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Oaxaca

$102+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Dec 30 — Jan 61
Tue 12/30
Tue 1/6
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 November 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$273
(Booking.com)

One-way from

$102
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$560
Provider with most accurate pricing for Chicago (CHI)-Oaxaca Xoxocotlan flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Oaxaca Xoxocotlan flights.
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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. 16% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Sun 12/143:47 pmORD - OAX
2 stops22h 26mMultiple Airlines
Tue 12/165:10 pmOAX - ORD
1 stop6h 40mMultiple Airlines
Deal found 11/29$395
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 12/59:14 pmORD - OAX
2 stops18h 58mMultiple Airlines
Tue 12/95:10 pmOAX - ORD
1 stop21h 50mMultiple Airlines
Deal found 11/28$398
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Sun 12/143:47 pmORD - OAX
2 stops22h 26mMultiple Airlines
Thu 12/185:10 pmOAX - ORD
1 stop6h 40mMultiple Airlines
Deal found 11/29$401
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Sun 12/143:47 pmORD - OAX
2 stops22h 26mMultiple Airlines
Fri 12/1911:35 pmOAX - ORD
1 stop24h 15mMultiple Airlines
Deal found 11/29$406
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Sun 12/143:47 pmORD - OAX
2 stops22h 26mMultiple Airlines
Tue 12/235:10 pmOAX - ORD
1 stop21h 50mMultiple Airlines
Deal found 11/29$412
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Fri 12/129:14 pmORD - OAX
3 stops19h 31mMultiple Airlines
Thu 12/185:10 pmOAX - ORD
1 stop6h 40mMultiple Airlines
Deal found 11/29$424
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Fri 12/129:14 pmORD - OAX
3 stops19h 31mMultiple Airlines
Tue 12/165:10 pmOAX - ORD
1 stop6h 40mMultiple Airlines
Deal found 11/29$426
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Sat 12/136:05 amORD - OAX
2 stops10h 40mMultiple Airlines
Tue 12/165:10 pmOAX - ORD
1 stop6h 40mMultiple Airlines
Deal found 11/29$429
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Sun 12/143:47 pmORD - OAX
2 stops22h 26mMultiple Airlines
Wed 12/2411:11 amOAX - ORD
1 stop27h 42mMultiple Airlines
Deal found 11/29$430
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Thu 12/115:00 amORD - OAX
2 stops11h 12mMultiple Airlines
Tue 12/235:10 pmOAX - ORD
1 stop21h 50mMultiple Airlines
Deal found 11/29$434
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Fri 12/129:14 pmORD - OAX
3 stops19h 31mMultiple Airlines
Fri 12/1911:35 pmOAX - ORD
1 stop24h 15mMultiple Airlines
Deal found 11/29$437
This Kiwi.com deal was found by Cheapflights users on 11/28. 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.
Mon 12/17:30 pmORD - PXM
2 stops20h 45mViva
Sat 12/64:55 pmPXM - ORD
1 stop22h 05mViva
Deal found 11/28$466

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 November 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 2/25

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Thu 3/5

1:10 pm-11:35 pm

1 stop10h 25m

$302

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Tue 1/13

6:23 am-9:35 pm

1 stop15h 12m

Puerto Escondido

Tue 1/20

10:25 pm-11:25 pm

1 stop25h 00m

$302

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sat 1/24

11:59 pm-3:05 pm

1 stop15h 06m

Puerto Escondido

Wed 1/28

10:25 pm-11:25 pm

1 stop25h 00m

$307

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sat 3/14

6:05 pm-3:15 pm

1 stop22h 10m

Puerto Escondido

Thu 3/19

2:00 pm-12:35 am

1 stop9h 35m

$309

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 1/24

11:59 pm-12:25 pm

2 stops12h 26m

Oaxaca Xoxocotlan

Sat 1/31

1:10 pm-11:25 pm

1 stop10h 15m

$314

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Thu 3/5

6:23 am-9:35 pm

1 stop15h 12m

Puerto Escondido

Mon 3/9

8:25 am-12:45 am

2 stops15h 20m

$315

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Tue 1/13

1:00 am-9:35 pm

1 stop20h 35m

Puerto Escondido

Wed 1/21

10:25 pm-11:25 pm

1 stop25h 00m

$325

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sat 1/10

11:59 pm-9:35 pm

2 stops45h 36m

Puerto Escondido

Thu 1/22

10:25 pm-11:25 pm

1 stop25h 00m

$325

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Mon 2/16

12:55 am-3:05 pm

1 stop14h 10m

Puerto Escondido

Sat 2/21

8:30 am-11:50 pm

2 stops39h 20m

$328

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Tue 1/27

1:00 am-2:55 pm

1 stop13h 55m

Santa Maria Huatulco

Fri 2/6

12:30 pm-11:50 pm

2 stops11h 20m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/29

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, March is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $202). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $428). 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 November 30, 2025.

One of the essential ways to save on airfare from Chicago to State of Oaxaca is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 42% on airfare.

What is the cheapest day to fly from Chicago to State of 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 State of Oaxaca flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday at noon 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 November 30, 2025.
Read through reviews of airlines operating flights from Chicago to Oaxaca, such as Delta, United Airlines, 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
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

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
8,011 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

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
9,057 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

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
11,042 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

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
789 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

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
6.7
Okay
1,155 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Crew

8.5

Entertainment

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.

  • 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 7h 33m. 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 O'Hare Intl - Santa Maria Huatulco 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, March is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $202). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $428). 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 November 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$247Average$381FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$266Average$405FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$453Average$822FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$455Average$530FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$465Average$954FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$543Average$786FlexibilityNo cancel feeOn-time71%

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