$98 Find Cheap Flights from Chicago to Riviera Maya

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 Riviera Maya 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

KAYAK searches hundreds of travel sites at once for deals on flights to Riviera Maya

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Riviera Maya.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Riviera Maya.
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Flight Deals

Book Cheap Chicago to Riviera Maya 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 Riviera Maya 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 Riviera Maya

Wed, Aug 26 - Thu, Sep 3
Volaris Logo
1:59 am - 3:33 pm
ORD
-
CUN
13h 34m
1 stop
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
$252Volaris
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
Fri, Apr 17 - Thu, Apr 30
Frontier Logo
6:30 am - 10:38 am
ORD
-
CUN
4h 08mnonstop
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$255Frontier
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
Wed, Jun 10 - Sun, Jun 14
Volaris Logo
2:19 am - 3:28 pm
ORD
-
CUN
13h 09m
1 stop
Volaris Logo
11:16 am - 12:06 am
CUN
-
ORD
12h 50m
1 stop
$258Volaris
Fri, Apr 24 - Tue, Apr 28
Frontier Logo
6:30 am - 10:38 am
ORD
-
CUN
4h 08mnonstop
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$259Frontier
Mon, Apr 27 - Mon, May 4
Southwest Logo
9:35 am - 1:10 pm
MDW
-
CUN
3h 35mnonstop
Southwest Logo
4:10 pm - 7:50 pm
CUN
-
MDW
3h 40mnonstop
$285Southwest
Sat, Apr 18 - Sat, Apr 25
Aeromexico Logo
6:00 am - 12:57 pm
MDW
-
CZM
7h 57m
1 stop
Aeromexico Logo
2:14 pm - 10:28 pm
CZM
-
MDW
7h 14m
1 stop
$701Aeromexico
Fri, Apr 17 - Sat, Apr 25
Delta Logo
6:38 pm - 12:57 pm
MDW
-
CZM
19h 19m
2 stops
Delta Logo
2:14 pm - 10:28 pm
CZM
-
MDW
7h 14m
1 stop
$706Delta
Booking Insights

KAYAK's insights & trends for Chicago to Riviera Maya flights

Get data-powered insights and trends into flights from Chicago to Riviera Maya to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Riviera Maya flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Riviera Maya from Chicago found in the last 72 hours was to Cancún, at $215 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Cancún (CUN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $215.

What is the cheapest time of day to fly to Riviera Maya?

The average price for all round-trip flights from Chicago to Riviera Maya depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Riviera Maya is generally in the morning, when round-trip flights cost $466 on average. Morning departures are around 16% cheaper than evening flights, on average. The most expensive time of day to fly to Riviera Maya is generally in the evening, which is peak travel time and where the average cost of a ticket is $558.

Can I save money by flying with a layover from Chicago to Riviera Maya?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $415, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Riviera Maya?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Riviera Maya, 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 Riviera Maya is September, when tickets cost $369 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $531 and $526 respectively.

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

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

When flying from Chicago to Riviera Maya, you should consider leaving on a Monday and avoid Thursdays 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 Mondays.

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

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 Riviera Maya, 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 Riviera Maya, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

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

FAQs - booking Riviera Maya flights

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

    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 Riviera Maya.

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

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

    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 Riviera Maya 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 Riviera Maya?

    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 Riviera Maya 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 Riviera Maya

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Riviera Maya. 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 Riviera Maya? 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
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
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 more than 3 hours, and the metro had stopped running by the time we got to the terminal well past midnight, so I was stranded, alone, with no way to get home until the metro started up the next morning.

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

When I arrived at the airport at 4:00 in the morning, I was notified that I "hadn't paid" for my ticket (I had paid and had a boarding pass). Then I was told that while I had paid, the ticket was $600 more than it actually was, and that I needed to pay that so I could board. None of this was true, of course, but it took 20 minutes, two crew members behind the desk, and one on the phone to clear up.

The flight was delayed by two hours, then by three hours. Then, at 10:01, a notification that the flight was back on schedule for the original time. I just happened to be getting on a train to go to the airport at 10 just to be extra early for the delayed departure when I saw the update come through. I got to the train terminal at the airport at 11:07. A shuttle immediately arrived and offloaded, but didn't show anyone on before speeding off. It was 30 minutes before another arrived. I finally got to the terminal and through security and to the gate just in time for them to tell me the door had just been locked. Flight closed. I had to wait until the next day to fly out. No or for a hotel, a meal, nothing.

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 .

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.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Everything you need to know for your flight to Riviera Maya

Cabin class types available on flights to Chicago

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