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Oaxaca

$191+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAX
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$508
(Delta)

One-way from

$191
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$375
From Chicago Midway to Oaxaca Xoxocotlan
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One-way flight from Chicago Midway to Oaxaca Xoxocotlan
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Highest demand for flights based on searches. 13% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 11/156:00 amMDW - OAX
2 stops12h 47mDelta
Tue 11/1810:28 amOAX - MDW
2 stops13h 04mDelta
Deal found 9/11$508
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:00 amMDW - OAX
2 stops11h 02mMultiple Airlines
Tue 9/234:36 pmOAX - MDW
1 stop25h 40mMultiple Airlines
Deal found 9/9$560
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/178:39 pmMDW - OAX
1 stop14h 59mVolaris
Tue 9/234:36 pmOAX - MDW
1 stop25h 40mVolaris
Deal found 9/9$581
This Aeromexico deal was found by Cheapflights users on 9/10. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/126:00 amMDW - OAX
2 stops17h 30mAeromexico
Tue 10/216:05 amOAX - MDW
2 stops15h 09mAeromexico
Deal found 9/10$615
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/108:39 pmMDW - OAX
1 stop14h 59mVolaris
Tue 10/149:17 pmOAX - MDW
2 stops20h 59mVolaris
Deal found 9/10$616
This Delta deal was found by Cheapflights users on 9/10. 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 9/256:00 amMDW - OAX
2 stops13h 16mDelta
Tue 9/308:10 amOAX - MDW
2 stops12h 26mDelta
Deal found 9/10$645
This Delta deal was found by Cheapflights users on 9/11. 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.
Mon 10/206:00 amMDW - OAX
2 stops10h 25mDelta
Fri 10/248:15 amOAX - MDW
2 stops12h 59mDelta
Deal found 9/11$728
This Aeromexico deal was found by Cheapflights users on 9/11. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:00 amMDW - OAX
2 stops17h 45mAeromexico
Wed 10/158:03 pmOAX - MDW
2 stops25h 11mAeromexico
Deal found 9/11$762
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:39 pmMDW - OAX
1 stop12h 04mMultiple Airlines
Fri 11/1410:25 pmOAX - MDW
2 stops14h 12mMultiple Airlines
Deal found 9/10$797
This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 10/246:00 amMDW - OAX
2 stops10h 25mDelta
Sat 11/88:27 amOAX - MDW
2 stops13h 47mDelta
Deal found 9/10$845
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 10/76:00 amMDW - OAX
2 stops10h 15mDelta
Mon 10/138:15 amOAX - MDW
2 stops12h 59mDelta
Deal found 9/11$847

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 September 11, 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

Sun 10/12

6:00 am-10:30 pm

2 stops17h 30m

Oaxaca Xoxocotlan

Tue 10/21

6:05 am-10:14 pm

2 stops15h 09m

$615

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 10/10

8:39 pm-10:38 am

1 stop14h 59m

Oaxaca Xoxocotlan

Tue 10/14

9:17 pm-7:16 pm

2 stops20h 59m

$616

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 9/30

6:00 am-6:16 pm

2 stops13h 16m

Oaxaca Xoxocotlan

Sun 10/5

6:05 am-9:36 pm

2 stops14h 31m

$645

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Thu 9/25

6:00 am-6:16 pm

2 stops13h 16m

Oaxaca Xoxocotlan

Tue 9/30

8:10 am-9:36 pm

2 stops12h 26m

$645

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 10/6

10:35 am-10:45 pm

2 stops13h 10m

Oaxaca Xoxocotlan

Sat 10/11

8:15 am-10:14 pm

2 stops12h 59m

$645

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 1/5

6:00 am-7:23 pm

2 stops13h 23m

Oaxaca Xoxocotlan

Sun 1/18

6:01 am-4:25 pm

2 stops10h 24m

$649

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 10/20

6:00 am-3:25 pm

2 stops10h 25m

Oaxaca Xoxocotlan

Fri 10/24

8:15 am-10:14 pm

2 stops12h 59m

$728

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 10/3

6:00 am-10:45 pm

2 stops17h 45m

Oaxaca Xoxocotlan

Wed 10/15

8:03 pm-10:14 pm

2 stops25h 11m

$762

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 10/7

6:00 am-3:15 pm

2 stops10h 15m

Oaxaca Xoxocotlan

Sun 10/12

10:01 am-10:14 pm

2 stops11h 13m

$762

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 10/24

6:00 am-3:25 pm

2 stops10h 25m

Oaxaca Xoxocotlan

Sat 11/8

8:27 am-10:14 pm

2 stops13h 47m

$845

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 20 results
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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 $645, Aeromexico can have you in Oaxaca from Chicago Midway Airport in 13h 16m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Oaxaca?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Oaxaca (average of $510). Flying from Chicago Midway Airport to 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

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