$100 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 9/11. 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

Sat, Sep 27 - Thu, Oct 2
 Logo
12:45 pm - 9:49 pmORD-CUN
9h 04m1 stop
 Logo
10:20 am - 7:50 pmCUN-ORD
9h 30m1 stop
Wed, Sep 24 - Sat, Oct 4
Spirit Airlines Logo
5:05 am - 12:59 pmORD-CUN
7h 54m1 stop
Spirit Airlines Logo
10:44 am - 2:49 pmCUN-ORD
4h 05mnonstop
$236Spirit Airlines
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Sat, Oct 18 - Tue, Oct 21
 Logo
12:25 pm - 7:50 pmORD-CUN
7h 25m1 stop
 Logo
1:49 pm - 11:45 pmCUN-ORD
9h 56m1 stop
Mon, Nov 10 - Fri, Nov 14
United Airlines Logo
7:34 am - 12:30 pmORD-CUN
3h 56mnonstop
United Airlines Logo
3:18 pm - 6:09 pmCUN-ORD
3h 51mnonstop
$271United Airlines
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Sat, Oct 25 - Fri, Oct 31
Southwest Logo
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
Southwest Logo
3:15 pm - 6:50 pmCUN-MDW
3h 35mnonstop
$271Southwest
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Sat, Oct 11 - Fri, Oct 17
Viva Logo
12:25 pm - 10:15 pmORD-CUN
9h 50m1 stop
Viva Logo
7:10 am - 11:35 pmCUN-ORD
16h 25m1 stop
$276Viva
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Mon, Oct 27 - Fri, Oct 31
United Airlines Logo
7:34 am - 11:30 amORD-CUN
3h 56mnonstop
United Airlines Logo
4:55 pm - 12:15 amCUN-ORD
7h 20m1 stop
$281United Airlines
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Sun, Sep 14 - Thu, Sep 18
Southwest Logo
10:35 am - 2:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
3:10 pm - 6:50 pmCUN-MDW
3h 40mnonstop
$281Southwest
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Sat, Oct 4 - Sat, Oct 11
Frontier Logo
6:15 am - 12:40 pmMDW-CUN
6h 25m1 stop
Frontier Logo
1:41 pm - 10:47 pmCUN-MDW
9h 06m1 stop
$364Frontier
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Sat, Oct 4 - Sat, Oct 11
Frontier Logo
6:15 am - 12:40 pmMDW-CUN
6h 25m1 stop
Frontier Logo
1:41 pm - 10:47 pmCUN-MDW
9h 06m1 stop
$367Frontier
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Good to know

Low seasonSeptember
Cheapest flight$100
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 21% 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 30m.

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

    7 direct flights run between Chicago and Playa del Carmen on a daily basis. On average, there are about 52 departures each week.

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

    Consider leaving on a Saturday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Fridays.

  • 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 Spirit Airlines for $100. Spirit Airlines offered a round-trip connection from $236 and Southwest from $271.

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 3 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 4242 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

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.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

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 flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

I will use spirit more New clean aircraft Excellent crew ! Quick boarding process !

Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.

Flight was late, after my first leg was cancelled altogether causing me to spend $$$ with another carrier. Seating is ridiculously tight, I can't recommend spirit if I cant depend on them to get me there and back on time.

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

The incoming plane ✈️ was delayed 5 hours en route to Raleigh. My flight was delayed for 5 hours 😢. Finally boarded and then de boarded due to an AC problem. A very tough and long night.

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

I liked the check in procedure. The luggage charges and overweight cost can be better.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

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