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MDW - CUN

$94 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 5/18. 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
0 bags
Sun 6/9
Sun 6/16

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 43,895,468 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
7:05 am - 4:11 pmMDW-CUN
9h 06m1 stop
7:54 am - 2:34 pmCUN-MDW
6h 40m1 stop
$271Frontier
Find Deal
Tue, Jun 4 - Wed, Jun 12
7:53 am - 4:05 pmMDW-CUN
8h 12m1 stop
11:59 am - 9:20 pmCUN-MDW
9h 21m1 stop
$272Frontier
Find Deal
Wed, May 29 - Tue, Jun 11
2:26 pm - 3:42 pmMDW-CUN
25h 16m1 stop
7:54 am - 2:34 pmCUN-MDW
6h 40m1 stop
$279Frontier
Find Deal
Sun, Jun 9 - Wed, Jun 12
7:05 am - 4:11 pmMDW-CUN
9h 06m1 stop
7:54 am - 2:34 pmCUN-MDW
6h 40m1 stop
$280Frontier
Find Deal
Tue, Jun 4 - Wed, Jun 19
5:54 am - 4:34 pmMDW-CUN
10h 40m1 stop
11:08 am - 10:41 pmCUN-MDW
11h 33m1 stop
Tue, Jul 30 - Wed, Aug 7
2:35 pm - 10:24 amMDW-CUN
19h 49m1 stop
12:31 pm - 7:53 pmCUN-MDW
7h 22m1 stop
Sat, Jun 1 - Sat, Jun 8
6:00 am - 6:43 pmMDW-CUN
12h 43m2 stops
7:52 am - 9:44 pmCUN-MDW
13h 52m2 stops
$390Delta
Find Deal
Tue, Sep 17 - Tue, Sep 24
10:11 am - 7:53 pmMDW-CUN
9h 42m1 stop
9:00 am - 9:44 pmCUN-MDW
12h 44m2 stops
$400Delta
Find Deal
Fri, Sep 13 - Mon, Sep 16
2:05 pm - 10:22 amMDW-CUN
20h 17m2 stops
8:15 am - 9:44 pmCUN-MDW
13h 29m1 stop
$444Aeromexico
Find Deal
Fri, Sep 6 - Mon, Sep 9
10:11 am - 11:42 pmMDW-CUN
13h 31m2 stops
11:00 am - 5:59 pmCUN-MDW
6h 59m1 stop
$477Aeromexico
Find Deal
Fri, Jul 19 - Wed, Jul 24

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 $271 on Frontier, followed by Delta ($390). One-way flight deals have also been found from as low as $94 on Frontier and from $180 on Aeromexico.

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 Sunday, when 22% of all weekly flights depart. The fewest flights depart on a Monday.

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

$94
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 $94 for a one-way ticket and $271 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 10768 reviews
8.2Boarding
7.9Comfort
7.4Food
8.0Entertainment
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

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!

I had a great travel experience as there weren't any delays and I was able to get to Mexico City on time for conference.

I like using the Delta app to keep informed, boarding was smooth, and flight attendants were awesome and on top of everything, good communication from pilots.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

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."

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!

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.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

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 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…

Very bad. Plane delayed. Crew not nice. Luggage weight limit is 40lbs and they overcharge for over weight

Seats could use more padding. Kind of hard on the tush.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

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.

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.
5/18Sat
1 stopFrontier
11h 39mMDW-CUN
$94
5/17Fri
1 stopFrontier
17h 28mMDW-CUN
$103
5/25Sat
1 stop
22h 20mMDW-CUN
$133
5/25Sat
2 stops
20h 45mMDW-CUN
$159
5/15Wed
2 stopsAeromexico
12h 51mMDW-CUN
$180
5/15Wed
2 stopsAeromexico
19h 33mMDW-CUN
$185
7/23Tue
2 stopsDelta
10h 20mMDW-CUN
$289
6/2Sun
2 stopsVolaris
15h 55mMDW-CUN
$312
5/30Thu
2 stopsDelta
10h 19mMDW-CUN
$320
6/27Thu
2 stopsVolaris
15h 55mMDW-CUN
$338

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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.
5/14Tue
multi-stopFrontier
9h 06mMDW-CUN
5/17Fri
multi-stopFrontier
23h 45mCUN-MDW
$274
5/13Mon
multi-stopFrontier
26h 36mMDW-CUN
5/15Wed
multi-stopFrontier
12h 31mCUN-MDW
$279
5/12Sun
multi-stopDelta
6h 55mMDW-CUN
5/15Wed
multi-stopDelta
8h 56mCUN-MDW
$394
5/11Sat
multi-stopDelta
10h 19mMDW-CUN
5/15Wed
multi-stopDelta
8h 56mCUN-MDW
$451
5/14Tue
multi-stop
9h 06mMDW-CUN
5/17Fri
multi-stop
14h 09mCUN-MDW
$526
5/15Wed
multi-stop
23h 45mMDW-CUN
5/18Sat
multi-stop
8h 18mCUN-MDW
$573
5/15Wed
multi-stopAeromexico
7h 09mMDW-CUN
5/19Sun
multi-stopAeromexico
13h 51mCUN-MDW
$706
5/15Wed
multi-stopAeromexico
7h 09mMDW-CUN
5/19Sun
multi-stopAeromexico
6h 45mCUN-MDW
$707
5/14Tue
multi-stopVolaris
15h 55mMDW-CUN
5/17Fri
multi-stopVolaris
17h 59mCUN-MDW
$790
5/15Wed
multi-stopVolaris
12h 14mMDW-CUN
5/20Mon
multi-stopVolaris
11h 08mCUN-MDW
$1,204

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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: