$104 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 1/17. 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 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

Thu, Jan 8 - Sat, Jan 10
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
Frontier Logo
3:34 pm - 10:27 pm
CUN
-
MDW
7h 53m1 stop
$231Frontier
Thu, Jan 22 - Mon, Jan 26
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$233Frontier
Mon, Feb 2 - Thu, Feb 12
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
Frontier Logo
2:49 pm - 10:34 pm
CUN
-
MDW
8h 45m1 stop
$235Frontier
Mon, Jan 12 - Sat, Jan 17
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
Frontier Logo
4:25 pm - 8:03 am
CUN
-
MDW
16h 38m1 stop
$241Frontier
Wed, Jan 7 - Mon, Jan 12
Frontier Logo
5:10 pm - 2:04 pm
MDW
-
CUN
19h 54m1 stop
Frontier Logo
3:24 pm - 10:17 pm
CUN
-
MDW
7h 53m1 stop
$247Frontier
Mon, Jan 26 - Thu, Feb 5
Southwest Logo
9:15 am - 1:55 pm
MDW
-
CUN
3h 40mnonstop
Southwest Logo
3:00 pm - 5:45 pm
CUN
-
MDW
3h 45mnonstop
$269Southwest
Wed, Jan 28 - Wed, Feb 4
Aeromexico Logo
6:00 am - 1:50 pm
MDW
-
CZM
7h 50m1 stop
Aeromexico Logo
3:05 pm - 10:22 pm
CZM
-
MDW
7h 17m1 stop
$420Aeromexico
Mon, Jan 12 - Wed, Jan 21
Delta Logo
6:45 am - 1:50 pm
MDW
-
CZM
7h 05m1 stop
Delta Logo
3:05 pm - 10:22 pm
CZM
-
MDW
7h 17m1 stop
$447Delta
Thu, Jan 29 - Thu, Feb 5
Aeromexico Logo
6:00 am - 1:50 pm
MDW
-
CZM
7h 50m1 stop
Aeromexico Logo
3:05 pm - 10:22 pm
CZM
-
MDW
7h 17m1 stop
$449Aeromexico
Mon, Jan 12 - Tue, Jan 20
Delta Logo
6:14 pm - 1:50 pm
MDW
-
CZM
19h 36m2 stops
Delta Logo
3:05 pm - 8:52 am
CZM
-
MDW
17h 47m2 stops
$452Delta
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 $304 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 $304.

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 $398, 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 September, when tickets cost $371 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $710 and $695 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 Friday, 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 5 weeks before departure, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$104
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 26% 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.

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

    The cheapest time of day to fly to Riviera Maya is generally at night, when round-trip flights cost $385 on average. Morning departures are around 14% 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 $653.

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 $165 one-way - $362 round-trip

Reviews of the top 5 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.
7.9
SouthwestOverall score based on 4249 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

I booked a flight through Kayak to Brazil I have traveled to Brazil several times before Kayak Delta or LATAM never mentioned during the booking or in the pre flight process that the visa requirements to visit Brazil have changed earlier this year. I was unaware of this change and as such never got a visa and was unable to fly from JFK to Sao Paulo Add to this that Delta allowed me to fly from Boston to JFK which they should not have as I didn’t have a visa. It has been a terrible experience and a huge loss of money

Wish the seats were a little more comfortable.. it was a 6 hrs nonstop trip. But the crew was courteous and w a smile

Latam may be the worst airline in the world, far worse than even the lowest of low cost airlines in the USA. I wasted hours trying to PAY THEM TO CHECK A BAG! Then they misled me at the terminal, sent me through the wrong security line, the list goes on and on... Just absolutely terrible in every way. Avoid at all costs.

The plane broke down at the Lima stopover and they offered to put me on a flight the be t day but I had to be back in LA that morning and so I had to buy another ticket from Avianca and United for $2k I asked LATAM for compensation and received none. Very bad experience

Poor handling of carry on luggage. We had a 8 hour stop in Santiago, are over 70 and, in spite of paying full fare they wanted to send carry on to luggage hold. No empathy. We had to show that several group 4/5 passengers were not sending their carry ons before they finally let Is keep them. Very poor .

Really bad experience – delayed for 6 hours without any notice, no food or drinks provided, and stuck in the horrible Cartagena airport.

I’m entitled to a refund per LATAM due to the mid flight itinerary change and being stuck in São Paulo for 24 hours and needing to get a hotel. The airline was dismissive and of no help.

The flight was late. Please do not delay next time.

I couldn't travel, now I can't get a refund and to change the date I have to pay an absurd fine.

My biggest complaint is the comfort. I am not tall and there was no legroom. It was very uncomfortable. During my transfer in Sao Paola, the flight was slightly delayed so boarding was confusing because there were no instructions in English.

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

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.

My wife's entertainment system did not work. Payed for flight upgrade but did not receive advertised "free WiFi".

Annoying that we had to go to departures and get boarding passes. Should allow us to be booked all the way through, this is the only airline i have this problem with in MEX. Late boarding and take off

Lousy No wheelchair. As normal at Atlanta Cheap airline Cheap aero plane. - Neither entertainment nor food on a 5 hour saga

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

This is not a low cost airline. Stop acting like o e.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

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

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

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.

Everything you need to know for your flight to Riviera Maya

Information on your arrival and departure airports