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Oaxaca

$108+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Oaxaca Xoxocotlan are usually found in September or August, booked 67 days in advance, depart on a Monday or Tuesday and return on a Tuesday

Cheap 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 September 15, 2025.

Round-trip from

$313
(CheapOair)

One-way from

$108
(Booking.com)

Popular in

December

Cheapest in

September

Average price

$375
From Chicago (CHI) to Oaxaca Xoxocotlan
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One-way flight from Chicago (CHI) to Oaxaca Xoxocotlan
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Highest demand for flights based on searches. 12% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Oaxaca

Cheapest flights from Chicago to Oaxaca
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 15, 2025.

This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/154:40 pmORD - OAX
1 stop23h 50mViva
Wed 11/191:10 pmOAX - ORD
1 stop10h 20mViva
Deal found 9/13$290
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/31:40 amORD - OAX
1 stop7h 28mVolaris
Wed 10/224:36 pmOAX - ORD
1 stop6h 39mVolaris
Deal found 9/13$311
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/96:34 pmORD - OAX
1 stop20h 12mMultiple Airlines
Wed 10/152:25 pmOAX - ORD
1 stop8h 10mMultiple Airlines
Deal found 9/14$320
This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/1112:25 pmORD - OAX
1 stop26h 20mViva
Fri 10/177:20 pmOAX - ORD
1 stop27h 15mViva
Deal found 9/13$326
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 9/291:40 amORD - OAX
1 stop12h 13mVolaris
Sat 10/49:19 amOAX - ORD
1 stop13h 13mVolaris
Deal found 9/15$327
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/154:40 pmORD - OAX
1 stop23h 50mViva
Fri 11/2110:25 pmOAX - ORD
1 stop16h 45mViva
Deal found 9/14$328
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/191:55 amORD - OAX
1 stop9h 43mVolaris
Fri 10/249:19 amOAX - ORD
1 stop13h 13mVolaris
Deal found 9/13$332
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/101:40 amORD - OAX
1 stop11h 28mVolaris
Sat 10/189:19 amOAX - ORD
1 stop13h 13mVolaris
Deal found 9/13$340
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/105:05 amORD - OAX
2 stops11h 07mMultiple Airlines
Fri 11/2110:25 pmOAX - ORD
1 stop16h 45mMultiple Airlines
Deal found 9/14$342
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/126:00 amMDW - OAX
2 stops10h 59mDelta
Thu 11/2010:25 amOAX - MDW
2 stops13h 07mDelta
Deal found 9/14$504
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 9/276:00 amMDW - OAX
2 stops13h 16mDelta
Tue 9/308:10 amOAX - MDW
2 stops12h 26mDelta
Deal found 9/13$505
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/156:00 amMDW - OAX
2 stops12h 47mDelta
Wed 11/1911:09 amOAX - MDW
2 stops12h 23mDelta
Deal found 9/13$508

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 September 15, 2025.
Use the filters below to find and compare flights from Chicago to Oaxaca that are best for you.

Fly from

Chicago

Fly to

Oaxaca

Route

Depart

Return

Price

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 10/10

1:40 am-12:20 pm

1 stop11h 40m

Oaxaca Xoxocotlan

Fri 10/17

7:20 pm-11:35 pm

1 stop27h 15m

$370

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 10/12

12:25 pm-8:50 am

1 stop21h 25m

Oaxaca Xoxocotlan

Fri 10/17

7:20 pm-11:35 pm

1 stop27h 15m

$387

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 9/30

5:30 am-6:16 pm

2 stops13h 46m

Oaxaca Xoxocotlan

Sat 10/4

8:15 am-11:55 pm

1 stop14h 40m

$432

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 11/12

12:33 am-2:58 pm

1 stop14h 25m

Oaxaca Xoxocotlan

Fri 11/21

6:00 am-6:47 pm

2 stops12h 47m

$444

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 10/12

5:20 am-2:45 pm

2 stops10h 25m

Oaxaca Xoxocotlan

Sat 10/18

6:15 am-1:55 pm

1 stop6h 40m

$452

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 11/13

10:05 pm-4:12 pm

2 stops18h 07m

Oaxaca Xoxocotlan

Tue 11/18

1:10 pm-11:30 pm

1 stop10h 20m

$456

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 10/11

6:10 pm-2:45 pm

2 stops21h 35m

Oaxaca Xoxocotlan

Fri 10/17

8:15 am-9:24 pm

2 stops12h 09m

$462

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 10/12

5:20 am-6:16 pm

2 stops13h 56m

Oaxaca Xoxocotlan

Fri 10/17

6:05 am-9:24 pm

2 stops14h 19m

$462

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 2/26

7:10 am-7:03 pm

2 stops11h 53m

Oaxaca Xoxocotlan

Mon 3/2

3:38 pm-11:18 pm

1 stop7h 40m

$480

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 11/12

10:35 am-10:46 pm

2 stops12h 11m

Oaxaca Xoxocotlan

Thu 11/20

6:00 am-6:47 pm

2 stops12h 47m

$504

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 36 results
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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.
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

How far ahead should I book a flight from Chicago to Oaxaca?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Oaxaca. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Oaxaca, you should look to book at least 67 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Oaxaca?

Currently, August is the cheapest month in which you can book a flight from Chicago to Oaxaca (average of $510). Flying from Chicago to Oaxaca in December is currently the most expensive (average of $803). 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.

What is the cheapest time of day to fly from CHI to OAX?

Find hourly flight availability from Chicago to Oaxaca. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 24% on flights from Chicago to Oaxaca by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Chicago to Oaxaca?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Oaxaca. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Oaxaca flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago to Oaxaca?

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 15, 2025.
Read reviews from past customers who have flown Delta, Aeromexico, and American 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.
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Aeromexico
7.5
Good
1,697 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Viva
7.0
Good
787 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Volaris
6.6
Okay
1,154 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What airport do you fly into for flights to Oaxaca from Chicago?

    Oaxaca Xoxocotlan (OAX) is the airport you will fly into if you book a flight from Chicago to Oaxaca. You should not have trouble finding flights to Xoxocotlan from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 6 airlines have flights to the Oaxaca airport from Chicago. It is only a 4.4 mi journey from Xoxocotlan (OAX) to Oaxaca’s city center.

  • How long is the flight from Chicago to Oaxaca?

    Viva and Delta can get you from Chicago to Oaxaca in just under 13h 46m. Your travel time can differ by up to 7h 39m. There are 1802 mi between Chicago and Oaxaca. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Oaxaca round-trip?

    Flying on Viva is currently your cheapest option to Oaxaca, with prices starting at $239. Additional round-trip tickets that might be worth considering are offered by Volaris and Aeromexico, with the lowest prices starting at $272 and $449, respectively. Viva is 56% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Chicago to Oaxaca that include hotel bookings?

    Yes. In addition to deals on Chicago to Oaxaca flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Oaxaca?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Oaxaca.

  • Can I find deals for business class flights from Chicago to Oaxaca?

    Yes. Cheapflights offers flight deals from Chicago to Oaxaca by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Oaxaca?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Oaxaca (average of $510). Flying from Chicago to Oaxaca in December is currently the most expensive (average of $803). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$239Average$408FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$272Average$413FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$449Average$540FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$465Average$652FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$702FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$551Average$865FlexibilityNo cancel feeOn-time69%

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