$213+ Cheap flights from Cancún (CUN) to Chicago (CHI)
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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Cancún to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Cancun to Chicago are usually found in April or January, booked 23 days in advance, depart on a Thursday or Sunday and return on a Sunday
Cheap flight deals from Cancún to Chicago
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Cheapest flights from Cancún to ChicagoExplore the most affordable flight options available from Cancún to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from Cancún to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Frontier deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/1011:38 am -
Nonstop4h 00m
Thu 12/105:24 pm -
2 stops17h 20m
Deal found 10/29![Frontier logo]()
$291
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2211:38 am -
Nonstop4h 00m
Tue 1/57:40 am -
Nonstop4h 18m
Deal found 10/28![Frontier logo]()
$330
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/211:44 am -
Nonstop4h 01m
Mon 11/96:10 am -
Nonstop3h 58m
Deal found 10/29![Frontier logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/1011:38 am -
Nonstop4h 00m
Mon 12/147:42 am -
Nonstop4h 18m
Deal found 10/29![Frontier logo]()
$341
This Frontier deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/1011:28 am -
1 stop11h 14m
Sun 12/139:34 pm -
1 stop13h 10m
Deal found 10/27![Frontier logo]()
$346
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:44 am -
Nonstop4h 01m
Mon 11/307:59 am -
Nonstop3h 56m
Deal found 10/28![Frontier logo]()
$350
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:44 am -
Nonstop4h 01m
Tue 11/176:10 am -
Nonstop3h 58m
Deal found 10/28![Frontier logo]()
$355
This Air Canada deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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.
Fri 12/1110:30 am -
1 stop10h 22m
Mon 12/1410:05 am -
1 stop12h 25m
Deal found 10/30![Air Canada logo]()
$367
This Air Canada deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Thu 12/1010:30 am -
1 stop10h 22m
Mon 12/1410:05 am -
1 stop12h 25m
Deal found 10/29![Air Canada logo]()
$369
This Air Canada deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/258:00 am -
1 stop8h 38m
Sun 11/297:05 am -
1 stop14h 40m
Deal found 10/27![Air Canada logo]()
$370
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:15 am -
2 stops10h 29m
Fri 1/19:58 am -
1 stop5h 37m
Deal found 10/29![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/2711:20 am -
1 stop12h 02m
Wed 1/610:47 am -
1 stop9h 43m
Deal found 10/25![Delta logo]()
$431
Best flights from Cancún to ChicagoDiscover carefully curated flight deals from Cancún to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Cancún to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Viva deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/610:50 am -
1 stop26h 40m
Fri 2/121:10 am -
1 stop23h 00m
Deal found 10/29![Viva logo]()
$400
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/42:55 pm -
Nonstop4h 04m
Tue 12/88:40 am -
Nonstop4h 03m
Deal found 10/29![United Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/39:24 am -
1 stop15h 15m
Mon 12/77:45 pm -
1 stop16h 52m
Deal found 10/25![Delta logo]()
$426
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/106:00 pm -
Nonstop3h 35m
Mon 12/146:00 am -
1 stop10h 00m
Deal found 10/29![Southwest logo]()
$491
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/311:16 am -
1 stop13h 23m
Tue 12/88:04 am -
1 stop12h 04m
Deal found 10/25![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:15 am -
2 stops13h 03m
Tue 1/59:50 am -
1 stop10h 40m
Deal found 10/30![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/242:45 pm -
Nonstop3h 40m
Tue 12/16:00 am -
1 stop10h 00m
Deal found 10/25![Southwest logo]()
$510
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/248:15 am -
2 stops13h 02m
Thu 11/2611:18 am -
2 stops8h 37m
Deal found 10/25![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:15 am -
1 stop12h 48m
Sun 1/37:00 am -
1 stop8h 10m
Deal found 10/26![Delta logo]()
$431
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/249:40 am -
1 stop8h 00m
Sun 2/285:00 am -
1 stop10h 00m
Deal found 10/26![Southwest logo]()
$541
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 1/218:00 am -
2 stops9h 26m
Thu 1/287:00 am -
2 stops13h 30m
Deal found 10/25![Delta logo]()
$431
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/2511:35 am -
2 stops9h 35m
Sun 11/2911:00 pm -
1 stop16h 00m
Deal found 10/27![Southwest logo]()
$542
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/271:10 pm -
1 stop9h 29m
Sun 1/37:00 am -
1 stop8h 10m
Deal found 10/27![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/186:04 am -
2 stops12h 01m
Thu 11/268:00 am -
1 stop11h 55m
Deal found 10/25![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/108:05 am -
1 stop9h 11m
Mon 12/146:00 am -
1 stop6h 50m
Deal found 10/29![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/128:15 am -
2 stops10h 49m
Tue 11/179:30 am -
2 stops10h 25m
Deal found 10/26![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/214:20 pm -
1 stop7h 02m
Tue 12/296:00 am -
1 stop9h 35m
Deal found 10/29![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/288:15 am -
1 stop9h 04m
Sat 1/26:00 am -
1 stop8h 07m
Deal found 10/28![Delta logo]()
$547
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/2711:20 am -
1 stop12h 02m
Sun 1/36:00 am -
1 stop5h 42m
Deal found 10/26![Delta logo]()
$558
Last-minute flights from Cancún to ChicagoDiscover last-minute flight deals from Cancún to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Cancún to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/211:44 am -
Nonstop4h 01m
Mon 11/96:10 am -
Nonstop3h 58m
Deal found 10/29![Frontier logo]()
$331
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:51 pm -
1 stop9h 56m
Mon 11/96:08 am -
1 stop6h 33m
Deal found 10/29![Frontier logo]()
$461
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:44 am -
Nonstop4h 01m
Mon 11/307:59 am -
Nonstop3h 56m
Deal found 10/28![Frontier logo]()
$350
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:44 am -
Nonstop4h 01m
Tue 11/176:10 am -
Nonstop3h 58m
Deal found 10/28![Frontier logo]()
$355
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:44 am -
Nonstop4h 01m
Sun 11/156:10 am -
Nonstop3h 58m
Deal found 10/27![Frontier logo]()
$374
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:51 pm -
1 stop9h 56m
Sun 11/156:08 am -
1 stop6h 33m
Deal found 10/29![Frontier logo]()
$436
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/128:15 am -
2 stops10h 49m
Tue 11/179:30 am -
2 stops10h 25m
Deal found 10/27![Delta logo]()
$452
This Frontier deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Fri 11/2011:44 am -
1 stop12h 34m
Mon 11/235:25 am -
1 stop10h 43m
Deal found 10/29![Frontier logo]()
$387
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/2111:10 am -
1 stop12h 44m
Sat 11/286:00 am -
1 stop5h 30m
Deal found 10/25![Delta logo]()
$431
This Frontier deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Tue 11/2411:44 am -
1 stop12h 34m
Tue 12/13:55 pm -
2 stops18h 09m
Deal found 10/28![Frontier logo]()
$378
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:37 am -
1 stop7h 53m
