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MDW - CUN

$93 Find cheap flights from Chicago Midway Airport to Cancun

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 Cancún 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
Fri 6/7
Fri 6/14

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cancún.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cancún.
In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Cancún (MDW-CUN)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Cancún 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 and deals for you by selecting your travel dates.
Choose your dates
9:08 pm - 8:47 amMDW-CUN
11h 39m1 stop
3:06 pm - 11:50 pmCUN-MDW
8h 44m1 stop
$220Frontier
Find Deal
Sat, May 18 - Wed, May 22
5:11 am - 12:59 pmMDW-CUN
7h 48m1 stop
3:06 pm - 11:50 pmCUN-MDW
8h 44m1 stop
$222Frontier
Find Deal
Mon, May 20 - Wed, May 22
5:11 am - 12:59 pmMDW-CUN
7h 48m1 stop
9:06 am - 9:31 pmCUN-MDW
12h 25m1 stop
$225Frontier
Find Deal
Mon, May 20 - Tue, May 21
7:23 pm - 3:42 pmMDW-CUN
20h 19m1 stop
9:06 am - 9:31 pmCUN-MDW
12h 25m1 stop
$231Frontier
Find Deal
Sun, May 19 - Tue, May 21
10:33 pm - 4:16 pmMDW-CUN
17h 43m1 stop
1:36 pm - 1:46 pmCUN-MDW
24h 10m1 stop
$244Frontier
Find Deal
Sat, May 18 - Wed, May 22
7:05 am - 4:16 pmMDW-CUN
9h 11m1 stop
11:05 am - 7:55 pmCUN-MDW
8h 50m1 stop
Tue, May 21 - Tue, May 28
9:44 pm - 7:07 amMDW-CUN
9h 23m1 stop
9:10 am - 9:10 pmCUN-MDW
12h 00m2 stops
Thu, Aug 15 - Tue, Aug 20
1:05 pm - 7:53 pmMDW-CUN
6h 48m1 stop
6:57 am - 9:44 pmCUN-MDW
14h 47m2 stops
$390Delta
Find Deal
Tue, Oct 22 - Tue, Oct 29
9:32 am - 7:51 pmMDW-CUN
10h 19m2 stops
9:34 am - 9:46 pmCUN-MDW
12h 12m2 stops
$394Delta
Find Deal
Wed, Jun 5 - Wed, Jun 12
6:00 am - 11:19 amMDW-CUN
5h 19m1 stop
8:15 am - 5:59 pmCUN-MDW
9h 44m1 stop
$452Aeromexico
Find Deal
Tue, Jul 23 - Wed, Jul 31

Flights from Midway to Cancún - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Cancún to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Cancún?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Cancún, 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 Cancún is January, where tickets cost $299 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $522 and $389 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Cancún?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Cancún, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Cancún, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 9 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Cancún?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago Midway Airport to Cancún found by KAYAK users in the last 72 hours was for $220 on Frontier, followed by Delta ($390). One-way flight deals have also been found from as low as $93 on Frontier and from $180 on Delta.

How many flights are there between Chicago Midway Airport and Cancún per day?

Each day, there are between 1 and 2 nonstop flights that take off from Chicago Midway Airport and land in Cancún, with an average flight time of 3h 38m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 9 flights. The most frequent day of departure is Saturday, when 22% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between Chicago Midway Airport and Cancún?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Chicago Midway Airport to Cancún?

Early birds can take the earliest flight from Chicago Midway Airport at 6:15 am and will be landing in Cancún at 9:55 am.

What’s the latest departure time from Chicago Midway Airport to Cancún?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Cancún jets off at 1:00 pm and lands at 4:40 pm.

Good to know

Low season

September

High season

December

Cheapest flight

$93
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Chicago Midway Airport to Cancún

When to book flights from Midway to Cancún

Are your dates flexible? Find out the best times to travel from Midway to Cancún based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Cancun flights

  • What is the cheapest flight from Chicago Midway Airport to Cancún?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Cancún was $93 for a one-way ticket and $220 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Cancún?

    Yes

  • Which airports will I be using when flying from Chicago Midway Airport to Cancún?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Cancún is Cancun.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Cancún?

