Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago Midway Airport to Riviera Maya from $121

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 7/30. 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
0 bags
Sun 6/30
Sun 7/7

Search hundreds of travel sites at once for deals on flights to Riviera Maya

In the last 7 days travelers have searched 42,787,818 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

Best Riviera Maya Flight Deals

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

Cancún
Cancún1 stop$278

Good to know

Low season

September

High season

December

Cheapest flight

$121
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Chicago Midway Airport to Cancún

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 to Riviera Maya from Chicago Midway Airport 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 to Riviera Maya with an airline and back to Chicago Midway Airport 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 to Riviera Maya from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 5 airlines serving from Midway to Riviera Maya

 
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
DeltaOverall score based on 10419 reviews
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
7.4Food
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

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.

Planes seat could be bigger very uncomfortable for tall humans.

Atraso de dos horas y media con vuelos sobre vendidos

Great airplane The confort was within the high standards. My only little problem was That all the movies ( only 3) was on Spanish, even though I was selecting the audio on English it didn't happen. After that I highly recommend aeromexico

1 hour waiting for suitcases to come out traveling in business class and food in business class is a sandwich? Avoid Aeromexico .

Newer plane with large seats. No meal, but snacks were plentiful. Inflight entertainment was good but movies were dated.

No space reserved for anyone who didn’t have underseat in front of them. Made it inconvenient to get the backs secured. No inflight entertainment in the 190. Bring your own! Food was excellent and we were surprised to get a full breakfast.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

Book cheap flights from Chicago to Riviera Maya

Recent round-trip flight deals

7/30Tue
1 stopFrontier
9h 21mMDW-CUN
8/7Wed
1 stopFrontier
6h 43mCUN-MDW
$278
8/7Wed
1 stop
10h 21mMDW-CUN
8/14Wed
1 stop
11h 36mCUN-MDW
$291
6/19Wed
1 stopFrontier
7h 15mMDW-CUN
6/26Wed
1 stopFrontier
6h 40mCUN-MDW
$293
9/22Sun
1 stopFrontier
9h 23mMDW-CUN
9/26Thu
1 stopFrontier
11h 38mCUN-MDW
$299
8/24Sat
1 stopAeromexico
13h 55mMDW-CUN
8/31Sat
1 stopAeromexico
11h 46mCUN-MDW
$378
9/14Sat
1 stopDelta
9h 42mMDW-CUN
9/21Sat
2 stopsDelta
12h 10mCUN-MDW
$390
9/14Sat
2 stopsDelta
10h 18mMDW-CUN
9/21Sat
2 stopsDelta
12h 10mCUN-MDW
$394
8/20Tue
1 stopAeromexico
8h 07mMDW-CUN
8/27Tue
1 stopAeromexico
13h 46mCUN-MDW
$434
7/7Sun
2 stopsVolaris
19h 41mMDW-CZM
7/14Sun
2 stopsVolaris
16h 02mCZM-MDW
$1,155
6/20Thu
2 stopsVolaris
19h 41mMDW-CZM
6/23Sun
2 stopsVolaris
16h 02mCZM-MDW
$1,202

Search by stops

Search by airline

Search by price

Recent one-way flight deals

7/30Tue
1 stopFrontier
9h 21mMDW-CUN
$121
7/30Tue
1 stopFrontier
9h 21mMDW-CUN
$122
6/15Sat
1 stop
28h 04mMDW-CUN
$148
8/22Thu
1 stop
16h 56mMDW-CUN
$156
6/5Wed
2 stopsDelta
10h 19mMDW-CUN
$180
8/17Sat
1 stopAeromexico
18h 13mMDW-CUN
$182
7/5Fri
1 stopAeromexico
13h 55mMDW-CUN
$191
6/18Tue
2 stopsDelta
10h 21mMDW-CUN
$282
7/2Tue
1 stopVolaris
11h 34mMDW-CUN
$333
7/30Tue
1 stopVolaris
12h 19mMDW-CUN
$334

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Riviera Maya

Last minute flight, train and bus deals

6/3Mon
multi-stopFrontier
11h 51mMDW-CUN
6/10Mon
multi-stopFrontier
15h 08mCUN-MDW
$350
6/3Mon
multi-stopFrontier
11h 51mMDW-CUN
6/5Wed
multi-stopFrontier
22h 06mCUN-MDW
$357
6/5Wed
multi-stopFrontier
7h 15mMDW-CUN
6/9Sun
multi-stopFrontier
25h 39mCUN-MDW
$358
6/5Wed
multi-stop
7h 15mMDW-CUN
6/9Sun
multi-stop
23h 33mCUN-MDW
$369
6/1Sat
multi-stop
22h 20mMDW-CUN
6/8Sat
multi-stop
13h 36mCUN-MDW
$375
6/1Sat
multi-stopDelta
10h 19mMDW-CUN
6/4Tue
multi-stopDelta
9h 28mCUN-MDW
$451
6/3Mon
multi-stopAeromexico
15h 44mMDW-CUN
6/5Wed
multi-stopAeromexico
14h 56mCUN-MDW
$491
6/2Sun
multi-stopAeromexico
16h 58mMDW-CUN
6/4Tue
multi-stopAeromexico
10h 52mCUN-MDW
$595
6/2Sun
multi-stopVolaris
24h 09mMDW-CUN
6/4Tue
multi-stopVolaris
24h 22mCUN-MDW
$646
6/5Wed
multi-stopDelta
10h 19mMDW-CUN
6/8Sat
multi-stopDelta
9h 04mCUN-MDW
$706

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Riviera Maya Flights

Departure:

Chicago Midway Airport (MDW)United States

Cabin classes:

$639
$728
$477
$37