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Oaxaca

$266+ Cheap flights from Midway (MDW) to Oaxaca, Mexico (OAX)

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAX
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Midway to Oaxaca

Cheapest flights from Midway to Oaxaca
Explore the most affordable flight options available from Midway to Oaxaca. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Delta deal was found by Cheapflights users on 12/10. 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.
Thu 12/256:00 amMDW - OAX
2 stops16h 40mDelta
Thu 1/112:07 pmOAX - MDW
2 stops20h 58mDelta
Deal found 12/10$1,292
This Delta deal was found by Cheapflights users on 12/10. 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.
Thu 12/256:00 amMDW - OAX
2 stops16h 40mDelta
Mon 1/511:32 amOAX - MDW
2 stops10h 35mDelta
Deal found 12/10$1,467
This Delta deal was found by Cheapflights users on 12/11. 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.
Sat 12/276:00 amMDW - OAX
2 stops9h 53mDelta
Wed 12/318:13 amOAX - MDW
2 stops14h 09mDelta
Deal found 12/11$1,647
This Delta deal was found by Cheapflights users on 12/10. 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.
Thu 12/256:00 amMDW - OAX
2 stops13h 49mDelta
Sat 1/36:04 amOAX - MDW
2 stops9h 24mDelta
Deal found 12/10$2,039
This Delta deal was found by Cheapflights users on 12/10. 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.
Sun 12/219:50 amMDW - OAX
2 stops12h 50mDelta
Sun 12/288:13 amOAX - MDW
2 stops14h 09mDelta
Deal found 12/10$2,064
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 12/206:00 amMDW - OAX
2 stops13h 52mDelta
Sun 12/288:13 amOAX - MDW
2 stops14h 09mDelta
Deal found 12/10$2,114
This Delta deal was found by Cheapflights users on 12/10. 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.
Sun 12/286:00 amMDW - OAX
2 stops13h 49mDelta
Sat 1/36:04 amOAX - MDW
2 stops9h 24mDelta
Deal found 12/10$2,214
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 12/206:00 amMDW - OAX
2 stops13h 52mDelta
Sat 12/276:04 amOAX - MDW
2 stops9h 24mDelta
Deal found 12/10$2,217
This Delta deal was found by Cheapflights users on 12/11. 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.
Sat 12/276:00 amMDW - OAX
2 stops9h 53mDelta
Sat 1/36:04 amOAX - MDW
2 stops9h 24mDelta
Deal found 12/11$2,424
This Delta deal was found by Cheapflights users on 12/11. 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.
Fri 12/266:00 amMDW - OAX
2 stops13h 49mDelta
Fri 1/26:04 amOAX - MDW
2 stops10h 16mDelta
Deal found 12/11$2,602

Find flight deals from Midway to Oaxaca

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Oaxaca (OAX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$451
(Delta)

One-way from

$266
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$924
Provider with most accurate pricing for Chicago Midway-Oaxaca Xoxocotlan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Oaxaca Xoxocotlan flights.
Search Deals
From Chicago Midway to Oaxaca Xoxocotlan
Search Deals
One-way flight from Chicago Midway to Oaxaca Xoxocotlan
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 December 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Oaxaca that are best for you.

Fly from

Midway

Fly to

Oaxaca

Route

Depart

Return

Price

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 1/19

12:48 pm-7:41 am

2 stops18h 53m

Oaxaca Xoxocotlan

Mon 1/26

8:19 pm-5:29 pm

2 stops21h 10m

$451

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 1/13

6:45 am-10:40 pm

2 stops15h 55m

Oaxaca Xoxocotlan

Wed 1/21

10:37 am-10:22 pm

2 stops11h 45m

$451

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 1/13

6:45 am-7:36 am

2 stops24h 51m

Oaxaca Xoxocotlan

Tue 1/20

8:19 pm-5:29 pm

2 stops21h 10m

$451

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 1/14

6:45 am-7:03 pm

2 stops12h 18m

Oaxaca Xoxocotlan

Wed 1/21

10:37 am-10:22 pm

2 stops11h 45m

$473

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 3/10

10:49 am-10:44 pm

2 stops12h 55m

Oaxaca Xoxocotlan

Wed 3/18

8:06 am-10:29 pm

2 stops13h 23m

$520

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 2/9

10:46 am-7:25 am

2 stops20h 39m

Oaxaca Xoxocotlan

Fri 2/13

8:25 pm-10:42 pm

2 stops26h 17m

$547

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 3/7

6:00 am-8:18 pm

2 stops14h 18m

Oaxaca Xoxocotlan

Wed 3/11

10:37 am-10:29 pm

2 stops10h 52m

$603

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 3/14

6:30 am-7:08 pm

2 stops13h 38m

Oaxaca Xoxocotlan

Wed 3/18

8:06 am-10:29 pm

2 stops13h 23m

$603

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 2/10

12:48 pm-7:25 am

2 stops18h 37m

Oaxaca Xoxocotlan

Mon 2/23

8:25 pm-10:44 pm

2 stops26h 19m

$609

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 2/2

6:00 am-7:03 pm

2 stops13h 03m

Oaxaca Xoxocotlan

Wed 3/4

6:00 am-5:45 pm

2 stops11h 45m

$609

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 19 results
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Compare providers for flights from Midway to Oaxaca

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Oaxaca in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Oaxaca flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Oaxaca flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Oaxaca flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Oaxaca flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Oaxaca flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Oaxaca

Have a flexible travel schedule? Discover the best time to fly to Oaxaca from Midway 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Oaxaca. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Oaxaca from Chicago Midway?

    Located just 4.4 mi from the city center, Oaxaca Xoxocotlan is the airport most travelers will use when flying to Oaxaca from Chicago Midway. Booking flights from Chicago Midway to Xoxocotlan (OAX) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 0 different airlines.

  • How long is the flight from Chicago Midway Airport to Oaxaca?

    For as low as $451, Aeromexico can have you in Oaxaca from Chicago Midway Airport in 15h 55m. The distance from Chicago Midway Airport to Oaxaca is about 1792 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Oaxaca that include hotel bookings?

    Yes. In addition to deals on Midway to Oaxaca flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Oaxaca?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Oaxaca.

  • Can I find deals for business class flights from Midway to Oaxaca?

    Yes. Cheapflights offers flight deals from Midway 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.

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