$177+ Cheap flights from Quintana Roo to Chicago (CHI)
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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Jul 22 — Jul 291
Round-trip
1 adult, Economy
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Cheapest flights from Quintana Roo to ChicagoExplore the most affordable flight options available from Quintana Roo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 22, 2026.
Explore the most affordable flight options available from Quintana Roo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 22, 2026.
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1010:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Fri 10/161:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/21![Volaris logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Tue 7/71:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/18![Volaris logo]()
$288
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Sat 10/31:40 am
ORD
- CUN
1 stop12h 48m
Volaris
Deal found 6/21![Volaris logo]()
$289
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Tue 7/147:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/19![Volaris logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/73:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Fri 7/106:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Deal found 6/17![Volaris logo]()
$300
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Mon 8/317:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/20![Volaris logo]()
$308
This Despegar 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 Despegar is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Sun 10/187:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/19![Volaris logo]()
$310
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Sun 7/192:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Deal found 6/21![Volaris logo]()
$313
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:20 pm
CUN
- ORD
1 stop14h 32m
Volaris
Fri 9/117:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/20![Volaris logo]()
$315
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Mon 7/208:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/21![Volaris logo]()
$356
This CheapOair deal was found by Cheapflights users on 6/17. 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.
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Mon 6/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/17![Volaris logo]()
$361
This OneTravel deal was found by Cheapflights users on 6/17. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Wed 7/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/17![Volaris logo]()
$376
Best flights from Quintana Roo to ChicagoDiscover carefully curated flight deals from Quintana Roo to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 22, 2026.
Discover carefully curated flight deals from Quintana Roo to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 22, 2026.
This Volaris deal was found by Cheapflights users on 6/18. 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 9/89:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Thu 9/101:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/18![Volaris logo]()
$308
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.
Thu 10/83:38 pm
CUN
- ORD
Nonstop3h 57m
United Airlines
Mon 10/129:38 pm
ORD
- CUN
1 stop14h 55m
United Airlines
Deal found 6/19![United Airlines logo]()
$383
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.
Thu 10/112:38 pm
CUN
- ORD
1 stop11h 15m
Delta
Sun 10/411:17 am
ORD
- CUN
2 stops8h 58m
Delta
Deal found 6/19![Delta logo]()
$393
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:10 am
CUN
- MDW
1 stop9h 22m
Frontier
Mon 8/176:05 am
MDW
- CUN
1 stop7h 41m
Frontier
Deal found 6/21![Frontier logo]()
$395
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:10 pm
CUN
- MDW
1 stop8h 45m
Southwest
Sun 9/207:20 am
MDW
- CUN
1 stop7h 30m
Southwest
Deal found 6/19![Southwest logo]()
$457
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 8/49:09 am
CTM
- ORD
2 stops36h 11m
Multiple Airlines
Tue 8/117:35 am
ORD
- CTM
1 stop29h 50m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$533
This Viva 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:30 pm
CZM
- ORD
1 stop27h 15m
Viva
Wed 12/212:30 am
ORD
- CZM
1 stop18h 12m
Viva
Deal found 6/20![Viva logo]()
$563
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.
Thu 10/292:11 pm
CUN
- ORD
Nonstop4h 02m
United Airlines
Mon 11/29:02 am
ORD
- CUN
Nonstop3h 57m
United Airlines
Deal found 6/21![United Airlines logo]()
$387
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/244:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Fri 7/316:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Deal found 6/21![Volaris logo]()
$389
This Delta deal was found by Cheapflights users on 6/18. 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 9/242:31 pm
CUN
- ORD
1 stop9h 22m
Delta
Mon 9/2811:17 am
ORD
- CUN
2 stops8h 58m
Delta
Deal found 6/18![Delta logo]()
$396
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Thu 10/812:11 pm
CUN
- ORD
Nonstop3h 53m
United Airlines
Tue 10/1310:46 am
ORD
- CUN
Nonstop3h 40m
United Airlines
Deal found 6/17![United Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 6/18. 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 10/812:30 pm
CUN
- ORD
1 stop7h 54m
Delta
Tue 10/138:55 am
ORD
- CUN
2 stops11h 20m
Delta
Deal found 6/18![Delta logo]()
$401
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.
Thu 8/205:09 pm
CTM
- ORD
1 stop21h 02m
Aeromexico
Sun 8/235:30 am
ORD
- CTM
2 stops10h 21m
Aeromexico
Deal found 6/21![Aeromexico logo]()
$909
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2311:10 am
CUN
- MDW
1 stop9h 22m
Volaris
Tue 7/288:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Deal found 6/21![Volaris logo]()
$423
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.
Tue 7/2112:40 pm
CUN
- MDW
1 stop6h 25m
Southwest
Tue 7/2810:05 am
MDW
- CUN
Nonstop3h 35m
Southwest
Deal found 6/21![Southwest logo]()
$477
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2711:40 am
CUN
- MDW
2 stops8h 40m
Southwest
Mon 8/39:55 am
MDW
- CUN
Nonstop3h 35m
Southwest
Deal found 6/19![Southwest logo]()
$499
This Volaris deal was found by Cheapflights users on 6/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Sun 7/268:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 6/17![Volaris logo]()
$494
This Delta deal was found by Cheapflights users on 6/18. 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 9/208:00 am
CUN
- MDW
1 stop8h 11m
Delta
Thu 9/241:00 pm
MDW
- CUN
1 stop7h 15m
Delta
Deal found 6/18![Delta logo]()
$532
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Fri 7/248:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 6/19![Volaris logo]()
$494
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/211:40 am
CUN
- MDW
1 stop8h 25m
Southwest
Tue 7/1410:05 am
MDW
- CUN
Nonstop3h 35m
Southwest
Deal found 6/19![Southwest logo]()
$595
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.
Sat 7/1111:00 am
CUN
- MDW
2 stops22h 13m
Delta
Wed 7/226:00 am
MDW
- CUN
2 stops14h 26m
Delta
Deal found 6/20![Delta logo]()
$590
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Wed 8/53:52 pm
CZM
- ORD
1 stop7h 23m
United Airlines
Tue 8/115:30 am
ORD
- CZM
1 stop9h 12m
United Airlines
Deal found 6/17![United Airlines logo]()
$656
This Delta deal was found by Cheapflights users on 6/17. 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.
Tue 7/288:00 am
CUN
- MDW
2 stops10h 25m
Delta
Fri 7/3112:41 pm
MDW
- CUN
1 stop7h 42m
Delta
Deal found 6/17![Delta logo]()
$595
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Thu 8/63:52 pm
CZM
- ORD
1 stop7h 23m
United Airlines
Wed 8/126:30 am
ORD
- CZM
1 stop8h 12m
United Airlines
Deal found 6/17![United Airlines logo]()
$656
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:52 pm
CZM
- ORD
1 stop7h 35m
United Airlines
Wed 10/147:30 am
ORD
- CZM
1 stop7h 12m
United Airlines
Deal found 6/18![United Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:52 pm
CZM
- ORD
1 stop7h 35m
United Airlines
Sun 10/47:30 am
ORD
- CZM
1 stop7h 12m
United Airlines
Deal found 6/18![United Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:25 pm
CZM
- ORD
1 stop7h 46m
United Airlines
Tue 11/36:00 am
ORD
- CZM
1 stop6h 23m
United Airlines
Deal found 6/18![United Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Fri 7/243:52 pm
CZM
- ORD
1 stop8h 53m
United Airlines
Sun 8/25:30 am
ORD
- CZM
1 stop9h 12m
United Airlines
Deal found 6/17![United Airlines logo]()
$666
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.
Wed 7/223:52 pm
CZM
- ORD
1 stop8h 53m
United Airlines
Sun 7/266:29 am
ORD
- CZM
1 stop8h 13m
United Airlines
Deal found 6/22![United Airlines logo]()
$667
Last-minute flights from Quintana Roo to ChicagoDiscover last-minute flight deals from Quintana Roo to Chicago. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from Quintana Roo to Chicago. Data last updated June 22, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1812:49 pm
CUN
- ORD
1 stop12h 06m
Volaris
Mon 6/227:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/17![Volaris logo]()
$324
This CheapOair deal was found by Cheapflights users on 6/17. 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.
Thu 6/1810:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Mon 6/228:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/17![Volaris logo]()
$361
This CheapOair deal was found by Cheapflights users on 6/17. 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.
Thu 6/253:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Sun 6/287:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/17![Volaris logo]()
$321
This CheapOair deal was found by Cheapflights users on 6/17. 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.
Mon 6/293:20 pm
CUN
- ORD
1 stop14h 32m
Volaris
Sun 7/51:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Deal found 6/17![Volaris logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Tue 7/71:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/18![Volaris logo]()
$288
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Tue 7/147:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 6/19![Volaris logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/73:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Fri 7/106:21 am
ORD
- CUN
1 stop9h 07m
Volaris
Deal found 6/17![Volaris logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Tue 7/79:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Fri 7/172:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Deal found 6/17![Volaris logo]()
$325
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Fri 7/101:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 6/19![Volaris logo]()
$327
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.
Sat 7/114:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Mon 7/202:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Deal found 6/20![Volaris logo]()
$323
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Sun 7/192:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Deal found 6/21![Volaris logo]()
$313
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Mon 7/208:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/21![Volaris logo]()
$356
One-way flights from Quintana Roo to ChicagoSearch for one-way flight options from Quintana Roo to Chicago. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
Search for one-way flight options from Quintana Roo to Chicago. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 6/17![Volaris logo]()
$177
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 6/17![Volaris logo]()
$180
This CheapOair deal was found by Cheapflights users on 6/17. 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 7/44:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Deal found 6/17![Volaris logo]()
$182
This OneTravel deal was found by Cheapflights users on 6/17. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Deal found 6/17![Volaris logo]()
$184
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 6/19![Volaris logo]()
$186
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.
