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Oaxaca

$103+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Chicago to Oaxaca with Cheapflights

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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

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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amORD - OAX
1 stop10h 12mMultiple Airlines
Fri 12/510:20 pmOAX - ORD
1 stop16h 40mMultiple Airlines
Deal found 10/28$312
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amORD - OAX
1 stop10h 12mMultiple Airlines
Sat 12/63:20 pmOAX - ORD
1 stop23h 40mMultiple Airlines
Deal found 10/28$314
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/110:32 amORD - OAX
1 stop29h 40mMultiple Airlines
Sat 12/63:20 pmOAX - ORD
1 stop23h 40mMultiple Airlines
Deal found 10/29$323
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:53 pmORD - OAX
2 stops43h 52mMultiple Airlines
Fri 12/1210:20 pmOAX - ORD
1 stop16h 40mMultiple Airlines
Deal found 10/28$329
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:00 amORD - OAX
1 stop10h 12mMultiple Airlines
Mon 12/85:15 pmOAX - ORD
1 stop29h 00mMultiple Airlines
Deal found 10/28$334
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amORD - OAX
1 stop10h 12mMultiple Airlines
Wed 12/35:15 pmOAX - ORD
1 stop29h 00mMultiple Airlines
Deal found 10/28$337
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amORD - OAX
1 stop10h 12mMultiple Airlines
Mon 12/110:20 pmOAX - ORD
2 stops31h 12mMultiple Airlines
Deal found 10/28$344
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:53 pmORD - OAX
2 stops39h 32mMultiple Airlines
Thu 12/115:15 pmOAX - ORD
1 stop16h 50mMultiple Airlines
Deal found 10/28$349
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:58 pmORD - OAX
1 stop12h 27mMultiple Airlines
Wed 11/195:15 pmOAX - ORD
1 stop29h 00mMultiple Airlines
Deal found 10/28$353
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amORD - OAX
1 stop10h 12mMultiple Airlines
Thu 12/41:10 pmOAX - ORD
1 stop10h 20mMultiple Airlines
Deal found 10/28$354
This Delta deal was found by Cheapflights users on 10/30. 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 11/76:00 amMDW - OAX
2 stops12h 47mDelta
Wed 11/1211:09 amOAX - MDW
2 stops12h 31mDelta
Deal found 10/30$584
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:24 pmMDW - OAX
2 stops24h 18mFrontier
Sun 12/219:40 amOAX - MDW
2 stops36h 18mFrontier
Deal found 10/30$713

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$295
(Booking.com)

One-way from

$103
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$601
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. 13% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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

Wed 4/22

12:58 am-8:08 am

1 stop8h 10m

Oaxaca Xoxocotlan

Wed 4/29

3:30 pm-12:45 am

1 stop8h 15m

$261

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 1/18

11:58 pm-7:19 am

1 stop7h 21m

Oaxaca Xoxocotlan

Mon 2/9

4:55 pm-11:50 pm

1 stop6h 55m

$270

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 4/22

12:58 am-8:08 am

1 stop8h 10m

Oaxaca Xoxocotlan

Sun 4/26

8:52 am-11:07 pm

1 stop13h 15m

$279

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 1/17

1:00 am-12:25 pm

1 stop11h 25m

Oaxaca Xoxocotlan

Mon 2/9

4:55 pm-11:50 pm

1 stop6h 55m

$291

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 1/15

11:59 pm-8:35 am

1 stop8h 36m

Oaxaca Xoxocotlan

Tue 1/20

1:10 pm-11:25 pm

1 stop10h 15m

$300

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 1/20

1:00 am-12:25 pm

1 stop11h 25m

Oaxaca Xoxocotlan

Tue 2/10

1:10 pm-11:25 pm

1 stop10h 15m

$301

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 4/21

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sun 4/26

3:30 pm-12:45 am

1 stop8h 15m

$327

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 1/21

6:23 am-5:39 am

2 stops23h 16m

Oaxaca Xoxocotlan

Tue 2/10

1:10 pm-11:25 pm

1 stop10h 15m

$341

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 2/7

1:00 am-12:25 pm

1 stop11h 25m

Oaxaca Xoxocotlan

Sun 2/15

3:25 pm-11:50 pm

1 stop8h 25m

$348

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 4/21

2:19 am-4:35 am

3 stops27h 16m

Oaxaca Xoxocotlan

Sun 4/26

7:34 pm-5:57 am

1 stop9h 23m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 40 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 October.
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 October 24, 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 $202). Flying from Chicago to Oaxaca in December is currently the most expensive (average of $402). 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 October 30, 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.

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 October 30, 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
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,993 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,030 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Viva
7.0
Good
790 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Volaris
6.7
Okay
1,151 reviews
Delta
7.9
Good
7,993 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 and Viva can get you from Chicago to Oaxaca in just under 8h 10m. Your travel time can differ by up to 3h 15m. 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 $151. Volaris flights start at $251 while deals on Delta start at $288 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 $202). Flying from Chicago to Oaxaca in December is currently the most expensive (average of $402). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$247Average$387FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$271Average$406FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$453Average$800FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$455Average$540FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$465Average$660FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$531Average$695FlexibilityNo cancel feeOn-time71%

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