    American Airlines, Aeromexico, British Airways, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to Cancun flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Cancún?

    The Airbus A320neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Cancun flight route.

  • On which days can I fly direct from Chicago Midway Airport to Cancún?

    There are nonstop flights from Chicago Midway Airport to Cancún on a daily basis.

  • Which is the best airline for flights from Chicago to Cancún, Delta or Aeromexico?

    The two airlines most popular with KAYAK users for flights from Chicago to Cancún are Delta and Aeromexico. With an average price for the route of $507 and an overall rating of 8.0, Delta is the most popular choice. Aeromexico is also a great choice for the route, with an average price of $596 and an overall rating of 7.6.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Cancún?

    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 Cancún.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Cancún?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cancún 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 Cancún?

    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 Cancún with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and CUN can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Cancún?

    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 Cancún 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 tips for finding a cheap flight from MDW to Cancun

  • Looking for a cheap flight? 25% of our users found flights on this route for $133 or less round-trip.

Prefer to fly non-stop from Chicago Midway Airport to Cancún?

Find which airlines fly direct from Midway to Cancun, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Cancun

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Cancun to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 5 airlines serving from Midway to Cancún

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Cancún. 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 Cancún? 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 10789 reviews
8.0Entertainment
7.9Comfort
8.2Boarding
7.4Food
8.6Crew
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

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!

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.

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."

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.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

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 flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

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.

Book cheap flights from Chicago to Cancun

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Cancún found on KAYAK in the last 72 hours.
5/14Tue
1 stopFrontier
9h 06mMDW-CUN
$93
5/18Sat
1 stopFrontier
11h 39mMDW-CUN
$94
5/31Fri
1 stop
21h 08mMDW-CUN
$144
5/14Tue
2 stops
30h 19mMDW-CUN
$179
5/15Wed
1 stopDelta
7h 09mMDW-CUN
$180
7/12Fri
1 stopDelta
13h 53mMDW-CUN
$185
5/16Thu
2 stopsAeromexico
12h 51mMDW-CUN
$258
5/27Mon
2 stopsAeromexico
19h 38mMDW-CUN
$283
6/16Sun
2 stopsVolaris
15h 55mMDW-CUN
$329
6/15Sat
2 stopsVolaris
18h 05mMDW-CUN
$336

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Last minute flights from Midway to Cancún

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Cancún that are departing in the next 10 days.
5/13Mon
multi-stopFrontier
26h 36mMDW-CUN
5/18Sat
multi-stopFrontier
12h 05mCUN-MDW
$261
5/11Sat
multi-stopFrontier
11h 12mMDW-CUN
5/15Wed
multi-stopFrontier
12h 31mCUN-MDW
$272
5/12Sun
multi-stopFrontier
14h 53mMDW-CUN
5/15Wed
multi-stopFrontier
12h 31mCUN-MDW
$273
5/13Mon
multi-stopDelta
12h 00mMDW-CUN
5/22Wed
multi-stopDelta
10h 52mCUN-MDW
$390
5/12Sun
multi-stopDelta
5h 23mMDW-CUN
5/15Wed
multi-stopDelta
8h 56mCUN-MDW
$394
5/9Thu
multi-stop
14h 27mMDW-CUN
5/12Sun
multi-stop
12h 08mCUN-MDW
$559
5/11Sat
multi-stopAeromexico
5h 23mMDW-CUN
5/11Sat
multi-stopAeromexico
6h 41mCUN-MDW
$722
5/10Fri
multi-stopAeromexico
12h 51mMDW-CUN
5/12Sun
multi-stopAeromexico
13h 41mCUN-MDW
$816
5/11Sat
multi-stop
25h 39mMDW-CUN
5/15Wed
multi-stop
21h 56mCUN-MDW
$938
5/11Sat
multi-stopLATAM Airlines
29h 14mMDW-CUN
5/14Tue
multi-stopLATAM Airlines
30h 30mCUN-MDW
$2,332

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Chicago Midway Airport - Cancún Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Cancun (CUN)Mexico

Return flight deals:

Cancun - Chicago Midway Airport

Cabin classes:

$79

Browse destinations: