MDW - CUN

$124 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 9/1. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Cancún

 
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.
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Flights Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Cancún

Mon, Oct 27 - Sun, Nov 2
Southwest Logo
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
$270Southwest
Find Deal
Sun, Sep 14 - Thu, Sep 18
Southwest Logo
10:35 am - 2:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
3:10 pm - 6:50 pmCUN-MDW
3h 40mnonstop
$280Southwest
Find Deal
Sat, Sep 6 - Thu, Sep 11
Aeromexico Logo
6:00 am - 11:30 amMDW-CUN
5h 30m1 stop
Aeromexico Logo
12:25 pm - 9:36 pmCUN-MDW
9h 11m1 stop
$303Aeromexico
Find Deal
Sun, Oct 26 - Sat, Nov 1
Delta Logo
10:35 am - 8:20 pmMDW-CUN
9h 45m1 stop
Delta Logo
1:58 pm - 10:14 pmCUN-MDW
8h 16m1 stop
$324Delta
Find Deal
Sun, Nov 2 - Tue, Nov 18
Aeromexico Logo
5:00 am - 8:20 pmMDW-CUN
14h 20m1 stop
Aeromexico Logo
2:56 pm - 9:44 pmCUN-MDW
7h 48m1 stop
$325Aeromexico
Find Deal
Mon, Oct 27 - Fri, Nov 7
Delta Logo
6:23 pm - 8:20 pmMDW-CUN
25h 57m2 stops
Delta Logo
12:05 pm - 8:40 amCUN-MDW
21h 35m2 stops
$329Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
 Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
 Logo
2:41 pm - 11:09 pmCUN-MDW
9h 28m1 stop
Sat, Aug 30 - Sat, Sep 6
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:55 pm - 11:17 pmCUN-MDW
9h 22m1 stop
$342Frontier
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
6:10 am - 1:26 pmMDW-CUN
6h 16m1 stop
Frontier Logo
2:41 pm - 11:09 pmCUN-MDW
9h 28m1 stop
$343Frontier
Find Deal
Thu, Sep 11 - Thu, Sep 18
 Logo
6:20 am - 12:40 pmMDW-CUN
6h 20m1 stop
 Logo
12:25 pm - 9:36 pmCUN-MDW
9h 11m1 stop
Booking Insights

KAYAK's insights & trends for Midway to Cancún flights

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’s the cheapest day of the week to fly from Chicago Midway Airport to Cancun?

The average price of all round-trip flights from Chicago Midway Airport to Cancún clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Cancun, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Wednesdays.

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 round-trip 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 September, where tickets cost $450 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $711 and $694 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Cancún?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $419, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Chicago Midway Airport to Cancún, you should book around 5 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$124
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago Midway Airport to Cancun

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 $124 for a one-way ticket and $270 for a round-trip.

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

    Yes

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

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

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

    American Airlines, Delta, and Aeromexico 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 Cancun?

    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 Cancun?

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Cancún are Southwest and Delta. With an average price for the route of $579 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $610 and an overall rating of 8.0.

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

    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 Cancun.

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

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

    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 Cancun 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 Cancun?

    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 Cancun from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Cancún

  • Looking for a cheap flight? 25% of our users found flights on this route for $122 or less one-way and $309 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Cancun?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Cancun.
Find which airlines fly direct from Chicago Midway Airport to Cancun Airport, which days they fly and book direct flights.

Direct 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

Direct 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

Reviews of the 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
SouthwestOverall score based on 4241 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

I never got this flight. You sent me to Chile!!! And from Chile I got the other flight to São Paulo... I've arrived 7h latter than I was supposed to arrive because of Delta delays.

Because the flight was late, we lost the connection to Brazil. You, Delta delayed, and you Delta anticipated the door closing in 15 min from Miami to GRU. Why? It caused a lot of stress! I almost could not see my mother in law alive because of your delay.

My entertainment did not work. I was very tired from the botched connection, and the poor sleep

Lost ,y connection due to a mechanical delay, huge line to get new connection and vouchers

It’s a delta flight operated by LATAM. The whole ticket sale is a mess, delta changed my flight but didn’t update it in LATAM system, I couldn’t get my boarding pass, it took me hours to resolve this issue with delta. I had to change my travel plan. No apology from Delta even though it’s their fault.

Boarding was done by woman who insisted on strict standing in line policy; food was ok; entertainment minimal

Wider seats, better seat cushions, (I felt like there was a board I was sitting on). I had the chicken to eat but It neither tasted nor looked like chicken. The fruit was good.

I was in the last row and they sent me to check in my luggage last minute after boarding. I had to go through the crowd.

Our flight was cancelled and it took them 5 hours to reschedule and the next morning they said we still didn’t have a new ticket.

We didn’t have any entertainment. I tried to go online without success. The airplane was extremely cold and they didn’t have blankets.

The ground staff were not as friendly and nice to the passengers as the air crew. Flight attendants, cockpit crew were great and very nice to everyone on board.

My flight was delayed, then I got transferred to a new flight that was also delayed- which wasn’t Aeromexico’s fault, it was because of weather conditions. Most of the crew was very nice and patient, except for one or two flight attendants who were rude. The entertainment wasn’t on, so all the screens were off.

My wife's entertainment system did not work. Payed for flight upgrade but did not receive advertised "free WiFi".

Annoying that we had to go to departures and get boarding passes. Should allow us to be booked all the way through, this is the only airline i have this problem with in MEX. Late boarding and take off

Lousy No wheelchair. As normal at Atlanta Cheap airline Cheap aero plane. - Neither entertainment nor food on a 5 hour saga

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

This is not a low cost airline. Stop acting like o e.

Aeromexico crew made me check my hand luggage in the door of the plane. As soon as I reach Mexico City, I notice that my luggage was opened and 8 games of Nintendo Switch were stolen (700 dllrs value aprox) (the console was there) but the games were stolen. I am very dissapointed of Aeromexico and all the crew. Instead of being a good trip, It was a sad trip

Ok. But we arrived to a remote terminal which meant that a bus had to take us to the terminal building

Old aircraft the audio of the entertainment dosent work Dirty seats

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

Everything you need to know for your flight from Midway to Cancún

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