Fri 9/189:52 am
CZM
- ORD
1 stop13h 55m
Volaris
Deal found 6/20![Volaris logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/104:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 6/17![Volaris logo]()
$188
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.
Thu 9/179:52 am
CZM
- ORD
1 stop13h 55m
Volaris
Deal found 6/20![Volaris logo]()
$194
This Volaris deal was found by Cheapflights users on 6/18. 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 9/154:47 pm
CZM
- ORD
1 stop13h 05m
Volaris
Deal found 6/18![Volaris logo]()
$201
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/19![Volaris logo]()
$211
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/20![Volaris logo]()
$212
This CheapOair deal was found by Cheapflights users on 6/17. 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 6/2610:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/17![Volaris logo]()
$216
Find flight deals from Quintana Roo to Chicago
Keep the following information in mind while searching for Quintana Roo to Chicago flight deals. Data was last updated June 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $283 (Super.com) |
One-way from | $177 (Super.com) |
Popular in | September |
Cheapest in | April |
Average price | $415 |
Good round-trip deal | $356 or less |
Good one-way deal | $252 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Quintana Roo to Chicago 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 22, 2026.
Use the filters below to find and compare flights from Quintana Roo to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CancúnChicago
CUN - ORD
CUNORD
Cancun
Tue 9/8
9:50 pm-5:52 am
1 stop8h 02m
Chicago O'Hare Intl
Thu 9/10
1:40 am-10:03 am
1 stop8h 23m
$308
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 10/8
3:38 pm-7:35 pm
Nonstop3h 57m
Chicago O'Hare Intl
Mon 10/12
9:38 pm-12:33 pm
1 stop14h 55m
$383
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 10/29
2:11 pm-6:13 pm
Nonstop4h 02m
Chicago O'Hare Intl
Mon 11/2
9:02 am-1:59 pm
Nonstop3h 57m
$387
CancúnChicago
CUN - ORD
CUNORD
Cancun
Fri 7/24
4:32 pm-12:55 am
1 stop8h 23m
Chicago O'Hare Intl
Fri 7/31
6:21 am-3:28 pm
1 stop9h 07m
$389
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 10/1
12:38 pm-11:53 pm
1 stop11h 15m
Chicago O'Hare Intl
Sun 10/4
11:17 am-8:15 pm
2 stops8h 58m
$393
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 8/13
11:10 am-8:32 pm
1 stop9h 22m
Chicago Midway
Mon 8/17
6:05 am-1:46 pm
1 stop7h 41m
$395
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 9/24
2:31 pm-11:53 pm
1 stop9h 22m
Chicago O'Hare Intl
Mon 9/28
11:17 am-8:15 pm
2 stops8h 58m
$396
Quickest round-trip
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 10/8
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Tue 10/13
10:46 am-2:26 pm
Nonstop3h 40m
$396
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 10/8
12:30 pm-8:24 pm
1 stop7h 54m
Chicago O'Hare Intl
Tue 10/13
8:55 am-8:15 pm
2 stops11h 20m
$401
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 7/23
11:10 am-8:32 pm
1 stop9h 22m
Chicago Midway
Tue 7/28
8:49 pm-10:55 am
1 stop14h 06m
$423
Showing 1-10 of 59 resultsSorted by cheapest first
Best time to book a flight from Quintana Roo to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Quintana Roo with our price prediction graph.
CZM-ORD
CUN-ORD
CUN-MDW
CTM-ORD
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 Quintana Roo to Chicago
MXQR-CHI
CZM-ORD
CUN-ORD
CUN-MDW
CTM-ORD
What is the cheapest month to book a flight from Quintana Roo to Chicago?
Currently, August is the cheapest month in which you can book a flight from Quintana Roo to Chicago (average of $78). Flying from Quintana Roo to Chicago in September is currently the most expensive (average of $167). 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 QR to CHI?
Find hourly flight availability from Quintana Roo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 22, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Quintana Roo to Chicago as you normally would.
Weekly flight availability from Quintana Roo to Chicago
Explore weekly flight availability from Quintana Roo to Chicago. 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 22, 2026.
The most flights from MXQR to CHI are scheduled on a Saturday (14 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Quintana Roo to Chicago?
How far ahead should I book a flight from Quintana Roo to Chicago?
Booking 79 days in advance of your planned departure date is, on average, the best time to get cheap flights from Quintana Roo to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Quintana Roo to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
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Alternative routes for Quintana Roo to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 22, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Quintana Roo to Chicago by cabin class
Find flights from Quintana Roo to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Quintana Roo and Chicago flights
Browse other Quintana Roo and Chicago flight options. Last updated on June 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Quintana Roo to Chicago
Discover the top 3 airlines that operate flights from Quintana Roo to Chicago. 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$184 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$209 | Average$251 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$271 | Average$374 | FlexibilityNo cancel fee | On-time71% |