$117+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Oct 8 — Oct 151
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 September 8, 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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/51:40 am -
1 stop11h 24m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sun 10/41:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$335
This CheapOair deal was found by Cheapflights users on 9/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/812:35 am -
1 stop17h 28m
Sun 11/152:20 pm -
1 stop8h 35m
Deal found 9/5![Viva logo]()
$336
This FlightHub deal was found by Cheapflights users on 9/3. 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.
Sun 11/812:35 am -
1 stop17h 28m
Sat 11/147:46 pm -
1 stop8h 57m
Deal found 9/3![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/6![Volaris logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/51:40 am -
1 stop11h 24m
Sat 10/107:34 pm -
1 stop9h 18m
Deal found 9/3![Multiple Airlines logo]()
$341
This Mytrip deal was found by Cheapflights users on 9/4. 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.
Fri 10/21:40 am -
1 stop7h 33m
Thu 10/157:34 pm -
1 stop9h 18m
Deal found 9/4![Volaris logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 9/211:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 9/211:40 am -
1 stop7h 33m
Thu 10/157:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/31:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sun 10/41:40 am -
1 stop7h 33m
Mon 10/127:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/106:29 am -
1 stop15h 09m
Fri 11/133:57 pm -
1 stop6h 53m
Deal found 9/7![Multiple Airlines logo]()
$349
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 September 8, 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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:35 am -
2 stops12h 35m
Fri 11/133:57 pm -
1 stop6h 53m
Deal found 9/7![Viva logo]()
$374
This Volaris deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 2/91:24 am -
1 stop11h 15m
Mon 2/151:27 pm -
1 stop8h 46m
Deal found 9/7![Volaris logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 2/201:24 am -
1 stop11h 15m
Sat 2/278:20 am -
2 stops15h 24m
Deal found 9/6![Multiple Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/177:45 am -
2 stops14h 53m
Mon 11/2310:22 am -
1 stop13h 17m
Deal found 9/6![Delta logo]()
$624
This CheapOair deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/912:25 am -
1 stop14h 42m
Sat 1/3010:30 pm -
1 stop25h 05m
Deal found 9/8![Viva logo]()
$409
This CheapOair deal was found by Cheapflights users on 9/3. 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 CheapOair 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 2/133:24 pm -
1 stop6h 49m
Deal found 9/3![Multiple Airlines logo]()
$456
This deal was found by Cheapflights users on 9/3. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:30 am -
1 stop11h 34m
Sat 11/286:04 am -
1 stop7h 08m
Deal found 9/3![Aeromexico logo]()
$951
This Expedia deal was found by Cheapflights users on 9/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/226:29 am -
1 stop8h 02m
Mon 3/83:24 pm -
1 stop13h 19m
Deal found 9/3![Volaris logo]()
$480
This Volaris deal was found by Cheapflights users on 9/5. 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.
Fri 1/2212:04 am -
1 stop14h 27m
Sat 2/133:24 pm -
1 stop6h 49m
Deal found 9/5![Volaris logo]()
$489
This CheapOair deal was found by Cheapflights users on 9/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:04 am -
1 stop12h 20m
Tue 11/310:32 pm -
1 stop25h 03m
Deal found 9/5![Multiple Airlines logo]()
$537
This Volaris deal was found by Cheapflights users on 9/3. 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.
Mon 3/16:29 am -
1 stop8h 02m
Tue 3/93:24 pm -
1 stop13h 19m
Deal found 9/3![Volaris logo]()
$495
This Volaris deal was found by Cheapflights users on 9/4. 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.
Sat 10/311:04 am -
1 stop14h 27m
Wed 11/43:24 pm -
1 stop13h 19m
Deal found 9/4![Volaris logo]()
$496
This Delta deal was found by Cheapflights users on 9/4. 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.
Sat 10/34:30 pm -
2 stops16h 01m
Thu 10/158:10 am -
2 stops13h 23m
Deal found 9/4![Delta logo]()
$719
This CheapOair deal was found by Cheapflights users on 9/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/252:53 am -
1 stop10h 53m
Mon 11/91:27 pm -
1 stop8h 46m
Deal found 9/4![Volaris logo]()
$499
This Delta deal was found by Cheapflights users on 9/3. 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.
Thu 9/241:54 am -
1 stop10h 27m
Wed 9/306:05 am -
2 stops13h 51m
Deal found 9/3![Delta logo]()
$725
This Volaris deal was found by Cheapflights users on 9/4. 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 11/1212:04 am -
1 stop14h 27m
Sat 11/213:24 pm -
1 stop6h 49m
Deal found 9/4![Volaris logo]()
$537
This Delta deal was found by Cheapflights users on 9/3. 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.
Thu 9/246:05 am -
2 stops26h 26m
Sat 10/108:14 am -
2 stops13h 19m
Deal found 9/3![Delta logo]()
$729
This Delta deal was found by Cheapflights users on 9/3. 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 10/56:05 am -
2 stops17h 25m
Sat 10/108:14 am -
2 stops13h 19m
Deal found 9/3![Delta logo]()
$749
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sun 11/16:17 pm -
1 stop18h 22m
Wed 11/44:54 pm -
2 stops19h 36m
Deal found 9/3![Multiple Airlines logo]()
$838
This Volaris deal was found by Cheapflights users on 9/3. 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.
Thu 11/1912:04 am -
1 stop12h 20m
Mon 11/301:27 pm -
1 stop8h 46m
Deal found 9/3![Volaris logo]()
$588
This Delta deal was found by Cheapflights users on 9/5. 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.
Sun 9/276:10 am -
2 stops11h 56m
Thu 10/111:58 am -
2 stops11h 01m
Deal found 9/5![Delta logo]()
$759
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 12/199:41 pm -
2 stops34h 36m
Tue 12/294:03 pm -
1 stop24h 44m
Deal found 9/7![Multiple Airlines logo]()
$847
This Volaris deal was found by Cheapflights users on 9/4. 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 9/4![Volaris logo]()
$594
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 1/96:00 am -
2 stops11h 43m
Sat 2/279:26 am -
2 stops12h 44m
Deal found 9/6![Delta logo]()
$767
This Mytrip deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/48:23 pm -
1 stop17h 23m
Sun 10/112:45 pm -
3 stops27h 19m
Deal found 9/6![Volaris logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 12/186:17 pm -
1 stop18h 22m
Tue 12/2210:30 pm -
2 stops18h 17m
Deal found 9/7![Multiple Airlines logo]()
$895
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:45 am -
2 stops14h 53m
Sun 11/156:54 am -
2 stops17h 00m
Deal found 9/8![Delta logo]()
$779
This Delta deal was found by Cheapflights users on 9/3. 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 9/1910:25 am -
2 stops25h 23m
Thu 10/1511:58 am -
1 stop11h 03m
Deal found 9/3![Delta logo]()
$789
This Delta deal was found by Cheapflights users on 9/4. 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.
Sun 10/41:54 am -
1 stop13h 17m
Mon 10/266:04 am -
2 stops14h 39m
Deal found 9/4![Delta logo]()
$835
This Mytrip deal was found by Cheapflights users on 9/3. 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.
Sun 11/16:17 pm -
2 stops18h 07m
Wed 11/41:27 pm -
3 stops25h 21m
Deal found 9/3![Volaris logo]()
$818
Last-minute flights from Chicago to OaxacaDiscover last-minute flight deals from Chicago to Oaxaca. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oaxaca. Data last updated September 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 9/211:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 9/211:40 am -
1 stop7h 33m
Thu 10/157:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 9/211:40 am -
1 stop7h 33m
Sat 10/107:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$352
This Mytrip deal was found by Cheapflights users on 9/4. 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.
Fri 10/21:40 am -
1 stop7h 33m
Thu 10/157:34 pm -
1 stop9h 18m
Deal found 9/4![Volaris logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/31:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sun 10/41:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sun 10/41:40 am -
1 stop7h 33m
Mon 10/127:34 pm -
1 stop9h 18m
Deal found 9/3![Volaris logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/51:40 am -
1 stop11h 24m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/3![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:40 am -
1 stop7h 33m
Tue 10/137:34 pm -
1 stop9h 18m
Deal found 9/6![Volaris logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 10/51:40 am -
1 stop11h 24m
Sat 10/107:34 pm -
1 stop9h 18m
Deal found 9/3![Multiple Airlines logo]()
$341
This Trip.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Thu 10/151:40 am -
1 stop12h 46m
Sat 10/242:24 pm -
1 stop14h 19m
Deal found 9/7![Volaris logo]()
$387
This Mytrip deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/201:40 am -
1 stop12h 46m
Wed 10/281:27 pm -
1 stop8h 46m
Deal found 9/6![Volaris logo]()
$367
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 September 8, 2026.
Search for one-way flight options from Chicago to Oaxaca. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Booking.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/6![Viva logo]()
$117
This Mytrip deal was found by Cheapflights users on 9/4. 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.
Fri 10/21:40 am -
1 stop7h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Volaris logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Fri 10/22:53 am -
2 stops37h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$159
This Booking.com deal was found by Cheapflights users on 9/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:30 am -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Viva logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/2712:35 am -
2 stops21h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Viva logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:30 pm -
2 stops27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Viva logo]()
$173
This Gotogate deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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.
Fri 10/21:40 am -
1 stop14h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Volaris logo]()
$179
This CheapOair deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/2712:04 am -
1 stop12h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Volaris logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:41 am -
2 stops37h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$211
This Jetabroad deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:23 pm -
1 stop13h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Volaris logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Mon 12/142:41 am -
1 stop13h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Volaris logo]()
$217
This Trip.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Fri 10/91:40 am -
1 stop7h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Volaris logo]()
$220
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 September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $315 (Mytrip) |
One-way from | $117 (Booking.com) |
Popular in | December |
Cheapest in | April |
Average price | $431 |
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 September 8, 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
Quickest round-trip
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Fri 10/2
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Fri 10/2
2:53 am-10:20 pm
2 stops44h 27m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
ChicagoPuerto Escondido
ORD Chicago O'Hare Intl - PXM Puerto Escondido
ORDPXM
Chicago O'Hare Intl
Fri 11/27
12:35 am-9:38 pm
2 stops21h 03m
Puerto Escondido
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
ChicagoSanta Maria Huatulco
ORD Chicago O'Hare Intl - HUX Santa Maria Huatulco
ORDHUX
Chicago O'Hare Intl
Fri 10/2
1:40 am-2:55 pm
1 stop14h 15m
Santa Maria Huatulco
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
ChicagoPuerto Escondido
ORD Chicago O'Hare Intl - PXM Puerto Escondido
ORDPXM
Chicago O'Hare Intl
Fri 11/27
12:04 am-12:24 pm
1 stop12h 20m
Puerto Escondido
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
ChicagoSanta Maria Huatulco
ORD Chicago O'Hare Intl - HUX Santa Maria Huatulco
ORDHUX
Chicago O'Hare Intl
Tue 10/27
12:30 pm-3:12 pm
2 stops27h 42m
Santa Maria Huatulco
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Fri 10/9
1:40 am-8:13 am
1 stop7h 33m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$220
ChicagoSanta Maria Huatulco
ORD Chicago O'Hare Intl - HUX Santa Maria Huatulco
ORDHUX
Chicago O'Hare Intl
Fri 10/2
2:53 am-3:12 pm
2 stops13h 19m
Santa Maria Huatulco
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$226
ChicagoSanta Maria Huatulco
MDW Chicago Midway - HUX Santa Maria Huatulco
MDWHUX
Chicago Midway
Sun 10/25
8:23 pm-5:24 pm
2 stops22h 01m
Santa Maria Huatulco
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$242
ChicagoOaxaca
MDW Chicago Midway - OAX Oaxaca Xoxocotlan
MDWOAX
Chicago Midway
Sat 10/17
7:30 pm-7:47 am
2 stops37h 17m
Oaxaca Xoxocotlan
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$248
Showing 1-10 of 60 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
MDW-OAX
MDW-PXM
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
MDW-OAX
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 $363). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $729). 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 $368 and $451 in February.The cheapest round-trip price found within the last 5 days was $315 on Volaris (Feb 5-Feb 15).
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 40 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 September 8, 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.
Overall
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
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Chicago and Oaxaca flights
Browse other Chicago and Oaxaca flight options. Last updated on September 8, 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 7,457,451 searches. Data last updated September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$269 | Average$423 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$288 | Average$427 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$378 | Average$754 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$453 | Average$750 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$475 | Average$1,014 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$546 | Average$775 | FlexibilityNo cancel fee | On-time71% |