MDW - CUN

$102 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 1/12. 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, 0 bags

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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$213
Overall average: $667
Frontier
Sat 3/7Sat 3/14
MDW - CUN • Non-stop
Cheapest non-stop
$214
Typical prices: $365-$667
Frontier
Sat 3/7Sat 3/14
MDW - CUN • Non-stop
Top airlines
Southwest
Cheapest • from $314 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
5 weeks
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 33% price drop
January
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Cancún!
Flight Deals
Booking Insights
Flight 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

Sat, Mar 7 - Sat, Mar 14
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
2:07 pm - 6:14 pm
CUN
-
MDW
4h 07mnonstop
$213Frontier
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
2:07 pm - 6:14 pm
CUN
-
MDW
4h 07mnonstop
$214Frontier
Fri, Feb 27 - Sat, Mar 7
Frontier Logo
6:00 am - 1:36 pm
MDW
-
CUN
6h 36m1 stop
Frontier Logo
3:07 pm - 6:14 pm
CUN
-
MDW
4h 07mnonstop
$220Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
Frontier Logo
3:24 pm - 10:17 pm
CUN
-
MDW
7h 53m1 stop
$231Frontier
Sun, Jan 11 - Sat, Jan 17
Frontier Logo
12:41 pm - 2:04 pm
MDW
-
CUN
24h 23m1 stop
Frontier Logo
4:25 pm - 8:03 am
CUN
-
MDW
16h 38m1 stop
$232Frontier
Sat, Jan 17 - Thu, Jan 22
Frontier Logo
6:10 am - 3:10 pm
MDW
-
CUN
8h 00m1 stop
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$233Frontier
Sat, Jan 31 - Fri, Feb 6
Frontier Logo
9:38 am - 3:20 pm
MDW
-
CUN
28h 42m1 stop
Frontier Logo
4:30 pm - 8:43 am
CUN
-
MDW
17h 13m1 stop
$234Frontier
Fri, Jan 9 - Thu, Jan 15
Frontier Logo
3:05 pm - 5:36 pm
MDW
-
CUN
25h 31m1 stop
Frontier Logo
4:12 pm - 10:19 pm
CUN
-
MDW
7h 07m1 stop
$238Frontier
Wed, Jan 7 - Sun, Jan 11
Frontier Logo
5:10 pm - 2:04 pm
MDW
-
CUN
19h 54m1 stop
Frontier Logo
4:15 pm - 10:17 pm
CUN
-
MDW
7h 02m1 stop
$247Frontier
Wed, Feb 4 - Sun, Feb 8
Frontier Logo
1:20 pm - 1:47 pm
MDW
-
CUN
23h 27m1 stop
Frontier Logo
4:30 pm - 11:45 am
CUN
-
MDW
20h 15m1 stop
$253Frontier
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 Mondays and the most expensive ones on Tuesdays.

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 $371 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $710 and $695 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $450 on average.

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 33% 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$102
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 26% 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 $102 for a one-way ticket and $214 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, JetBlue, 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 A321-100/200 is the aircraft model that flies most regularly on the Chicago Midway Airport to Cancun flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to Cancun?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago Midway Airport and Cancun, with oneworld being the most commonly used for this 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 $570 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $615 and an overall rating of 7.9.

  • 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 $214 or less one-way and $412 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.
7.9
SouthwestOverall score based on 4252 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Latam may be the worst airline in the world, far worse than even the lowest of low cost airlines in the USA. I wasted hours trying to PAY THEM TO CHECK A BAG! Then they misled me at the terminal, sent me through the wrong security line, the list goes on and on... Just absolutely terrible in every way. Avoid at all costs.

Poor, the airline was not able to help me move flights.

Check in -- in business took over 30 mins as there was only one attendant. Boarding was also a mess. The seat was too narrow and was not working properly. Food was very bad and the entertainment very poor. Crew was very polite and helpful, in fairness.

we were missing our luggage, trying to find someone to have any empathy was pretty much not happening....

Poor handling of carry on luggage. We had a 8 hour stop in Santiago, are over 70 and, in spite of paying full fare they wanted to send carry on to luggage hold. No empathy. We had to show that several group 4/5 passengers were not sending their carry ons before they finally let Is keep them. Very poor .

I’m entitled to a refund per LATAM due to the mid flight itinerary change and being stuck in São Paulo for 24 hours and needing to get a hotel. The airline was dismissive and of no help.

The flight was late. Please do not delay next time.

I couldn't travel, now I can't get a refund and to change the date I have to pay an absurd fine.

My biggest complaint is the comfort. I am not tall and there was no legroom. It was very uncomfortable. During my transfer in Sao Paola, the flight was slightly delayed so boarding was confusing because there were no instructions in English.

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.

Unfortunately I had an awful boarding experience. Our first flight with Aeromexico was fine and landed on time however it couldn’t find a gate and we were late which made us lose our connecting flight with Aeromexico. The staff handled it horribly when we explained our situation and would not led us board when we missed the boarding time by a couple minutes. The staff were extremely rude and did not attempt to even help us. Because of this incident, my husband and I missed a full day of work which negatively impacted our salary which we need. Please compensate us for the work that we missed.

It was OK. The flight is pretty long for the airlines to only offer a simple sandwich on business class. The entertainment is similar to that on other Skyteam members. Ultimately the airline lost my bag and didn’t deliver it to me until the next day after a lengthy lost baggage report.

Aeroméxico cancelled my ticket without advice AND It make a last minute mess in my intinerary, no solving my situation, bad advice and bad customer service

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.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

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.

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

Other airlines flying from Midway to Cancún

Flights from the other most popular airlines that fly from Midway to Cancún according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.