$202+ Cheap flights from Cancún (CUN) 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Sep 12 — Sep 191
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 August 13, 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 August 13, 2026.
This CheapOair deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:35 pm -
1 stop11h 05m
Sun 10/187:35 am -
1 stop13h 28m
Deal found 8/12![Multiple Airlines logo]()
$264
This FlightHub deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/29:50 pm -
1 stop8h 02m
Wed 9/97:35 am -
1 stop13h 28m
Deal found 8/12![Volaris logo]()
$278
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/249:50 pm -
1 stop8h 02m
Mon 9/287:35 am -
1 stop13h 28m
Deal found 8/11![Volaris logo]()
$288
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 -
Nonstop3h 57m
Tue 10/139:29 am -
Nonstop3h 41m
Deal found 8/11![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/912:11 pm -
Nonstop3h 53m
Mon 10/129:38 pm -
1 stop12h 28m
Deal found 8/10![United Airlines logo]()
$300
This OneTravel deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/249:50 pm -
1 stop8h 02m
Sat 9/261:40 am -
1 stop8h 23m
Deal found 8/11![Volaris logo]()
$301
This Super.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:40 am -
1 stop14h 15m
Wed 9/27:35 am -
1 stop13h 28m
Deal found 8/12![Volaris logo]()
$305
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/95:22 pm -
1 stop7h 01m
Wed 10/146:25 am -
1 stop12h 54m
Deal found 8/10![United Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/2412:35 pm -
1 stop11h 05m
Mon 9/287:35 am -
1 stop13h 28m
Deal found 8/10![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/19:50 pm -
1 stop8h 02m
Mon 9/71:40 am -
1 stop8h 23m
Deal found 8/12![Volaris logo]()
$312
This Despegar deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Sat 11/149:55 pm -
1 stop7h 48m
Tue 11/176:29 am -
1 stop13h 28m
Deal found 8/11![Volaris logo]()
$313
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/241:05 pm -
Nonstop3h 35m
Sun 9/277:10 am -
1 stop6h 40m
Deal found 8/11![Southwest logo]()
$359
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 August 13, 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 August 13, 2026.
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/2512:11 pm -
Nonstop3h 53m
Tue 9/295:00 am -
1 stop9h 40m
Deal found 8/11![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/112:40 pm -
2 stops11h 19m
Sun 10/46:40 am -
1 stop13h 10m
Deal found 8/12![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/241:05 pm -
Nonstop3h 35m
Mon 9/285:30 am -
1 stop6h 40m
Deal found 8/10![Southwest logo]()
$456
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/112:11 pm -
Nonstop3h 53m
Sun 10/45:30 am -
1 stop9h 07m
Deal found 8/11![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/2412:41 pm -
2 stops11h 18m
Sun 9/276:10 am -
2 stops12h 39m
Deal found 8/12![Delta logo]()
$413
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/243:38 pm -
Nonstop3h 57m
Mon 9/289:38 pm -
1 stop12h 28m
Deal found 8/12![United Airlines logo]()
$379
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/151:05 pm -
Nonstop3h 40m
Mon 10/195:00 am -
1 stop10h 00m
Deal found 8/8![Southwest logo]()
$467
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/2412:11 pm -
Nonstop3h 53m
Sun 9/279:29 am -
Nonstop3h 41m
Deal found 8/8![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/23:22 pm -
1 stop7h 14m
Thu 9/1011:35 am -
1 stop8h 15m
Deal found 8/12![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:10 pm -
Nonstop3h 40m
Mon 12/147:35 am -
1 stop5h 50m
Deal found 8/9![Southwest logo]()
$467
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/43:38 pm -
Nonstop3h 57m
Mon 9/710:46 am -
Nonstop3h 40m
Deal found 8/8![United Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/101:00 pm -
2 stops9h 25m
Sun 9/137:55 am -
1 stop6h 05m
Deal found 8/10![Southwest logo]()
$476
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/212:11 pm -
Nonstop3h 53m
Mon 9/75:30 am -
1 stop7h 03m
Deal found 8/8![United Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:20 am -
2 stops9h 45m
Tue 12/156:40 am -
1 stop7h 50m
Deal found 8/9![Southwest logo]()
$477
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:05 am -
1 stop7h 19m
Sat 9/2611:35 am -
1 stop8h 15m
Deal found 8/10![Delta logo]()
$526
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 -
Nonstop3h 53m
Tue 10/1310:46 am -
Nonstop3h 40m
Deal found 8/9![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/28:00 am -
2 stops14h 36m
Sun 9/66:05 am -
2 stops12h 44m
Deal found 8/8![Delta logo]()
$532
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/33:10 pm -
2 stops8h 15m
Mon 9/75:25 am -
1 stop9h 35m
Deal found 8/8![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/2312:40 pm -
Nonstop3h 40m
Mon 9/288:25 am -
Nonstop3h 35m
Deal found 8/9![Southwest logo]()
$522
Last-minute flights from Cancún to ChicagoDiscover last-minute flight deals from Cancún to Chicago. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Cancún to Chicago. Data last updated August 13, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:40 am -
1 stop14h 15m
Wed 9/27:35 am -
1 stop13h 28m
Deal found 8/12![Volaris logo]()
$305
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/11:12 pm -
1 stop19h 57m
Wed 9/95:30 am -
1 stop9h 07m
Deal found 8/10![United Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/19:50 pm -
1 stop8h 02m
Mon 9/71:40 am -
1 stop8h 23m
Deal found 8/12![Volaris logo]()
$312
This FlightHub deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/29:50 pm -
1 stop8h 02m
Wed 9/97:35 am -
1 stop13h 28m
Deal found 8/12![Volaris logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:50 am -
1 stop12h 57m
Thu 9/107:35 am -
1 stop13h 28m
Deal found 8/12![Volaris logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/34:32 pm -
1 stop8h 23m
Thu 9/107:35 am -
1 stop13h 28m
Deal found 8/12![Volaris logo]()
$299
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/249:50 pm -
1 stop8h 02m
Mon 9/287:35 am -
1 stop13h 28m
Deal found 8/11![Volaris logo]()
$288
This OneTravel deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/249:50 pm -
1 stop8h 02m
Sat 9/261:40 am -
1 stop8h 23m
Deal found 8/11![Volaris logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/2412:35 pm -
1 stop11h 05m
Mon 9/287:35 am -
1 stop13h 28m
Deal found 8/10![Multiple Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/243:38 pm -
Nonstop3h 57m
Sun 9/276:00 am -
1 stop8h 40m
Deal found 8/12![United Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/241:05 pm -
Nonstop3h 35m
Sun 9/277:10 am -
1 stop6h 40m
Deal found 8/11![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/253:38 pm -
Nonstop3h 57m
Tue 9/299:29 am -
Nonstop3h 41m
Deal found 8/10![United Airlines logo]()
$300
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 August 13, 2026.
