$203+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Nov 1 — Nov 81
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 64 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 2, 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 2, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/511:44 am -
Nonstop4h 01m
Sun 11/86:10 am -
Nonstop3h 58m
Deal found 9/30![Frontier logo]()
$285
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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.
Wed 10/2810:44 am -
Nonstop4h 01m
Mon 11/96:10 am -
Nonstop3h 58m
Deal found 9/29![Frontier logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 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 1/57:29 am -
Nonstop4h 23m
Deal found 9/30![Frontier logo]()
$291
This Viva deal was found by Cheapflights users on 9/29. 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.
Fri 10/912:30 pm -
1 stop24h 40m
Sun 2/141:10 am -
1 stop23h 00m
Deal found 9/29![Viva logo]()
$307
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:49 am -
Nonstop4h 01m
Wed 10/286:10 am -
Nonstop3h 58m
Deal found 9/30![Frontier logo]()
$311
This Travelocity deal was found by Cheapflights users on 9/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:24 am -
Nonstop4h 01m
Sat 11/287:45 am -
Nonstop3h 56m
Deal found 9/30![Frontier logo]()
$316
This Viva deal was found by Cheapflights users on 9/28. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:30 am -
1 stop25h 40m
Thu 11/51:05 am -
1 stop24h 10m
Deal found 9/28![Viva logo]()
$324
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:49 am -
Nonstop4h 01m
Mon 10/196:10 am -
Nonstop3h 48m
Deal found 9/30![Frontier logo]()
$327
This Viva deal was found by Cheapflights users on 9/27. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:10 pm -
1 stop25h 40m
Sat 11/71:05 am -
1 stop22h 10m
Deal found 9/27![Viva logo]()
$334
This Booking.com deal was found by Cheapflights users on 9/29. 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 Booking.com 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 9/29![Frontier logo]()
$341
This Expedia deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:51 pm -
1 stop9h 56m
Mon 11/96:16 am -
1 stop6h 25m
Deal found 10/1![Frontier logo]()
$348
This Frontier deal was found by Cheapflights users on 9/29. 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 10/301:51 pm -
1 stop9h 56m
Mon 11/26:16 am -
1 stop6h 25m
Deal found 9/29![Frontier logo]()
$350
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 2, 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 2, 2026.
This Viva deal was found by Cheapflights users on 9/28. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2210:00 pm -
1 stop26h 35m
Sun 1/311:40 pm -
1 stop19h 20m
Deal found 9/28![Viva logo]()
$322
This Delta deal was found by Cheapflights users on 9/30. 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 12/42:21 pm -
1 stop10h 18m
Mon 12/145:30 am -
1 stop7h 20m
Deal found 9/30![Delta logo]()
$381
This United Airlines deal was found by Cheapflights users on 9/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:11 pm -
Nonstop4h 02m
Tue 11/37:20 am -
Nonstop4h 03m
Deal found 9/27![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 9/27. 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.
Thu 12/36:00 pm -
Nonstop3h 35m
Mon 12/75:20 am -
1 stop9h 40m
Deal found 9/27![Southwest logo]()
$450
This Viva deal was found by Cheapflights users on 9/28. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:25 am -
1 stop13h 30m
Sun 11/291:05 am -
1 stop20h 30m
Deal found 9/28![Viva logo]()
$324
This Viva deal was found by Cheapflights users on 9/27. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:10 pm -
1 stop25h 40m
Sat 11/71:05 am -
1 stop22h 10m
Deal found 9/27![Viva logo]()
$334
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 12/126:04 am -
1 stop8h 08m
Sat 1/25:25 am -
1 stop10h 10m
Deal found 10/2![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/223:38 pm -
Nonstop3h 57m
Sun 10/258:40 am -
Nonstop4h 03m
Deal found 10/1![United Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 9/28. 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.
Fri 1/2212:27 pm -
1 stop11h 33m
Sun 1/317:00 am -
2 stops8h 30m
Deal found 9/28![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 9/28. 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.
Fri 1/2212:27 pm -
1 stop11h 33m
Fri 1/297:00 am -
2 stops8h 30m
Deal found 9/28![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 9/27. 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.
Thu 11/56:55 pm -
1 stop7h 15m
Sun 11/87:50 am -
2 stops9h 05m
Deal found 9/27![Southwest logo]()
$479
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 11/129:24 am -
2 stops14h 30m
Tue 11/176:00 am -
1 stop8h 06m
Deal found 10/2![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/138:20 am -
2 stops9h 40m
Tue 11/1710:15 am -
1 stop8h 30m
Deal found 10/1![Southwest logo]()
$479
This Delta deal was found by Cheapflights users on 9/28. 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.
Fri 1/2211:00 am -
2 stops8h 37m
Fri 1/296:00 am -
1 stop9h 30m
Deal found 9/28![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 9/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/229:40 am -
2 stops11h 15m
Sun 1/317:50 am -
2 stops8h 35m
Deal found 9/28![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 stops11h 15m
Tue 11/175:30 am -
1 stop8h 36m
Deal found 10/1![Delta logo]()
$391
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 2/125:40 pm -
1 stop7h 10m
Tue 2/165:30 am -
2 stops13h 30m
Deal found 10/1![Delta logo]()
$391
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/131:40 pm -
1 stop10h 14m
Tue 11/176:00 am -
1 stop8h 06m
Deal found 10/1![Delta logo]()
$457
Last-minute flights from Cancún to ChicagoDiscover last-minute flight deals from Cancún to Chicago. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from Cancún to Chicago. Data last updated October 2, 2026 and is based on user searches.
