Oaxaca

$133+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAX
jul. 8 — jul. 151
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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 julio 3, 2025.

Round-trip from

$250
(Kiwi.com)

One-way from

$141
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$650
From Chicago (CHI) to Oaxaca
One-way flight from Chicago (CHI) to Oaxaca
Highest demand for flights based on searches. 7% potential increase in price ($46 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 julio 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
sáb. 8/161:40 amORD - OAX
2 stops13h 06mVolaris
dom. 8/249:19 amOAX - ORD
1 stop19h 23mVolaris
Deal found 7/3$220
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
sáb. 8/161:40 amORD - OAX
1 stop11h 35mMultiple Airlines
dom. 8/249:19 amOAX - ORD
1 stop19h 23mMultiple Airlines
Deal found 7/3$247
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
sáb. 8/161:40 amORD - PXM
1 stop11h 51mVolaris
dom. 8/2412:20 pmPXM - ORD
2 stops16h 22mVolaris
Deal found 7/3$307
This Booking.com deal was found by Cheapflights users on 7/2. 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.
vie. 10/312:25 pmORD - OAX
1 stop7h 25mViva
lun. 10/132:25 pmOAX - ORD
1 stop8h 10mViva
Deal found 7/2$315
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
sáb. 8/161:40 amORD - PXM
1 stop11h 51mMultiple Airlines
dom. 8/2410:25 pmPXM - ORD
1 stop30h 17mMultiple Airlines
Deal found 7/3$317
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
sáb. 8/161:40 amORD - HUX
1 stop14h 15mVolaris
dom. 8/243:45 pmHUX - ORD
1 stop12h 57mVolaris
Deal found 7/3$321
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
mié. 8/136:55 amORD - HUX
1 stop29h 15mMultiple Airlines
mié. 8/273:45 pmHUX - ORD
1 stop12h 57mMultiple Airlines
Deal found 7/3$339
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
sáb. 10/188:35 pmORD - PXM
1 stop21h 30mViva
sáb. 10/2510:20 amPXM - ORD
1 stop7h 45mViva
Deal found 7/2$378
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/196:04 amMDW - OAX
2 stops13h 02mDelta
mar. 8/266:01 amOAX - MDW
2 stops14h 43mDelta
Deal found 7/1$504
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
sáb. 7/198:39 pmMDW - OAX
1 stop12h 04mVolaris
mar. 8/124:36 pmOAX - MDW
1 stop25h 40mVolaris
Deal found 7/3$510
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
sáb. 7/198:39 pmMDW - OAX
1 stop12h 04mMultiple Airlines
mar. 8/124:36 pmOAX - MDW
2 stops23h 27mMultiple Airlines
Deal found 7/3$527
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
vie. 8/14:00 pmMDW - PXM
2 stops21h 31mMultiple Airlines
dom. 8/105:40 pmPXM - MDW
1 stop24h 36mMultiple Airlines
Deal found 7/1$529

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 julio 3, 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

sáb. 8/16

1:40 am-1:46 pm

2 stops13h 06m

Oaxaca Xoxocotlan

dom. 8/24

9:19 am-5:42 am

1 stop19h 23m

$220

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

sáb. 8/16

1:40 am-12:15 pm

1 stop11h 35m

Oaxaca Xoxocotlan

dom. 8/24

9:19 am-5:42 am

1 stop19h 23m

$247

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

sáb. 8/16

1:40 am-12:31 pm

1 stop11h 51m

Puerto Escondido

dom. 8/24

12:20 pm-5:42 am

2 stops16h 22m

$307

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

vie. 10/3

12:25 pm-6:50 pm

1 stop7h 25m

Oaxaca Xoxocotlan

lun. 10/13

2:25 pm-11:35 pm

1 stop8h 10m

$315

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

sáb. 8/16

1:40 am-12:31 pm

1 stop11h 51m

Puerto Escondido

dom. 8/24

10:25 pm-5:42 am

1 stop30h 17m

$317

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

sáb. 8/16

1:40 am-2:55 pm

1 stop14h 15m

Santa Maria Huatulco

dom. 8/24

3:45 pm-5:42 am

1 stop12h 57m

$321

ChicagoSanta Maria Huatulco

ORD - HUX

ORDHUX

Chicago O'Hare Intl

mié. 8/13

6:55 am-11:10 am

1 stop29h 15m

Santa Maria Huatulco

mié. 8/27

3:45 pm-5:42 am

1 stop12h 57m

$339

ChicagoPuerto Escondido

ORD - PXM

ORDPXM

Chicago O'Hare Intl

sáb. 10/18

8:35 pm-5:05 pm

1 stop21h 30m

Puerto Escondido

sáb. 10/25

10:20 am-7:05 pm

1 stop7h 45m

$378

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

mar. 8/19

6:04 am-6:06 pm

2 stops13h 02m

Oaxaca Xoxocotlan

mar. 8/26

6:01 am-9:44 pm

2 stops14h 43m

$504

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

sáb. 7/19

8:39 pm-7:43 am

1 stop12h 04m

Oaxaca Xoxocotlan

mar. 8/12

4:36 pm-7:16 pm

1 stop25h 40m

$510

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 43 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, August is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $510). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $803). 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 julio 3, 2025.

When flying from Chicago to State of Oaxaca, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

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 julio 3, 2025.
Read through reviews of airlines operating flights from Chicago to Oaxaca, such as Delta, Aeromexico, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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!
8.0
Very good
8.0
Very good

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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!
8.0
Very good

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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!
8.0
Very good

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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!
8.0
Very good

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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!
8.0
Very good

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

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

    $141 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 Frontier, with prices starting from $152 and $215, 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, August is the cheapest month in which you can book a flight from Chicago to State of Oaxaca (average of $510). Flying from Chicago to State of Oaxaca in December is currently the most expensive (average of $803). 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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Alternative routes for Chicago to Oaxaca

See prices for flight routes from nearby airports that may be better suited for you.

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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$240Average$382FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$277Average$419FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$418Average$564FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$465Average$707FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$781FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$551Average$935FlexibilityNo cancel feeOn-time69%

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