$118+ Cheap flights from Chicago (CHI) to Oaxaca
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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oaxaca with Cheapflights
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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
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Cheapest flights from Chicago to OaxacaExplore the most affordable flight options available from Chicago to Oaxaca. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Chicago to Oaxaca. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Wed 12/98:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$366
This Booking.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Sat 11/141:05 am -
1 stop10h 59m
Tue 11/248:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Fri 12/118:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Thu 12/108:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Mon 12/78:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Sun 12/68:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Sat 12/58:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$397
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:05 am -
1 stop10h 59m
Mon 12/78:01 pm -
1 stop8h 42m
Deal found 11/3![Multiple Airlines logo]()
$418
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Tue 11/101:05 am -
1 stop10h 59m
Wed 12/28:01 pm -
1 stop8h 42m
Deal found 11/3![Multiple Airlines logo]()
$423
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:05 am -
1 stop10h 59m
Tue 12/88:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$432
This Booking.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:05 am -
1 stop10h 59m
Sat 11/218:01 pm -
1 stop8h 42m
Deal found 10/30![Multiple Airlines logo]()
$433
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Mon 11/3012:35 am -
1 stop13h 03m
Tue 12/88:01 pm -
1 stop8h 42m
Deal found 11/3![Multiple Airlines logo]()
$436
Best flights from Chicago to OaxacaDiscover carefully curated flight deals from Chicago to Oaxaca that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Chicago to Oaxaca that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/712:04 am -
1 stop12h 05m
Sun 1/171:27 pm -
1 stop8h 46m
Deal found 10/30![Volaris logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/252:10 am -
1 stop10h 54m
Sat 4/37:34 pm -
1 stop9h 18m
Deal found 10/30![Multiple Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 2/46:30 am -
2 stops16h 10m
Mon 2/86:05 am -
1 stop7h 39m
Deal found 11/4![Delta logo]()
$642
This FlightHub deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Fri 1/221:05 am -
1 stop13h 46m
Sat 2/133:39 pm -
1 stop6h 34m
Deal found 11/4![Multiple Airlines logo]()
$468
This Volaris deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Sat 1/236:29 am -
1 stop8h 02m
Sat 2/133:39 pm -
1 stop13h 04m
Deal found 11/3![Volaris logo]()
$482
This Volaris deal was found by Cheapflights users on 11/2. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/206:29 am -
1 stop8h 02m
Mon 3/13:24 pm -
1 stop13h 19m
Deal found 11/2![Volaris logo]()
$482
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/81:24 am -
2 stops35h 00m
Sun 1/172:00 pm -
1 stop8h 13m
Deal found 10/30![Multiple Airlines logo]()
$489
This Volaris deal was found by Cheapflights users on 11/1. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1612:04 am -
1 stop14h 27m
Tue 2/233:39 pm -
1 stop13h 04m
Deal found 11/1![Volaris logo]()
$484
This Delta deal was found by Cheapflights users on 11/1. 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 3/46:20 am -
2 stops16h 20m
Tue 3/98:50 am -
2 stops13h 30m
Deal found 11/1![Delta logo]()
$653
This Volaris deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Mon 3/16:29 am -
1 stop8h 02m
Tue 3/93:24 pm -
1 stop13h 19m
Deal found 11/4![Volaris logo]()
$496
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 1/227:25 am -
2 stops15h 15m
Mon 1/254:12 pm -
1 stop6h 51m
Deal found 11/3![Delta logo]()
$672
This Volaris deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/106:29 am -
1 stop8h 02m
Sun 3/143:43 pm -
1 stop12h 53m
Deal found 11/4![Volaris logo]()
$506
This Delta deal was found by Cheapflights users on 11/2. 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.
Mon 1/115:30 am -
2 stops17h 10m
Fri 1/156:05 am -
1 stop7h 39m
Deal found 11/2![Delta logo]()
$672
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 2/46:30 am -
2 stops16h 10m
Sun 2/79:02 am -
1 stop14h 01m
Deal found 11/4![Delta logo]()
$672
This Volaris deal was found by Cheapflights users on 11/1. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1812:58 am -
1 stop8h 21m
Tue 3/237:31 pm -
1 stop9h 05m
Deal found 11/1![Volaris logo]()
$566
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 2/11:02 am -
1 stop10h 36m
Tue 2/912:37 pm -
1 stop10h 26m
Deal found 11/1![Delta logo]()
$704
This Volaris deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:29 am -
1 stop8h 02m
Fri 12/43:24 pm -
1 stop13h 19m
Deal found 11/3![Volaris logo]()
$620
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 2/11:02 am -
1 stop10h 36m
Sun 2/78:52 pm -
2 stops20h 27m
Deal found 11/1![Delta logo]()
$714
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 2/17:25 pm -
2 stops24h 34m
Sun 2/78:52 pm -
2 stops25h 36m
Deal found 11/1![Delta logo]()
$719
This Volaris deal was found by Cheapflights users on 11/1. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:04 am -
1 stop8h 08m
Mon 12/78:01 pm -
1 stop8h 42m
Deal found 11/1![Volaris logo]()
$657
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 2/17:25 pm -
2 stops24h 34m
Mon 2/88:52 pm -
2 stops20h 27m
Deal found 11/1![Delta logo]()
$719
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/81:24 am -
3 stops34h 35m
Sun 1/174:19 pm -
3 stops29h 54m
Deal found 10/30![Volaris logo]()
$815
This Volaris deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/251:24 am -
1 stop11h 15m
Sat 3/271:20 pm -
1 stop8h 46m
Deal found 11/4![Volaris logo]()
$815
Last-minute flights from Chicago to OaxacaDiscover last-minute flight deals from Chicago to Oaxaca. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oaxaca. Data last updated November 4, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Tue 11/101:05 am -
1 stop10h 59m
Wed 12/28:01 pm -
1 stop8h 42m
Deal found 11/3![Multiple Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Wed 12/98:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$366
This Booking.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Sat 11/141:05 am -
1 stop10h 59m
Tue 11/248:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Fri 12/118:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Thu 12/108:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Mon 12/78:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Sun 12/68:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:05 am -
1 stop10h 59m
Sat 12/58:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$397
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:05 am -
1 stop10h 59m
Tue 12/88:01 pm -
1 stop8h 42m
Deal found 10/31![Multiple Airlines logo]()
$432
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:05 am -
1 stop10h 59m
Mon 12/78:01 pm -
1 stop8h 42m
Deal found 11/3![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:55 pm -
2 stops16h 17m
Thu 12/108:01 pm -
1 stop8h 42m
Deal found 10/30![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:00 am -
2 stops22h 12m
Thu 12/108:01 pm -
1 stop8h 42m
Deal found 10/30![Multiple Airlines logo]()
$401
One-way flights from Chicago to OaxacaSearch for one-way flight options from Chicago to Oaxaca. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Chicago to Oaxaca. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1012:35 am -
1 stop17h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Viva logo]()
$118
This Booking.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/111:05 am -
1 stop10h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Viva logo]()
$127
This Booking.com deal was found by Cheapflights users on 11/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/141:05 am -
1 stop10h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Viva logo]()
$129
This Booking.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Fri 4/21:20 am -
1 stop14h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Viva logo]()
$132
This Booking.com deal was found by Cheapflights users on 11/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:35 am -
1 stop13h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Viva logo]()
$141
This Booking.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/712:35 am -
1 stop17h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Viva logo]()
$152
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/301:05 am -
1 stop20h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Viva logo]()
$161
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/301:05 am -
1 stop10h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Viva logo]()
$162
This Booking.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Sat 11/141:05 am -
1 stop10h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Viva logo]()
$177
This FlightHub deal was found by Cheapflights users on 11/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/142:10 am -
1 stop10h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Viva logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/128:25 am -
3 stops47h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/117:10 am -
3 stops49h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$195
Find flight deals from Chicago to Oaxaca
Keep the following information in mind while searching for Chicago to Oaxaca flight deals. Data was last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (Booking.com) |
One-way from | $118 (Mytrip) |
Popular in | October |
Cheapest in | April |
Average price | $514 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Oaxaca 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 November 4, 2026.
