$125+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Jun 4 — Jun 111
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 May 5, 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 May 5, 2026.
This Viva deal was found by Cheapflights users on 5/3. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:30 am
ORD
- OAX
1 stop14h 37m
Viva
Mon 10/1212:49 pm
OAX
- ORD
1 stop21h 11m
Viva
Deal found 5/3![Viva logo]()
$295
This Viva deal was found by Cheapflights users on 5/1. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/81:30 am
ORD
- OAX
1 stop14h 30m
Viva
Thu 6/183:30 pm
OAX
- ORD
1 stop7h 25m
Viva
Deal found 5/1![Viva logo]()
$303
This Viva deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 11/1612:30 am
ORD
- OAX
1 stop14h 37m
Viva
Mon 11/233:37 pm
OAX
- ORD
1 stop7h 08m
Viva
Deal found 5/5![Viva logo]()
$310
This Viva deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/81:30 am
ORD
- OAX
1 stop14h 30m
Viva
Wed 6/103:30 pm
OAX
- ORD
1 stop7h 25m
Viva
Deal found 5/5![Viva logo]()
$319
This Viva deal was found by Cheapflights users on 5/3. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:30 am
ORD
- OAX
1 stop14h 37m
Viva
Tue 9/2212:49 pm
OAX
- ORD
1 stop21h 11m
Viva
Deal found 5/3![Viva logo]()
$327
This Mytrip deal was found by Cheapflights users on 5/2. 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 9/91:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 9/147:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/2![Volaris logo]()
$329
This FlightHub deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Mon 8/171:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Sun 8/237:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/5![Volaris logo]()
$331
This Mytrip deal was found by Cheapflights users on 5/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Tue 9/227:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/4![Volaris logo]()
$333
This FlightHub deal was found by Cheapflights users on 5/1. 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.
Tue 5/261:40 am
ORD
- OAX
1 stop7h 33m
Multiple Airlines
Mon 6/13:30 pm
OAX
- ORD
1 stop7h 25m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$334
This Viva deal was found by Cheapflights users on 5/1. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:35 am
ORD
- OAX
1 stop11h 29m
Viva
Fri 10/23:37 pm
OAX
- ORD
1 stop7h 08m
Viva
Deal found 5/1![Viva logo]()
$335
This Viva deal was found by Cheapflights users on 5/3. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:30 am
ORD
- OAX
1 stop14h 37m
Viva
Tue 9/2912:49 pm
OAX
- ORD
1 stop21h 11m
Viva
Deal found 5/3![Viva logo]()
$336
This Delta deal was found by Cheapflights users on 5/1. 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.
Tue 9/291:05 pm
MDW
- OAX
2 stops10h 38m
Delta
Tue 10/68:55 am
OAX
- MDW
2 stops11h 50m
Delta
Deal found 5/1![Delta logo]()
$575
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 May 5, 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 May 5, 2026.
This Viva deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:35 am
ORD
- OAX
1 stop11h 29m
Viva
Tue 9/812:49 pm
OAX
- ORD
1 stop21h 11m
Viva
Deal found 5/5![Viva logo]()
$357
This Mytrip deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 9/21:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Tue 9/87:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/5![Volaris logo]()
$360
This Delta deal was found by Cheapflights users on 5/3. 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.
Mon 6/17:45 pm
ORD
- OAX
2 stops22h 04m
Delta
Tue 6/1610:31 am
OAX
- ORD
1 stop12h 36m
Delta
Deal found 5/3![Delta logo]()
$597
This Viva deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/91:30 am
ORD
- OAX
1 stop20h 05m
Viva
Sat 8/153:30 pm
OAX
- ORD
1 stop8h 10m
Viva
Deal found 5/5![Viva logo]()
$373
This Volaris deal was found by Cheapflights users on 5/4. 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.
Thu 10/221:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Tue 11/247:31 pm
OAX
- ORD
1 stop9h 05m
Volaris
Deal found 5/4![Volaris logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/98:48 pm
MDW
- OAX
1 stop12h 47m
Multiple Airlines
Mon 5/119:00 am
OAX
- MDW
2 stops12h 02m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$881
This Volaris deal was found by Cheapflights users on 5/3. 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.
Wed 6/171:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Thu 6/257:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/3![Volaris logo]()
$467
This Viva deal was found by Cheapflights users on 5/2. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/191:30 am
ORD
- OAX
1 stop20h 05m
Viva
Fri 7/319:15 pm
OAX
- ORD
1 stop26h 25m
Viva
Deal found 5/2![Viva logo]()
$490
This Delta deal was found by Cheapflights users on 5/3. 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.
Wed 6/35:30 am
ORD
- OAX
2 stops12h 19m
Delta
Thu 6/186:00 am
OAX
- ORD
1 stop17h 07m
Delta
Deal found 5/3![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 5/1. 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.
Wed 9/306:00 am
ORD
- OAX
2 stops13h 43m
Delta
Fri 10/26:05 am
OAX
- ORD
2 stops14h 40m
Delta
Deal found 5/1![Delta logo]()
$606
This Volaris deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/181:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Sat 8/110:00 pm
OAX
- ORD
1 stop13h 09m
Volaris
Deal found 5/5![Volaris logo]()
$571
This Delta deal was found by Cheapflights users on 5/3. 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.
Tue 6/26:24 am
ORD
- OAX
2 stops14h 16m
Delta
Sat 6/1310:27 am
OAX
- ORD
1 stop12h 40m
Delta
Deal found 5/3![Delta logo]()
$617
This Volaris deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 10/291:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Fri 11/67:31 pm
OAX
- ORD
1 stop9h 05m
Volaris
Deal found 5/5![Volaris logo]()
$599
This Delta deal was found by Cheapflights users on 5/4. 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.
Fri 5/812:53 pm
MDW
- OAX
2 stops10h 39m
Delta
Tue 5/1210:31 am
OAX
- MDW
2 stops9h 38m
Delta
Deal found 5/4![Delta logo]()
$712
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/236:23 am
MDW
- OAX
2 stops13h 54m
Delta
Sat 5/306:05 am
OAX
- MDW
2 stops14h 04m
Delta
Deal found 5/5![Delta logo]()
$742
This Delta deal was found by Cheapflights users on 5/1. 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.
Sat 8/16:00 am
MDW
- OAX
2 stops14h 58m
Delta
Sat 8/88:00 am
OAX
- MDW
2 stops13h 15m
Delta
Deal found 5/1![Delta logo]()
$758
This Delta deal was found by Cheapflights users on 5/3. 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.
Sun 5/3110:59 am
MDW
- OAX
2 stops12h 33m
Delta
Tue 6/1610:31 am
OAX
- MDW
2 stops10h 46m
Delta
Deal found 5/3![Delta logo]()
$808
This Delta deal was found by Cheapflights users on 5/1. 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 7/2312:41 pm
MDW
- OAX
2 stops10h 58m
Delta
Fri 8/76:02 am
OAX
- MDW
2 stops15h 13m
Delta
Deal found 5/1![Delta logo]()
$830
This Delta deal was found by Cheapflights users on 5/3. 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.
Wed 5/2012:53 pm
MDW
- OAX
2 stops10h 39m
Delta
Sun 5/246:00 am
OAX
- MDW
2 stops14h 09m
Delta
Deal found 5/3![Delta logo]()
$842
This Delta deal was found by Cheapflights users on 5/3. 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.
Sat 5/96:23 am
MDW
- OAX
2 stops13h 54m
Delta
Wed 5/136:00 am
OAX
- MDW
2 stops14h 09m
Delta
Deal found 5/3![Delta logo]()
$893
Last-minute flights from Chicago to OaxacaDiscover last-minute flight deals from Chicago to Oaxaca. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oaxaca. Data last updated May 5, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Sat 5/91:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 5/187:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/4![Volaris logo]()
$376
This FlightHub deal was found by Cheapflights users on 5/1. 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 5/171:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Fri 5/297:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/1![Volaris logo]()
$375
This Viva deal was found by Cheapflights users on 5/1. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/242:15 am
ORD
- OAX
1 stop13h 45m
Viva
Mon 7/63:30 pm
OAX
- ORD
1 stop7h 25m
Viva
Deal found 5/1![Viva logo]()
$359
This FlightHub deal was found by Cheapflights users on 5/1. 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.
Tue 5/261:40 am
ORD
- OAX
1 stop7h 33m
Multiple Airlines
Mon 6/13:30 pm
OAX
- ORD
1 stop7h 25m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$334
This FlightHub deal was found by Cheapflights users on 5/4. 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.
Tue 5/261:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 6/17:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 5/4![Volaris logo]()
$339
This Viva deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/11:30 am
ORD
- OAX
1 stop14h 30m
Viva
Tue 6/912:50 pm
OAX
- ORD
1 stop21h 05m
Viva
Deal found 5/5![Viva logo]()
$373
This Viva deal was found by Cheapflights users on 5/3. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:30 am
ORD
- OAX
1 stop20h 10m
Viva
Wed 6/103:30 pm
OAX
- ORD
1 stop7h 25m
Viva
Deal found 5/3![Viva logo]()
$331
This Viva deal was found by Cheapflights users on 5/4. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/71:30 am
ORD
- OAX
1 stop20h 10m
Viva
Thu 6/113:30 pm
OAX
- ORD
1 stop7h 25m
Viva
Deal found 5/4![Viva logo]()
$348
This Viva deal was found by Cheapflights users on 5/1. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/81:30 am
ORD
- OAX
1 stop14h 30m
Viva
Thu 6/183:30 pm
OAX
- ORD
1 stop7h 25m
Viva
Deal found 5/1![Viva logo]()
$303
This Viva deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/81:30 am
ORD
- OAX
1 stop14h 30m
Viva
Wed 6/103:30 pm
OAX
- ORD
1 stop7h 25m
Viva
Deal found 5/5![Viva logo]()
$319
This Trip.com deal was found by Cheapflights users on 5/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/241:40 am
ORD
- OAX
1 stop7h 33m
Multiple Airlines
Mon 7/63:30 pm
OAX
- ORD
1 stop7h 25m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$366
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Thu 7/92:29 pm
OAX
- ORD
1 stop13h 12m
Volaris
Deal found 5/3![Volaris logo]()
$372
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 May 5, 2026.
