Cheap flights from Oaxaca to Chicago

One-way fares from $247 · OAX → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Oaxaca
Cheapest fare
$247

Viva Aerobus · Fri, Nov 6

Cheapest month
November

from $247

Direct flights
Not recently

Usually 1+ stop

Quickest trip
5h 12m

2,890 km

Get a price alert

We'll email you when Oaxaca → Chicago drops to your price. It's free, and you can stop any time.

Today's cheapest fare is $247. We'll send one email to confirm. See our privacy policy.

Cheapest month to fly from Oaxaca to Chicago

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

  1. November 2026 Cheapest $247

Cheapest dates in November 2026

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

Viva Aerobus
Depart12:53 Fri, Nov 6OAX → ORD 5h 12m · 1 stop
$247one way, per person
View deal
Volaris
Depart20:01 Sun, Nov 8OAX → ORD 5h 12m · 1 stop
$311one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Chicago

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

Where to stay

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

Things to do

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

Getting around

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

Stay connected

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

About flights from Oaxaca to Chicago

Oaxaca (OAX) and Chicago (CHI) 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 12m. Over the next few months, one-way fares start from $247, 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 Oaxaca to Chicago?

The cheapest one-way fare we've seen recently is $247 with Viva Aerobus, departing Friday, November 6, 2026.

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

November 2026 currently has the lowest fares, from $247 one way.

Are there direct flights from Oaxaca to Chicago?

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

How long is the flight from Oaxaca to Chicago?

The quickest journey we've seen takes about 5h 12m. Oaxaca and Chicago are around 2,890 km apart.

Which airlines fly from Oaxaca to Chicago?

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

More cheap flights from Oaxaca

Compare flights to Chicago from other cities →