$138+ Cheap flights from Chicago (CHI) to Oaxaca
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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Jul 9 — Jul 161
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
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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 9, 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 9, 2026.
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Mon 8/241:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Tue 9/17:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/7![Volaris logo]()
$296
This CheapOair deal was found by Cheapflights users on 6/8. 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.
Wed 8/261:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Sat 9/57:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/8![Volaris logo]()
$301
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Mon 8/241:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Tue 9/87:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/7![Volaris logo]()
$303
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 8/317:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/8![Volaris logo]()
$311
This Viva deal was found by Cheapflights users on 6/6. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:30 am
ORD
- OAX
1 stop14h 37m
Viva
Sun 11/153:37 pm
OAX
- ORD
1 stop7h 08m
Viva
Deal found 6/6![Viva logo]()
$313
This CheapOair deal was found by Cheapflights users on 6/5. 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.
Thu 8/201:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Tue 9/17:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/5![Volaris logo]()
$315
This Justfly.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Sat 8/299:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/9![Volaris logo]()
$320
This CheapOair deal was found by Cheapflights users on 6/5. 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.
Thu 8/201:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Sat 8/297:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/5![Volaris logo]()
$321
This Gotogate deal was found by Cheapflights users on 6/6. 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.
Sun 9/271:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 10/57:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/6![Volaris logo]()
$324
This Mytrip deal was found by Cheapflights users on 6/6. 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.
Sat 10/31:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Sun 10/117:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/6![Volaris logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Fri 9/181:30 am
ORD
- PXM
1 stop21h 08m
Viva
Thu 9/243:55 pm
PXM
- ORD
1 stop7h 04m
Viva
Deal found 6/4![Viva logo]()
$330
This Viva deal was found by Cheapflights users on 6/6. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/412:30 pm
ORD
- PXM
1 stop27h 34m
Viva
Tue 10/2010:32 pm
PXM
- ORD
1 stop11h 28m
Viva
Deal found 6/6![Viva logo]()
$336
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 9, 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 9, 2026.
This Viva deal was found by Cheapflights users on 6/6. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/412:30 pm
ORD
- PXM
1 stop27h 34m
Viva
Tue 10/2010:32 pm
PXM
- ORD
1 stop11h 28m
Viva
Deal found 6/6![Viva logo]()
$336
This Volaris deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/181:40 am
ORD
- HUX
1 stop14h 15m
Volaris
Sat 9/263:40 pm
HUX
- ORD
1 stop13h 12m
Volaris
Deal found 6/9![Volaris logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Sat 9/57:35 am
ORD
- HUX
1 stop8h 37m
Multiple Airlines
Tue 9/83:53 pm
HUX
- ORD
1 stop18h 07m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 6/7. 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 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
1 stop12h 38m
Delta
Deal found 6/7![Delta logo]()
$566
This Viva deal was found by Cheapflights users on 6/4. 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.
Thu 9/241:30 am
ORD
- PXM
1 stop21h 08m
Viva
Wed 9/3010:32 pm
PXM
- ORD
1 stop11h 28m
Viva
Deal found 6/4![Viva logo]()
$369
This Volaris deal was found by Cheapflights users on 6/7. 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 11/1711:58 pm
ORD
- OAX
1 stop8h 21m
Volaris
Mon 11/232:44 pm
OAX
- ORD
1 stop8h 55m
Volaris
Deal found 6/7![Volaris logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Fri 7/32:53 am
ORD
- PXM
1 stop13h 12m
Multiple Airlines
Sat 7/118:30 am
PXM
- ORD
2 stops15h 25m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$427
This Viva deal was found by Cheapflights users on 6/5. 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.
Thu 10/151:30 am
ORD
- OAX
1 stop14h 37m
Viva
Wed 10/213:37 pm
OAX
- ORD
1 stop7h 08m
Viva
Deal found 6/5![Viva logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Wed 7/12:53 am
ORD
- OAX
2 stops35h 56m
Volaris
Fri 7/102:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/4![Volaris logo]()
$410
This Volaris deal was found by Cheapflights users on 6/4. 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 8/151:40 am
ORD
- HUX
1 stop14h 15m
Volaris
Wed 8/193:40 pm
HUX
- ORD
1 stop7h 07m
Volaris
Deal found 6/4![Volaris logo]()
$420
This Viva deal was found by Cheapflights users on 6/8. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:35 am
ORD
- HUX
1 stop14h 36m
Viva
Sat 10/173:47 pm
HUX
- ORD
1 stop18h 13m
Viva
Deal found 6/8![Viva logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 10/32:53 am
ORD
- PXM
2 stops18h 07m
Multiple Airlines
Tue 10/2010:32 pm
PXM
- ORD
1 stop30h 20m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$480
This Volaris deal was found by Cheapflights users on 6/8. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:58 pm
ORD
- OAX
1 stop8h 21m
Volaris
Mon 11/232:44 pm
OAX
- ORD
1 stop8h 55m
Volaris
Deal found 6/8![Volaris logo]()
$426
This Delta deal was found by Cheapflights users on 6/6. 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.
Wed 8/127:25 am
ORD
- OAX
2 stops13h 31m
Delta
Wed 8/268:05 am
OAX
- ORD
2 stops11h 45m
Delta
Deal found 6/6![Delta logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/31:49 pm
ORD
- PXM
1 stop23h 57m
Multiple Airlines
Sun 7/53:55 pm
PXM
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$507
This Gotogate deal was found by Cheapflights users on 6/6. 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.
Sat 7/47:35 am
ORD
- HUX
1 stop8h 20m
Volaris
Wed 7/83:40 pm
HUX
- ORD
1 stop7h 07m
Volaris
Deal found 6/6![Volaris logo]()
$429
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 9/296:05 am
MDW
- OAX
2 stops12h 18m
Delta
Tue 10/66:00 am
OAX
- MDW
2 stops15h 10m
Delta
Deal found 6/8![Delta logo]()
$576
This Volaris deal was found by Cheapflights users on 6/4. 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 9/247:35 am
ORD
- HUX
1 stop8h 20m
Volaris
Wed 9/303:40 pm
HUX
- ORD
1 stop13h 12m
Volaris
Deal found 6/4![Volaris logo]()
$431
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 11/236:00 am
MDW
- OAX
2 stops16h 44m
Delta
Sat 12/58:09 am
OAX
- MDW
2 stops14h 01m
Delta
Deal found 6/8![Delta logo]()
$606
This Volaris deal was found by Cheapflights users on 6/4. 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 11/1311:58 pm
ORD
- HUX
1 stop14h 31m
Volaris
Sat 11/213:43 pm
HUX
- ORD
1 stop12h 53m
Volaris
Deal found 6/4![Volaris logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Thu 7/238:49 pm
MDW
- PXM
1 stop19h 16m
Multiple Airlines
Thu 7/3010:30 pm
PXM
- MDW
2 stops17h 52m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$649
This Delta deal was found by Cheapflights users on 6/5. 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.
Fri 10/166:00 am
MDW
- OAX
2 stops12h 18m
Delta
Wed 10/216:00 am
OAX
- MDW
2 stops14h 45m
Delta
Deal found 6/5![Delta logo]()
$673
This Volaris deal was found by Cheapflights users on 6/8. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:53 am
ORD
- PXM
1 stop10h 53m
Volaris
Sun 11/81:14 pm
PXM
- ORD
1 stop10h 25m
Volaris
Deal found 6/8![Volaris logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Wed 7/228:23 pm
MDW
- PXM
1 stop17h 23m
Multiple Airlines
Wed 7/2910:30 pm
PXM
- MDW
2 stops21h 02m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$659
This Delta deal was found by Cheapflights users on 6/6. 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.
Wed 8/126:05 am
MDW
- OAX
2 stops14h 51m
Delta
Wed 8/268:05 am
OAX
- MDW
2 stops13h 31m
Delta
Deal found 6/6![Delta logo]()
$676
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Thu 6/251:40 am
ORD
- OAX
2 stops13h 09m
Volaris
Tue 8/119:45 pm
OAX
- ORD
1 stop13h 24m
Volaris
Deal found 6/4![Volaris logo]()
$470
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:00 am
MDW
- OAX
2 stops9h 30m
Delta
Fri 7/108:00 am
OAX
- MDW
2 stops13h 15m
Delta
Deal found 6/4![Delta logo]()
$694
This Volaris deal was found by Cheapflights users on 6/6. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:23 am
ORD
- HUX
1 stop8h 06m
Volaris
Tue 11/103:43 pm
HUX
- ORD
1 stop12h 53m
Volaris
Deal found 6/6![Volaris logo]()
$477
This Volaris deal was found by Cheapflights users on 6/6. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:23 am
ORD
- HUX
1 stop8h 06m
Volaris
Tue 11/173:43 pm
HUX
- ORD
1 stop12h 53m
Volaris
Deal found 6/6![Volaris logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/48:49 pm
MDW
- OAX
1 stop12h 44m
Multiple Airlines
Sat 8/88:56 am
OAX
- MDW
2 stops12h 07m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$825
Last-minute flights from Chicago to OaxacaDiscover last-minute flight deals from Chicago to Oaxaca. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oaxaca. Data last updated June 9, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 6/8. 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 6/131:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Tue 6/167:34 pm
OAX
- ORD
1 stop9h 18m
Volaris
Deal found 6/8![Volaris logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Thu 6/251:40 am
ORD
- PXM
1 stop12h 46m
Multiple Airlines
Fri 7/311:30 am
PXM
- ORD
2 stops12h 25m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$420
This CheapOair deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/301:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Mon 7/62:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/9![Volaris logo]()
$343
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Tue 6/301:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Sun 7/52:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/7![Volaris logo]()
$358
This Gotogate deal was found by Cheapflights users on 6/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:40 am
ORD
- OAX
1 stop7h 33m
Multiple Airlines
Wed 7/88:56 am
OAX
- ORD
1 stop29h 13m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$362
This CheapOair deal was found by Cheapflights users on 6/4. 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.
Thu 7/21:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Fri 7/102:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/4![Volaris logo]()
$360
This CheapOair deal was found by Cheapflights users on 6/8. 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.
Thu 7/21:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Wed 7/82:29 pm
OAX
- ORD
1 stop9h 26m
Volaris
Deal found 6/8![Volaris logo]()
$363
This CheapOair deal was found by Cheapflights users on 6/7. 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 7/36:21 am
ORD
- OAX
1 stop12h 56m
Volaris
Thu 7/92:29 pm
OAX
- ORD
1 stop13h 12m
Volaris
Deal found 6/7![Volaris logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Fri 7/32:53 am
ORD
- PXM
1 stop13h 12m
Multiple Airlines
Sat 7/118:30 am
PXM
- ORD
2 stops15h 25m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$427
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Sat 7/41:49 pm
ORD
- OAX
2 stops27h 46m
Multiple Airlines
Wed 7/82:29 pm
OAX
- ORD
1 stop9h 26m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Mon 7/61:49 pm
ORD
- PXM
1 stop23h 57m
Multiple Airlines
Wed 7/88:30 am
PXM
- ORD
2 stops15h 25m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$410
This CheapOair deal was found by Cheapflights users on 6/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Thu 8/202:29 pm
OAX
- ORD
1 stop13h 12m
Volaris
Deal found 6/6![Volaris logo]()
$355
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 9, 2026.
Search for one-way flight options from Chicago to Oaxaca. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This CheapOair deal was found by Cheapflights users on 6/4. 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.
Wed 9/21:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Deal found 6/4![Volaris logo]()
$138
This Mytrip deal was found by Cheapflights users on 6/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:35 am
ORD
- HUX
1 stop8h 20m
Volaris
Deal found 6/8![Volaris logo]()
$138
This CheapOair deal was found by Cheapflights users on 6/8. 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.
Tue 7/141:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Deal found 6/8![Volaris logo]()
$142
This Viva deal was found by Cheapflights users on 6/7. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:40 pm
ORD
- PXM
1 stop18h 27m
Viva
Deal found 6/7![Viva logo]()
$147
This CheapOair deal was found by Cheapflights users on 6/8. 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.
Tue 8/181:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Deal found 6/8![Volaris logo]()
$150
This CheapOair deal was found by Cheapflights users on 6/6. 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 CheapOair 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 6/6![Volaris logo]()
$151
This CheapOair deal was found by Cheapflights users on 6/5. 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 8/161:40 am
ORD
- OAX
1 stop7h 33m
Volaris
Deal found 6/5![Volaris logo]()
$155
This eDestinos deal was found by Cheapflights users on 6/6. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/261:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Deal found 6/6![Volaris logo]()
$158
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Sat 8/81:49 pm
ORD
- OAX
1 stop8h 20m
Volaris
Deal found 6/7![Volaris logo]()
$169
This Kissandfly.com deal was found by Cheapflights users on 6/5. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/171:40 am
ORD
- PXM
1 stop12h 46m
Volaris
Deal found 6/5![Volaris logo]()
$178
This Viva deal was found by Cheapflights users on 6/7. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:05 am
ORD
- PXM
1 stop12h 08m
Viva
Deal found 6/7![Viva logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 9/142:53 am
ORD
- OAX
2 stops34h 11m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$183
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 June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (CheapOair) |
One-way from | $138 (CheapOair) |
Popular in | December |
Cheapest in | April |
Average price | $527 |
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 9, 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
ChicagoPuerto Escondido
ORD - PXM
ORDPXM
Chicago O'Hare Intl
Sun 10/4
12:30 pm-3:04 pm
1 stop27h 34m
Puerto Escondido
Tue 10/20
10:32 pm-11:00 am
1 stop11h 28m
$336
ChicagoPuerto Escondido
ORD - PXM
ORDPXM
Chicago O'Hare Intl
Thu 9/24
1:30 am-9:38 pm
1 stop21h 08m
Puerto Escondido
Wed 9/30
10:32 pm-11:00 am
1 stop11h 28m
$369
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Thu 10/15
1:30 am-3:07 pm
1 stop14h 37m
Oaxaca Xoxocotlan
Wed 10/21
3:37 pm-11:45 pm
1 stop7h 08m
$389
ChicagoSanta Maria Huatulco
ORD - HUX
ORDHUX
Chicago O'Hare Intl
Fri 9/18
1:40 am-2:55 pm
1 stop14h 15m
Santa Maria Huatulco
Sat 9/26
3:40 pm-5:52 am
1 stop13h 12m
$395
ChicagoSanta Maria Huatulco
ORD - HUX
ORDHUX
Chicago O'Hare Intl
Sat 9/5
7:35 am-3:12 pm
1 stop8h 37m
Santa Maria Huatulco
Tue 9/8
3:53 pm-11:00 am
1 stop18h 07m
$404
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
2:44 pm-11:39 pm
1 stop8h 55m
$405
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Wed 7/1
2:53 am-1:49 pm
2 stops35h 56m
Oaxaca Xoxocotlan
Fri 7/10
2:29 pm-12:55 am
1 stop9h 26m
$410
ChicagoSanta Maria Huatulco
ORD - HUX
ORDHUX
Chicago O'Hare Intl
Sat 8/15
1:40 am-2:55 pm
1 stop14h 15m
Santa Maria Huatulco
Wed 8/19
3:40 pm-11:47 pm
1 stop7h 07m
$420
ChicagoSanta Maria Huatulco
ORD - HUX
ORDHUX
Chicago O'Hare Intl
Fri 10/9
1:35 am-3:11 pm
1 stop14h 36m
Santa Maria Huatulco
Sat 10/17
3:47 pm-11:00 am
1 stop18h 13m
$421
ChicagoOaxaca
ORD - OAX
ORDOAX
Chicago O'Hare Intl
Wed 11/18
11:58 pm-8:19 am
1 stop8h 21m
Oaxaca Xoxocotlan
Mon 11/23
2:44 pm-11:39 pm
1 stop8h 55m
$426
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 $119). Flying from Chicago to State of Oaxaca in October is currently the most expensive (average of $273). 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?
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 47 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 9, 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.
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Overall
7.9
Food
7.2
Crew
8.5
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.
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Alternative routes for Chicago to Oaxaca
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Complete your trip
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Find flights from Chicago to Oaxaca, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Oaxaca flights
Browse other Chicago and Oaxaca flight options. Last updated on June 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Oaxaca flights
Consider these flights traveling from Chicago to Oaxaca.
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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$466 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$266 | Average$412 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$472 | Average$581 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$520 | Average$809 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$524 | Average$1,060 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$543 | Average$703 | FlexibilityNo cancel fee | On-time71% |