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Find cheap flights from Chicago Midway Airport to Riviera Maya from $94

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 5/14. 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.
1 adult
0 bags
Sat 6/1
Sat 6/8

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Best Riviera Maya Flight Deals

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

Cancún
Cancún1 stop$214

Good to know

Low season

October

High season

December

Cheapest flight

$94
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 26% increase in price.
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 10858 reviews
8.0Entertainment
8.6Crew
7.9Comfort
8.2Boarding
7.4Food
Airline reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

8.0 ExcellentAnonymous, May 2024ATL - ATW
Read more about Delta reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

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.

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.

Cons: "left Houston more than 2 hours later, arrive in Mexico over 2 am"
Cons: "El problema es que nunca pude cambiar mi vuelo y con ustedes fue imposible comunicarse para que me auxiliaran. Muy mal por ustedes no por la línea."
Pros: "The crew was amazing , the site is ok"
Cons: "I love Aeroméxico , thanks for de service and the food."

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!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Book cheap flights from Chicago to Riviera Maya

Recent round-trip flight deals

5/11Sat
1 stopFrontier
11h 12mMDW-CUN
5/17Fri
1 stopFrontier
23h 45mCUN-MDW
$214
5/11Sat
2 stopsFrontier
27h 46mMDW-CUN
5/16Thu
1 stopFrontier
8h 11mCUN-MDW
$215
5/11Sat
1 stopFrontier
11h 12mMDW-CUN
5/21Tue
1 stopFrontier
12h 25mCUN-MDW
$216
6/9Sun
1 stop
11h 30mMDW-CUN
6/11Tue
1 stop
9h 22mCUN-MDW
$305
6/9Sun
1 stop
11h 30mMDW-CUN
6/12Wed
1 stop
6h 40mCUN-MDW
$309
7/14Sun
1 stopDelta
13h 53mMDW-CUN
7/24Wed
1 stopDelta
6h 59mCUN-MDW
$390
5/30Thu
2 stopsDelta
29h 21mMDW-CZM
6/6Thu
2 stopsDelta
30h 41mCZM-MDW
$400
6/1Sat
1 stopAeromexico
7h 50mMDW-CZM
6/5Wed
2 stopsAeromexico
30h 26mCZM-MDW
$522
5/18Sat
1 stopAeromexico
7h 50mMDW-CZM
5/25Sat
1 stopAeromexico
6h 51mCZM-MDW
$572
6/8Sat
2 stopsVolaris
20h 11mMDW-CZM
6/15Sat
2 stopsVolaris
16h 32mCZM-MDW
$811

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Recent one-way flight deals

5/14Tue
1 stopFrontier
11h 27mMDW-CUN
$94
5/11Sat
1 stopFrontier
11h 12mMDW-CUN
$98
6/13Thu
2 stops
20h 19mMDW-CUN
$175
5/10Fri
2 stops
33h 24mMDW-CUN
$183
5/15Wed
1 stopDelta
11h 06mMDW-CUN
$185
6/14Fri
2 stopsDelta
10h 21mMDW-CUN
$198
5/11Sat
1 stopAeromexico
7h 50mMDW-CZM
$225
5/31Fri
2 stopsAeromexico
32h 06mMDW-CZM
$265
6/6Thu
2 stopsVolaris
18h 05mMDW-CUN
$366
7/10Wed
1 stopVolaris
14h 18mMDW-CUN
$470

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Last minute flights from Midway to Riviera Maya

Last minute flight, train and bus deals

5/7Tue
multi-stopFrontier
11h 27mMDW-CUN
5/14Tue
multi-stopFrontier
10h 27mCUN-MDW
$235
5/6Mon
multi-stopFrontier
9h 11mMDW-CUN
5/15Wed
multi-stopFrontier
12h 31mCUN-MDW
$263
5/4Sat
multi-stopFrontier
16h 26mMDW-CUN
5/11Sat
multi-stopFrontier
10h 43mCUN-MDW
$264
5/6Mon
multi-stop
9h 11mMDW-CUN
5/29Wed
multi-stop
11h 43mCUN-MDW
$365
5/6Mon
multi-stopDelta
9h 58mMDW-CUN
5/15Wed
multi-stopDelta
8h 56mCUN-MDW
$404
5/6Mon
multi-stop
14h 21mMDW-CUN
5/29Wed
multi-stop
12h 49mCUN-MDW
$501
5/5Sun
multi-stopDelta
10h 58mMDW-CUN
5/7Tue
multi-stopDelta
8h 56mCUN-MDW
$514
5/6Mon
multi-stopAeromexico
11h 57mMDW-CUN
5/9Thu
multi-stopAeromexico
11h 56mCUN-MDW
$691
5/3Fri
multi-stopAeromexico
12h 48mMDW-CUN
5/7Tue
multi-stopAeromexico
14h 59mCUN-MDW
$693
5/7Tue
multi-stopLATAM Airlines
21h 44mMDW-CUN
5/11Sat
multi-stopLATAM Airlines
20h 07mCUN-MDW
$2,975

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Chicago Midway Airport - Riviera Maya Flights

Departure:

Chicago Midway Airport (MDW)United States

Cabin classes:

$527
$546
$292
$27