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Oaxaca

$104+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
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 July 24, 2026.

This Viva deal was found by Cheapflights users on 7/21. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/204:22 pm
ORD
-
OAX
1 stop23h 47m
Viva
Sat 9/263:39 pm
OAX
-
ORD
1 stop22h 13m
Viva
Deal found 7/21$265
This Booking.com deal was found by Cheapflights users on 7/18. 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 8/234:20 pm
ORD
-
OAX
1 stop23h 40m
Viva
Sat 8/293:30 pm
OAX
-
ORD
1 stop22h 20m
Viva
Deal found 7/18$268
This Viva deal was found by Cheapflights users on 7/22. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:35 am
ORD
-
OAX
1 stop13h 03m
Viva
Sun 11/82:20 pm
OAX
-
ORD
1 stop8h 35m
Viva
Deal found 7/22$276
This Viva deal was found by Cheapflights users on 7/22. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:40 pm
ORD
-
OAX
1 stop25h 29m
Viva
Wed 10/1412:53 pm
OAX
-
ORD
1 stop21h 07m
Viva
Deal found 7/22$278
This Viva deal was found by Cheapflights users on 7/18. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:22 pm
ORD
-
OAX
1 stop23h 47m
Viva
Wed 9/3012:53 pm
OAX
-
ORD
1 stop21h 07m
Viva
Deal found 7/18$279
This Mytrip deal was found by Cheapflights users on 7/18. 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 8/171:30 am
ORD
-
OAX
1 stop14h 30m
Multiple Airlines
Thu 8/272:29 pm
OAX
-
ORD
1 stop13h 12m
Multiple Airlines
Deal found 7/18$283
This Viva deal was found by Cheapflights users on 7/21. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/274:22 pm
ORD
-
OAX
1 stop23h 47m
Viva
Wed 9/3012:53 pm
OAX
-
ORD
1 stop21h 07m
Viva
Deal found 7/21$284
This Viva deal was found by Cheapflights users on 7/22. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:35 am
ORD
-
OAX
1 stop17h 28m
Viva
Tue 11/1012:53 pm
OAX
-
ORD
1 stop10h 42m
Viva
Deal found 7/22$289
This Viva deal was found by Cheapflights users on 7/20. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/204:22 pm
ORD
-
OAX
1 stop23h 47m
Viva
Wed 9/3012:53 pm
OAX
-
ORD
1 stop21h 07m
Viva
Deal found 7/20$293
This Viva deal was found by Cheapflights users on 7/18. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:40 pm
ORD
-
OAX
1 stop25h 29m
Viva
Mon 10/512:53 pm
OAX
-
ORD
1 stop21h 07m
Viva
Deal found 7/18$295
This Viva deal was found by Cheapflights users on 7/21. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2912:35 am
ORD
-
PXM
1 stop21h 32m
Viva
Sat 12/123:47 pm
PXM
-
ORD
1 stop7h 10m
Viva
Deal found 7/21$313
This Viva deal was found by Cheapflights users on 7/20. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:30 am
ORD
-
PXM
1 stop21h 08m
Viva
Sat 10/102:02 pm
PXM
-
ORD
1 stop19h 58m
Viva
Deal found 7/20$332

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 July 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$265
(Viva)

One-way from

$104
(Viva)

Popular in

December

Cheapest in

April

Average price

$527
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. 19% potential increase in price ($122 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 24, 2026.
Use the filters below to find and compare flights from Chicago to Oaxaca that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 8/23

4:20 pm-3:00 pm

1 stop23h 40m

Oaxaca Xoxocotlan

Sat 8/29

3:30 pm-2:50 pm

1 stop22h 20m

$268

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 9/25

4:22 pm-3:09 pm

1 stop23h 47m

Oaxaca Xoxocotlan

Wed 9/30

12:53 pm-11:00 am

1 stop21h 07m

$279

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 9/27

4:22 pm-3:09 pm

1 stop23h 47m

Oaxaca Xoxocotlan

Wed 9/30

12:53 pm-11:00 am

1 stop21h 07m

$284

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 10/3

2:40 pm-3:09 pm

1 stop25h 29m

Oaxaca Xoxocotlan

Tue 10/6

12:53 pm-11:00 am

1 stop21h 07m

$284

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 10/2

2:40 pm-3:09 pm

1 stop25h 29m

Oaxaca Xoxocotlan

Mon 10/5

12:53 pm-11:00 am

1 stop21h 07m

$295

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 10/7

4:20 pm-3:09 pm

1 stop23h 49m

Oaxaca Xoxocotlan

Wed 10/21

12:53 pm-11:00 am

1 stop21h 07m

$312

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Thu 10/1

1:30 am-9:38 pm

1 stop21h 08m

Puerto Escondido

Sat 10/10

2:02 pm-11:00 am

1 stop19h 58m

$332

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Thu 10/1

1:40 am-1:26 pm

1 stop12h 46m

Puerto Escondido

Sat 10/10

2:24 pm-11:47 pm

1 stop8h 23m

$352
Quickest round-trip

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Mon 9/28

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sun 10/4

7:34 pm-5:52 am

1 stop9h 18m

$357

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Mon 10/5

2:53 am-3:09 pm

2 stops13h 16m

Oaxaca Xoxocotlan

Fri 10/23

7:34 pm-5:52 am

1 stop9h 18m

$386

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/19

Showing 1-10 of 60 resultsSorted by cheapest first
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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, May is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $366). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $741). 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.

How much does it cost to fly round-trip from Chicago to State of Oaxaca?

Airfare is below average for this route at the moment.
Chicago to State of Oaxaca flights typically cost between $394 and $725 in September.
The cheapest round-trip price found within the last 5 days was $265 on Viva (Sep 20-Sep 26).

How far ahead should I book a flight from Chicago to State of Oaxaca?

To ensure you get the cheapest price possible for a flight from Chicago to State of Oaxaca, you should look to book at least 49 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.

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 July 24, 2026.
Read through reviews of airlines operating flights from Chicago to Oaxaca, such as Delta,United Airlines, andAmerican Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,481 reviews

Crew

8.5

Overall

7.8

Food

7.2

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,481 reviews
Delta
7.8
Good
8,481 reviews

Crew

8.5

Overall

7.8

Food

7.2

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
10,025 reviews
Delta
7.8
Good
8,481 reviews

Crew

8.5

Overall

7.8

Food

7.2

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,836 reviews
Delta
7.8
Good
8,481 reviews

Crew

8.5

Overall

7.8

Food

7.2

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Viva
7.0
Good
804 reviews
Delta
7.8
Good
8,481 reviews

Crew

8.5

Overall

7.8

Food

7.2

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Volaris
6.6
Okay
1,153 reviews
Delta
7.8
Good
8,481 reviews

Crew

8.5

Overall

7.8

Food

7.2

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 12h 46m. Fly via Viva, Volaris, or Frontier to get the fastest option. The distance between Chicago and State of Oaxaca is about 1883 mi. This flight may include one or multiple stops.

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

    $92 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on Viva and United Airlines, with prices starting from $104 and $295, 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 Midway - Oaxaca Xoxocotlan 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, May is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $366). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $741). 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

Browse thousands of different options on Cheapflights for your next trip

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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 July 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$261Average$470FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$278Average$418FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$453Average$806FlexibilityNo cancel feeOn-time69%
DeltaCheapest$475Average$1,013FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$475Average$601FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$543Average$731FlexibilityNo cancel feeOn-time71%

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