$118 Find Cheap Flights from Chicago to Oaxaca

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Oaxaca departing on 9/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oaxaca.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oaxaca.
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Cheap Flights from Chicago to Oaxaca

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Oaxaca
Oaxaca1 stop$252
Oaxaca
Oaxaca1 stop$252

Book Cheap Chicago to Oaxaca Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Oaxaca that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Oaxaca

Fri, Oct 10 - Thu, Oct 16
Viva Logo
12:25 pm - 6:50 pmORD-OAX
7h 25m1 stop
Viva Logo
2:25 pm - 11:35 pmOAX-ORD
8h 10m1 stop
$252Viva
Find Deal
Fri, Sep 12 - Fri, Sep 19
Viva Logo
12:25 pm - 8:35 pmORD-OAX
9h 10m1 stop
Viva Logo
9:15 pm - 11:50 pmOAX-ORD
25h 35m1 stop
$281Viva
Find Deal
Sat, Sep 13 - Sat, Sep 20
 Logo
7:25 am - 3:16 pmORD-PXM
8h 51m1 stop
 Logo
8:40 am - 11:50 pmPXM-ORD
14h 10m1 stop
Mon, Aug 18 - Tue, Aug 26
 Logo
1:40 am - 12:53 pmORD-OAX
12h 13m1 stop
 Logo
2:20 pm - 11:50 pmOAX-ORD
8h 30m1 stop
Mon, Sep 29 - Sat, Oct 4
Volaris Logo
1:40 am - 12:53 pmORD-OAX
12h 13m1 stop
Volaris Logo
9:19 am - 11:32 pmOAX-ORD
13h 13m1 stop
$310Volaris
Find Deal
Thu, Oct 16 - Sun, Oct 26
Volaris Logo
1:55 am - 10:38 amORD-OAX
9h 43m1 stop
Volaris Logo
4:36 pm - 12:15 amOAX-ORD
6h 39m1 stop
$324Volaris
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
6:00 am - 3:25 pmMDW-OAX
10h 25m2 stops
Delta Logo
8:15 am - 9:10 pmOAX-MDW
11h 55m2 stops
$544Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
12:43 pm - 10:45 pmMDW-OAX
11h 02m2 stops
Delta Logo
6:00 am - 5:35 pmOAX-MDW
10h 35m2 stops
$573Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Aeromexico Logo
6:00 am - 3:25 pmMDW-PXM
10h 25m2 stops
Aeromexico Logo
4:05 pm - 9:36 pmPXM-MDW
28h 31m2 stops
$1,235Aeromexico
Find Deal
Sat, Sep 13 - Sat, Sep 20
Aeromexico Logo
6:00 am - 3:25 pmMDW-PXM
10h 25m2 stops
Aeromexico Logo
4:05 pm - 9:36 pmPXM-MDW
28h 31m2 stops
$1,240Aeromexico
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Oaxaca flights

Get data-powered insights and trends into flights from Chicago to Oaxaca to help you find the cheapest flights, the best time to fly and much more.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Oaxaca, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Oaxaca is September, when tickets cost $359 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $857 and $608 respectively.

What’s the cheapest day of the week to fly from Chicago to Oaxaca?

The average price of all round-trip flights from Chicago to Oaxaca clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Oaxaca, look for departures on Mondays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Oaxaca, Tuesday is the cheapest day to fly and Friday is the most expensive.

How far in advance should I book a flight from Chicago to Oaxaca?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Oaxaca, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Oaxaca, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.


Good to know

Low seasonAugust
Cheapest flight$118
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Airport to Oaxaca

FAQs - booking Oaxaca flights

  • How does KAYAK find such low prices on flights from Chicago to Oaxaca?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Oaxaca.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Oaxaca?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Oaxaca is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Oaxaca?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Oaxaca with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Oaxaca?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Oaxaca up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Oaxaca?

    The cheapest time of day to fly to Oaxaca is generally in the evening, when round-trip flights cost $470 on average. Morning departures are around 42% more expensive than evening flights, on average. The most expensive time of day to fly to Oaxaca is generally in the morning, which is peak travel time and where the average cost of a ticket is $669.

Reviews of the top 5 airlines serving from Chicago to Oaxaca

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oaxaca. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Oaxaca? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 7980 reviews
7.3Food
7.9Entertainment
8.2Boarding
8.5Crew
7.9Comfort
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

The ground staff were not as friendly and nice to the passengers as the air crew. Flight attendants, cockpit crew were great and very nice to everyone on board.

My flight was delayed, then I got transferred to a new flight that was also delayed- which wasn’t Aeromexico’s fault, it was because of weather conditions. Most of the crew was very nice and patient, except for one or two flight attendants who were rude. The entertainment wasn’t on, so all the screens were off.

My wife's entertainment system did not work. Payed for flight upgrade but did not receive advertised "free WiFi".

Annoying that we had to go to departures and get boarding passes. Should allow us to be booked all the way through, this is the only airline i have this problem with in MEX. Late boarding and take off

Lousy No wheelchair. As normal at Atlanta Cheap airline Cheap aero plane. - Neither entertainment nor food on a 5 hour saga

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

This is not a low cost airline. Stop acting like o e.

Aeromexico crew made me check my hand luggage in the door of the plane. As soon as I reach Mexico City, I notice that my luggage was opened and 8 games of Nintendo Switch were stolen (700 dllrs value aprox) (the console was there) but the games were stolen. I am very dissapointed of Aeromexico and all the crew. Instead of being a good trip, It was a sad trip

Ok. But we arrived to a remote terminal which meant that a bus had to take us to the terminal building

Old aircraft the audio of the entertainment dosent work Dirty seats

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

The bad thing is they didnt send me the deatils about how much alowed bagage ehight 1 carryon or cheacking bag Also they just send in spanishlanfuage i couldnt understand emails

The boarding process was ridiculous. The boarded groups into a walkway just before the aerobridge (about 20 mins late), whilst we watch the crew stroll casually onto the plane, running late. And then they made us line up on then aerobridge with no aircon for 10 minutes before we boarded. Staff are just as ghetto as the customers. Wouldn’t fly again

They closed the gate over 25 minutes before departure and I didn’t get to board.

No empathy for my situation, arriving at the check-in counter 5 minutes after the deadline to deposit baggage due to a very delayed incoming intercontinental flight. The attendant simply stared past my shoulder and picked up the microphone to announce a "reminder that all passengers must arrive at least one hour before the flight" before speaking to the passenger behind me. I understand that there are rules above deadlines but at least show some damn empathy. It was Christmas morning and I'd been travelling for 20 hours for goodness sake!

They no longer offer anything free to eat or drink, everything is sold, not even a bottle of water is offered for free.

I paid for Viva play and most of the time didn’t work and also I order some drinks and the price was to expensive.

The terminal and gate was never the right one announced in the Viva App, neither in screens, moved from one terminal to another

The smart/express line to check in was a mess, employees not doing the process smooth and quick, using their mobile phones, talking to their coworkers

My flight was changed 4 tienes , delaying my arrival lore than 5 hours

Everything was okay, but boarding begins late and when I was returning there was a gate change. The app never showed the change.

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

Everything you need to know for your flight from Chicago to Oaxaca

Cabin class types available on flights to Oaxaca

Cabin classes available on flights to Oaxaca. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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