HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oaxaca

$111+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 January 29, 2026.

This Gotogate deal was found by Cheapflights users on 1/26. 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.
Mon 5/111:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Sun 5/177:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 1/26$271
This Gotogate deal was found by Cheapflights users on 1/28. 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.
Tue 5/121:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Mon 5/187:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 1/28$272
This Mytrip deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Sun 5/177:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 1/28$273
This Gotogate deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Sat 5/237:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 1/28$280
This Trip.com deal was found by Cheapflights users on 1/26. 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.
Tue 5/121:40 am
ORD
-
OAX
1 stop7h 33m
Multiple Airlines
Sun 5/173:30 pm
OAX
-
ORD
1 stop8h 15m
Multiple Airlines
Deal found 1/26$289
This Gotogate deal was found by Cheapflights users on 1/28. 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 3/111:58 pm
ORD
-
OAX
1 stop7h 21m
Volaris
Fri 3/68:56 am
OAX
-
ORD
1 stop13h 10m
Volaris
Deal found 1/28$294
This Mytrip deal was found by Cheapflights users on 1/26. 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 3/1411:59 pm
ORD
-
OAX
1 stop11h 36m
Volaris
Fri 3/208:56 am
OAX
-
ORD
1 stop13h 10m
Volaris
Deal found 1/26$307
This Booking.com deal was found by Cheapflights users on 1/27. 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 4/53:30 am
ORD
-
OAX
1 stop18h 05m
Viva
Mon 4/133:30 pm
OAX
-
ORD
1 stop8h 15m
Viva
Deal found 1/27$309
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/171:40 am
ORD
-
OAX
1 stop7h 33m
Multiple Airlines
Sun 4/263:30 pm
OAX
-
ORD
1 stop8h 15m
Multiple Airlines
Deal found 1/27$315
This Expedia deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/31:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Fri 5/87:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 1/27$318
This Travelocity deal was found by Cheapflights users on 1/27. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:19 am
ORD
-
OAX
1 stop7h 19m
Volaris
Sun 9/207:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 1/27$321
This Delta deal was found by Cheapflights users on 1/27. 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 3/46:00 am
MDW
-
OAX
2 stops13h 00m
Delta
Wed 3/117:56 am
OAX
-
MDW
2 stops13h 35m
Delta
Deal found 1/27$497

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$271
(Gotogate)

One-way from

$111
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$537
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. 20% potential increase in price ($138 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Mon 5/11

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sun 5/17

7:34 pm-5:52 am

1 stop9h 18m

$271

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 5/8

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sun 5/17

7:34 pm-5:52 am

1 stop9h 18m

$273

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 4/5

3:30 am-8:35 pm

1 stop18h 05m

Oaxaca Xoxocotlan

Mon 4/13

3:30 pm-12:45 am

1 stop8h 15m

$309

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 2/19

11:59 pm-8:35 am

1 stop8h 36m

Oaxaca Xoxocotlan

Mon 2/23

8:56 am-10:06 pm

1 stop13h 10m

$348

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 5/13

1:49 pm-8:13 am

2 stops19h 24m

Oaxaca Xoxocotlan

Mon 5/18

7:34 pm-5:52 am

1 stop9h 18m

$374

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 3/29

3:30 am-8:35 pm

1 stop18h 05m

Oaxaca Xoxocotlan

Thu 4/2

3:30 pm-12:45 am

1 stop8h 15m

$378

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 2/18

1:00 am-12:30 pm

1 stop11h 30m

Oaxaca Xoxocotlan

Mon 2/23

5:05 pm-11:50 pm

1 stop6h 45m

$379

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 2/22

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Mon 3/2

4:55 pm-11:45 pm

1 stop6h 50m

$379

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 3/14

11:59 pm-12:20 pm

2 stops13h 21m

Oaxaca Xoxocotlan

Fri 3/20

8:56 am-11:06 pm

1 stop13h 10m

$380

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 2/19

12:59 pm-2:13 pm

2 stops25h 14m

Oaxaca Xoxocotlan

Mon 2/23

5:05 pm-11:50 pm

1 stop6h 45m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 39 results
1
2
3
4

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 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.
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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Oaxaca, you should look to book at least 53 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 $219). 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.

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

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 January 29, 2026.
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
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

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
8,127 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

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
9,215 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

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
11,206 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

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
816 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

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
1,173 reviews
Delta
7.9
Good
8,127 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

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?

    Volaris, Viva, and Delta can get you from Chicago to Oaxaca in just under 7h 33m. Your travel time can differ by up to 10h 32m. 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 $261. Additional round-trip tickets that might be worth considering are offered by Volaris and United Airlines, with the lowest prices starting at $272 and $453, respectively. Viva is 52% 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 $140 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 $219). 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

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$261Average$348FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$272Average$400FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$453Average$750FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$455Average$525FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$484Average$740FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$505Average$623FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.