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$235+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAX
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$515
(Delta)

One-way from

$235
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$517
Provider with most accurate pricing for Chicago (CHI)-Oaxaca Xoxocotlan flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Oaxaca Xoxocotlan flights.
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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. 18% potential increase in price ($125 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 January 2026
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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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/7. 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 3/46:00 amMDW - OAX
2 stops13h 00mDelta
Wed 3/117:56 amOAX - MDW
2 stops13h 35mDelta
Deal found 1/7$515
This Delta deal was found by Cheapflights users on 1/5. 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 3/76:00 amMDW - OAX
2 stops12h 15mDelta
Wed 3/117:56 amOAX - MDW
2 stops13h 35mDelta
Deal found 1/5$535
This Delta deal was found by Cheapflights users on 1/7. 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 8/181:05 pmMDW - OAX
2 stops10h 38mDelta
Sat 8/226:05 amOAX - MDW
2 stops14h 41mDelta
Deal found 1/7$549
This Delta deal was found by Cheapflights users on 1/6. 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 2/206:00 amMDW - OAX
2 stops13h 00mDelta
Fri 2/278:01 amOAX - MDW
2 stops14h 30mDelta
Deal found 1/6$555
This Aeromexico deal was found by Cheapflights users on 1/6. 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.
Sat 2/1411:06 amMDW - OAX
2 stops21h 39mAeromexico
Tue 2/178:25 pmOAX - MDW
2 stops21h 20mAeromexico
Deal found 1/6$564
This Delta deal was found by Cheapflights users on 1/7. 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 2/236:00 amMDW - OAX
2 stops13h 00mDelta
Mon 3/910:12 amOAX - MDW
2 stops11h 19mDelta
Deal found 1/7$588
This Delta deal was found by Cheapflights users on 1/5. 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 3/266:25 amMDW - OAX
2 stops14h 20mDelta
Tue 3/3110:45 amOAX - MDW
2 stops10h 46mDelta
Deal found 1/5$595
This Delta deal was found by Cheapflights users on 1/6. 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 1/266:00 amMDW - OAX
2 stops13h 03mDelta
Fri 2/1310:14 amOAX - MDW
2 stops12h 17mDelta
Deal found 1/6$596
This Delta deal was found by Cheapflights users on 1/7. 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 2/226:00 amMDW - OAX
2 stops13h 00mDelta
Fri 2/278:01 amOAX - MDW
2 stops14h 30mDelta
Deal found 1/7$613
This Delta deal was found by Cheapflights users on 1/6. 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 2/156:00 amMDW - OAX
2 stops13h 00mDelta
Sat 2/288:01 amOAX - MDW
2 stops14h 30mDelta
Deal found 1/6$619
This Priceline deal was found by Cheapflights users on 1/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/96:00 amMDW - OAX
2 stops16h 38mAeromexico
Wed 2/118:25 pmOAX - MDW
2 stops21h 20mAeromexico
Deal found 1/7$629
This Aeromexico deal was found by Cheapflights users on 1/7. 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.
Sat 2/2811:06 amMDW - HUX
2 stops22h 46mAeromexico
Wed 3/410:12 amHUX - MDW
2 stops12h 19mAeromexico
Deal found 1/7$903

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 January 8, 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

Wed 3/4

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

Wed 3/11

7:56 am-10:31 pm

2 stops13h 35m

$515

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 2/23

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

Mon 3/9

10:12 am-10:31 pm

2 stops11h 19m

$588

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 3/25

6:25 am-5:04 pm

2 stops11h 39m

Oaxaca Xoxocotlan

Tue 3/31

10:45 am-10:31 pm

2 stops10h 46m

$588

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 1/26

6:00 am-7:03 pm

2 stops13h 03m

Oaxaca Xoxocotlan

Fri 2/13

10:14 am-10:31 pm

2 stops12h 17m

$596

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 2/27

6:00 am-7:25 am

2 stops25h 25m

Oaxaca Xoxocotlan

Tue 3/3

8:25 pm-5:45 pm

2 stops21h 20m

$599

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 2/22

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

Fri 2/27

8:01 am-10:31 pm

2 stops14h 30m

$613

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 2/15

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

Sat 2/28

8:01 am-10:31 pm

2 stops14h 30m

$619

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 2/9

6:00 am-10:38 pm

2 stops16h 38m

Oaxaca Xoxocotlan

Wed 2/11

8:25 pm-5:45 pm

2 stops21h 20m

$629

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 2/4

6:00 am-10:34 pm

2 stops16h 34m

Oaxaca Xoxocotlan

Wed 2/11

10:44 am-10:22 pm

2 stops11h 38m

$655

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 3/14

6:00 am-4:12 pm

2 stops35h 12m

Oaxaca Xoxocotlan

Fri 3/20

8:40 am-11:32 pm

2 stops37h 52m

$670

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 38 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.

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.

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

    Delta and Aeromexico can get you from Chicago Midway Airport to State of Oaxaca in just under 13h. Your travel time can differ by up to 9h 46m. There are 1792 mi between Chicago Midway Airport and State of Oaxaca. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

See more FAQs

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