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Oaxaca

$255+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAX
feb. 25 — mar. 41
mié. 2/25
mié. 3/4
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 enero 26, 2026.

This Delta deal was found by Cheapflights users on 1/24. 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.
mié. 3/46:00 am
MDW
-
OAX
2 stops13h 00m
Delta
mié. 3/117:56 am
OAX
-
MDW
2 stops13h 35m
Delta
Deal found 1/24$535
This Aeromexico deal was found by Cheapflights users on 1/24. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1710:45 am
MDW
-
OAX
2 stops21h 36m
Aeromexico
jue. 3/196:00 am
OAX
-
MDW
2 stops15h 31m
Aeromexico
Deal found 1/24$549
This Aeromexico deal was found by Cheapflights users on 1/24. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/76:00 am
MDW
-
OAX
2 stops26h 40m
Aeromexico
mié. 3/117:56 am
OAX
-
MDW
2 stops13h 35m
Aeromexico
Deal found 1/24$584
This Delta deal was found by Cheapflights users on 1/24. 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.
dom. 2/226:00 am
MDW
-
OAX
2 stops13h 00m
Delta
vie. 2/276:00 am
OAX
-
MDW
2 stops11h 45m
Delta
Deal found 1/24$633
This CheapOair deal was found by Cheapflights users on 1/25. 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.
jue. 3/55:16 pm
MDW
-
OAX
2 stops22h 56m
Frontier
vie. 3/138:40 am
OAX
-
MDW
2 stops36h 05m
Frontier
Deal found 1/25$645
This CheapOair deal was found by Cheapflights users on 1/24. 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.
sáb. 3/146:55 am
MDW
-
OAX
2 stops34h 17m
Frontier
lun. 3/238:40 am
OAX
-
MDW
2 stops29h 53m
Frontier
Deal found 1/24$657
This Aeromexico deal was found by Cheapflights users on 1/23. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/276:00 am
MDW
-
OAX
2 stops27h 29m
Aeromexico
mar. 3/38:25 pm
OAX
-
MDW
2 stops21h 20m
Aeromexico
Deal found 1/23$698
This Delta deal was found by Cheapflights users on 1/24. 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.
dom. 3/156:00 am
MDW
-
OAX
2 stops14h 00m
Delta
jue. 3/199:23 am
OAX
-
MDW
2 stops12h 08m
Delta
Deal found 1/24$740
This Delta deal was found by Cheapflights users on 1/25. 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.
lun. 2/236:00 am
MDW
-
OAX
2 stops13h 00m
Delta
lun. 3/28:01 am
OAX
-
MDW
2 stops14h 30m
Delta
Deal found 1/25$818
This Delta deal was found by Cheapflights users on 1/25. 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.
mié. 5/206:00 am
MDW
-
OAX
2 stops14h 15m
Delta
dom. 5/246:00 am
OAX
-
MDW
2 stops14h 45m
Delta
Deal found 1/25$838
This Delta deal was found by Cheapflights users on 1/25. 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.
vie. 2/276:00 am
MDW
-
OAX
2 stops13h 00m
Delta
mar. 3/310:14 am
OAX
-
MDW
2 stops12h 19m
Delta
Deal found 1/25$861

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 enero 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$535
(Delta)

One-way from

$255
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$537
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. 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 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 enero 26, 2026.
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

mié. 3/11

6:00 am-6:58 pm

2 stops13h 58m

Oaxaca Xoxocotlan

mié. 3/18

7:56 am-10:31 pm

2 stops13h 35m

$535

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

mié. 3/4

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

mié. 3/11

7:56 am-10:31 pm

2 stops13h 35m

$535

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

sáb. 3/7

6:00 am-8:40 am

2 stops26h 40m

Oaxaca Xoxocotlan

mié. 3/11

7:56 am-10:31 pm

2 stops13h 35m

$584

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

dom. 2/22

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

vie. 2/27

6:00 am-5:45 pm

2 stops11h 45m

$633

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

vie. 2/27

6:00 am-9:29 am

2 stops27h 29m

Oaxaca Xoxocotlan

mar. 3/3

8:25 pm-5:45 pm

2 stops21h 20m

$698

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

dom. 3/15

6:00 am-7:00 pm

2 stops14h 00m

Oaxaca Xoxocotlan

jue. 3/19

9:23 am-10:31 pm

2 stops12h 08m

$740

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

lun. 2/23

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

lun. 3/2

8:01 am-10:31 pm

2 stops14h 30m

$818

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

jue. 3/5

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

mié. 3/11

7:56 am-10:31 pm

2 stops13h 35m

$818

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

mié. 5/20

6:00 am-7:15 pm

2 stops14h 15m

Oaxaca Xoxocotlan

dom. 5/24

6:00 am-9:45 pm

2 stops14h 45m

$838

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

dom. 2/8

6:54 pm-8:35 am

1 stop13h 41m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 12 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Oaxaca flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $535, Aeromexico can have you in Oaxaca from Chicago Midway Airport in 13h. 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.

See more FAQs

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