Tue 12/11:44 pm -
1 stop6h 30m
Deal found 10/28![American Airlines logo]()
$395
This Air Canada deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/258:00 am -
1 stop8h 38m
Sun 11/297:05 am -
1 stop14h 40m
Deal found 10/27![Air Canada logo]()
$370
One-way flights from Cancún to ChicagoSearch for one-way flight options from Cancún to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Cancún to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/245:24 pm -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Volaris logo]()
$213
This Super.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/192:51 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$214
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/1610:25 am -
1 stop12h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Volaris logo]()
$225
This Booking.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Thu 12/1712:35 pm -
1 stop11h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Arajet logo]()
$226
This Super.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/163:44 pm -
1 stop13h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Volaris logo]()
$227
This Justfly.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/1111:28 am -
1 stop25h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$228
This Air Canada deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 1/283:00 pm -
2 stops18h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Air Canada logo]()
$228
This Trip.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Sun 11/89:30 pm -
1 stop23h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Air Canada logo]()
$229
This Volaris deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 4/29:50 pm -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Volaris logo]()
$230
This OneTravel deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Fri 12/411:26 am -
1 stop25h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/1410:48 pm -
1 stop25h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Viva logo]()
$231
This Justfly.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 2/48:00 am -
2 stops25h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Air Canada logo]()
$232
Find flight deals from Cancún to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Cancún (CUN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Frontier) |
One-way from | $213 (FlightHub) |
Popular in | August |
Cheapest in | April |
Average price | $390 |
Good round-trip deal | $397 or less |
Good one-way deal | $288 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Cancún 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 7,457,451 searches. Data last updated October 30, 2026.
Use the filters below to find and compare flights from Cancún to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Sat 12/19
2:00 pm-10:22 pm
2 stops9h 22m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$250
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Sat 12/26
8:15 am-8:03 pm
1 stop12h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$250
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Sat 1/23
12:17 pm-8:32 pm
2 stops9h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$251
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Mon 12/21
12:20 pm-8:18 pm
2 stops8h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$251
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Thu 11/19
8:15 am-6:04 pm
2 stops10h 49m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 1/7
8:00 am-4:27 pm
2 stops9h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
Quickest round-trip
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Thu 11/19
6:00 pm-8:35 pm
Nonstop3h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$260
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Fri 11/20
8:20 am-5:00 pm
2 stops9h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Wed 11/4
8:00 am-8:30 pm
2 stops13h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$272
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Tue 11/10
2:10 pm-9:20 pm
1 stop8h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$281
Showing 1-10 of 36 resultsSorted by cheapest first
Compare providers for flights from Cancún to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cancún to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Cancún-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cancún-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cancún-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Cancún-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cancún-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Cancún to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Cancún with our price prediction graph.
CUN-CHI
CUN-ORD
CUN-MDW
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 Cancún to Chicago
CUN-CHI
CUN-ORD
CUN-MDW
What is the cheapest month to book a flight from Cancún to Chicago?
Currently, January is the cheapest month in which you can book a flight from Cancún to Chicago (average of $222). Flying from Cancún to Chicago in July is currently the most expensive (average of $435). 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 CUN to CHI?
Find hourly flight availability from Cancún 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 October 30, 2026.
When flying from Cancún to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Cancún to Chicago?
Airfare is typical for this route at the moment.
Cancún to Chicago flights typically cost between $205 and $406 in December.The cheapest round-trip price found within the last 5 days was $291 on Frontier (Dec 10-Dec 10).
How often are flights from Cancún to Chicago delayed?
About 19% of weekly flights between Cancún and Chicago have experienced delays in the past year, with the average delay time being 151 minutes.
What is the most punctual flight time for Cancún to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Cancún to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 16% of flights being delayed.
How far ahead should I book a flight from Cancún to Chicago?
The price you pay for your flight from Cancún to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 52 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
The best insider tips for Cancún to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Cancún to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 30, 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andVolaris from Cancún to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Entertainment
7.1
Food
6.7
Comfort
7.3
Overall
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Cancún 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Cancún and Chicago flights
Browse other Cancún and Chicago flight options. Last updated on October 30, 2026.
Other flights from Cancún
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Top 3 airlines flying from Cancún to Chicago
Discover the top 3 airlines that operate flights from Cancún 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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$212 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$220 | Average$334 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$306 | Average$398 | FlexibilityNo cancel fee | On-time79% |