MDW - CUN

$101 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 4/10. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cancún, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$285
Overall average: $662
Southwest
Sat 5/9Sat 5/16
MDW - CUN • Non-stop
Cheapest one-way
$100
Typical prices: $253-$327
Volaris
Fri 4/10
MDW - CUN • 1 stop
Top airlines
Cheapest • from $285 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest and Frontier. Average duration is 3h 43m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 87% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $449 (round-trip)
Shortest trip • 5h 41m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 53% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 37% price drop
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, May 9 - Sat, May 16
Southwest Logo
10:40 am - 2:10 pm
MDW
-
CUN
3h 30mnonstop
Southwest Logo
4:00 pm - 7:40 pm
CUN
-
MDW
3h 40mnonstop
$285Southwest
Sat, Apr 11 - Thu, Apr 16
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
12:04 pm - 10:22 pm
CUN
-
MDW
10h 18m
1 stop
$289Frontier
Sat, Apr 11 - Fri, Apr 17
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
4:07 pm - 6:37 pm
CUN
-
MDW
26h 30m
1 stop
$290Frontier
Wed, Jul 1 - Wed, Jul 8
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$292Volaris
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:14 pm
CUN
-
MDW
8h 49m
1 stop
$296Frontier
Sat, Apr 11 - Thu, Apr 16
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
12:04 pm - 10:22 pm
CUN
-
MDW
10h 18m
1 stop
$297Frontier
Sat, Apr 11 - Tue, Apr 14
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
4:07 pm - 7:31 pm
CUN
-
MDW
27h 24m
1 stop
$301Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:14 pm
CUN
-
MDW
8h 49m
1 stop
$302Frontier
Sat, Apr 11 - Thu, Apr 16
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
12:04 pm - 10:22 pm
CUN
-
MDW
10h 18m
1 stop
$304Frontier
Sat, Apr 4 - Tue, Apr 14
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
4:07 pm - 7:31 pm
CUN
-
MDW
27h 24m
1 stop
$305Frontier
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 Saturdays 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 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 October, where tickets cost $313 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $686 and $662 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 2 weeks before departure, which saves you about 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$100
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 4% 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 $101 for a one-way ticket and $285 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, Aeromexico, 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 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?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Cancun.

  • 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 $516 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 $3,633 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 $184 or less one-way and $408 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

Frontier,Southwest

Frontier,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

Frontier,Southwest

Frontier,Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 4 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 4321 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

No WiFi. Arrival was early but gate was occupied and had to sit on jet 30 min to deplane.

No WiFi on flight. Arrival was early but gate was occupied and had to sit on jet for nearly 30 min to deplane.

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

All went very well. We used the AIFI Airport, such a lovely facility. Definitely needs better transportation options to get there.

Both ground crew and flight crew were rude, and did not provide any level of service. They made it very difficult as we were traveling with a passenger the required assistance.

From the check-in, to the flight, and arriving, everything went very smoothly. Unfortunately, when I received my baggage it was severely damaged. I have a hard shelled suitcase and it was completely smashed it. I’m not sure how this could happened but I am extremely disappointed that my belongings were damaged beyond repair and continued use.

Really nice, all good, nice crew and all on time

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.

Good, the flight from Miami to Mexico City was better than Mexico City to Miami

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

Flight was on time, good service, but there was no free WiFi, even for first class passengers

It was good in general. The Crew during the flight were very nice at all times.

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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.