$203+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Sep 28 — Oct 51
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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Best
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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 August 29, 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 29, 2026.
This eDestinos deal was found by Cheapflights users on 8/25. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:35 pm -
1 stop11h 05m
Fri 10/306:45 am -
1 stop10h 04m
Deal found 8/25![Arajet logo]()
$280
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair 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 8/25![Multiple Airlines logo]()
$303
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2412:35 pm -
1 stop11h 05m
Sat 10/31:40 am -
1 stop8h 23m
Deal found 8/24![Multiple Airlines logo]()
$306
This eDestinos deal was found by Cheapflights users on 8/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:35 pm -
1 stop11h 05m
Mon 10/264:30 am -
1 stop12h 27m
Deal found 8/27![Arajet logo]()
$307
This Booking.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2412:35 pm -
1 stop11h 05m
Mon 9/285:30 am -
1 stop11h 42m
Deal found 8/24![Arajet logo]()
$310
This Expedia deal was found by Cheapflights users on 8/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:49 am -
Nonstop4h 01m
Mon 10/266:10 am -
Nonstop3h 48m
Deal found 8/26![Frontier logo]()
$313
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/19:50 pm -
1 stop8h 02m
Mon 10/57:35 am -
1 stop13h 28m
Deal found 8/24![Volaris logo]()
$327
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/175:40 pm -
1 stop11h 14m
Mon 9/217:35 am -
1 stop13h 28m
Deal found 8/24![Volaris logo]()
$329
This Super.com deal was found by Cheapflights users on 8/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:50 pm -
1 stop8h 02m
Mon 10/52:53 am -
1 stop9h 11m
Deal found 8/25![Volaris logo]()
$330
This Frontier deal was found by Cheapflights users on 8/28. 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.
Thu 10/221:51 pm -
1 stop9h 52m
Mon 10/266:15 am -
1 stop6h 26m
Deal found 8/28![Frontier logo]()
$334
This Frontier deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/81:51 pm -
1 stop9h 52m
Mon 10/126:15 am -
1 stop6h 26m
Deal found 8/24![Frontier logo]()
$336
This Expedia deal was found by Cheapflights users on 8/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:51 pm -
1 stop8h 31m
Mon 10/126:15 am -
1 stop6h 26m
Deal found 8/28![Frontier logo]()
$342
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 29, 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 29, 2026.
This Volaris deal was found by Cheapflights users on 8/28. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:50 pm -
1 stop8h 02m
Sat 10/31:40 am -
1 stop8h 23m
Deal found 8/28![Volaris logo]()
$372
This Viva deal was found by Cheapflights users on 8/27. 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 12/1710:35 pm -
1 stop25h 25m
Fri 1/812:35 am -
1 stop13h 30m
Deal found 8/27![Viva logo]()
$375
This United Airlines deal was found by Cheapflights users on 8/28. 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 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 10/46:25 am -
1 stop8h 12m
Deal found 8/28![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 8/26. 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.
Tue 10/272:26 pm -
1 stop10h 13m
Tue 11/37:00 am -
2 stops12h 55m
Deal found 8/26![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/11:05 pm -
Nonstop3h 40m
Mon 10/59:05 am -
Nonstop3h 35m
Deal found 8/24![Southwest logo]()
$462
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:11 pm -
Nonstop3h 53m
Mon 10/265:30 am -
1 stop6h 24m
Deal found 8/28![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 8/25. 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 10/279:24 am -
2 stops13h 09m
Tue 11/39:29 am -
2 stops10h 26m
Deal found 8/25![Delta logo]()
$413
This United Airlines deal was found by Cheapflights users on 8/27. 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 9/2512:11 pm -
Nonstop3h 53m
Tue 9/299:29 am -
Nonstop3h 41m
Deal found 8/27![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 8/26. 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.
