Cheap Flights from Chicago to Oaxaca

Compare Chicago to Oaxaca flight deals

Find the cheapest month or even day of the year to fly to Oaxaca

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Flight deals from Chicago to Oaxaca

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Oaxaca Airport? If you want to travel next month, round-trip fares start from AED 1,311. Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Chicago to Oaxaca

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Oaxaca flights are currently cheapest in February.

Chicago to Oaxaca: Alternative routes

Compare routes from Chicago to Oaxaca below. You may find an airport to fly into that's cheaper, faster, or easier than Oaxaca.

Chicago to Oaxaca: Flight information

The things to know before you go.
Cheapest flight foundAED 374
Cheapest month to flyFebruary

Finding cheap flights from Chicago to Oaxaca: Frequently asked questions

The best price we found for a round-trip flight from Chicago to Oaxaca is AED 779. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Oaxaca. But we found flights with one stop from AED 779.
There are no flights flying from Chicago to Oaxaca, as of May 2026.
The cheapest month to fly from Chicago to Oaxaca is usually February.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Oaxaca Airport on Thursday, February 4, 2027.
No airlines currently offer direct flights between Chicago and Oaxaca Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Oaxaca but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Oaxaca is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Oaxaca is Viva.

Traveling from Chicago to Oaxaca Xoxocotlan International Airport (OAX): What you need to know

  • Chicago and Oaxaca (where Oaxaca Xoxocotlan International Airport is located) share the UTC-6 timezone. That means you won't have to change your watch on arrival.

  • To ensure you catch your flight from Chicago to OAX, leave plenty of time for things like check-in and baggage drop. Turning up two hours ahead of international departures and one hour before domestic flights is the general travel rule.

  • If you're going away during a popular month like July, get to the terminal even earlier. It's smart to arrive up to four hours before international flights and two hours ahead of a domestic departure. Expect lines to be longer during high seasons like Christmas, New Year and spring break.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Consider adding a stopover to find cheap flights from Chicago to OAX. Simply deselect 'Direct flights only' when searching for departures from Chicago O'Hare International Airport (ORD). Break the trip up (and maybe score a better deal) by stopping at one of these popular airports:

    • Dallas Fort Worth International Airport (DFW)

    • Houston George Bush Intercontinental Airport (IAH)

    • Mexico City Benito Juarez International Airport (MEX)

  • ORD is around 27 kilometers from central Chicago. If you're driving, catching a cab or ride-sharing from the center, it'll take you 30 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the travel time to be around 45 minutes.

  • Looking for a comfortable hotel near Chicago O'Hare International Airport? If you've booked an early flight from Chicago to Oaxaca Xoxocotlan International Airport, these stays will have you sleeping moments from check-in:

  • When it comes to Chicago O'Hare International Airport's on-time performance, 70% of flights arrive within the expected time frame.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Work a stopover into your journey at Dallas Fort Worth International Airport (DFW). It's a key transfer point for flights from Chicago to Oaxaca Xoxocotlan International Airport (OAX) out of Chicago Midway International Airport.

  • MDW is about 16 kilometers from central Chicago. It takes 25 minutes or so to get to the airport driving from the city center. Public transport takes roughly 30 minutes.

  • Want to treat yourself to an extra night away before catching your Chicago to OAX flight? Kick back in a hotel near Chicago Midway International Airport before your trip officially begins. These stays are expecting you:

  • As far as flight punctuality goes, Chicago Midway International Airport has an on-time arrival performance of 76%.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey to RFD from central Chicago is around 2 hours by public transport. If you're in a car, it'll take you roughly 1 hour 40 minutes to cover the 145 kilometers or so.

  • Make catching an early Chicago to Oaxaca Xoxocotlan International Airport flight the easiest part of your trip. Stay at one of these accommodation options close to Chicago Rockford International Airport and get to the check-in counter with plenty of time to spare:

  • The on-time performance rate of RFD is 71%. In other words, that's how frequently flights from this airport arrive at their final stop as planned.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Oaxaca Xoxocotlan International Airport (OAX)

  • Reserve a hotel close to OAX if you're catching a late flight from Chicago to Oaxaca Xoxocotlan International Airport. Pick one of these options and be in bed in no time flat:

  • Booking your ride around one week in advance of your Chicago to Oaxaca Xoxocotlan International Airport flight can help you find the best deal.

Getting from Oaxaca Xoxocotlan International Airport (OAX) to central Oaxaca

  • From Oaxaca Xoxocotlan International Airport, central Oaxaca is around 8 kilometers away. It takes about 20 minutes to reach the city center by car.

  • Traveling on public transport will take you around 35 minutes.

How to find the cheapest flights from Chicago to Oaxaca Xoxocotlan International Airport (OAX)

  • Right now, AED 374 is the best price we've found for a one-way ticket from Chicago to Oaxaca Xoxocotlan International Airport. The cheapest price for a return flight is AED 779. Remember fares can change due to demand at the time of booking.

  • To find cheap flights from Chicago to OAX, book in advance. Airlines generally offer the most competitive fares when tickets are first released.

  • Cheap Chicago to Oaxaca Xoxocotlan International Airport tickets are easier to find if you're not locked into specific dates. Try using the 'Whole month' search function to compare fares across the month and then pick the cheapest day.

  • Locking in a cheap plane ticket from Chicago to OAX is a breeze with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch when a better deal is available.

  • Filters make it easier to dig up a deal for your flight from Chicago to Oaxaca Xoxocotlan International Airport. Choose the airlines, flight times and stops that match your plans. Then sort the results by 'Cheapest' to find the most affordable option fast.

The best time to fly from Chicago to Oaxaca Xoxocotlan International Airport (OAX)

  • November is the quietest month for flights from Chicago to Oaxaca Xoxocotlan International Airport (OAX), while January is the most popular. Choose the ideal time to visit Oaxaca based on whether you prefer a bustling atmosphere or a more laid-back vibe.

  • Before locking in your Chicago to OAX plane ticket, consider the kind of weather you prefer. April is the warmest month in Oaxaca, with temperatures ranging from 12ºC (54ºF) to 30ºC (86ºF).

  • For cooler conditions, search for a cheap ticket from Chicago to Oaxaca Xoxocotlan International Airport in January when temperatures are between 7ºC (45ºF) and 24ºC (75ºF).

More about Oaxaca

  • Start your Oaxaca trip right by choosing the perfect place to stay. After booking your flight from Chicago to Oaxaca Xoxocotlan International Airport, explore our selection of accommodation options including:

  • There are so many things to do and see in this city, it can be hard to work out where to start. Centro Histórico de Oaxaca de Juárez, Templo de Santo Domingo and Zócalo (Plaza de la Constitución) are top sights which should feature on every Oaxaca itinerary.

Explore more of Mexico

  • Puebla is just one of the many cities in Mexico waiting to be explored after you've seen Oaxaca. Around 274 kilometers away to the northwest, check out popular attractions including Zócalo de Puebla, Temple of Our Lady of Guadalupe and Centro Histórico de Puebla.

  • If you're eager to discover another well-known destination in Mexico, consider Veracruz, roughly 257 kilometers north of Oaxaca. Veracruz Cathedral, San Juan de Ulúa and Malecón Veracruz Puerto are among the biggest draws.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.