$128+ Cheap flights from Chicago (CHI) to Oaxaca, Mexico (OAX)
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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oaxaca 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.Cheap flight deals from Chicago to Oaxaca
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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 June 23, 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 June 23, 2026.
This CheapOair deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/261:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 8/312:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/20![Volaris logo]()
$305
This CheapOair deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/241:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Wed 9/307:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/20![Volaris logo]()
$310
This FlightHub deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Sat 8/151:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Sat 8/297:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/21![Volaris logo]()
$311
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/91:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Tue 7/149:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/21![Volaris logo]()
$318
This FlightHub deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/261:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Sun 8/302:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/21![Volaris logo]()
$321
This Gotogate deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 10/57:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/20![Volaris logo]()
$323
This CheapOair deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Tue 7/79:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/22![Volaris logo]()
$329
This CheapOair deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Wed 7/82:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/19![Volaris logo]()
$330
This FlightHub deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Sat 8/151:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Sun 8/232:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/23![Volaris logo]()
$331
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/291:00 pm
MDW
- OAX
2 stops10h 39m
Delta
Tue 10/66:00 am
OAX
- MDW
2 stops9h 25m
Delta
Deal found 6/23![Delta logo]()
$576
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/210:54 am
MDW
- OAX
2 stops12h 45m
Delta
Sat 9/58:05 am
OAX
- MDW
2 stops13h 31m
Delta
Deal found 6/23![Delta logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/248:23 pm
MDW
- OAX
1 stop25h 46m
Multiple Airlines
Sat 10/33:37 pm
OAX
- MDW
2 stops43h 30m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$634
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 June 23, 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 June 23, 2026.
This Trip.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Sat 10/31:40 am
ORD
- OAX
1 stop7h 33m
Multiple Airlines
Fri 10/93:37 pm
OAX
- ORD
1 stop22h 13m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$329
This Volaris deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 11/1711:58 pm
ORD
- OAX
1 stop8h 21m
Volaris
Mon 11/237:31 pm
OAX
- ORD
1 stop9h 05m
Volaris
Deal found 6/23![Volaris logo]()
$435
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:35 am
ORD
- OAX
2 stops15h 09m
Delta
Mon 11/2310:22 am
OAX
- ORD
2 stops13h 28m
Delta
Deal found 6/22![Delta logo]()
$576
This Viva deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Mon 10/261:35 am
ORD
- OAX
1 stop11h 29m
Viva
Wed 11/43:37 pm
OAX
- ORD
1 stop7h 08m
Viva
Deal found 6/23![Viva logo]()
$590
This Mytrip deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Sat 10/31:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Fri 10/92:31 pm
OAX
- ORD
3 stops32h 16m
Volaris
Deal found 6/23![Volaris logo]()
$474
This CheapOair deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/309:27 pm
MDW
- OAX
2 stops23h 06m
Frontier
Sun 8/28:56 am
OAX
- MDW
2 stops25h 11m
Frontier
Deal found 6/18![Frontier logo]()
$1,032
This Volaris deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/11:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Sat 8/82:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/20![Volaris logo]()
$509
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/296:05 am
MDW
- OAX
2 stops12h 18m
Delta
Tue 10/66:00 am
OAX
- MDW
2 stops15h 10m
Delta
Deal found 6/20![Delta logo]()
$576
This Volaris deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/161:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Fri 7/312:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/20![Volaris logo]()
$528
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:35 am
ORD
- OAX
2 stops15h 09m
Delta
Tue 11/176:01 am
OAX
- ORD
2 stops10h 36m
Delta
Deal found 6/19![Delta logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/198:23 pm
MDW
- OAX
1 stop22h 54m
Multiple Airlines
Tue 7/288:56 am
OAX
- MDW
2 stops12h 07m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$670
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/98:23 pm
MDW
- OAX
1 stop13h 10m
Multiple Airlines
Sat 8/158:56 am
OAX
- MDW
2 stops12h 07m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$732
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/286:05 am
MDW
- OAX
2 stops12h 13m
Delta
Mon 10/58:05 am
OAX
- MDW
2 stops13h 40m
Delta
Deal found 6/23![Delta logo]()
$676
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/146:05 am
MDW
- OAX
2 stops15h 14m
Delta
Mon 8/246:00 am
OAX
- MDW
2 stops15h 36m
Delta
Deal found 6/21![Delta logo]()
$736
This Volaris deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 10/281:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 11/22:44 pm
OAX
- ORD
1 stop8h 55m
Volaris
Deal found 6/22![Volaris logo]()
$772
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:00 am
ORD
- OAX
2 stops16h 44m
Delta
Mon 11/2310:22 am
OAX
- ORD
2 stops13h 28m
Delta
Deal found 6/19![Delta logo]()
$742
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/2710:54 am
MDW
- OAX
2 stops12h 45m
Delta
Mon 8/318:05 am
OAX
- MDW
2 stops13h 31m
Delta
Deal found 6/20![Delta logo]()
$840
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:54 am
MDW
- OAX
2 stops12h 45m
Delta
Wed 9/28:05 am
OAX
- MDW
2 stops13h 31m
Delta
Deal found 6/23![Delta logo]()
$840
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/156:05 am
MDW
- OAX
2 stops14h 53m
Delta
Sat 8/298:05 am
OAX
- MDW
2 stops13h 31m
Delta
Deal found 6/21![Delta logo]()
$931
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/156:05 am
MDW
- OAX
2 stops12h 08m
Delta
Sun 8/236:00 am
OAX
- MDW
2 stops15h 36m
Delta
Deal found 6/21![Delta logo]()
$1,071
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:00 am
MDW
- OAX
2 stops16h 44m
Delta
Sun 11/157:00 am
OAX
- MDW
2 stops15h 10m
Delta
Deal found 6/21![Delta logo]()
$1,104
Last-minute flights from Chicago to OaxacaDiscover last-minute flight deals from Chicago to Oaxaca. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oaxaca. Data last updated June 23, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/21:30 am
ORD
- OAX
2 stops11h 35m
Multiple Airlines
Tue 7/79:45 pm
OAX
- ORD
1 stop13h 24m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$370
This CheapOair deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/41:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Tue 7/79:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/23![Volaris logo]()
$335
This CheapOair deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Tue 7/79:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/22![Volaris logo]()
$329
This CheapOair deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Wed 7/82:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/19![Volaris logo]()
$330
This CheapOair deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Thu 7/99:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/23![Volaris logo]()
$354
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/71:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Sat 7/182:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/21![Volaris logo]()
$337
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/91:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Tue 7/149:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/21![Volaris logo]()
$318
This CheapOair deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/106:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Fri 7/172:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/19![Volaris logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/198:23 pm
MDW
- OAX
1 stop22h 54m
Multiple Airlines
Tue 7/288:56 am
OAX
- MDW
2 stops12h 07m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$670
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/218:49 pm
MDW
- OAX
1 stop12h 44m
Multiple Airlines
Tue 7/288:56 am
OAX
- MDW
2 stops12h 07m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$650
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/248:23 pm
MDW
- OAX
1 stop25h 46m
Multiple Airlines
Sat 10/33:37 pm
OAX
- MDW
2 stops43h 30m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$634
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/248:23 pm
MDW
- OAX
1 stop25h 46m
Volaris
Sat 10/32:29 pm
OAX
- MDW
1 stop27h 35m
Volaris
Deal found 6/18![Volaris logo]()
$692
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 June 23, 2026.
Search for one-way flight options from Chicago to Oaxaca. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Mytrip deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Tue 11/1711:58 pm
ORD
- OAX
1 stop8h 21m
Volaris
Deal found 6/22![Volaris logo]()
$128
This CheapOair deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/261:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Deal found 6/23![Volaris logo]()
$129
This CheapOair deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/131:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Deal found 6/22![Volaris logo]()
$142
This Mytrip deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/316:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Deal found 6/21![Volaris logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/262:53 am
ORD
- OAX
2 stops29h 52m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/281:49 pm
ORD
- OAX
2 stops26h 01m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Deal found 6/21![Volaris logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/288:23 pm
MDW
- OAX
2 stops16h 42m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/288:23 pm
MDW
- OAX
1 stop25h 46m
Volaris
Deal found 6/23![Volaris logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/279:26 pm
MDW
- OAX
3 stops42h 24m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$233
This Mytrip deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/318:23 pm
MDW
- OAX
2 stops18h 26m
Volaris
Deal found 6/22![Volaris logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/3112:11 pm
MDW
- OAX
3 stops57h 58m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$285
Find flight deals from Chicago to Oaxaca