Wed 9/168:05 am -
1 stop8h 10m
Tue 9/2210:48 am -
1 stop9h 02m
Deal found 8/26![Delta logo]()
$414
This Southwest deal was found by Cheapflights users on 8/27. 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 11/52:10 pm -
Nonstop3h 40m
Sun 11/85:15 am -
1 stop8h 10m
Deal found 8/27![Southwest logo]()
$467
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/212:11 pm -
Nonstop3h 53m
Mon 10/59:29 am -
Nonstop3h 41m
Deal found 8/24![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 8/26. 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.
Fri 10/91:45 pm -
1 stop7h 55m
Sun 10/185:00 am -
2 stops7h 40m
Deal found 8/26![Southwest logo]()
$481
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/3012:11 pm -
Nonstop3h 53m
Sun 10/45:30 am -
1 stop7h 03m
Deal found 8/24![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 2/123:40 pm -
Nonstop3h 45m
Tue 2/167:30 am -
1 stop11h 15m
Deal found 8/24![Southwest logo]()
$482
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:10 pm -
1 stop9h 49m
Tue 10/136:25 am -
1 stop6h 08m
Deal found 8/28![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/236:25 pm -
1 stop12h 15m
Wed 12/3010:05 am -
2 stops8h 40m
Deal found 8/24![Southwest logo]()
$541
This Southwest deal was found by Cheapflights users on 8/27. 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 12/241:45 pm -
2 stops8h 45m
Tue 12/298:00 am -
1 stop7h 25m
Deal found 8/27![Southwest logo]()
$546
Last-minute flights from Cancún to ChicagoDiscover last-minute flight deals from Cancún to Chicago. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Cancún to Chicago. Data last updated August 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:49 pm -
1 stop12h 06m
Tue 9/87:35 am -
1 stop13h 28m
Deal found 8/26![Volaris logo]()
$347
This Super.com deal was found by Cheapflights users on 8/26. 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 9/312:49 pm -
1 stop12h 06m
Thu 9/107:35 am -
1 stop13h 28m
Deal found 8/26![Volaris logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:49 pm -
1 stop12h 06m
Tue 9/81:40 am -
1 stop8h 23m
Deal found 8/26![Volaris logo]()
$354
This Frontier deal was found by Cheapflights users on 8/28. 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 9/111:51 pm -
1 stop9h 53m
Mon 9/146:25 am -
1 stop6h 12m
Deal found 8/28![Frontier logo]()
$408
This Delta deal was found by Cheapflights users on 8/25. 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 9/1612:35 pm -
1 stop10h 09m
Tue 9/229:29 am -
2 stops10h 21m
Deal found 8/25![Delta logo]()
$413
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/175:40 pm -
1 stop11h 14m
Mon 9/217:35 am -
1 stop13h 28m
Deal found 8/24![Volaris logo]()
$329
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/1810:50 am -
1 stop12h 57m
Mon 9/217:35 am -
1 stop13h 28m
Deal found 8/24![Volaris logo]()
$341
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Fri 9/183:20 pm -
1 stop8h 27m
Tue 9/227:35 am -
1 stop13h 28m
Deal found 8/27![Volaris logo]()
$348
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair 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 8/25![Multiple Airlines logo]()
$303
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2412:35 pm -
1 stop11h 05m
Sat 10/31:40 am -
1 stop8h 23m
Deal found 8/24![Multiple Airlines logo]()
$306
This Booking.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2412:35 pm -
1 stop11h 05m
Mon 9/285:30 am -
1 stop11h 42m
Deal found 8/24![Arajet logo]()
$310
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 8/24![Volaris logo]()
$336
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 29, 2026.
Search for one-way flight options from Cancún to Chicago. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Tue 11/2410:45 am -
1 stop12h 28m
Deal found 8/27![Volaris logo]()
$203
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:51 pm -
1 stop9h 52m
Deal found 8/25![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:44 am -
Nonstop4h 01m
Deal found 8/26![Frontier logo]()
$204
This Super.com deal was found by Cheapflights users on 8/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:51 pm -
1 stop9h 53m
Deal found 8/25![Frontier logo]()
$205
This Super.com deal was found by Cheapflights users on 8/27. 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.
