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Oaxaca

$239+ Cheap flights from Midway (MDW) 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAX
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Midway to Oaxaca

Keep the following information in mind while searching for Midway to Oaxaca flight deals. Data was last updated July 30, 2025.

Round-trip from

$504
(Delta)

One-way from

$254
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$608
From Chicago Midway to Oaxaca
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One-way flight from Chicago Midway to Oaxaca
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Highest demand for flights based on searches. 11% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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 9/410:31 amMDW - OAX
2 stops13h 14mDelta
Thu 9/118:05 amOAX - MDW
2 stops12h 31mDelta
Deal found 7/28$504
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 10/98:39 pmMDW - OAX
1 stop12h 04mMultiple Airlines
Mon 10/139:20 amOAX - MDW
2 stops37h 51mMultiple Airlines
Deal found 7/29$655
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:00 amMDW - PXM
2 stops16h 35mMultiple Airlines
Fri 9/1910:25 pmPXM - MDW
2 stops21h 45mMultiple Airlines
Deal found 7/29$707
This Aeromexico deal was found by Cheapflights users on 7/27. 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 9/1212:43 pmMDW - OAX
2 stops11h 02mAeromexico
Sat 9/206:00 amOAX - MDW
2 stops14h 10mAeromexico
Deal found 7/27$739
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sat 8/28:39 pmMDW - OAX
1 stop12h 04mVolaris
Mon 8/47:40 pmOAX - MDW
1 stop22h 36mVolaris
Deal found 7/29$899
This Delta deal was found by Cheapflights users on 7/30. 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.
Wed 9/106:00 amMDW - PXM
2 stops10h 05mDelta
Sun 9/212:20 pmPXM - MDW
2 stops42h 20mDelta
Deal found 7/30$947
This Expedia deal was found by Cheapflights users on 7/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:00 amMDW - PXM
2 stops10h 10mAeromexico
Thu 9/254:00 pmPXM - MDW
2 stops28h 36mAeromexico
Deal found 7/27$1,014
This Aeromexico deal was found by Cheapflights users on 7/29. 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.
Mon 8/46:00 amMDW - HUX
2 stops13h 24mAeromexico
Tue 8/57:29 amHUX - MDW
2 stops13h 13mAeromexico
Deal found 7/29$1,367
This WestJet deal was found by Cheapflights users on 7/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:10 pmMDW - HUX
2 stops49h 29mWestJet
Tue 1/67:00 pmHUX - MDW
2 stops23h 08mWestJet
Deal found 7/29$4,045

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 July 30, 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

Thu 9/4

10:31 am-10:45 pm

2 stops13h 14m

Oaxaca Xoxocotlan

Thu 9/11

8:05 am-9:36 pm

2 stops12h 31m

$504

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Thu 10/9

8:39 pm-7:43 am

1 stop12h 04m

Oaxaca Xoxocotlan

Mon 10/13

9:20 am-12:11 am

2 stops37h 51m

$655

ChicagoPuerto Escondido

MDW - PXM

MDWPXM

Chicago Midway

Fri 9/12

6:00 am-9:35 pm

2 stops16h 35m

Puerto Escondido

Fri 9/19

10:25 pm-9:10 pm

2 stops21h 45m

$707

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 9/12

12:43 pm-10:45 pm

2 stops11h 02m

Oaxaca Xoxocotlan

Sat 9/20

6:00 am-9:10 pm

2 stops14h 10m

$739

ChicagoSanta Maria Huatulco

MDW - HUX

MDWHUX

Chicago Midway

Sat 1/3

6:00 am-5:26 pm

2 stops11h 26m

Santa Maria Huatulco

Sat 1/17

11:51 am-9:46 pm

2 stops9h 55m

$881

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 8/2

8:39 pm-7:43 am

1 stop12h 04m

Oaxaca Xoxocotlan

Mon 8/4

7:40 pm-7:16 pm

1 stop22h 36m

$899

ChicagoPuerto Escondido

MDW - PXM

MDWPXM

Chicago Midway

Wed 9/10

6:00 am-3:05 pm

2 stops10h 05m

Puerto Escondido

Sun 9/21

2:20 pm-9:40 am

2 stops42h 20m

$947

ChicagoPuerto Escondido

MDW - PXM

MDWPXM

Chicago Midway

Sat 9/20

6:00 am-3:10 pm

2 stops10h 10m

Puerto Escondido

Thu 9/25

4:00 pm-9:36 pm

2 stops28h 36m

$1,014

ChicagoSanta Maria Huatulco

MDW - HUX

MDWHUX

Chicago Midway

Sat 9/13

6:00 am-6:19 pm

2 stops13h 19m

Santa Maria Huatulco

Sat 9/20

12:15 pm-9:36 pm

2 stops32h 21m

$1,486

ChicagoSanta Maria Huatulco

MDW - HUX

MDWHUX

Chicago Midway

Tue 12/30

12:10 pm-1:39 pm

2 stops49h 29m

Santa Maria Huatulco

Tue 1/6

7:00 pm-6:08 pm

2 stops23h 08m

$4,045

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 15 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Oaxaca
No data available for this route at this time. Please check back soon.

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 July 30, 2025.
Get a feel of what it's like to fly with Delta, Aeromexico, and WestJet from Chicago Midway Airport to Oaxaca by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

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!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

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!
Aeromexico
7.5
Good
1,721 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

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!
WestJet
7.2
Good
2,975 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

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!
Volaris
6.6
Okay
1,164 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

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 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 are the cheapest airlines to fly from Chicago Midway Airport to State of Oaxaca one-way?

    To fly one-way, consider booking your trip with Volaris, which is currently one of the cheapest options available, starting at $254. Delta flights start at $502 while deals on Aeromexico start at $1,369 one-way.

  • What are the most popular routes from Chicago Midway Airport to State of Oaxaca?

    When deciding which route to take from Chicago Midway Airport to State of Oaxaca consider Chicago Midway - Oaxaca Xoxocotlan, Chicago Midway - Santa Maria Huatulco or Chicago Midway - Puerto Escondido as they are the most popular.

  • 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 State of Oaxaca?

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

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