Use the filters below to find and compare flights from Chicago to Oaxaca that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Sun 1/10
12:35 am-6:01 pm
1 stop17h 26m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$118
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Mon 1/11
7:10 am-8:12 am
3 stops49h 02m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$195
ChicagoSanta Maria Huatulco
ORD Chicago O'Hare Intl - HUX Santa Maria Huatulco
ORDHUX
Chicago O'Hare Intl
Wed 12/9
1:05 am-2:51 pm
1 stop13h 46m
Santa Maria Huatulco
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Fri 1/8
1:30 pm-7:41 am
3 stops42h 11m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$238
ChicagoSanta Maria Huatulco
ORD Chicago O'Hare Intl - HUX Santa Maria Huatulco
ORDHUX
Chicago O'Hare Intl
Sat 1/2
1:05 am-9:52 pm
1 stop20h 47m
Santa Maria Huatulco
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$258
ChicagoPuerto Escondido
ORD Chicago O'Hare Intl - PXM Puerto Escondido
ORDPXM
Chicago O'Hare Intl
Thu 12/31
11:19 am-12:22 pm
2 stops25h 03m
Puerto Escondido
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$266
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Thu 12/31
8:22 am-8:12 am
3 stops23h 50m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
ChicagoPuerto Escondido
ORD Chicago O'Hare Intl - PXM Puerto Escondido
ORDPXM
Chicago O'Hare Intl
Thu 12/31
4:08 pm-12:09 pm
3 stops20h 01m
Puerto Escondido
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$285
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Thu 11/12
12:35 am-8:01 pm
2 stops19h 26m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$291
ChicagoPuerto Escondido
ORD Chicago O'Hare Intl - PXM Puerto Escondido
ORDPXM
Chicago O'Hare Intl
Thu 12/3
10:29 pm-9:38 pm
3 stops47h 09m
Puerto Escondido
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$294
Showing 1-10 of 53 resultsSorted by cheapest first
Best time to book a flight from Chicago to Oaxaca
Have a flexible travel schedule? Discover the best time to fly to Oaxaca from Chicago with our price prediction graph.
ORD-OAX
ORD-PXM
ORD-HUX
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 Chicago to Oaxaca
CHI-MXOA
ORD-OAX
ORD-PXM
ORD-HUX
What is the cheapest month to book a flight from Chicago to State of Oaxaca?
Currently, May is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $381). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $738). 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.
How much does it cost to fly round-trip from Chicago to State of Oaxaca?
Airfare is below average for this route at the moment.
Chicago to State of Oaxaca flights typically cost between $397 and $604 in February.The cheapest round-trip price found within the last 5 days was $339 on Multiple Airlines (Feb 12-Feb 21).
How far ahead should I book a flight from Chicago to State of Oaxaca?
To ensure you get the cheapest price possible for a flight from Chicago to State of Oaxaca, you should look to book at least 49 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Oaxaca
Get insights into the airlines that provide service to Oaxaca. 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 Oaxaca. Reviews last updated November 4, 2026.
Read through reviews of airlines operating flights from Chicago to Oaxaca, such as Delta,United Airlines, andAmerican Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Food
7.2
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Related info for your journey
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Chicago and Oaxaca flights
Browse other Chicago and Oaxaca flight options. Last updated on November 4, 2026.
Popular flight searches
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Top 6 airlines flying from Chicago to Oaxaca
Discover the top 6 airlines that operate flights from Chicago to Oaxaca. 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$262 | Average$459 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$292 | Average$430 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$476 | Average$702 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$557 | Average$1,078 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$587 | Average$768 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$598 | Average$820 | FlexibilityNo cancel fee | On-time71% |