Cheap flights from Chicago to Oaxaca

One-way fares from $153 · CHI → OAX · prices found by travellers in the last 48 hours

Compare all dates Oaxaca → Chicago
Cheapest fare
$153

Viva Aerobus · Tue, Nov 10

Cheapest month
November

from $153

Direct flights
Not recently

Usually 1+ stop

Quickest trip
5h 19m

2,890 km

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Cheapest month to fly from Chicago to Oaxaca

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $153

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Viva Aerobus
Depart01:05 Tue, Nov 10ORD → OAX 5h 19m · 1 stop
$153one way, per person
View deal
Volaris
Depart06:29 Fri, Nov 13ORD → OAX 5h 25m · 1 stop
$279one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Oaxaca

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in OaxacaCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in OaxacaTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in OaxacaPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in OaxacaCompare rental cars from major brands on EconomyBookings Compare cars →

Stay connected

eSIM for MexicoMobile data from the moment you land, by Airalo Get eSIM →

About flights from Chicago to Oaxaca

Chicago (CHI) and Oaxaca (OAX) are about 2,890 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 5h 19m. Over the next few months, one-way fares start from $153, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Oaxaca?

The cheapest one-way fare we've seen recently is $153 with Viva Aerobus, departing Tuesday, November 10, 2026.

What is the cheapest month to fly from Chicago to Oaxaca?

November 2026 currently has the lowest fares, from $153 one way.

Are there direct flights from Chicago to Oaxaca?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Chicago to Oaxaca?

The quickest journey we've seen takes about 5h 19m. Chicago and Oaxaca are around 2,890 km apart.

Which airlines fly from Chicago to Oaxaca?

Recent fares on this route were with Viva Aerobus and Volaris.

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