$106 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 1/27. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Sun, Nov 30 - Thu, Dec 4
Multiple Airlines Logo
10:32 am - 3:35 pmORD-CUN
4h 03mnonstop
Multiple Airlines Logo
12:31 pm - 8:09 pmCUN-ORD
8h 38m1 stop
$243Multiple Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Multiple Airlines Logo
9:22 pm - 11:16 amORD-CUN
12h 54m1 stop
Multiple Airlines Logo
6:02 pm - 9:12 pmCUN-ORD
4h 10mnonstop
$244Multiple Airlines
Find Deal
Sat, Nov 15 - Tue, Nov 18
Spirit Airlines Logo
6:00 am - 10:44 amORD-CUN
3h 44mnonstop
Spirit Airlines Logo
2:44 pm - 12:27 amCUN-ORD
10h 43m1 stop
$246Spirit Airlines
Find Deal
Fri, Jan 2 - Fri, Jan 9
Spirit Airlines Logo
6:05 am - 10:55 amORD-CUN
3h 50mnonstop
Spirit Airlines Logo
10:15 am - 9:23 pmCUN-ORD
12h 08m1 stop
$248Spirit Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
Frontier Logo
10:37 am - 3:48 pmORD-CUN
4h 11mnonstop
Frontier Logo
5:02 pm - 9:12 pmCUN-ORD
4h 10mnonstop
$254Frontier
Find Deal
Mon, Dec 1 - Fri, Dec 5
American Airlines Logo
10:00 am - 2:49 pmORD-CUN
3h 49mnonstop
American Airlines Logo
2:35 pm - 5:40 pmCUN-ORD
4h 05mnonstop
$262American Airlines
Find Deal
Thu, Nov 27 - Thu, Dec 4
Frontier Logo
7:00 am - 5:20 pmORD-CUN
9h 20m1 stop
Frontier Logo
6:02 pm - 9:12 pmCUN-ORD
4h 10mnonstop
$268Frontier
Find Deal
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
Find Deal
Sat, Nov 29 - Sat, Dec 6
United Airlines Logo
7:34 am - 12:30 pmORD-CUN
3h 56mnonstop
United Airlines Logo
3:18 pm - 6:09 pmCUN-ORD
3h 51mnonstop
$272United Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
9:50 am - 2:46 pmORD-CZM
4h 56mnonstop
American Airlines Logo
4:05 pm - 7:19 pmCZM-ORD
3h 14mnonstop
$424American Airlines
Find Deal
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 $229 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 $229.

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 $402, 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 March and December, when the average cost of round-trip tickets is $524 and $482 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 Wednesdays.

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 2 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$106
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 Cozumel

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 28% 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 $643.

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 4241 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

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

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.

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.