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Find cheap flights from Chicago Midway Airport to Riviera Maya from $103

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 6/21. 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
Thu 7/11
Thu 7/18

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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$246

Good to know

Low season

September

High season

December

Cheapest flight

$103
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 10277 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.6Crew
8.2Boarding
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

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 .

Aeromexico es siempre una buena opción, relación precio calidad adecuada!

Business class was economy with a table in the middle seat. That is worse than economy. No food and no entertainment. Very poor representation.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

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?

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

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

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…

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

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!!!

Book cheap flights from Chicago to Riviera Maya

Recent round-trip flight deals

6/21Fri
1 stopFrontier
15h 03mMDW-CUN
6/24Mon
1 stopFrontier
15h 08mCUN-MDW
$246
7/24Wed
1 stopFrontier
20h 00mMDW-CUN
7/29Mon
1 stopFrontier
14h 58mCUN-MDW
$259
6/20Thu
1 stopFrontier
13h 35mMDW-CUN
6/24Mon
1 stopFrontier
15h 08mCUN-MDW
$260
8/11Sun
1 stop
6h 35mMDW-CUN
8/14Wed
1 stop
11h 31mCUN-MDW
$313
8/4Sun
1 stop
11h 09mMDW-CUN
8/9Fri
1 stop
12h 32mCUN-MDW
$336
9/6Fri
2 stopsDelta
12h 57mMDW-CUN
9/11Wed
1 stopDelta
6h 43mCUN-MDW
$390
9/6Fri
2 stopsDelta
11h 57mMDW-CUN
9/13Fri
2 stopsDelta
12h 04mCUN-MDW
$401
8/13Tue
1 stopAeromexico
8h 07mMDW-CUN
8/20Tue
1 stopAeromexico
10h 05mCUN-MDW
$434
8/20Tue
1 stopAeromexico
8h 07mMDW-CUN
8/27Tue
1 stopAeromexico
8h 08mCUN-MDW
$487
11/22Fri
2 stopsWestJet
27h 40mMDW-CZM
11/30Sat
2 stopsWestJet
24h 11mCZM-MDW
$3,347

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Recent one-way flight deals

6/21Fri
1 stopFrontier
15h 03mMDW-CUN
$103
7/18Thu
1 stopFrontier
6h 25mMDW-CUN
$113
8/31Sat
1 stop
16h 07mMDW-CUN
$128
9/4Wed
2 stops
14h 22mMDW-CUN
$146
7/6Sat
1 stopAeromexico
9h 14mMDW-CUN
$171
7/31Wed
1 stopDelta
5h 19mMDW-CUN
$190
7/9Tue
2 stopsDelta
10h 22mMDW-CUN
$224
8/28Wed
2 stopsAeromexico
25h 41mMDW-CZM
$245
8/12Mon
1 stopVolaris
14h 21mMDW-CUN
$330
8/14Wed
1 stopVolaris
14h 21mMDW-CUN
$363

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Last minute flights from Midway to Riviera Maya

Last minute flight, train and bus deals

6/16Sun
multi-stopFrontier
10h 32mMDW-CUN
6/19Wed
multi-stopFrontier
22h 06mCUN-MDW
$317
6/14Fri
multi-stopFrontier
15h 03mMDW-CUN
6/18Tue
multi-stopFrontier
9h 21mCUN-MDW
$329
6/15Sat
multi-stopFrontier
25h 51mMDW-CUN
6/18Tue
multi-stopFrontier
9h 21mCUN-MDW
$338
6/16Sun
multi-stop
19h 28mMDW-CUN
6/20Thu
multi-stop
7h 57mCUN-MDW
$546
6/14Fri
multi-stop
17h 46mMDW-CUN
6/17Mon
multi-stop
12h 08mCUN-MDW
$623
6/14Fri
multi-stopAeromexico
13h 48mMDW-CUN
6/18Tue
multi-stopAeromexico
13h 46mCUN-MDW
$667
6/12Wed
multi-stopAeromexico
19h 40mMDW-CUN
6/14Fri
multi-stopAeromexico
13h 46mCUN-MDW
$682
6/12Wed
multi-stopDelta
9h 14mMDW-CUN
6/18Tue
multi-stopDelta
9h 04mCUN-MDW
$805
6/14Fri
multi-stopDelta
11h 44mMDW-CUN
6/19Wed
multi-stopDelta
13h 46mCUN-MDW
$811
6/12Wed
multi-stopVolaris
12h 14mMDW-CUN
6/16Sun
multi-stopVolaris
13h 16mCUN-MDW
$1,482

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Chicago Midway Airport - Riviera Maya Flights

Departure:

Chicago Midway Airport (MDW)United States

Cabin classes:

$702
$630
$404
$37