$216 Cheap Flights from Chicago (MDW) to Oaxaca Intl. (OAX)

View $216 flight on Sat, Aug 16, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Oaxaca Intl. Airport

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Cheap Flights from Chicago to Oaxaca Intl. (MDW-OAX)

Prices were available within the past 7 days and start at $216 for one-way flights and $503 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aeromexico
Tue, Sep 23 - Tue, Sep 30
MDW
Chicago
OAX
Oaxaca
$503 Roundtrip, found 3 days ago
$503
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Tue, Sep 23 from Chicago to Oaxaca, returning Tue, Sep 30, priced at $503 found 3 days ago
Delta
Wed, Apr 29 - Wed, May 6
MDW
Chicago
OAX
Oaxaca
$503 Roundtrip, found 10 hours ago
$503
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, Apr 29 from Chicago to Oaxaca, returning Wed, May 6, priced at $503 found 10 hours ago
Delta
Fri, Jan 16 - Wed, Jan 21
MDW
Chicago
OAX
Oaxaca
$523 Roundtrip, found 3 days ago
$523
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 16 from Chicago to Oaxaca, returning Wed, Jan 21, priced at $523 found 3 days ago
Delta
Tue, Sep 23 - Tue, Sep 30
MDW
Chicago
OAX
Oaxaca
$528 Roundtrip, found 3 days ago
$528
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 23 from Chicago to Oaxaca, returning Tue, Sep 30, priced at $528 found 3 days ago
Delta
Wed, Apr 15 - Wed, Apr 22
MDW
Chicago
OAX
Oaxaca
$548 Roundtrip, found 11 hours ago
$548
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Apr 15 from Chicago to Oaxaca, returning Wed, Apr 22, priced at $548 found 11 hours ago
Aeromexico
Sat, Sep 13 - Fri, Sep 19
MDW
Chicago
OAX
Oaxaca
$572 Roundtrip, found 3 days ago
$572
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Sat, Sep 13 from Chicago to Oaxaca, returning Fri, Sep 19, priced at $572 found 3 days ago
Delta
Wed, Apr 29 - Wed, May 6
MDW
Chicago
OAX
Oaxaca
$593 Roundtrip, found 10 hours ago
$593
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, Apr 29 from Chicago to Oaxaca, returning Wed, May 6, priced at $593 found 10 hours ago
Aeromexico
Sat, Sep 13 - Fri, Sep 19
MDW
Chicago
OAX
Oaxaca
$601 Roundtrip, found 3 days ago
$601
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Sat, Sep 13 from Chicago to Oaxaca, returning Fri, Sep 19, priced at $601 found 3 days ago
Volaris
Sat, Aug 9 - Thu, Aug 14
MDW
Chicago
OAX
Oaxaca
$604 Roundtrip, found 1 day ago
$604
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Aug 9 from Chicago to Oaxaca, returning Thu, Aug 14, priced at $604 found 1 day ago
Delta
Tue, Aug 26 - Wed, Sep 3
MDW
Chicago
OAX
Oaxaca
$610 Roundtrip, found 1 day ago
$610
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Oaxaca, returning Wed, Sep 3, priced at $610 found 1 day ago

Alternative airports near Oaxaca

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Xoxocotlan Intl. OAX. Cheapest and Closest option available. Average driving time to city center is 12 minutes. Flights from $1,452
OAX
Xoxocotlan Intl.
CheapestClosest
Average driving time to city center12 min
Flights from $1,452
Flights from Chicago (MDW) to Oaxaca Intl. (OAX)
Origin airport
Midway Intl.
Destination airport
Oaxaca Intl.
Airlines serving
Aeromexico, Delta
Roundtrip price
$502
Distance
1793 mi

Chicago to Oaxaca Intl. Flights

The cheapest times to fly from Chicago to Oaxaca Intl.

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Oaxaca Intl. are during the month of September. You can find some of the cheapest flights from Chicago to Oaxaca Intl. with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Oaxaca Intl.

Sunday is one of the best days to book for cheap flights from Chicago to Oaxaca Intl.: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Oaxaca Intl.

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Oaxaca Intl. in 2025. You can also book with separate airlines for your outbound and return journeys, from $216 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Oaxaca Intl. flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Oaxaca Intl. airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Xoxocotlan Intl. Airport (OAX) cost?
Discover the latest flight deals from MDW to OAX by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to OAX?
The cheapest flights from MDW to OAX are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to OAX?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to OAX. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Xoxocotlan Intl. Airport (OAX)?
Nonstop flights from Midway Intl. Airport (MDW) to Xoxocotlan Intl. Airport (OAX) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to OAX?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Xoxocotlan Intl. Airport (OAX)?
Select a flight from Midway Intl. Airport (MDW) to Xoxocotlan Intl. Airport (OAX) that leaves before 3 PM to reduce the likelihood of delays. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Xoxocotlan Intl. Airport (OAX) last-minute?
Holding off until just before your departure to book a ticket from MDW to OAX generally means paying more. While you might find some last-minute offers, they aren't always guaranteed. Allow some flexibility in your schedule for the best chance of scoring a bargain.
Is it cheaper to book a MDW to OAX flight and hotel package?
Opting for a MDW to OAX flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our wide range of accommodations and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Xoxocotlan Intl. Airport (OAX)?
You can usually cancel or reschedule your MDW to OAX flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.