This Viva deal was found by Cheapflights users on 9/29. 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.
Fri 10/912:30 pm -
1 stop24h 40m
Sun 2/141:10 am -
1 stop23h 00m
Deal found 9/29![Viva logo]()
$307
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:49 am -
Nonstop4h 01m
Mon 10/196:10 am -
Nonstop3h 48m
Deal found 9/30![Frontier logo]()
$327
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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.
Tue 10/2010:49 am -
Nonstop4h 01m
Tue 10/276:10 am -
Nonstop3h 58m
Deal found 9/29![Frontier logo]()
$345
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:49 am -
Nonstop4h 01m
Wed 10/286:10 am -
Nonstop3h 58m
Deal found 9/30![Frontier logo]()
$311
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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.
Wed 10/2810:44 am -
Nonstop4h 01m
Mon 11/96:10 am -
Nonstop3h 58m
Deal found 9/29![Frontier logo]()
$286
This OneTravel deal was found by Cheapflights users on 9/29. 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.
Wed 10/2810:44 am -
Nonstop4h 01m
Sun 11/81:24 am -
1 stop13h 07m
Deal found 9/29![Multiple Airlines logo]()
$347
This Viva deal was found by Cheapflights users on 9/28. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:30 am -
1 stop25h 40m
Thu 11/51:05 am -
1 stop24h 10m
Deal found 9/28![Viva logo]()
$324
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/511:44 am -
Nonstop4h 01m
Sun 11/86:10 am -
Nonstop3h 58m
Deal found 9/30![Frontier logo]()
$285
This Viva deal was found by Cheapflights users on 9/27. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:10 pm -
1 stop25h 40m
Sat 11/71:05 am -
1 stop22h 10m
Deal found 9/27![Viva logo]()
$334
This Expedia deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:51 pm -
1 stop9h 56m
Mon 11/96:16 am -
1 stop6h 25m
Deal found 10/1![Frontier logo]()
$348
This Booking.com deal was found by Cheapflights users on 9/29. 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 Booking.com 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 9/29![Frontier logo]()
$341
This Travelocity deal was found by Cheapflights users on 9/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:24 am -
Nonstop4h 01m
Sat 11/287:45 am -
Nonstop3h 56m
Deal found 9/30![Frontier logo]()
$316
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 2, 2026.
Search for one-way flight options from Cancún to Chicago. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
This CheapOair deal was found by Cheapflights users on 9/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1211:16 am -
1 stop12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Volaris logo]()
$203
This FlightHub deal was found by Cheapflights users on 9/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:20 am -
1 stop14h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Volaris logo]()
$204
This Super.com deal was found by Cheapflights users on 9/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1111:16 am -
1 stop12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Volaris logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:45 am -
1 stop12h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Viva logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:06 pm -
1 stop11h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Volaris logo]()
$209
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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.
Sun 12/610:15 am -
1 stop13h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Viva logo]()
$210
This Frontier deal was found by Cheapflights users on 9/28. 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.
Fri 10/301:51 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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.
Tue 10/135:40 pm -
1 stop10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Volaris logo]()
$213
This Super.com deal was found by Cheapflights users on 9/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:51 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$214
This Super.com deal was found by Cheapflights users on 9/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:51 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$215
This FlightHub deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 10/2810:40 am -
1 stop14h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Volaris logo]()
$215
This Super.com deal was found by Cheapflights users on 9/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:51 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$216
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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $285 (Cheapflightsfares) |
One-way from | $203 (CheapOair) |
Popular in | August |
Cheapest in | April |
Average price | $386 |
Good round-trip deal | $297 or less |
Good one-way deal | $285 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 2, 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 - ORD Chicago O'Hare Intl
CUNORD
Cancun
Mon 12/28
2:50 pm-11:00 pm
1 stop9h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Wed 2/17
9:55 pm-4:43 am
1 stop7h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$215
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 10/29
7:56 am-12:29 am
1 stop16h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Tue 10/27
4:46 pm-12:29 am
1 stop7h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
Quickest round-trip
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Fri 12/18
1:16 pm-4:18 pm
Nonstop4h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$229
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Fri 11/13
1:16 pm-4:18 pm
Nonstop4h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$229
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Wed 10/21
8:00 am-6:00 pm
2 stops10h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$229
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Fri 12/25
8:15 am-5:44 pm
2 stops10h 29m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$229
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Wed 12/2
8:15 am-4:16 pm
1 stop9h 01m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Wed 11/4
8:00 am-6:00 pm
2 stops11h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
Showing 1-10 of 39 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 $221). 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 2, 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.
Weekly flight availability from Cancún to Chicago
Explore weekly flight availability from Cancún 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 October 2, 2026.
The most flights from CUN to CHI are scheduled on a Thursday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Cancún to Chicago?
Airfare is below average for this route at the moment.
Cancún to Chicago flights typically cost between $317 and $403 in November.The cheapest round-trip price found within the last 5 days was $285 on Frontier (Nov 5-Nov 8).
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 2, 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
Food
6.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Food
6.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Food
6.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Food
6.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Boarding
7.7
Food
6.7
Entertainment
7.1
Overall
7.4
Comfort
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Complete your trip
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Cancún and Chicago flights
Browse other Cancún and Chicago flight options. Last updated on October 2, 2026.
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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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$209 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$209 | Average$319 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$306 | Average$466 | FlexibilityNo cancel fee | On-time79% |