CHI - OAX

$138 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 2/8. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$271
Typical prices: $345-$573
Volaris
Mon 5/11Sun 5/17
ORD - OAX • 1 stop
Cheapest one-way
$128
Typical prices: $180-$336
Volaris
Sun 2/8
ORD - OAX • 1 stop
Top airlines
Volaris
Cheapest • from $271 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 32% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Oaxaca (CHI-OAX)

 
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

Mon, May 11 - Sun, May 17
Volaris Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Volaris Logo
7:34 pm - 5:52 am
OAX
-
ORD
9h 18m
1 stop
$271Volaris
Sun, Feb 22 - Mon, Mar 2
Viva Logo
1:20 am - 4:25 pm
ORD
-
OAX
15h 05m
1 stop
Viva Logo
4:55 pm - 11:45 pm
OAX
-
ORD
6h 50m
1 stop
$280Viva
Tue, May 12 - Sun, May 17
Multiple Airlines Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Multiple Airlines Logo
3:30 pm - 12:45 am
OAX
-
ORD
8h 15m
1 stop
$289Multiple Airlines
Sat, Mar 14 - Fri, Mar 20
Volaris Logo
11:59 pm - 10:35 am
ORD
-
OAX
11h 36m
1 stop
Volaris Logo
8:56 am - 11:06 pm
OAX
-
ORD
13h 10m
1 stop
$307Volaris
Tue, Mar 3 - Wed, Mar 11
Viva Logo
1:05 am - 12:20 pm
ORD
-
OAX
11h 15m
1 stop
Viva Logo
4:55 pm - 12:45 am
OAX
-
ORD
6h 50m
1 stop
$308Viva
Wed, Mar 4 - Wed, Mar 11
Delta Logo
6:00 am - 5:05 pm
MDW
-
OAX
11h 05m
2 stops
Delta Logo
7:56 am - 10:31 pm
OAX
-
MDW
13h 35m
2 stops
$497Delta
Sat, Apr 11 - Wed, Apr 22
Aeromexico Logo
6:00 am - 9:10 pm
MDW
-
OAX
16h 10m
2 stops
Aeromexico Logo
10:30 am - 10:28 pm
OAX
-
MDW
10h 58m
2 stops
$508Aeromexico
Wed, Mar 4 - Wed, Mar 11
Delta Logo
6:00 am - 7:00 pm
MDW
-
OAX
13h 00m
2 stops
Delta Logo
7:56 am - 10:31 pm
OAX
-
MDW
13h 35m
2 stops
$535Delta
Thu, Mar 19 - Wed, Mar 25
Frontier Logo
6:05 am - 4:12 pm
MDW
-
OAX
35h 07m
2 stops
Frontier Logo
8:40 am - 12:19 pm
OAX
-
MDW
26h 39m
2 stops
$641Frontier
Thu, Mar 5 - Fri, Mar 13
Frontier Logo
5:16 pm - 4:12 pm
MDW
-
OAX
22h 56m
2 stops
Frontier Logo
8:40 am - 9:45 pm
OAX
-
MDW
36h 05m
2 stops
$645Frontier
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.

How much is a round-trip flight from Chicago to Oaxaca?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Oaxaca departing in May.

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, where tickets cost $375 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $930 and $637 respectively.

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 22 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$128
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago O'Hare Airport to Oaxaca

When to book flights from Chicago to Oaxaca

Are your dates flexible? Find out the best times to travel from Chicago to Oaxaca based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Oaxaca

  • What is the cheapest flight from Chicago to Oaxaca?

    In the last 3 days, the lowest price for a flight from Chicago to Oaxaca was $128 for a one-way ticket and $271 for a round-trip.

  • Do I need a passport to fly between Chicago and Oaxaca?

    A passport is required to fly from Chicago to Oaxaca.

  • Which airports will I be using when flying from Chicago to Oaxaca?

    Chicago is served by 2 major airports and there is only 1 main airport in Oaxaca. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Oaxaca Xoxocotlan.

  • Which aircraft models fly most regularly from Chicago to Oaxaca?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Oaxaca?

    Star Alliance, oneworld, and SkyTeam are the airline alliances operating flights between Chicago and Oaxaca, with Star Alliance being the most commonly used for this route.

  • What is the most popular layover when flying to Oaxaca from Chicago?

    Mexico City is the most popular layover city among KAYAK users traveling from Chicago to Oaxaca.

  • Which is the best airline for flights from Chicago to Oaxaca, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Oaxaca are Delta and United Airlines. With an average price for the route of $574 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $678 and an overall rating of 7.4.

  • 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 to Oaxaca from Chicago 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 to Oaxaca with an airline and back to Chicago 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 to Oaxaca from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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.
7.9
DeltaOverall score based on 8119 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.9Comfort
7.2Food
Airline reviews

The flight was comfortable and uneventful, which is what I desire

8.0 ExcellentLarry, Jan 2026
JFK - SJD
Read more Delta reviews

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

It was cancelled at the last moment and the customer services seemed unnoticed to this change and hanged me off the phone the first time I called.

Staff especially Alan Hernandez was a great help with arrangements for my partner and me sit together. This made the trip do much more enjoyable. Thanks so much.

One of the flight was delayed an hour. We then boarded a new flight. We were told to unboard after some other time. To wait for the next flight for another hour. I paid for a short flight that turned in to half a day of travel.

No entertainment, charging, nor wifi on board but I napped for basically the entire time so it was alright. Was allowed to switch seats because the flight was not full but everyone was assigned to the back. Comfortable seats and we got moved to the emergency exit so the extra room was nice.

Painless trip. Only downside: No entertainment system (which we know with Viva & Volaris) and very small seat space. I'm petite and felt squizzed. I'm not sure how most overweight passengers do.

I was charge $90 for my bag more then the fight crazy!! And the plain hit a couple of birds on the take off bird strikes we returned back and had to change planes bad customer service everyone has an attitude problem!!! Bad experience!!!

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!

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

It’s a 2 1/2 hour flight so good and comfort was not my real concern. Safety, easy, fast was what I was looking for. The crews were great, plane was clean, boarding from CBX was fantastic! Definitely traveling this way again.

The money you save flying volaris is not worth it

Is was a good short flight with some turbulence! I would fly Volaris again.

We had boarding passes for the next flight but we could not catch the flight in the small airport just because volaris closed the boarding at the counters an hour before for which we had to sepnd almost 3+ hours to catch next flight. There are hardly anyone who can speak english, but thank God, we have found an young man who could not only speak English but helped us book for the next flight. The air crafts are noisy and scary sometimes to hear that squeeking noises during the take off and during the flight. They do not even offer a cup of coffee for free in flight. The prices are super high and the services are zero. That’s pretty much for this airlines in summary.

Unfortunately it was not a good flight got canceled had to be at the airport all night long to get a different flight to another airport my first flight with Volaris was very bad. Poor services

The boarding , and it would be nice if they would let us know head of time about flight changes

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

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

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

Information on your arrival and departure airports