$115+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Sep 7 — Sep 141
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 August 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 August 8, 2026.
This Viva deal was found by Cheapflights users on 8/3. 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 11/512:35 am -
1 stop17h 28m
Sun 11/152:20 pm -
1 stop8h 35m
Deal found 8/3![Viva logo]()
$288
This Viva deal was found by Cheapflights users on 8/7. 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.
Fri 10/22:40 pm -
1 stop25h 29m
Fri 10/93:39 pm -
1 stop20h 31m
Deal found 8/7![Viva logo]()
$289
This Mytrip deal was found by Cheapflights users on 8/3. 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 -
1 stop7h 33m
Wed 9/2312:53 pm -
1 stop21h 07m
Deal found 8/3![Multiple Airlines logo]()
$307
This Mytrip deal was found by Cheapflights users on 8/4. 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 9/151:30 am -
1 stop11h 34m
Wed 9/3012:53 pm -
1 stop21h 07m
Deal found 8/4![Viva logo]()
$310
This Viva deal was found by Cheapflights users on 8/3. 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.
Sun 9/274:22 pm -
1 stop23h 47m
Wed 9/3012:53 pm -
1 stop21h 07m
Deal found 8/3![Viva logo]()
$312
This Viva deal was found by Cheapflights users on 8/6. 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.
Mon 11/3012:35 am -
1 stop13h 03m
Wed 12/92:20 pm -
1 stop8h 40m
Deal found 8/6![Viva logo]()
$313
This CheapOair deal was found by Cheapflights users on 8/7. 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 9/261:40 am -
1 stop7h 33m
Wed 9/307:34 pm -
1 stop9h 18m
Deal found 8/7![Volaris logo]()
$314
This Mytrip deal was found by Cheapflights users on 8/4. 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.
Mon 8/311:30 am -
1 stop11h 34m
Tue 9/812:53 pm -
1 stop21h 07m
Deal found 8/4![Viva logo]()
$315
This CheapOair deal was found by Cheapflights users on 8/4. 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.
Sat 9/261:40 am -
1 stop7h 33m
Thu 10/17:34 pm -
1 stop9h 18m
Deal found 8/4![Volaris logo]()
$318
This CheapOair deal was found by Cheapflights users on 8/5. 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.
Wed 9/91:40 am -
1 stop7h 33m
Mon 9/147:34 pm -
1 stop9h 18m
Deal found 8/5![Volaris logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Wed 9/28:23 pm -
1 stop22h 54m
Wed 9/93:39 pm -
2 stops43h 20m
Deal found 8/3![Multiple Airlines logo]()
$569
This Kiwi.com deal was found by Cheapflights users on 8/4. 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.
Mon 8/108:23 pm -
1 stop25h 46m
Tue 8/259:45 pm -
1 stop20h 19m
Deal found 8/4![Volaris logo]()
$570
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 August 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 August 8, 2026.
This Viva deal was found by Cheapflights users on 8/7. 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.
Fri 10/22:40 pm -
1 stop25h 29m
Fri 10/93:39 pm -
1 stop20h 31m
Deal found 8/7![Viva logo]()
$289
This Delta deal was found by Cheapflights users on 8/4. 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 9/274:30 pm -
1 stop7h 03m
Wed 9/3012:01 pm -
1 stop10h 58m
Deal found 8/4![Delta logo]()
$611
This Viva deal was found by Cheapflights users on 8/6. 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 9/274:22 pm -
1 stop23h 47m
Wed 9/3012:53 pm -
1 stop21h 07m
Deal found 8/6![Viva logo]()
$315
This Viva deal was found by Cheapflights users on 8/3. 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 10/214:20 pm -
1 stop23h 49m
Sun 10/2512:53 pm -
1 stop21h 07m
Deal found 8/3![Viva logo]()
$373
This Viva deal was found by Cheapflights users on 8/7. 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 10/312:40 pm -
1 stop23h 58m
Sat 11/712:53 pm -
1 stop10h 42m
Deal found 8/7![Viva logo]()
$402
This Viva deal was found by Cheapflights users on 8/5. 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.
Sat 11/281:05 am -
1 stop10h 59m
Wed 12/302:20 pm -
1 stop8h 40m
Deal found 8/5![Viva logo]()
$408
This Delta deal was found by Cheapflights users on 8/3. 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 9/26:05 am -
2 stops17h 28m
Wed 9/96:05 am -
2 stops15h 39m
Deal found 8/3![Delta logo]()
$618
This Delta deal was found by Cheapflights users on 8/4. 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 11/276:45 am -
2 stops12h 23m
Thu 12/39:37 am -
2 stops14h 22m
Deal found 8/4![Delta logo]()
$687
This Delta deal was found by Cheapflights users on 8/6. 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 9/110:33 am -
2 stops13h 00m
Tue 9/83:12 pm -
1 stop7h 47m
Deal found 8/6![Delta logo]()
$698
This Viva deal was found by Cheapflights users on 8/7. 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 10/311:05 am -
1 stop11h 59m
Sun 11/12:20 pm -
1 stop8h 35m
Deal found 8/7![Viva logo]()
$595
This Delta deal was found by Cheapflights users on 8/7. 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.
Sat 8/293:25 pm -
2 stops16h 59m
Wed 9/28:08 am -
2 stops14h 49m
Deal found 8/7![Delta logo]()
$728
This Delta deal was found by Cheapflights users on 8/4. 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 11/276:00 am -
2 stops13h 08m
Thu 12/39:37 am -
2 stops13h 19m
Deal found 8/4![Delta logo]()
$850
This Delta deal was found by Cheapflights users on 8/4. 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.
Tue 9/16:05 am -
2 stops12h 40m
Tue 9/88:08 am -
2 stops13h 36m
Deal found 8/4![Delta logo]()
$861
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 12/66:00 am -
2 stops13h 08m
Sat 12/126:01 am -
2 stops9h 18m
Deal found 8/7![Delta logo]()
$880
This Delta deal was found by Cheapflights users on 8/6. 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 9/264:30 pm -
2 stops16h 01m
Fri 10/98:10 am -
2 stops13h 23m
Deal found 8/6![Delta logo]()
$880
This Delta deal was found by Cheapflights users on 8/5. 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 8/3010:54 am -
2 stops12h 45m
Wed 9/28:08 am -
2 stops13h 28m
Deal found 8/5![Delta logo]()
$921
This Delta deal was found by Cheapflights users on 8/6. 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 12/16:00 am -
2 stops13h 08m
Wed 12/98:06 am -
2 stops14h 50m
Deal found 8/6![Delta logo]()
$985
This Delta deal was found by Cheapflights users on 8/7. 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.
Mon 10/56:05 am -
2 stops12h 10m
Mon 10/268:06 am -
2 stops13h 27m
Deal found 8/7![Delta logo]()
$985
Last-minute flights from Chicago to OaxacaDiscover last-minute flight deals from Chicago to Oaxaca. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oaxaca. Data last updated August 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/4. 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.
Mon 8/108:23 pm -
1 stop25h 46m
Tue 8/259:45 pm -
1 stop20h 19m
Deal found 8/4![Volaris logo]()
$570
This CheapOair deal was found by Cheapflights users on 8/3. 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.
Sun 8/306:21 am -
1 stop12h 56m
Wed 9/27:34 pm -
1 stop9h 18m
Deal found 8/3![Volaris logo]()
$327
This Mytrip deal was found by Cheapflights users on 8/4. 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.
Mon 8/311:30 am -
1 stop11h 34m
Tue 9/812:53 pm -
1 stop21h 07m
Deal found 8/4![Viva logo]()
$315
This CheapOair deal was found by Cheapflights users on 8/6. 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 8/311:40 am -
1 stop7h 33m
Tue 9/87:34 pm -
1 stop9h 18m
Deal found 8/6![Volaris logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Wed 9/28:23 pm -
1 stop22h 54m
Wed 9/93:39 pm -
2 stops43h 20m
Deal found 8/3![Multiple Airlines logo]()
$569
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 9/51:40 am -
1 stop7h 33m
Tue 9/87:34 pm -
1 stop9h 18m
Deal found 8/6![Volaris logo]()
$323
This CheapOair deal was found by Cheapflights users on 8/5. 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.
Wed 9/91:40 am -
1 stop7h 33m
Mon 9/147:34 pm -
1 stop9h 18m
Deal found 8/5![Volaris logo]()
$319
This Mytrip deal was found by Cheapflights users on 8/3. 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 -
1 stop7h 33m
Wed 9/2312:53 pm -
1 stop21h 07m
Deal found 8/3![Multiple Airlines logo]()
$307
This Mytrip deal was found by Cheapflights users on 8/4. 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 9/151:30 am -
1 stop11h 34m
Wed 9/3012:53 pm -
1 stop21h 07m
Deal found 8/4![Viva logo]()
$310
This CheapOair deal was found by Cheapflights users on 8/7. 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 9/261:40 am -
1 stop7h 33m
Wed 9/307:34 pm -
1 stop9h 18m
Deal found 8/7![Volaris logo]()
$314
This CheapOair deal was found by Cheapflights users on 8/4. 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.
Sat 9/261:40 am -
1 stop7h 33m
Thu 10/17:34 pm -
1 stop9h 18m
Deal found 8/4![Volaris logo]()
$318
This Viva deal was found by Cheapflights users on 8/3. 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.
Sun 9/274:22 pm -
1 stop23h 47m
Wed 9/3012:53 pm -
1 stop21h 07m
Deal found 8/3![Viva logo]()
$312
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 August 8, 2026.
Search for one-way flight options from Chicago to Oaxaca. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This Booking.com deal was found by Cheapflights users on 8/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:40 pm -
1 stop25h 29m
Deal found 8/5![Viva logo]()
$115
This Booking.com deal was found by Cheapflights users on 8/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/712:35 am -
1 stop13h 03m
Deal found 8/5![Viva logo]()
$118
This Viva deal was found by Cheapflights users on 8/6. 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.
Thu 11/512:35 am -
1 stop17h 28m
Deal found 8/6![Viva logo]()
$124
This Trip.com deal was found by Cheapflights users on 8/3. 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.
Mon 9/141:40 am -
1 stop7h 33m
Deal found 8/3![Volaris logo]()
$136
This Viva deal was found by Cheapflights users on 8/5. 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 8/171:30 am -
1 stop14h 30m
Deal found 8/5![Viva logo]()
$138
This CheapOair deal was found by Cheapflights users on 8/6. 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 10/51:40 am -
1 stop7h 33m
Deal found 8/6![Volaris logo]()
$144
This Booking.com deal was found by Cheapflights users on 8/4. 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.
Sun 12/2712:35 am -
1 stop17h 26m
Deal found 8/4![Viva logo]()
$152
This CheapOair deal was found by Cheapflights users on 8/3. 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.
Thu 9/171:40 am -
1 stop7h 33m
Deal found 8/3![Volaris logo]()
$154
This Booking.com deal was found by Cheapflights users on 8/3. 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.
Wed 10/214:20 pm -
1 stop23h 49m
Deal found 8/3![Viva logo]()
$159
This Booking.com deal was found by Cheapflights users on 8/4. 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.
Fri 9/181:30 am -
1 stop11h 34m
Deal found 8/4![Viva logo]()
$165
This Booking.com deal was found by Cheapflights users on 8/4. 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.
