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Oaxaca

$112+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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”

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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

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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:20 amORD - OAX
1 stop12h 53mMultiple Airlines
Tue 12/305:15 pmOAX - ORD
2 stops21h 38mMultiple Airlines
Deal found 12/16$549
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/274:30 pmORD - OAX
1 stop21h 43mMultiple Airlines
Tue 12/305:15 pmOAX - ORD
2 stops21h 38mMultiple Airlines
Deal found 12/16$566
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/1711:43 amORD - OAX
2 stops50h 30mMultiple Airlines
Sat 12/203:20 pmOAX - ORD
1 stop8h 30mMultiple Airlines
Deal found 12/16$568
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:20 amORD - OAX
1 stop12h 53mMultiple Airlines
Mon 12/295:15 pmOAX - ORD
2 stops21h 38mMultiple Airlines
Deal found 12/16$569
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:43 amORD - OAX
1 stop28h 29mMultiple Airlines
Mon 12/2210:20 pmOAX - ORD
1 stop25h 30mMultiple Airlines
Deal found 12/15$578
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/274:30 pmORD - OAX
1 stop21h 43mMultiple Airlines
Wed 12/318:28 pmOAX - ORD
1 stop14h 51mMultiple Airlines
Deal found 12/16$580
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/271:20 amORD - OAX
1 stop12h 53mMultiple Airlines
Tue 12/305:15 pmOAX - ORD
2 stops21h 38mMultiple Airlines
Deal found 12/16$583
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/274:30 pmORD - OAX
1 stop21h 43mMultiple Airlines
Mon 12/295:15 pmOAX - ORD
2 stops21h 38mMultiple Airlines
Deal found 12/16$587
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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.
Tue 12/239:01 pmMDW - OAX
1 stop13h 34mVolaris
Wed 12/318:28 pmOAX - MDW
1 stop13h 12mVolaris
Deal found 12/17$1,092
This Mytrip deal was found by Cheapflights users on 12/17. 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 12/226:54 pmMDW - OAX
1 stop13h 19mVolaris
Mon 12/298:28 pmOAX - MDW
1 stop13h 12mVolaris
Deal found 12/17$1,309
This Aeromexico deal was found by Cheapflights users on 12/16. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amMDW - OAX
2 stops16h 35mAeromexico
Sat 12/206:04 amOAX - MDW
2 stops16h 18mAeromexico
Deal found 12/16$1,512
This Delta deal was found by Cheapflights users on 12/17. 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 12/276:00 amMDW - OAX
2 stops13h 52mDelta
Wed 12/318:13 amOAX - MDW
2 stops14h 09mDelta
Deal found 12/17$1,537

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$238
(Booking.com)

One-way from

$103
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$924
Provider with most accurate pricing for Chicago (CHI)-Oaxaca Xoxocotlan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Oaxaca Xoxocotlan flights.
Search Deals
From Chicago (CHI) to Oaxaca Xoxocotlan
Search Deals
One-way flight from Chicago (CHI) to Oaxaca Xoxocotlan
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($112 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Sun 2/1

7:11 am-4:12 pm

1 stop9h 01m

Oaxaca Xoxocotlan

Fri 2/6

4:55 pm-11:50 pm

1 stop6h 55m

$269

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 1/30

6:05 am-4:12 pm

1 stop10h 07m

Oaxaca Xoxocotlan

Fri 2/6

4:55 pm-11:50 pm

1 stop6h 55m

$295

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 1/17

11:59 pm-10:35 am

1 stop10h 36m

Oaxaca Xoxocotlan

Sat 1/24

1:10 pm-11:25 pm

1 stop10h 15m

$300

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 2/7

1:00 am-12:30 pm

1 stop11h 30m

Oaxaca Xoxocotlan

Tue 2/17

1:10 pm-11:25 pm

1 stop10h 15m

$307

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 3/14

2:05 am-12:20 pm

1 stop11h 15m

Oaxaca Xoxocotlan

Fri 3/20

4:55 pm-12:45 am

1 stop6h 50m

$309

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Mon 2/16

8:42 pm-4:12 pm

2 stops19h 30m

Oaxaca Xoxocotlan

Mon 2/23

4:55 pm-11:50 pm

1 stop6h 55m

$324

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 1/30

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Wed 2/4

4:55 pm-11:50 pm

1 stop6h 55m

$325

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 2/6

1:20 am-12:30 pm

2 stops35h 10m

Oaxaca Xoxocotlan

Sun 2/15

3:25 pm-11:50 pm

1 stop8h 25m

$326

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 2/1

7:11 am-7:19 am

2 stops24h 08m

Oaxaca Xoxocotlan

Thu 2/26

1:10 pm-11:25 pm

1 stop10h 15m

$328

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 2/24

1:00 am-12:30 pm

1 stop11h 30m

Oaxaca Xoxocotlan

Wed 3/4

4:55 pm-11:45 pm

1 stop6h 50m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 41 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Oaxaca flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Oaxaca flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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 December 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, March is the cheapest month in which you can book a flight from Chicago to Oaxaca (average of $192). Flying from Chicago to Oaxaca in August is currently the most expensive (average of $361). 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 December 18, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 21% 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. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

What’s the top layover airport for flights from Chicago to Oaxaca?

Share of 1-stop round-trip flights from Chicago to Oaxaca chosen by Cheapflights users in the past 12 months, using the same layover each way.

Mexico City (MEX) – chosen by Cheapflights users on 83% of 1-stop itineraries from Chicago to Oaxaca on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Oaxaca?

Average round-trip fare for 1-stop flights from Chicago to Oaxaca, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Mexico City (MEX) is the most affordable 1-stop option, with an average round-trip price of $490.

What’s the fastest layover option from Chicago to Oaxaca?

Shortest average travel time for 1-stop one-way flights from Chicago to Oaxaca, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Mexico City (MEX) have the shortest average one-way travel time for 1-stop routes: 7h 23m.

Which airport typically offers the quickest layover for flights from Chicago to Oaxaca?

Average layover duration for 1-stop one-way flights from Chicago to Oaxaca, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Mexico City (MEX) offer the fastest connection on this route, with an average layover time of 1h 33m.

Reviews of airlines servicing Oaxaca

Get insights into the airlines that provide service to Oaxaca. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oaxaca. Reviews last updated December 18, 2025.
Read reviews from past customers who have flown Delta, United Airlines, 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
7.9
Good
8,008 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,093 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,055 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Viva
7.0
Good
797 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Volaris
6.6
Okay
1,155 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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, Volaris, and Aeromexico can get you from Chicago to Oaxaca in just under 8h 36m. Your travel time can differ by up to 6h 29m. 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 $247. Additional round-trip tickets that might be worth considering are offered by Volaris and United Airlines, with the lowest prices starting at $271 and $453, respectively. Viva is 55% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Oaxaca one-way?

    To fly one-way, consider booking your trip with Viva, which is currently one of the cheapest options available, starting at $77. Volaris flights start at $156 while deals on United Airlines start at $178 one-way.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Oaxaca (average of $192). Flying from Chicago to Oaxaca in August is currently the most expensive (average of $361). 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

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$247Average$352FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$271Average$387FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$455Average$530FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$465Average$670FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$520Average$769FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$543Average$688FlexibilityNo cancel feeOn-time71%

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