$123 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 7/18. 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

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$269
Cancún
Cancúnnonstop$269

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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Riviera Maya

Thu, Jul 10 - Tue, Jul 15
Southwest Logo
4:35 pm - 8:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
8:30 am - 12:05 pmCUN-MDW
3h 35mnonstop
$269Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:54 pm - 11:11 pmCUN-MDW
9h 17m1 stop
$292Frontier
Find Deal
Tue, Jun 24 - Sat, Sep 6
Aeromexico Logo
12:44 pm - 8:20 pmMDW-CUN
7h 36m1 stop
Aeromexico Logo
12:40 pm - 9:12 pmCUN-MDW
8h 32m1 stop
$305Aeromexico
Find Deal
Fri, Aug 22 - Sat, Aug 30
Aeromexico Logo
12:43 pm - 8:20 pmMDW-CUN
7h 37m1 stop
Aeromexico Logo
8:00 am - 3:28 pmCUN-MDW
7h 28m1 stop
$314Aeromexico
Find Deal
Tue, Jun 24 - Wed, Jun 25
 Logo
12:44 pm - 8:20 pmMDW-CUN
7h 36m1 stop
 Logo
3:25 pm - 8:53 pmCUN-MDW
29h 28m1 stop
Mon, Sep 8 - Sat, Sep 13
Delta Logo
6:00 am - 2:10 pmMDW-CUN
8h 10m1 stop
Delta Logo
8:15 am - 3:30 pmCUN-MDW
7h 15m1 stop
$323Delta
Find Deal
Thu, Sep 11 - Wed, Sep 17
Delta Logo
9:30 am - 8:02 pmMDW-CUN
10h 32m2 stops
Delta Logo
12:25 pm - 9:44 pmCUN-MDW
9h 19m1 stop
$328Delta
Find Deal
Tue, Jul 8 - Sat, Jul 19
 Logo
6:00 am - 12:50 pmMDW-CUN
6h 50m1 stop
 Logo
9:09 am - 8:22 pmCUN-MDW
11h 13m1 stop
Fri, Jul 25 - Fri, Aug 1
Volaris Logo
8:39 pm - 4:52 pmMDW-CZM
21h 13m2 stops
Volaris Logo
5:42 pm - 7:16 pmCZM-MDW
24h 34m2 stops
$948Volaris
Find Deal
Fri, Jul 25 - Fri, Aug 1
Volaris Logo
8:39 pm - 4:52 pmMDW-CZM
21h 13m2 stops
Volaris Logo
5:42 pm - 7:16 pmCZM-MDW
24h 34m2 stops
$952Volaris
Find Deal
Useful Info

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 $268 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 $268.

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 $342, 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 July, when tickets cost $441 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $717 and $694 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, Wednesday is the cheapest day to fly and Thursday 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.


Good to know

Low seasonAugust
High seasonJanuary
Cheapest flight$123
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 18% 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 23% 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 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 $121 one-way - $346 round-trip

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 4287 reviews
8.6Crew
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

We departed and landed on time, the aircraft was clean and comfortable, the crew were lovely. Online checkin worked well and the self service bag drop at the airport worked well. The a/c was an Airbus A330 and has been fitted with a good entertainment system with lots of choice in many languages. The price I paid for the flight was competitive with other airlines apart from the budget carriers, none of whom I was familiar with so I stuck to an airline I have used in previous visits to South America.

We didn’t have any entertainment. I tried to go online without success. The airplane was extremely cold and they didn’t have blankets.

It was good, however the airplane was really cold. We received snacks and the crew was friendly.

Delta has an outstanding service. They are courteous and punctual most of the time. The flight departed a half hour late but we arrived 15 minutes early.

Not sure why there are so many security checks at this airport. Consistently annoying showing passport over and over, checking carryons at gate all the while trying to make tight connection. Basically it was uncomfortable crowded cabin with meidiocre service

Although the flight is goof and the crew is good, the way the airline charges you for every service is ridiculous.

They didi not provide wheelchair though we had requested. We had to run around for 40 minutes and arrange it from the airport!

I liked everything, this was classed as premium economy but it was much better than Lufthansas business class. Lovely staff, comfortable plane and an excellent seat arrangement. A very pleasant surprise.

No entertainment but not expected. Unless you are referring to monitor that you can use. Then Al, was fine on all flights.

Friendly staff, It was the first flight out for our plane, so had to be deiced from the frost. Only delayed a few minutes,

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.

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

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

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