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Oaxaca (OAX). 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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (CheapOair) |
One-way from | $128 (Mytrip) |
Popular in | December |
Cheapest in | April |
Average price | $482 |
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 2,558,603 searches. Data last updated June 23, 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 - OAX
ORDOAX
Chicago O'Hare Intl
Sat 10/3
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Fri 10/9
3:37 pm-2:50 pm
1 stop22h 13m
$329
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Tue 11/17
11:58 pm-8:19 am
1 stop8h 21m
Oaxaca Xoxocotlan
Mon 11/23
7:31 pm-4:36 am
1 stop9h 05m
$435
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Sat 10/3
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Fri 10/9
2:31 pm-11:47 pm
3 stops32h 16m
$474
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Sat 8/1
1:49 pm-9:09 pm
1 stop8h 20m
Oaxaca Xoxocotlan
Sat 8/8
2:29 pm-12:55 am
1 stop9h 26m
$509
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Thu 7/16
1:49 pm-9:09 pm
1 stop8h 20m
Oaxaca Xoxocotlan
Fri 7/31
2:29 pm-12:55 am
1 stop9h 26m
$528
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Tue 11/17
7:35 am-10:44 pm
2 stops15h 09m
Oaxaca Xoxocotlan
Mon 11/23
10:22 am-11:50 pm
2 stops13h 28m
$576
ChicagoOaxaca
MDW - OAX
MDWOAX
Chicago Midway
Tue 9/29
6:05 am-5:23 pm
2 stops12h 18m
Oaxaca Xoxocotlan
Tue 10/6
6:00 am-10:10 pm
2 stops15h 10m
$576
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Mon 10/26
1:35 am-12:04 pm
1 stop11h 29m
Oaxaca Xoxocotlan
Wed 11/4
3:37 pm-10:45 pm
1 stop7h 08m
$590
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Fri 11/13
7:35 am-10:44 pm
2 stops15h 09m
Oaxaca Xoxocotlan
Tue 11/17
6:01 am-4:37 pm
2 stops10h 36m
$606
ChicagoOaxaca
MDW - OAX
MDWOAX
Chicago Midway
Sun 7/19
8:23 pm-6:17 pm
1 stop22h 54m
Oaxaca Xoxocotlan
Tue 7/28
8:56 am-10:03 pm
2 stops12h 07m
$670
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Chicago to Oaxaca
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 Chicago to Oaxaca in June.
| 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 Accuracy1 star | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Oaxaca flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Oaxaca flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Oaxaca flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Oaxaca 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 Chicago-Oaxaca 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 Chicago to Oaxaca
Have a flexible travel schedule? Discover the best time to fly to Oaxaca from Chicago with our price prediction graph.
CHI-OAX
ORD-OAX
MDW-OAX
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-OAX
ORD-OAX
MDW-OAX
What is the cheapest month to book a flight from Chicago to Oaxaca?
Currently, May is the cheapest month in which you can book a flight from Chicago to Oaxaca (average of $119). Flying from Chicago to Oaxaca in November is currently the most expensive (average of $373). 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 Oaxaca?
What’s the top layover airport for flights from Chicago to Oaxaca?
Share of 1-stop round-trip flights from Chicago to Oaxaca chosen by Cheapflights users in the past 12 months, using the same layover each way.
Mexico City (MEX) – chosen by Cheapflights users on 83% of 1-stop itineraries from Chicago to Oaxaca on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Oaxaca?
Average round-trip fare for 1-stop flights from Chicago to Oaxaca, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Mexico City (MEX) is the most affordable 1-stop option, with an average round-trip price of $490.
What’s the fastest layover option from Chicago to Oaxaca?
Shortest average travel time for 1-stop one-way flights from Chicago to Oaxaca, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Mexico City (MEX) have the shortest average one-way travel time for 1-stop routes: 7h 23m.
Which airport typically offers the quickest layover for flights from Chicago to Oaxaca?
Average layover duration for 1-stop one-way flights from Chicago to Oaxaca, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Mexico City (MEX) offer the fastest connection on this route, with an average layover time of 1h 33m.
How far ahead should I book a flight from Chicago to Oaxaca?
To ensure you get the cheapest price possible for a flight from Chicago to Oaxaca, you should look to book at least 46 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 June 23, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Chicago to Oaxaca. 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.
Food
7.2
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Oaxaca. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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.
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Complete your trip
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Other flights to Oaxaca
Explore flights to Oaxaca departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 23, 2026.
Chicago and Oaxaca flights
Browse other Chicago and Oaxaca flight options. Last updated on June 23, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$261 | Average$375 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$426 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$472 | Average$623 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$520 | Average$750 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$524 | Average$778 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$543 | Average$616 | FlexibilityNo cancel fee | On-time71% |