Search for one-way flight options from Chicago to Oaxaca. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Deal found 5/3![Volaris logo]()
$125
This Mytrip deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Mon 7/271:30 am
ORD
- OAX
1 stop14h 30m
Viva
Deal found 5/5![Viva logo]()
$154
This Mytrip deal was found by Cheapflights users on 5/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Deal found 5/4![Volaris logo]()
$173
This Viva deal was found by Cheapflights users on 5/3. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/231:30 am
ORD
- OAX
1 stop20h 05m
Viva
Deal found 5/3![Viva logo]()
$176
This Booking.com deal was found by Cheapflights users on 5/3. 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.
Sun 7/191:30 am
ORD
- OAX
1 stop20h 05m
Viva
Deal found 5/3![Viva logo]()
$177
This Booking.com deal was found by Cheapflights users on 5/3. 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 7/201:30 am
ORD
- OAX
1 stop14h 30m
Viva
Deal found 5/3![Viva logo]()
$182
This Mytrip deal was found by Cheapflights users on 5/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Deal found 5/4![Volaris logo]()
$190
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Deal found 5/3![Volaris logo]()
$196
This Mytrip deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 8/158:49 pm
MDW
- OAX
1 stop12h 47m
Volaris
Deal found 5/5![Volaris logo]()
$253
This FlightHub deal was found by Cheapflights users on 5/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:48 pm
MDW
- OAX
1 stop12h 47m
Volaris
Deal found 5/3![Volaris logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 am
MDW
- OAX
3 stops27h 04m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$294
This FlightHub deal was found by Cheapflights users on 5/3. 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 FlightHub 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 47m
Volaris
Deal found 5/3![Volaris logo]()
$297
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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (Viva) |
One-way from | $125 (Mytrip) |
Popular in | December |
Cheapest in | April |
Average price | $454 |
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 May 5, 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
Wed 9/2
1:35 am-12:04 pm
1 stop11h 29m
Oaxaca Xoxocotlan
Tue 9/8
12:49 pm-11:00 am
1 stop21h 11m
$357
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Wed 9/2
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Tue 9/8
7:34 pm-5:52 am
1 stop9h 18m
$360
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Sun 8/9
1:30 am-8:35 pm
1 stop20h 05m
Oaxaca Xoxocotlan
Sat 8/15
3:30 pm-12:40 am
1 stop8h 10m
$373
Quickest round-trip
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Thu 10/22
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Tue 11/24
7:31 pm-4:36 am
1 stop9h 05m
$437
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Wed 6/17
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Thu 6/25
7:34 pm-5:52 am
1 stop9h 18m
$467
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Sun 7/19
1:30 am-8:35 pm
1 stop20h 05m
Oaxaca Xoxocotlan
Fri 7/31
9:15 pm-12:40 am
1 stop26h 25m
$490
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Sat 7/18
1:49 pm-9:09 pm
1 stop8h 20m
Oaxaca Xoxocotlan
Sat 8/1
10:00 pm-12:09 pm
1 stop13h 09m
$571
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Mon 6/1
7:45 pm-4:49 pm
2 stops22h 04m
Oaxaca Xoxocotlan
Tue 6/16
10:31 am-12:07 am
1 stop12h 36m
$597
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Wed 6/3
5:30 am-4:49 pm
2 stops12h 19m
Oaxaca Xoxocotlan
Thu 6/18
6:00 am-12:07 am
1 stop17h 07m
$597
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Thu 10/29
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Fri 11/6
7:31 pm-4:36 am
1 stop9h 05m
$599
Showing 1-10 of 37 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 May.
| 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 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
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 51 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.
What is the cheapest month to book a flight from Chicago to Oaxaca?
Currently, March is the cheapest month in which you can book a flight from Chicago to Oaxaca (average of $182). 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.
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 May 5, 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.
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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.
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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 May 5, 2026.
Chicago and Oaxaca flights
Browse other Chicago and Oaxaca flight options. Last updated on May 5, 2026.
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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 May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$261 | Average$360 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$385 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$472 | Average$581 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$520 | Average$750 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$524 | Average$775 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$543 | Average$623 | FlexibilityNo cancel fee | On-time71% |