$103 Find Cheap Flights from Chicago to Playa del Carmen

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 Playa del Carmen departing on 2/9. 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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Cheap Flights from Chicago to Playa del Carmen (CHI-CUN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Playa del Carmen 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 Playa del Carmen

Wed, Jan 21 - Wed, Jan 28
Spirit Airlines Logo
5:05 am - 12:27 pmORD-CUN
6h 22m1 stop
Spirit Airlines Logo
10:15 am - 9:23 pmCUN-ORD
12h 08m1 stop
$241Spirit Airlines
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Fri, Jan 23 - Wed, Feb 11
Spirit Airlines Logo
6:00 am - 10:37 amORD-CUN
3h 37mnonstop
Spirit Airlines Logo
1:35 pm - 9:00 pmCUN-ORD
8h 25m1 stop
$242Spirit Airlines
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Thu, Jan 22 - Thu, Feb 5
Spirit Airlines Logo
6:00 am - 10:37 amORD-CUN
3h 37mnonstop
Spirit Airlines Logo
11:42 am - 2:50 pmCUN-ORD
4h 08mnonstop
$243Spirit Airlines
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Wed, Mar 11 - Tue, Mar 17
Southwest Logo
12:15 pm - 4:05 pmORD-CUN
3h 50mnonstop
Southwest Logo
5:05 pm - 9:05 pmCUN-ORD
4h 00mnonstop
$252Southwest
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Sun, Jan 11 - Thu, Jan 15
American Airlines Logo
7:00 am - 11:49 amORD-CUN
3h 49mnonstop
American Airlines Logo
12:53 pm - 3:52 pmCUN-ORD
3h 59mnonstop
$262American Airlines
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Sat, Nov 15 - Fri, Nov 21
United Airlines Logo
7:10 am - 5:50 pmORD-CUN
9h 40m1 stop
United Airlines Logo
3:18 pm - 6:09 pmCUN-ORD
3h 51mnonstop
$271United Airlines
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Fri, Feb 20 - Fri, Feb 27
Volaris Logo
1:00 am - 2:00 pmORD-CUN
12h 00m1 stop
Volaris Logo
10:43 am - 10:06 pmCUN-ORD
12h 23m1 stop
$277Volaris
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Wed, Feb 4 - Tue, Feb 10
Volaris Logo
6:23 am - 9:26 pmORD-CUN
14h 03m1 stop
Volaris Logo
10:13 pm - 4:36 amCUN-ORD
7h 23m1 stop
$280Volaris
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Sun, Nov 16 - Sat, Nov 22
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
4:25 pm - 7:10 pmCUN-MDW
3h 45mnonstop
$282Southwest
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Sun, Nov 16 - Tue, Nov 18
American Airlines Logo
5:18 am - 3:22 pmORD-CUN
9h 04m1 stop
American Airlines Logo
3:54 pm - 6:59 pmCUN-ORD
4h 05mnonstop
$286American Airlines
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Everything you should know

Cheapest round-trip
$241
Typical prices: $246-$526
Spirit Airlines
Wed 1/21Wed 1/28
ORD - CUN • 1 stop
Cheapest non-stop
$243
Typical prices: $256-$546
Spirit Airlines
Thu 1/22Fri 2/6
ORD - CUN • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Playa del Carmen!
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$103
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Chicago O'Hare Airport to Cancun

When to book flights from Chicago to Playa del Carmen

Are your dates flexible? Find out the best times to travel from Chicago to Playa del Carmen based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Playa del Carmen

  • Which airports will I be using when flying from Chicago to Playa del Carmen?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Playa del Carmen does not have its own airport so you’ll be flying into nearby Cancun airport, which is 31.1 mi away.

  • How long does a flight from Chicago to Playa del Carmen take?

    Direct flights cover the 1,440 miles separating Chicago and Playa del Carmen in about 3h 37m.

  • How many flights are there between Chicago and Playa del Carmen?

    10 direct flights run between Chicago and Playa del Carmen on a daily basis. On average, there are about 75 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Playa del Carmen?

    Consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Playa del Carmen?

    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 Playa del Carmen.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Playa del Carmen 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 Playa del Carmen?

    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 Playa del Carmen 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 Playa del Carmen?

    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 Playa del Carmen from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Playa del Carmen?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Playa del Carmen found on KAYAK was with Volaris for $103. Spirit Airlines offered a round-trip connection from $241 and Southwest from $252.

Top tips for finding cheap flights from Chicago to Playa del Carmen

  • There is no airport in Playa del Carmen. Instead, you’ll be flying into Cancun Airport when flying between Chicago and Playa del Carmen.
  • The cheapest flight from Chicago to Playa del Carmen was found 66 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Playa del Carmen

 
Need help choosing which airline to fly with from Chicago to Playa del Carmen? 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
SouthwestOverall score based on 4240 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 ExcellentMargaret, Oct 2025SAV - HOU
Read more Southwest reviews

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

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

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

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

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!

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

The gate agents for spirit at EWR wouldn’t give me my ticket to board when I arrived 50 min from the flight, saying that I wouldn’t make my flight. They tried to reschedule me to arrive at my destination 14 hours after the original flight, which included a 10 hr layover in another city. I rebooked with another airline and it took me a total of 5 min to go through security. Then I see a charge on my card for a $100 change fee that I did not approve. Beware of this horrible place and these horrible people

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

Waited at the airport for over 4 hours to board this flight. Terrible airline

Was supposed to take off 8:00 last night. Got delayed till 8:00 this morning

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

When the flight ticket is expensive and you have to purchase check in luggage and there is no snacks, no entertainment, tight seats stuffed in the back of the plane not such good experience. I would like some to reach out to me . I paid for check luggage when I bought the ticket they made me pay again on the return flight extra $70. Very frustrating.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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