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Oaxaca

$113+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(CheapOair)

One-way from

$113
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$602
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. 14% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 6, 2025.

This Booking.com deal was found by Cheapflights users on 10/4. 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 11/164:40 pmORD - OAX
1 stop29h 15mViva
Fri 11/2110:45 pmOAX - ORD
1 stop16h 25mViva
Deal found 10/4$273
This Booking.com deal was found by Cheapflights users on 10/4. 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.
Mon 11/101:15 amORD - OAX
1 stop11h 10mViva
Sat 11/152:15 pmOAX - ORD
1 stop24h 55mViva
Deal found 10/4$302
This Booking.com deal was found by Cheapflights users on 10/4. 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 11/164:40 pmORD - OAX
1 stop29h 15mViva
Thu 11/201:10 pmOAX - ORD
1 stop10h 20mViva
Deal found 10/4$307
This Mytrip deal was found by Cheapflights users on 10/5. 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 11/157:30 pmORD - PXM
1 stop19h 30mViva
Thu 11/208:30 amPXM - ORD
1 stop13h 45mViva
Deal found 10/5$309
This Booking.com deal was found by Cheapflights users on 10/5. 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 11/157:30 pmORD - PXM
1 stop19h 30mViva
Wed 11/2610:25 pmPXM - ORD
1 stop25h 05mViva
Deal found 10/5$310
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 11/117:25 amORD - OAX
1 stop8h 47mMultiple Airlines
Sat 11/152:15 pmOAX - ORD
1 stop24h 55mMultiple Airlines
Deal found 10/4$313
This Booking.com deal was found by Cheapflights users on 10/4. 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 11/1811:45 pmORD - OAX
1 stop17h 00mViva
Tue 11/255:00 pmOAX - ORD
1 stop22h 10mViva
Deal found 10/4$326
This Trip.com deal was found by Cheapflights users on 10/5. 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.
Sat 11/156:23 amORD - PXM
2 stops32h 37mMultiple Airlines
Wed 11/2610:25 pmPXM - ORD
1 stop25h 05mMultiple Airlines
Deal found 10/5$330
This CheapOair deal was found by Cheapflights users on 10/5. 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.
Sat 11/154:40 pmORD - HUX
1 stop23h 35mViva
Thu 11/2012:30 pmHUX - ORD
1 stop9h 45mViva
Deal found 10/5$330
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/1911:58 pmORD - PXM
1 stop16h 01mMultiple Airlines
Sat 11/224:40 pmPXM - ORD
1 stop22h 30mMultiple Airlines
Deal found 10/6$332
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/1911:58 pmORD - PXM
1 stop16h 01mMultiple Airlines
Wed 11/2610:25 pmPXM - ORD
1 stop25h 05mMultiple Airlines
Deal found 10/6$333
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/1911:58 pmORD - PXM
1 stop16h 01mMultiple Airlines
Tue 11/258:30 amPXM - ORD
1 stop13h 45mMultiple Airlines
Deal found 10/6$334

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 6, 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

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Wed 3/4

11:58 pm-10:29 am

1 stop10h 31m

Santa Maria Huatulco

Mon 3/9

12:18 pm-11:06 pm

1 stop9h 48m

$318

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Wed 11/19

11:58 pm-3:59 pm

1 stop16h 01m

Puerto Escondido

Mon 11/24

8:30 am-10:15 pm

1 stop13h 45m

$345

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Wed 1/28

6:23 am-9:35 pm

1 stop15h 12m

Puerto Escondido

Sat 1/31

2:00 pm-11:25 pm

1 stop9h 25m

$351

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Fri 11/14

12:55 am-3:00 pm

1 stop14h 05m

Puerto Escondido

Thu 11/20

8:30 am-10:15 pm

1 stop13h 45m

$357

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Thu 1/29

11:59 pm-12:39 pm

1 stop12h 40m

Puerto Escondido

Mon 5/4

1:24 pm-11:32 pm

1 stop9h 08m

$358

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Thu 1/29

11:59 pm-12:39 pm

1 stop12h 40m

Puerto Escondido

Sat 2/28

4:35 pm-11:19 am

2 stops42h 44m

$364

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Fri 1/23

11:58 pm-10:29 am

1 stop10h 31m

Santa Maria Huatulco

Mon 2/2

12:18 pm-10:06 pm

1 stop9h 48m

$376

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Wed 1/28

12:55 am-3:05 pm

1 stop14h 10m

Puerto Escondido

Mon 5/4

10:30 pm-10:50 am

1 stop11h 20m

$392

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 1/28

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Wed 2/4

1:10 pm-10:06 pm

1 stop8h 56m

$392

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Wed 1/28

12:55 am-3:05 pm

1 stop14h 10m

Puerto Escondido

Sat 2/28

2:00 pm-11:25 pm

1 stop9h 25m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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 $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 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 October 6, 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 October 6, 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
8.0
Very good
7,967 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

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
7,967 reviews
Delta
8.0
Very good
7,967 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

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!
United Airlines
7.4
Good
8,957 reviews
Delta
8.0
Very good
7,967 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

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
11,040 reviews
Delta
8.0
Very good
7,967 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

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
786 reviews
Delta
8.0
Very good
7,967 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

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
6.7
Okay
1,151 reviews
Delta
8.0
Very good
7,967 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

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 8h 13m. Fly via Volaris, Viva, or Delta 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 $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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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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$246Average$380FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$266Average$409FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$449Average$540FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$465Average$731FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$531Average$788FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$551Average$867FlexibilityNo cancel feeOn-time69%

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