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Oaxaca

$103+ Cheap flights from Chicago (CHI) to Oaxaca

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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Chicago to Oaxaca

Keep the following information in mind while searching for Chicago to Oaxaca flight deals. Data was last updated August 20, 2025.

Round-trip from

$278
(Mytrip)

One-way from

$103
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$386
From Chicago (CHI) to Oaxaca
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One-way flight from Chicago (CHI) to Oaxaca
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Highest demand for flights based on searches. 13% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 20, 2025.

This Mytrip deal was found by Cheapflights users on 8/19. 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 9/1912:25 pmORD - OAX
1 stop9h 10mViva
Mon 9/299:10 amOAX - ORD
1 stop13h 40mViva
Deal found 8/19$278
This Booking.com deal was found by Cheapflights users on 8/18. 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 9/1412:25 pmORD - OAX
1 stop21h 05mViva
Fri 9/199:15 pmOAX - ORD
1 stop25h 35mViva
Deal found 8/18$282
This Gotogate deal was found by Cheapflights users on 8/19. 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.
Sat 10/1112:25 pmORD - OAX
1 stop26h 30mViva
Sat 10/182:25 pmOAX - ORD
1 stop8h 10mViva
Deal found 8/19$291
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Thu 9/181:55 amORD - OAX
1 stop9h 43mVolaris
Mon 9/294:36 pmOAX - ORD
1 stop6h 39mVolaris
Deal found 8/19$296
This Flightnetwork deal was found by Cheapflights users on 8/18. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/211:55 amORD - OAX
1 stop9h 43mVolaris
Fri 9/264:36 pmOAX - ORD
1 stop6h 39mVolaris
Deal found 8/18$302
This Booking.com deal was found by Cheapflights users on 8/20. 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 10/312:25 pmORD - OAX
1 stop26h 30mViva
Mon 10/139:20 amOAX - ORD
1 stop13h 15mViva
Deal found 8/20$306
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/207:25 amORD - PXM
1 stop15h 05mMultiple Airlines
Sat 10/258:40 amPXM - ORD
1 stop13h 55mMultiple Airlines
Deal found 8/18$309
This Mytrip deal was found by Cheapflights users on 8/18. 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 9/152:00 amORD - PXM
1 stop16h 10mViva
Tue 9/235:40 pmPXM - ORD
1 stop29h 35mViva
Deal found 8/18$313
This Booking.com deal was found by Cheapflights users on 8/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/68:40 pmORD - PXM
1 stop21h 30mViva
Tue 9/910:25 pmPXM - ORD
1 stop11h 30mViva
Deal found 8/17$316
This Kiwi.com deal was found by Cheapflights users on 8/19. 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
Mon 10/209:20 amOAX - ORD
1 stop13h 15mMultiple Airlines
Deal found 8/19$317
This CheapOair deal was found by Cheapflights users on 8/19. 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 8/19$319
This Booking.com deal was found by Cheapflights users on 8/19. 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.
Tue 9/212:25 pmORD - OAX
1 stop26h 25mViva
Fri 9/52:20 pmOAX - ORD
1 stop8h 30mViva
Deal found 8/19$322

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 20, 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 9/19

12:25 pm-8:35 pm

1 stop9h 10m

Oaxaca Xoxocotlan

Mon 9/29

9:10 am-11:50 pm

1 stop13h 40m

$278

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 9/14

12:25 pm-8:30 am

1 stop21h 05m

Oaxaca Xoxocotlan

Fri 9/19

9:15 pm-11:50 pm

1 stop25h 35m

$282

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 10/11

12:25 pm-1:55 pm

1 stop26h 30m

Oaxaca Xoxocotlan

Sat 10/18

2:25 pm-11:35 pm

1 stop8h 10m

$291

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 9/18

1:55 am-10:38 am

1 stop9h 43m

Oaxaca Xoxocotlan

Mon 9/29

4:36 pm-12:15 am

1 stop6h 39m

$296

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 9/21

1:55 am-10:38 am

1 stop9h 43m

Oaxaca Xoxocotlan

Fri 9/26

4:36 pm-12:15 am

1 stop6h 39m

$302

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Mon 10/20

7:25 am-9:30 pm

1 stop15h 05m

Puerto Escondido

Sat 10/25

8:40 am-11:35 pm

1 stop13h 55m

$309

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 10/3

12:25 pm-1:55 pm

1 stop26h 30m

Oaxaca Xoxocotlan

Mon 10/13

9:20 am-11:35 pm

1 stop13h 15m

$311

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Mon 9/15

2:00 am-5:10 pm

1 stop16h 10m

Puerto Escondido

Tue 9/23

5:40 pm-12:15 am

1 stop29h 35m

$313

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sat 9/6

8:40 pm-5:10 pm

1 stop21h 30m

Puerto Escondido

Tue 9/9

10:25 pm-10:55 am

1 stop11h 30m

$316

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 10/9

6:34 pm-1:46 pm

1 stop20h 12m

Oaxaca Xoxocotlan

Mon 10/20

9:20 am-11:35 pm

1 stop13h 15m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 60 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

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

Currently, August is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $510). Flying from Chicago to State of 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 OA?

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 August 20, 2025.

When flying from Chicago to State of Oaxaca, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 20, 2025.
Read through reviews of airlines operating flights from Chicago to Oaxaca, such as Delta, Aeromexico, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

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
1,718 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

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
7,982 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

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
789 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

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
1,161 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

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.

  • How long is the flight from Chicago to State of Oaxaca?

    There are many flights that can get you from Chicago to State of Oaxaca in 9h 10m. Fly via Viva, Volaris, or Aeromexico to get the fastest option. The distance between Chicago and State of Oaxaca is about 1802 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago to State of Oaxaca?

    When deciding which route to take from Chicago to State of Oaxaca consider Chicago O'Hare Intl - Oaxaca Xoxocotlan, Chicago O'Hare Intl - Puerto Escondido or Chicago Midway - Oaxaca Xoxocotlan as they are the most popular.

  • 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 State of Oaxaca?

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

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Alternative routes for Chicago to Oaxaca

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$239Average$373FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$269Average$411FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$418Average$539FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$465Average$730FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$799FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$551Average$902FlexibilityNo cancel feeOn-time69%

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