Oaxaca

$138+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
Jul 9 — Jul 161
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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 June 9, 2026.

This CheapOair deal was found by Cheapflights users on 6/7. 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 8/241:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Tue 9/17:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/7$296
This CheapOair deal was found by Cheapflights users on 6/8. 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.
Wed 8/261:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Sat 9/57:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/8$301
This CheapOair deal was found by Cheapflights users on 6/7. 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 8/241:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Tue 9/87:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/7$303
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Mon 8/317:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/8$311
This Viva deal was found by Cheapflights users on 6/6. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:30 am
ORD
-
OAX
1 stop14h 37m
Viva
Sun 11/153:37 pm
OAX
-
ORD
1 stop7h 08m
Viva
Deal found 6/6$313
This CheapOair deal was found by Cheapflights users on 6/5. 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.
Thu 8/201:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Tue 9/17:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/5$315
This Justfly.com deal was found by Cheapflights users on 6/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Sat 8/299:45 pm
OAX
-
ORD
1 stop13h 24m
Volaris
Deal found 6/9$320
This CheapOair deal was found by Cheapflights users on 6/5. 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.
Thu 8/201:49 pm
ORD
-
OAX
1 stop8h 20m
Volaris
Sat 8/297:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/5$321
This Gotogate deal was found by Cheapflights users on 6/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Mon 10/57:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/6$324
This Mytrip deal was found by Cheapflights users on 6/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:40 am
ORD
-
OAX
1 stop7h 33m
Volaris
Sun 10/117:34 pm
OAX
-
ORD
1 stop9h 18m
Volaris
Deal found 6/6$327
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Fri 9/181:30 am
ORD
-
PXM
1 stop21h 08m
Viva
Thu 9/243:55 pm
PXM
-
ORD
1 stop7h 04m
Viva
Deal found 6/4$330
This Viva deal was found by Cheapflights users on 6/6. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/412:30 pm
ORD
-
PXM
1 stop27h 34m
Viva
Tue 10/2010:32 pm
PXM
-
ORD
1 stop11h 28m
Viva
Deal found 6/6$336

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$296
(CheapOair)

One-way from

$138
(CheapOair)

Popular in

December

Cheapest in

April

Average price

$527
Provider with most accurate pricing for Chicago (CHI)-Oaxaca Xoxocotlan flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Oaxaca Xoxocotlan flights.
From Chicago (CHI) to Oaxaca
One-way flight from Chicago (CHI) to Oaxaca
Highest demand for flights based on searches. 22% potential increase in price ($150 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 June 9, 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

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Sun 10/4

12:30 pm-3:04 pm

1 stop27h 34m

Puerto Escondido

Tue 10/20

10:32 pm-11:00 am

1 stop11h 28m

$336

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

Thu 9/24

1:30 am-9:38 pm

1 stop21h 08m

Puerto Escondido

Wed 9/30

10:32 pm-11:00 am

1 stop11h 28m

$369

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 10/15

1:30 am-3:07 pm

1 stop14h 37m

Oaxaca Xoxocotlan

Wed 10/21

3:37 pm-11:45 pm

1 stop7h 08m

$389

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Fri 9/18

1:40 am-2:55 pm

1 stop14h 15m

Santa Maria Huatulco

Sat 9/26

3:40 pm-5:52 am

1 stop13h 12m

$395

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Sat 9/5

7:35 am-3:12 pm

1 stop8h 37m

Santa Maria Huatulco

Tue 9/8

3:53 pm-11:00 am

1 stop18h 07m

$404

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 11/17

11:58 pm-8:19 am

1 stop8h 21m

Oaxaca Xoxocotlan

Mon 11/23

2:44 pm-11:39 pm

1 stop8h 55m

$405

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 7/1

2:53 am-1:49 pm

2 stops35h 56m

Oaxaca Xoxocotlan

Fri 7/10

2:29 pm-12:55 am

1 stop9h 26m

$410

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Sat 8/15

1:40 am-2:55 pm

1 stop14h 15m

Santa Maria Huatulco

Wed 8/19

3:40 pm-11:47 pm

1 stop7h 07m

$420

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

Fri 10/9

1:35 am-3:11 pm

1 stop14h 36m

Santa Maria Huatulco

Sat 10/17

3:47 pm-11:00 am

1 stop18h 13m

$421

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 11/18

11:58 pm-8:19 am

1 stop8h 21m

Oaxaca Xoxocotlan

Mon 11/23

2:44 pm-11:39 pm

1 stop8h 55m

$426

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 60 resultsSorted by cheapest first
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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, May is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $119). Flying from Chicago to State of Oaxaca in October is currently the most expensive (average of $273). 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?

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 47 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 June 9, 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.

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Food

7.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

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

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Food

7.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

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

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Food

7.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

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

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Food

7.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

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

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Food

7.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

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

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Overall

7.9

Food

7.2

Crew

8.5

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 18m. Fly via Viva, Volaris, or Delta to get the fastest option. The distance between Chicago and State of Oaxaca is about 1792 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?

  • 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 $119). Flying from Chicago to State of Oaxaca in October is currently the most expensive (average of $273). 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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$179Average$466FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$266Average$412FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$472Average$581FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$520Average$809FlexibilityNo cancel feeOn-time69%
DeltaCheapest$524Average$1,060FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$543Average$703FlexibilityNo cancel feeOn-time71%

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