Search for one-way flight options from Cancún to Chicago. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This OneTravel deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/3110:40 am -
1 stop8h 24m
Deal found 8/10![Volaris logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:50 am -
1 stop12h 57m
Deal found 8/11![Volaris logo]()
$203
This Super.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/910:40 am -
1 stop8h 24m
Deal found 8/9![Volaris logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/911:30 am -
1 stop25h 40m
Deal found 8/9![Viva logo]()
$204
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/111:00 pm -
1 stop8h 35m
Deal found 8/12![Southwest logo]()
$205
This Viva deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Sun 9/277:00 am -
1 stop7h 52m
Deal found 8/11![Viva logo]()
$205
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/2110:40 am -
1 stop8h 24m
Deal found 8/11![Volaris logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:55 pm -
1 stop7h 48m
Deal found 8/11![Volaris logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 8/2910:40 am -
1 stop14h 15m
Deal found 8/12![Volaris logo]()
$207
This Air Canada deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:30 am -
1 stop10h 22m
Deal found 8/11![Air Canada logo]()
$208
This Super.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 10/812:35 pm -
1 stop11h 05m
Deal found 8/9![Arajet logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:32 pm -
1 stop8h 23m
Deal found 8/12![Volaris logo]()
$212
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 August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $264 (CheapOair) |
One-way from | $202 (OneTravel) |
Popular in | September |
Cheapest in | April |
Average price | $401 |
Good round-trip deal | $429 or less |
Good one-way deal | $296 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 2,558,603 searches. Data last updated August 13, 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
Fri 9/25
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Tue 9/29
5:00 am-2:40 pm
1 stop9h 40m
$299
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 10/1
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Sun 10/4
5:30 am-2:37 pm
1 stop9h 07m
$299
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 9/24
3:38 pm-7:35 pm
Nonstop3h 57m
Chicago O'Hare Intl
Mon 9/28
9:38 pm-10:06 am
1 stop12h 28m
$379
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 9/24
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Sun 9/27
9:29 am-1:10 pm
Nonstop3h 41m
$408
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Fri 9/4
3:38 pm-7:35 pm
Nonstop3h 57m
Chicago O'Hare Intl
Mon 9/7
10:46 am-2:26 pm
Nonstop3h 40m
$408
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Wed 9/2
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Mon 9/7
5:30 am-12:33 pm
1 stop7h 03m
$408
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
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
$409
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 10/1
12:40 pm-11:59 pm
2 stops11h 19m
Chicago O'Hare Intl
Sun 10/4
6:40 am-7:50 pm
1 stop13h 10m
$413
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 9/24
12:41 pm-11:59 pm
2 stops11h 18m
Chicago O'Hare Intl
Sun 9/27
6:10 am-6:49 pm
2 stops12h 39m
$413
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Thu 9/24
1:05 pm-4:40 pm
Nonstop3h 35m
Chicago Midway
Mon 9/28
5:30 am-12:10 pm
1 stop6h 40m
$456
Showing 1-10 of 41 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 August.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | 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 August 13, 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 August 13, 2026.
The most flights from CUN to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
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 $260 and $448 in October.The cheapest round-trip price found within the last 5 days was $264 on Multiple Airlines (Oct 15-Oct 18).
How often are flights from Cancún to Chicago delayed?
About 17% of weekly flights between Cancún and Chicago have experienced delays in the past year, with the average delay time being 152 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 15% 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 August 13, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines 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.
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
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
Flights by cabin class
Other flight options
Other flights from Cancún
Popular flights
Alternative routes for Cancún 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 August 13, 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 Cancún to Chicago by cabin class
Find flights from Cancún to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Cancún and Chicago flights
Browse other Cancún and Chicago flight options. Last updated on August 13, 2026.
Other flights from Cancún
Browse through other flights departing from Cancún. Flights are based on user searches made on Cheapflights and were last updated on August 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$175 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$209 | Average$251 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$306 | Average$387 | FlexibilityNo cancel fee | On-time79% |