) |
One-way from | $157 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $538 |
Good round-trip deal | $551 or less |
Good one-way deal | $266 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 7,457,451 searches. Data last updated September 20, 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
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Sun 10/25
9:02 am-12:59 pm
Nonstop3h 57m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$174
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Mon 12/14
7:20 am-12:23 pm
Nonstop4h 03m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$174
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Mon 11/2
7:00 am-1:58 pm
1 stop5h 58m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Tue 12/8
7:00 am-4:15 pm
1 stop8h 15m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$176
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Sun 11/15
7:00 am-1:58 pm
1 stop5h 58m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$176
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Tue 10/20
10:46 am-2:26 pm
Nonstop3h 40m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Fri 11/13
6:29 am-8:57 pm
1 stop13h 28m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$212
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Tue 12/8
11:28 am-9:08 pm
1 stop8h 40m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$231
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Wed 12/16
7:00 am-4:15 pm
1 stop8h 15m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$231
ChicagoCancún
ORD Chicago O'Hare Intl - CUN Cancun
ORDCUN
Chicago O'Hare Intl
Tue 12/15
7:20 am-12:23 pm
Nonstop4h 03m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
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, January is the cheapest month in which you can book a flight from Chicago to Quintana Roo (average of $369). Flying from Chicago to Quintana Roo in December is currently the most expensive (average of $568). 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 September 20, 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 18% 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 September 20, 2026.
The most flights from CHI to MXQR are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Chicago to Quintana Roo?
Airfare is below average for this route at the moment.
Chicago to Quintana Roo flights typically cost between $412 and $638 in November.The cheapest round-trip price found within the last 5 days was $385 on Multiple Airlines (Nov 7-Nov 11).
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 77 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 September 20, 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.
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
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
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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 September 20, 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 7,457,451 searches. Data last updated September 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$129 | Average$414 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$158 | Average$483 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$190 | Average$432 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$193 | Average$435 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$253 | Average$420 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$500 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$292 | Average$585 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$490 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$323 | Average$570 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$492 | FlexibilityNo cancel fee | On-time67% |