$98 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 4/13. 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

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Everything you should know

Cheapest round-trip
$254
Overall average: $458
Frontier, Spirit Airlines
Wed 4/8Tue 4/14
ORD - CUN • Non-stop
Cheapest one-way
$98
Typical prices: $113-$230
Frontier
Mon 4/13
ORD - CUN • Non-stop
Arrival airport
You can't fly directly to Playa del Carmen. It is served by Cancún (CUN), located 31.1 miles from Playa del Carmen.
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Flight Deals
Useful Info
Flight Deals

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, Apr 8 - Tue, Apr 14
Multiple Airlines Logo
6:30 am - 10:38 am
ORD
-
CUN
4h 08mnonstop
Multiple Airlines Logo
11:06 am - 3:06 pm
CUN
-
ORD
4h 00mnonstop
$254Multiple Airlines
Wed, Apr 8 - Tue, Apr 14
Spirit Airlines Logo
6:05 am - 9:51 am
ORD
-
CUN
3h 46mnonstop
Spirit Airlines Logo
11:06 am - 3:06 pm
CUN
-
ORD
4h 00mnonstop
$255Spirit Airlines
Tue, Mar 31 - Wed, Apr 8
Multiple Airlines Logo
2:35 am - 3:28 pm
ORD
-
CUN
12h 53m
1 stop
Multiple Airlines Logo
11:06 am - 3:06 pm
CUN
-
ORD
4h 00mnonstop
$256Multiple Airlines
Wed, May 13 - Sun, May 17
Frontier Logo
6:30 am - 10:33 am
ORD
-
CUN
4h 03mnonstop
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$257Frontier
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Multiple Airlines Logo
10:25 am - 2:35 pm
CUN
-
ORD
4h 10mnonstop
$258Multiple Airlines
Thu, May 14 - Mon, May 18
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Multiple Airlines Logo
10:25 am - 2:35 pm
CUN
-
ORD
4h 10mnonstop
$259Multiple Airlines
Thu, Apr 23 - Sat, Apr 25
Frontier Logo
6:30 am - 10:38 am
ORD
-
CUN
4h 08mnonstop
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$260Frontier
Fri, Sep 4 - Tue, Sep 8
Volaris Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
$261Volaris
Fri, May 1 - Sat, May 9
Southwest Logo
9:35 am - 1:10 pm
MDW
-
CUN
3h 35mnonstop
Southwest Logo
4:00 pm - 7:40 pm
CUN
-
MDW
3h 40mnonstop
$285Southwest
Wed, Jul 1 - Wed, Jul 8
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$292Volaris
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$98
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 18% 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?

    16 direct flights run between Chicago and Playa del Carmen on a daily basis. On average, there are about 116 departures each week.

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

    Consider leaving on a Friday and avoid Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays 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 $64. Volaris offered a round-trip connection from $112 and Spirit Airlines from $138.

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 November, December and January. 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 4318 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

Flight was delayed, then undelayed, then delayed again. Gate was changed to the other side of the airport. Horrible seats with no screens. Spirit os truly awful, even for a budget option.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

30 minute delay, Also there was a medical emergency on the flight. The flight crew was on top of the situation and assisted the medical professionals that happened to be on the flight.

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Everything you need to know for your flight from Chicago to Playa del Carmen

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