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$200+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAX
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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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 octubre 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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.
vie. 11/76:00 amMDW - OAX
2 stops12h 47mDelta
mié. 11/1211:09 amOAX - MDW
2 stops12h 31mDelta
Deal found 10/30$584
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
lun. 11/106:54 pmMDW - PXM
1 stop17h 45mMultiple Airlines
vie. 11/1410:25 pmPXM - MDW
2 stops14h 12mMultiple Airlines
Deal found 10/29$652
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:54 pmMDW - PXM
1 stop17h 45mVolaris
vie. 12/194:35 pmPXM - MDW
3 stops27h 05mVolaris
Deal found 10/28$712
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/147:24 pmMDW - OAX
2 stops24h 18mFrontier
dom. 12/219:40 amOAX - MDW
2 stops36h 18mFrontier
Deal found 10/30$713
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/66:00 amMDW - OAX
2 stops12h 47mDelta
vie. 12/1210:23 amOAX - MDW
2 stops13h 24mDelta
Deal found 10/29$727
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/236:00 amMDW - OAX
2 stops10h 06mDelta
vie. 11/2810:23 amOAX - MDW
2 stops13h 17mDelta
Deal found 10/29$741
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/139:01 pmMDW - OAX
1 stop13h 34mVolaris
sáb. 12/209:08 amOAX - MDW
1 stop10h 32mVolaris
Deal found 10/29$794
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/126:54 pmMDW - PXM
2 stops21h 05mVolaris
dom. 11/161:14 pmPXM - MDW
3 stops27h 04mVolaris
Deal found 10/29$806
This Aeromexico deal was found by Cheapflights users on 10/29. 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.
lun. 11/106:00 amMDW - OAX
2 stops25h 32mAeromexico
lun. 12/18:19 pmOAX - MDW
2 stops27h 28mAeromexico
Deal found 10/29$853
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/246:54 pmMDW - PXM
2 stops21h 05mVolaris
lun. 12/294:35 pmPXM - MDW
2 stops17h 05mVolaris
Deal found 10/29$862
This Aeromexico deal was found by Cheapflights users on 10/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/86:00 amMDW - OAX
2 stops10h 55mAeromexico
sáb. 11/156:10 amOAX - MDW
2 stops17h 30mAeromexico
Deal found 10/30$868
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/169:01 pmMDW - HUX
2 stops12h 34mMultiple Airlines
mié. 12/1712:18 pmHUX - MDW
3 stops21h 22mMultiple Airlines
Deal found 10/30$913

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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$529
(Kiwi.com)

One-way from

$200
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$601
Provider with most accurate pricing for Chicago (CHI)-Oaxaca Xoxocotlan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Oaxaca Xoxocotlan flights.
Search Deals
From Chicago Midway to Oaxaca
Search Deals
One-way flight from Chicago Midway to Oaxaca
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 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

ChicagoPuerto Escondido

MDW - PXM

MDWPXM

Chicago Midway

lun. 11/10

6:54 pm-12:39 pm

1 stop17h 45m

Puerto Escondido

vie. 11/14

10:25 pm-12:37 pm

2 stops14h 12m

$652

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

mié. 4/22

10:35 am-9:11 pm

2 stops11h 36m

Oaxaca Xoxocotlan

dom. 4/26

6:05 am-9:45 pm

2 stops14h 40m

$664

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

jue. 1/29

1:42 pm-10:35 am

3 stops20h 53m

Oaxaca Xoxocotlan

mar. 2/10

4:24 pm-5:34 pm

2 stops25h 10m

$665

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

sáb. 4/18

6:00 am-7:13 pm

2 stops14h 13m

Oaxaca Xoxocotlan

dom. 4/26

6:05 am-9:45 pm

2 stops14h 40m

$684

ChicagoPuerto Escondido

MDW - PXM

MDWPXM

Chicago Midway

vie. 12/12

6:54 pm-12:39 pm

1 stop17h 45m

Puerto Escondido

vie. 12/19

4:35 pm-7:40 pm

3 stops27h 05m

$712

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

sáb. 12/6

6:00 am-6:47 pm

2 stops12h 47m

Oaxaca Xoxocotlan

vie. 12/12

10:23 am-11:47 pm

2 stops13h 24m

$727

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

jue. 1/29

6:00 am-7:08 pm

2 stops13h 08m

Oaxaca Xoxocotlan

mar. 2/10

6:01 am-5:32 pm

2 stops11h 31m

$733

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

dom. 11/23

6:00 am-4:06 pm

2 stops10h 06m

Oaxaca Xoxocotlan

vie. 11/28

10:23 am-11:40 pm

2 stops13h 17m

$741

ChicagoSanta Maria Huatulco

MDW - HUX

MDWHUX

Chicago Midway

lun. 2/16

10:35 am-9:39 am

2 stops23h 04m

Santa Maria Huatulco

mié. 2/25

10:26 am-9:46 pm

2 stops11h 20m

$743

ChicagoSanta Maria Huatulco

MDW - HUX

MDWHUX

Chicago Midway

mar. 4/21

6:00 am-2:59 pm

2 stops9h 59m

Santa Maria Huatulco

mar. 4/28

10:44 am-9:45 pm

2 stops10h 01m

$788

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 47 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 Volaris can get you from Chicago Midway Airport to State of Oaxaca in just under 11h 36m. Your travel time can differ by up to 9h 17m. 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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