$89 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 5/16. 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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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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Flights Deals

Best Riviera Maya Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Cancún
Cancúnnonstop$203
Cancún
Cancúnnonstop$203

Cheap Flights from Chicago to Riviera Maya

 
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.

Recent round-trip flight deals from Chicago to Riviera Maya

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Riviera Maya.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
6:10 am - 9:44 amORD-CUN
3h 34mnonstop
Spirit Airlines Logo
10:52 am - 2:49 pmCUN-ORD
3h 57mnonstop
$203Spirit Airlines
Find Deal
Sat, May 10 - Sat, May 17
 Logo
6:10 am - 9:44 amORD-CUN
3h 34mnonstop
 Logo
11:05 am - 3:02 pmCUN-ORD
3h 57mnonstop
Mon, May 19 - Thu, May 22
Frontier Logo
7:15 am - 11:22 amORD-CUN
4h 07mnonstop
Frontier Logo
11:05 am - 3:02 pmCUN-ORD
3h 57mnonstop
$219Frontier
Find Deal
Sun, May 18 - Thu, May 22
Frontier Logo
7:35 am - 11:30 amORD-CUN
3h 55mnonstop
Frontier Logo
11:05 am - 3:06 pmCUN-ORD
4h 01mnonstop
$220Frontier
Find Deal
Tue, Jul 29 - Thu, Aug 7
United Airlines Logo
10:42 am - 2:28 pmORD-CUN
3h 46mnonstop
United Airlines Logo
3:30 pm - 12:15 amCUN-ORD
8h 45m1 stop
$296United Airlines
Find Deal
Sun, May 11 - Thu, May 15
American Airlines Logo
7:05 am - 1:45 pmORD-CUN
6h 40m1 stop
American Airlines Logo
10:20 am - 7:23 pmCUN-ORD
9h 03m1 stop
$339American Airlines
Find Deal
Thu, Jul 24 - Thu, Jul 31
Volaris Logo
1:40 am - 4:52 pmORD-CZM
16h 12m1 stop
Volaris Logo
5:42 pm - 5:42 amCZM-ORD
11h 00m1 stop
$400Volaris
Find Deal
Mon, May 26 - Tue, Jun 3
Volaris Logo
1:40 am - 4:52 pmORD-CZM
16h 12m1 stop
Volaris Logo
4:33 pm - 5:37 amCZM-ORD
12h 04m1 stop
$424Volaris
Find Deal
Mon, Oct 20 - Tue, Oct 28
American Airlines Logo
8:05 am - 3:23 pmORD-CZM
8h 18m1 stop
American Airlines Logo
4:23 pm - 10:10 amCZM-ORD
16h 47m1 stop
$482American Airlines
Find Deal
Fri, Jun 13 - Fri, Jun 20
United Airlines Logo
9:40 pm - 12:19 pmORD-CZM
15h 39m1 stop
United Airlines Logo
1:21 pm - 11:12 pmCZM-ORD
8h 51m1 stop
$583United Airlines
Find Deal
Sat, Jun 7 - Thu, Jun 12
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Riviera Maya.

The cheapest ticket to Riviera Maya from Chicago found in the last 72 hours was to Cancún, at $246 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 $249.

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 $325 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $521 and $493 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 Fridays and the most expensive ones on Thursdays.

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 1 week before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$89
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 26% 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.

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

    The cheapest time of day to fly to Riviera Maya is generally in the afternoon, when round-trip flights cost $192 on average. Morning departures are around 27% 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 $581.

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.
7.4
United AirlinesOverall score based on 8696 reviews
7.7Boarding
7.1Entertainment
8.1Crew
7.3Comfort
6.6Food
Airline reviews

A bit rush for transit. Food and entertainment are not available

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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.

Better communication about delayed flight. I am thankful for a small credit for late flight.

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.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

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.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

We had an 8 hr delay so it was not good

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

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.

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