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Oaxaca

$94+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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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 20, 2026.

This Booking.com deal was found by Cheapflights users on 1/19. 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.
Fri 2/271:20 am
ORD
-
OAX
1 stop15h 05m
Viva
Wed 3/44:55 pm
OAX
-
ORD
1 stop6h 50m
Viva
Deal found 1/19$270
This Trip.com deal was found by Cheapflights users on 1/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:59 pm
ORD
-
OAX
1 stop8h 36m
Multiple Airlines
Wed 3/44:55 pm
OAX
-
ORD
1 stop6h 50m
Multiple Airlines
Deal found 1/19$290
This Booking.com deal was found by Cheapflights users on 1/18. 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.
Mon 3/21:05 am
ORD
-
OAX
1 stop11h 15m
Viva
Wed 3/44:55 pm
OAX
-
ORD
1 stop6h 50m
Viva
Deal found 1/18$291
This Mytrip deal was found by Cheapflights users on 1/19. 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 5/151:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Mon 5/257:34 pm
OAX
-
ORD
1 stop9h 23m
Volaris
Deal found 1/19$298
This Booking.com deal was found by Cheapflights users on 1/19. 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.
Sun 2/221:00 am
ORD
-
PXM
1 stop20h 35m
Viva
Thu 2/263:55 pm
PXM
-
ORD
1 stop7h 30m
Viva
Deal found 1/19$302
This Booking.com deal was found by Cheapflights users on 1/18. 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.
Tue 3/31:05 am
ORD
-
OAX
1 stop11h 15m
Viva
Wed 3/114:55 pm
OAX
-
ORD
1 stop6h 50m
Viva
Deal found 1/18$304
This Booking.com deal was found by Cheapflights users on 1/19. 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.
Sat 2/211:00 am
ORD
-
OAX
1 stop11h 30m
Viva
Wed 2/255:05 pm
OAX
-
ORD
1 stop6h 45m
Viva
Deal found 1/19$307
This Orbitz deal was found by Cheapflights users on 1/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Sat 4/257:34 pm
OAX
-
ORD
1 stop9h 23m
Volaris
Deal found 1/18$315
This eDestinos deal was found by Cheapflights users on 1/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:58 pm
ORD
-
HUX
1 stop10h 31m
Volaris
Wed 3/111:18 pm
HUX
-
ORD
1 stop8h 48m
Volaris
Deal found 1/17$322
This Booking.com deal was found by Cheapflights users on 1/18. 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.
Wed 4/812:20 pm
ORD
-
PXM
1 stop27h 45m
Viva
Thu 4/164:00 pm
PXM
-
ORD
1 stop6h 45m
Viva
Deal found 1/18$325
This Booking.com deal was found by Cheapflights users on 1/19. 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.
Wed 3/412:55 am
ORD
-
PXM
1 stop14h 20m
Viva
Thu 3/123:55 pm
PXM
-
ORD
1 stop7h 30m
Viva
Deal found 1/19$327
This Trip.com deal was found by Cheapflights users on 1/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1311:59 pm
ORD
-
OAX
1 stop11h 36m
Multiple Airlines
Wed 3/184:55 pm
OAX
-
ORD
1 stop6h 50m
Multiple Airlines
Deal found 1/17$328

Find flight deals from Chicago to Oaxaca

Keep the following information in mind while searching for Chicago to Oaxaca flight deals. Data was last updated January 20, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$270
(Booking.com)

One-way from

$94
(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
Search Deals
One-way flight from Chicago (CHI) to Oaxaca
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 20, 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

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Wed 4/8

12:20 pm-3:05 pm

1 stop27h 45m

Puerto Escondido

Thu 4/16

4:00 pm-11:45 pm

1 stop6h 45m

$325

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Wed 3/4

12:55 am-3:15 pm

1 stop14h 20m

Puerto Escondido

Thu 3/12

3:55 pm-12:25 am

1 stop7h 30m

$327

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Wed 4/8

7:40 am-2:55 pm

1 stop8h 15m

Santa Maria Huatulco

Thu 4/16

3:40 pm-11:47 pm

1 stop7h 07m

$335

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sat 2/28

1:05 am-9:35 pm

1 stop20h 30m

Puerto Escondido

Tue 3/3

3:55 pm-11:25 pm

1 stop7h 30m

$336

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sat 1/31

12:55 am-3:05 pm

1 stop14h 10m

Puerto Escondido

Wed 2/4

10:25 pm-11:25 pm

1 stop25h 00m

$340

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Tue 3/24

2:05 am-9:35 pm

1 stop20h 30m

Puerto Escondido

Tue 3/31

3:55 pm-11:45 pm

1 stop6h 50m

$344

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sun 3/1

11:58 pm-1:00 pm

1 stop13h 02m

Puerto Escondido

Tue 3/3

8:25 am-11:25 pm

2 stops15h 00m

$359

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Mon 2/23

11:58 pm-10:29 am

1 stop10h 31m

Santa Maria Huatulco

Thu 2/26

8:53 am-10:29 pm

1 stop13h 36m

$362

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Mon 2/23

11:58 pm-2:55 pm

1 stop14h 57m

Santa Maria Huatulco

Thu 2/26

12:30 pm-11:25 pm

2 stops34h 55m

$367

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 2/8

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Wed 2/18

5:05 pm-11:50 pm

1 stop6h 45m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 60 results
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6

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 $219). Flying from Chicago to State of 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.

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 20, 2026.
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
8,085 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

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
8,085 reviews
Delta
7.9
Good
8,085 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

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
9,189 reviews
Delta
7.9
Good
8,085 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

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
11,169 reviews
Delta
7.9
Good
8,085 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

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
818 reviews
Delta
7.9
Good
8,085 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

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
8,085 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

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 8h 15m. Fly via Viva, Volaris, or Delta to get the fastest option. The distance between Chicago and State of Oaxaca is about 1876 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to State of Oaxaca one-way?

    $69 is the cheapest one-way deal found within the past few days, from Viva. You may also be able to find cheap deals on Volaris and United Airlines, with prices starting from $92 and $178, respectively.

  • 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 - Santa Maria Huatulco or Chicago O'Hare Intl - Puerto Escondido 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 $219). Flying from Chicago to State of 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

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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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$259Average$396FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$266Average$398FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$453Average$809FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$455Average$525FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$484Average$957FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$543Average$787FlexibilityNo cancel feeOn-time71%

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