$100 Find Cheap Flights from Chicago Midway Airport 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 Midway to Riviera Maya departing on 4/10. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Riviera Maya, as well as popular online travel agencies
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Flight Deals

Book Cheap Midway 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 Midway 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 Midway to Riviera Maya

sáb., abr. 11 - mié., abr. 15
Multiple Airlines Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Multiple Airlines Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$281Multiple Airlines
lun., abr. 27 - lun., 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
mié., jul. 1 - mié., 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
sáb., abr. 11 - sáb., abr. 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:14 pm
CUN
-
MDW
8h 49m
1 stop
$297Frontier
sáb., abr. 11 - jue., abr. 16
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
12:04 pm - 10:22 pm
CUN
-
MDW
10h 18m
1 stop
$300Frontier
dom., jun. 28 - vie., jul. 3
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
$301Volaris
sáb., abr. 11 - sáb., abr. 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:14 pm
CUN
-
MDW
8h 49m
1 stop
$303Frontier
sáb., abr. 11 - jue., abr. 16
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
12:04 pm - 10:22 pm
CUN
-
MDW
10h 18m
1 stop
$304Frontier
sáb., abr. 18 - sáb., abr. 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
vie., abr. 17 - sáb., abr. 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 Midway to Riviera Maya flights

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

What is the cheapest Chicago Midway Airport 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 Midway Airport found in the last 72 hours was to Cancún, at $258 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Cancún (CUN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $258.

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

The average price for all round-trip flights from Chicago Midway Airport 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 evening, when round-trip flights cost $430 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Riviera Maya is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $704.

Can I save money by flying with a layover from Chicago Midway Airport 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 $380, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Riviera Maya is October, when tickets cost $313 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $686 and $683 respectively.

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

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

If you are looking for a flight deal from Chicago Midway Airport to Riviera Maya, look for departures on Mondays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Riviera Maya, Thursday is the cheapest day to fly and Tuesday is the most expensive.

How far in advance should I book a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Riviera Maya, you should book around 2 weeks before departure, which saves you about 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$100
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago Midway Airport to Cancun

FAQs - booking Riviera Maya flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport 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 Midway Airport to Riviera Maya.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport to Riviera Maya up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Riviera Maya

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Cancun $258 one-way - $439 round-trip

Reviews of the top 4 airlines serving from Midway 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 Midway 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 4317 reviews
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
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

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

All went very well. We used the AIFI Airport, such a lovely facility. Definitely needs better transportation options to get there.

Both ground crew and flight crew were rude, and did not provide any level of service. They made it very difficult as we were traveling with a passenger the required assistance.

From the check-in, to the flight, and arriving, everything went very smoothly. Unfortunately, when I received my baggage it was severely damaged. I have a hard shelled suitcase and it was completely smashed it. I’m not sure how this could happened but I am extremely disappointed that my belongings were damaged beyond repair and continued use.

Really nice, all good, nice crew and all on time

Unfortunately I had an awful boarding experience. Our first flight with Aeromexico was fine and landed on time however it couldn’t find a gate and we were late which made us lose our connecting flight with Aeromexico. The staff handled it horribly when we explained our situation and would not led us board when we missed the boarding time by a couple minutes. The staff were extremely rude and did not attempt to even help us. Because of this incident, my husband and I missed a full day of work which negatively impacted our salary which we need. Please compensate us for the work that we missed.

It was OK. The flight is pretty long for the airlines to only offer a simple sandwich on business class. The entertainment is similar to that on other Skyteam members. Ultimately the airline lost my bag and didn’t deliver it to me until the next day after a lengthy lost baggage report.

Aeroméxico cancelled my ticket without advice AND It make a last minute mess in my intinerary, no solving my situation, bad advice and bad customer service

Flight was on time, good service, but there was no free WiFi, even for first class passengers

The ground staff were not as friendly and nice to the passengers as the air crew. Flight attendants, cockpit crew were great and very nice to everyone on board.

My flight was delayed, then I got transferred to a new flight that was also delayed- which wasn’t Aeromexico’s fault, it was because of weather conditions. Most of the crew was very nice and patient, except for one or two flight attendants who were rude. The entertainment wasn’t on, so all the screens were off.

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

Information on your arrival and departure airports