Sun 10/1811:16 am -
1 stop12h 50m
Deal found 8/27![Volaris logo]()
$205
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Sun 1/176:30 pm -
1 stop11h 13m
Deal found 8/27![Volaris logo]()
$206
This CheapOair deal was found by Cheapflights users on 8/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1610:45 am -
1 stop12h 28m
Deal found 8/26![Volaris logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:50 am -
1 stop12h 57m
Deal found 8/26![Volaris logo]()
$208
This Frontier deal was found by Cheapflights users on 8/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:51 pm -
1 stop9h 52m
Deal found 8/26![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:50 pm -
1 stop8h 02m
Deal found 8/27![Volaris logo]()
$210
This FlightHub deal was found by Cheapflights users on 8/27. 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.
Sun 9/1310:40 am -
1 stop8h 24m
Deal found 8/27![Volaris logo]()
$211
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Sat 10/3110:44 am -
Nonstop4h 01m
Deal found 8/27![Frontier logo]()
$211
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (eDestinos) |
One-way from | $203 (CheapOair) |
Popular in | July |
Cheapest in | April |
Average price | $426 |
Good round-trip deal | $475 or less |
Good one-way deal | $318 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 August 29, 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
Thu 10/1
9:50 pm-5:52 am
1 stop8h 02m
Chicago O'Hare Intl
Sat 10/3
1:40 am-10:03 am
1 stop8h 23m
$372
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 12/17
10:35 pm-11:00 pm
1 stop25h 25m
Chicago O'Hare Intl
Fri 1/8
12:35 am-3:05 pm
1 stop13h 30m
$375
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
6:25 am-2:37 pm
1 stop8h 12m
$407
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Thu 10/22
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Mon 10/26
5:30 am-11:54 am
1 stop6h 24m
$407
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Tue 10/27
2:26 pm-12:39 am
1 stop10h 13m
Chicago O'Hare Intl
Tue 11/3
7:00 am-8:55 pm
2 stops12h 55m
$408
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
9:29 am-1:10 pm
Nonstop3h 41m
$408
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Fri 10/2
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Mon 10/5
9:29 am-1:10 pm
Nonstop3h 41m
$409
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Wed 9/30
12:11 pm-4:04 pm
Nonstop3h 53m
Chicago O'Hare Intl
Sun 10/4
5:30 am-12:33 pm
1 stop7h 03m
$409
CancúnChicago
CUN Cancun - MDW Chicago Midway
CUNMDW
Cancun
Tue 10/27
9:24 am-10:33 pm
2 stops13h 09m
Chicago Midway
Tue 11/3
9:29 am-8:55 pm
2 stops10h 26m
$413
CancúnChicago
CUN Cancun - ORD Chicago O'Hare Intl
CUNORD
Cancun
Fri 10/9
2:10 pm-11:59 pm
1 stop9h 49m
Chicago O'Hare Intl
Tue 10/13
6:25 am-12:33 pm
1 stop6h 08m
$413
Showing 1-10 of 38 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 |
- 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 29, 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 29, 2026.
The most flights from CUN to CHI are scheduled on a Monday (7 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 $364 and $513 in October.The cheapest round-trip price found within the last 5 days was $253 on Arajet (Oct 22-Oct 26).
How often are flights from Cancún to Chicago delayed?
About 18% 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 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 51 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 29, 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.
Comfort
7.3
Food
6.7
Boarding
7.7
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.7
Boarding
7.7
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.7
Boarding
7.7
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.7
Boarding
7.7
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.7
Boarding
7.7
Crew
8.1
Overall
7.4
Entertainment
7.1
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
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 29, 2026.
Complete your trip
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Cancún and Chicago flights
Browse other Cancún and Chicago flight options. Last updated on August 29, 2026.
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Browse through other flights departing from Cancún. Flights are based on user searches made on Cheapflights and were last updated on August 29, 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 August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$209 | Average$315 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$306 | Average$466 | FlexibilityNo cancel fee | On-time79% |