$100 Find Cheap Flights from Chicago to Yucatan

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 Yucatan departing on 1/18. 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 Yucatan

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Yucatan, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Yucatan, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Yucatan 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 Yucatan 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 Yucatan

Thu, Jan 8 - Sat, Jan 31
Multiple Airlines Logo
6:05 am - 10:54 am
ORD
-
CUN
3h 49mnonstop
Multiple Airlines Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$213Multiple Airlines
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
2:07 pm - 6:14 pm
CUN
-
MDW
4h 07mnonstop
$214Frontier
Sat, Jan 10 - Wed, Feb 4
Multiple Airlines Logo
8:36 pm - 12:00 pm
ORD
-
CUN
14h 24m1 stop
Multiple Airlines Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$214Multiple Airlines
Sat, Jan 17 - Sat, Jan 31
Spirit Airlines Logo
8:36 pm - 12:00 pm
ORD
-
CUN
14h 24m1 stop
Spirit Airlines Logo
11:59 am - 2:53 pm
CUN
-
ORD
3h 54mnonstop
$222Spirit Airlines
Wed, Feb 4 - Mon, Feb 9
Viva Logo
1:20 am - 9:25 pm
ORD
-
MID
20h 05m1 stop
Viva Logo
5:45 am - 11:50 pm
MID
-
ORD
18h 05m1 stop
$233Viva
Mon, Jan 19 - Wed, Mar 4
Viva Logo
1:20 am - 11:59 pm
ORD
-
MID
22h 39m1 stop
Viva Logo
6:00 am - 11:45 pm
MID
-
ORD
17h 45m1 stop
$245Viva
Sat, Mar 7 - Sat, Mar 14
Volaris Logo
11:59 pm - 8:45 am
ORD
-
MID
8h 46m1 stop
Volaris Logo
8:17 pm - 11:09 am
MID
-
ORD
13h 52m1 stop
$260Volaris
Fri, Jan 23 - Tue, Feb 3
Delta Logo
6:00 am - 6:30 pm
MDW
-
MID
12h 30m2 stops
Delta Logo
5:46 am - 5:29 pm
MID
-
MDW
11h 43m2 stops
$471Delta
Sun, Feb 1 - Mon, Feb 9
Volaris Logo
6:54 pm - 8:45 am
MDW
-
MID
13h 51m1 stop
Volaris Logo
9:29 am - 5:34 pm
MID
-
MDW
8h 05m1 stop
$479Volaris
Fri, Jan 23 - Fri, Jan 30
Delta Logo
6:00 am - 5:08 pm
MDW
-
MID
11h 08m2 stops
Delta Logo
5:46 am - 5:29 pm
MID
-
MDW
11h 43m2 stops
$491Delta
Booking Insights

KAYAK's insights & trends for Chicago to Yucatan flights

Get data-powered insights and trends into flights from Chicago to Yucatan 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 Yucatan?

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 Yucatan departing in February.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Yucatan, 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 Yucatan is September, when tickets cost $331 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $647 and $647 respectively.

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

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

For Chicago to Yucatan, Friday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Yucatan back to Chicago, the best deals are generally found on Monday, with Thursday being the most expensive.

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

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 Yucatan, 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 Yucatan, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$100
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago O'Hare Airport to Cancun

FAQs - booking Yucatan flights

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

    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 Yucatan.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Yucatan 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 Yucatan?

    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 Yucatan 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 Yucatan?

    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 Yucatan 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 Yucatan?

    The cheapest time of day to fly to Yucatan is generally in the evening, when round-trip flights cost $382 on average. Morning departures are around 58% more expensive than evening flights, on average. The most expensive time of day to fly to Yucatan is generally in the morning, which is peak travel time and where the average cost of a ticket is $602.

Reviews of the top 5 airlines serving from Chicago to Yucatan

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Yucatan. 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 Yucatan? 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 8009 reviews
7.9Entertainment
8.1Boarding
7.9Comfort
8.5Crew
7.3Food
Airline reviews

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

10.0 ExcellentVenkata Krishna, Dec 2025
ATL - SDF
Read more Delta reviews

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

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.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

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.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

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

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!

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

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

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.

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

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 Yucatan

Cabin class types available on flights to Yucatan

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