$111 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 7/14. 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 Midway

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

Cancún
Cancúnnonstop$246
Cancún
Cancúnnonstop$246

Cheap Flights from Midway to Riviera Maya

 
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.

Recent round-trip flight deals from Midway to Riviera Maya

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Riviera Maya.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
10:45 am - 2:25 pmMDW-CUN
3h 40mnonstop
Southwest Logo
9:00 am - 12:40 pmCUN-MDW
3h 40mnonstop
$246Southwest
Find Deal
Sun, May 11 - Thu, May 15
Southwest Logo
5:10 am - 1:20 pmMDW-CUN
8h 10m1 stop
Southwest Logo
9:00 am - 12:40 pmCUN-MDW
3h 40mnonstop
$299Southwest
Find Deal
Mon, May 19 - Fri, May 23
Aeromexico Logo
12:44 pm - 8:20 pmMDW-CUN
7h 36m1 stop
Aeromexico Logo
11:00 am - 6:02 pmCUN-MDW
7h 02m1 stop
$306Aeromexico
Find Deal
Sat, Jul 5 - Thu, Jul 10
Delta Logo
6:00 am - 2:25 pmMDW-CUN
8h 25m1 stop
Delta Logo
8:00 am - 3:20 pmCUN-MDW
7h 20m1 stop
$321Delta
Find Deal
Tue, May 13 - Tue, May 20
Delta Logo
6:00 am - 2:25 pmMDW-CUN
8h 25m1 stop
Delta Logo
8:00 am - 6:45 pmCUN-MDW
10h 45m2 stops
$325Delta
Find Deal
Sat, May 10 - Tue, May 13
Aeromexico Logo
6:00 am - 12:50 pmMDW-CUN
6h 50m1 stop
Aeromexico Logo
11:00 am - 9:41 pmCUN-MDW
10h 41m1 stop
$341Aeromexico
Find Deal
Fri, Jul 25 - Wed, Jul 30
 Logo
9:12 pm - 8:16 amMDW-CUN
11h 04m1 stop
 Logo
12:35 pm - 11:51 pmCUN-MDW
11h 16m1 stop
Sun, Jun 8 - Fri, Jun 13
 Logo
9:12 pm - 8:16 amMDW-CUN
11h 04m1 stop
 Logo
12:39 pm - 10:18 pmCUN-MDW
9h 39m1 stop
Sat, May 31 - Fri, Jun 6
Frontier Logo
6:40 am - 1:00 pmMDW-CUN
6h 20m1 stop
Frontier Logo
1:47 pm - 11:18 pmCUN-MDW
9h 31m1 stop
$417Frontier
Find Deal
Tue, Jun 3 - Sun, Jun 8
Frontier Logo
6:20 am - 12:55 pmMDW-CUN
6h 35m1 stop
Frontier Logo
1:47 pm - 11:18 pmCUN-MDW
9h 31m1 stop
$427Frontier
Find Deal
Thu, May 29 - Thu, Jun 5
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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?

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

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

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 $466 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $724 and $710 respectively.

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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.


Good to know

Low seasonAugust
High seasonJanuary
Cheapest flight$111
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 17% 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 7% 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 $713.

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.
8.0
SouthwestOverall score based on 4294 reviews
8.0Comfort
8.2Boarding
7.1Food
8.6Crew
7.6Entertainment
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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.

Aeromexico crew made me check my hand luggage in the door of the plane. As soon as I reach Mexico City, I notice that my luggage was opened and 8 games of Nintendo Switch were stolen (700 dllrs value aprox) (the console was there) but the games were stolen. I am very dissapointed of Aeromexico and all the crew. Instead of being a good trip, It was a sad trip

Ok. But we arrived to a remote terminal which meant that a bus had to take us to the terminal building

Old aircraft the audio of the entertainment dosent work Dirty seats

The plane was so outdated, that it made it uncomfortable. The temperature was hot during the whole flight

Happy attentive flight crew. All in all good flight the night flight works well. Getting into Mexico City early so you don't get caught up it all the immigration and custom ques, additionally, this helps when exiting the airport and crossing the city to your final destination. All works very well and would do it again

Some entertainment and food/snack service would have been nice

All the pessengers should be wait in a line útil the creo and piloto are arrived.

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 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

Stood inside the plane for more than an hour before take off

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

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