Sat 12/2612:35 am -
1 stop13h 03m
Deal found 8/4![Viva logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 9/197:30 pm -
2 stops20h 39m
Deal found 8/4![Multiple Airlines logo]()
$238
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 August 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $288 (Viva) |
One-way from | $115 (Booking.com) |
Popular in | December |
Cheapest in | April |
Average price | $426 |
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 August 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
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Fri 10/2
2:40 pm-3:09 pm
1 stop25h 29m
Oaxaca Xoxocotlan
Fri 10/9
3:39 pm-1:10 pm
1 stop20h 31m
$289
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Sun 9/27
4:22 pm-3:09 pm
1 stop23h 47m
Oaxaca Xoxocotlan
Wed 9/30
12:53 pm-11:00 am
1 stop21h 07m
$315
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Wed 10/21
4:20 pm-3:09 pm
1 stop23h 49m
Oaxaca Xoxocotlan
Sun 10/25
12:53 pm-11:00 am
1 stop21h 07m
$373
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Sat 10/31
2:40 pm-1:38 pm
1 stop23h 58m
Oaxaca Xoxocotlan
Sat 11/7
12:53 pm-11:35 pm
1 stop10h 42m
$402
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Sat 11/28
1:05 am-12:04 pm
1 stop10h 59m
Oaxaca Xoxocotlan
Wed 12/30
2:20 pm-11:00 pm
1 stop8h 40m
$408
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Sat 10/31
1:05 am-12:04 pm
1 stop11h 59m
Oaxaca Xoxocotlan
Sun 11/1
2:20 pm-10:55 pm
1 stop8h 35m
$595
Quickest round-trip
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Sun 9/27
4:30 pm-10:33 pm
1 stop7h 03m
Oaxaca Xoxocotlan
Wed 9/30
12:01 pm-11:59 pm
1 stop10h 58m
$611
ChicagoOaxaca
MDW Chicago Midway - OAX Oaxaca Xoxocotlan
MDWOAX
Chicago Midway
Wed 9/2
6:05 am-10:33 pm
2 stops17h 28m
Oaxaca Xoxocotlan
Wed 9/9
6:05 am-10:44 pm
2 stops15h 39m
$618
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Fri 11/27
6:45 am-7:08 pm
2 stops12h 23m
Oaxaca Xoxocotlan
Thu 12/3
9:37 am-11:59 pm
2 stops14h 22m
$687
ChicagoOaxaca
ORD Chicago O'Hare Intl - OAX Oaxaca Xoxocotlan
ORDOAX
Chicago O'Hare Intl
Tue 9/1
10:33 am-10:33 pm
2 stops13h 00m
Oaxaca Xoxocotlan
Tue 9/8
3:12 pm-11:59 pm
1 stop7h 47m
$698
Showing 1-10 of 42 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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Oaxaca flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Oaxaca flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Oaxaca flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Oaxaca flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Oaxaca flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Oaxaca
Have a flexible travel schedule? Discover the best time to fly to Oaxaca from Chicago with our price prediction graph.
CHI-OAX
ORD-OAX
MDW-OAX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Oaxaca
CHI-OAX
ORD-OAX
MDW-OAX
What is the cheapest month to book a flight from Chicago to Oaxaca?
Currently, April is the cheapest month in which you can book a flight from Chicago to Oaxaca (average of $344). Flying from Chicago to Oaxaca in December is currently the most expensive (average of $722). 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?
Airfare is below average for this route at the moment.
Chicago to Oaxaca flights typically cost between $384 and $519 in November.The cheapest round-trip price found within the last 5 days was $288 on Viva (Nov 5-Nov 15).
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 80% 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 $457.
What’s the fastest layover option from Chicago to Oaxaca?
Shortest average travel time for 1-stop one-way flights from Chicago to Oaxaca, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Mexico City (MEX) have the shortest average one-way travel time for 1-stop routes: 7h 23m.
Which airport typically offers the quickest layover for flights from Chicago to Oaxaca?
Average layover duration for 1-stop one-way flights from Chicago to Oaxaca, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Mexico City (MEX) offer the fastest connection on this route, with an average layover time of 1h 33m.
How far ahead should I book a flight from Chicago to Oaxaca?
To ensure you get the cheapest price possible for a flight from Chicago to Oaxaca, you should look to book at least 49 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Oaxaca
Get insights into the airlines that provide service to Oaxaca. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oaxaca. Reviews last updated August 8, 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.
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Comfort
7.8
Food
7.2
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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Complete your trip
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Search flights from Chicago to Oaxaca by cabin class
Find flights from Chicago to Oaxaca, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 August 8, 2026.
Chicago and Oaxaca flights
Browse other Chicago and Oaxaca flight options. Last updated on August 8, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 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 2,558,603 searches. Data last updated August 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$261 | Average$389 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$288 | Average$435 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$453 | Average$750 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$475 | Average$686 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$475 | Average$601 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$546 | Average$712 | FlexibilityNo cancel fee | On-time71% |