HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oaxaca

$225+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAX
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Oaxaca with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 28, 2025.

This Aeromexico deal was found by Cheapflights users on 10/26. 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 11/810:35 amMDW - OAX
2 stops20h 48mAeromexico
Wed 12/38:09 pmOAX - MDW
2 stops20h 09mAeromexico
Deal found 10/26$497
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:54 pmMDW - OAX
1 stop15h 41mMultiple Airlines
Fri 11/141:10 pmOAX - MDW
2 stops23h 27mMultiple Airlines
Deal found 10/28$529
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:24 pmMDW - OAX
2 stops24h 18mFrontier
Sun 12/149:40 amOAX - MDW
2 stops25h 28mFrontier
Deal found 10/28$578
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:00 amMDW - OAX
2 stops10h 55mDelta
Wed 11/1911:09 amOAX - MDW
2 stops12h 31mDelta
Deal found 10/28$617
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:00 amMDW - OAX
2 stops10h 55mAeromexico
Wed 11/1911:09 amOAX - MDW
2 stops12h 31mAeromexico
Deal found 10/28$655
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.
Sun 11/96:54 pmMDW - OAX
1 stop15h 41mVolaris
Fri 11/144:52 pmOAX - MDW
3 stops23h 26mVolaris
Deal found 10/28$679
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amMDW - OAX
2 stops12h 47mDelta
Sat 12/66:10 amOAX - MDW
2 stops9h 34mDelta
Deal found 10/27$691
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:54 pmMDW - OAX
1 stop13h 41mVolaris
Sun 11/302:48 pmOAX - MDW
2 stops46h 16mVolaris
Deal found 10/27$692
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:00 amMDW - OAX
2 stops10h 55mDelta
Sat 11/156:10 amOAX - MDW
2 stops9h 33mDelta
Deal found 10/27$773
This Gotogate deal was found by Cheapflights users on 10/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:54 pmMDW - OAX
1 stop13h 41mVolaris
Wed 12/178:28 pmOAX - MDW
1 stop13h 12mVolaris
Deal found 10/26$780
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 amMDW - OAX
2 stops12h 47mDelta
Fri 11/78:07 amOAX - MDW
2 stops14h 07mDelta
Deal found 10/27$788

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$497
(Aeromexico)

One-way from

$225
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$601
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. 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 October 28, 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

Sat 11/8

10:35 am-7:23 am

2 stops20h 48m

Oaxaca Xoxocotlan

Wed 12/3

8:09 pm-4:18 pm

2 stops20h 09m

$497

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 11/9

6:54 pm-10:35 am

1 stop15h 41m

Oaxaca Xoxocotlan

Fri 11/14

1:10 pm-12:37 pm

2 stops23h 27m

$529

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 12/7

7:24 pm-7:42 pm

2 stops24h 18m

Oaxaca Xoxocotlan

Sun 12/14

9:40 am-11:08 am

2 stops25h 28m

$578

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 11/8

6:00 am-4:55 pm

2 stops10h 55m

Oaxaca Xoxocotlan

Wed 11/19

11:09 am-11:40 pm

2 stops12h 31m

$617

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 11/8

6:00 am-4:55 pm

2 stops10h 55m

Oaxaca Xoxocotlan

Wed 11/19

11:09 am-11:40 pm

2 stops12h 31m

$655

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 12/2

6:00 am-4:59 pm

2 stops10h 59m

Oaxaca Xoxocotlan

Mon 12/8

10:28 am-11:47 pm

2 stops13h 19m

$679

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 11/9

11:10 am-5:39 am

2 stops18h 29m

Oaxaca Xoxocotlan

Fri 11/14

4:52 pm-4:18 pm

3 stops23h 26m

$680

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 12/3

6:00 am-6:47 pm

2 stops12h 47m

Oaxaca Xoxocotlan

Sat 12/6

6:10 am-3:44 pm

2 stops9h 34m

$691

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 11/23

6:54 pm-8:35 am

1 stop13h 41m

Oaxaca Xoxocotlan

Sun 11/30

2:48 pm-1:04 pm

2 stops46h 16m

$692

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 1/7

6:54 pm-8:35 am

1 stop13h 41m

Oaxaca Xoxocotlan

Wed 3/11

8:06 am-9:46 pm

2 stops12h 40m

$756

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 22 results
1
2
3

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Oaxaca flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $617, Aeromexico can have you in Oaxaca from Chicago Midway Airport in 10h 55m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Oaxaca

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Oaxaca flights
O'Hare Intl to Puerto Escondido flights
O'Hare Intl to Santa Maria Huatulco flights
Midway to Santa Maria Huatulco flights
Midway to Puerto Escondido flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.