$102 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 5/16. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Oaxaca

 
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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Best Oaxaca Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Oaxaca
Oaxaca1 stop$309
Oaxaca
Oaxaca1 stop$309

Cheap Flights from Chicago to Oaxaca

 
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.

Recent round-trip flight deals from Chicago to Oaxaca

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Oaxaca.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
6:34 pm - 1:50 pmORD-OAX
20h 16m1 stop
 Logo
1:53 pm - 11:35 pmOAX-ORD
8h 42m1 stop
Sun, May 11 - Tue, May 13
 Logo
6:34 pm - 1:16 pmORD-OAX
19h 42m1 stop
 Logo
2:20 pm - 11:45 pmOAX-ORD
8h 25m1 stop
Fri, May 30 - Sun, Jun 8
Viva Logo
12:35 pm - 1:50 pmORD-OAX
26h 15m1 stop
Viva Logo
2:20 pm - 11:35 pmOAX-ORD
8h 15m1 stop
$329Viva
Find Deal
Tue, May 13 - Wed, May 21
Volaris Logo
1:55 am - 11:40 amORD-PXM
10h 45m1 stop
Volaris Logo
1:24 pm - 11:32 pmPXM-ORD
9h 08m1 stop
$331Volaris
Find Deal
Mon, Aug 11 - Fri, Aug 22
Volaris Logo
1:40 am - 12:31 pmORD-PXM
11h 51m1 stop
Volaris Logo
12:20 pm - 12:15 amPXM-ORD
10h 55m1 stop
$360Volaris
Find Deal
Sat, May 17 - Sun, May 25
Viva Logo
12:35 pm - 12:10 pmORD-OAX
24h 35m2 stops
Viva Logo
2:20 pm - 11:35 pmOAX-ORD
8h 15m1 stop
$367Viva
Find Deal
Tue, May 13 - Wed, May 21
Delta Logo
4:06 pm - 10:43 pmORD-OAX
7h 37m1 stop
Delta Logo
8:25 am - 11:58 pmOAX-ORD
14h 33m2 stops
$466Delta
Find Deal
Thu, May 15 - Tue, May 20
Delta Logo
11:07 am - 10:43 pmORD-OAX
12h 36m2 stops
Delta Logo
8:19 am - 11:58 pmOAX-ORD
14h 39m2 stops
$470Delta
Find Deal
Tue, May 20 - Thu, May 29
American Airlines Logo
5:00 am - 12:09 pmORD-OAX
8h 09m1 stop
American Airlines Logo
1:07 pm - 8:50 amOAX-ORD
18h 43m1 stop
$483American Airlines
Find Deal
Mon, Jun 9 - Wed, Jun 18
American Airlines Logo
10:05 pm - 12:09 pmORD-OAX
15h 04m1 stop
American Airlines Logo
1:07 pm - 11:43 pmOAX-ORD
9h 36m1 stop
$605American Airlines
Find Deal
Sat, Jun 7 - Sun, Jun 15
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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 Chicago to Oaxaca flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Oaxaca.

The cheapest ticket to Oaxaca from Chicago found in the last 72 hours was to Santa Maria Huatulco, at $1,321 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Santa Maria Huatulco (HUX), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $1,321.

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 $428 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $779 and $601 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 16 weeks before departure.


Good to know

Low seasonAugust
High seasonNovember
Cheapest flight$102
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 0% 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.

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 7936 reviews
7.9Entertainment
8.5Crew
8.2Boarding
7.3Food
7.9Comfort
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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

The plane was so outdated, that it made it uncomfortable. The temperature was hot during the whole flight

Happy attentive flight crew. All in all good flight the night flight works well. Getting into Mexico City early so you don't get caught up it all the immigration and custom ques, additionally, this helps when exiting the airport and crossing the city to your final destination. All works very well and would do it again

Some entertainment and food/snack service would have been nice

All the pessengers should be wait in a line útil the creo and piloto are arrived.

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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.

Flights were delayed both ways, with no communication provided by the boarding desk. Delay time kept changing and the boarding process is a pain, as it is so disorganized. Would not recommend.

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 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.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

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.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

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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