MDW - CUN

$123 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 7/18. 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
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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% 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.

Flights Deals
Useful Info
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

Thu, Jul 10 - Tue, Jul 15
Southwest Logo
4:35 pm - 8:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
8:30 am - 12:05 pmCUN-MDW
3h 35mnonstop
$269Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:54 pm - 11:11 pmCUN-MDW
9h 17m1 stop
$292Frontier
Find Deal
Sat, Aug 30 - Thu, Oct 2
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:41 pm - 11:25 pmCUN-MDW
9h 44m1 stop
$298Frontier
Find Deal
Sat, Oct 4 - Sat, Oct 11
Frontier Logo
6:10 am - 12:26 pmMDW-CUN
6h 16m1 stop
Frontier Logo
10:50 am - 12:11 amCUN-MDW
13h 21m1 stop
$301Frontier
Find Deal
Tue, Jun 24 - Sat, Sep 6
Aeromexico Logo
12:44 pm - 8:20 pmMDW-CUN
7h 36m1 stop
Aeromexico Logo
12:40 pm - 9:12 pmCUN-MDW
8h 32m1 stop
$305Aeromexico
Find Deal
Fri, Aug 22 - Sat, Aug 30
Aeromexico Logo
12:43 pm - 8:20 pmMDW-CUN
7h 37m1 stop
Aeromexico Logo
8:00 am - 3:28 pmCUN-MDW
7h 28m1 stop
$314Aeromexico
Find Deal
Tue, Jun 24 - Wed, Jun 25
 Logo
12:44 pm - 8:20 pmMDW-CUN
7h 36m1 stop
 Logo
3:25 pm - 8:53 pmCUN-MDW
29h 28m1 stop
Mon, Sep 8 - Sat, Sep 13
Delta Logo
6:00 am - 2:10 pmMDW-CUN
8h 10m1 stop
Delta Logo
8:15 am - 3:30 pmCUN-MDW
7h 15m1 stop
$323Delta
Find Deal
Thu, Sep 11 - Wed, Sep 17
Delta Logo
9:30 am - 8:02 pmMDW-CUN
10h 32m2 stops
Delta Logo
12:25 pm - 9:44 pmCUN-MDW
9h 19m1 stop
$328Delta
Find Deal
Tue, Jul 8 - Sat, Jul 19
 Logo
6:00 am - 12:50 pmMDW-CUN
6h 50m1 stop
 Logo
9:09 am - 8:22 pmCUN-MDW
11h 13m1 stop
Useful Info

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 Wednesdays and the most expensive ones on Thursdays.

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 July, where tickets cost $441 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $717 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 $432, 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonAugust
High seasonJanuary
Cheapest flight$123
Best time to beat the crowds with an average 4% 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 $123 for a one-way ticket and $269 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 $582 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 $121 or less one-way and $346 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
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
SouthwestOverall score based on 4287 reviews
8.2Boarding
7.6Entertainment
8.0Comfort
8.6Crew
7.1Food
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

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

It was good, however the airplane was really cold. We received snacks and the crew was friendly.

Delta has an outstanding service. They are courteous and punctual most of the time. The flight departed a half hour late but we arrived 15 minutes early.

Not sure why there are so many security checks at this airport. Consistently annoying showing passport over and over, checking carryons at gate all the while trying to make tight connection. Basically it was uncomfortable crowded cabin with meidiocre service

Although the flight is goof and the crew is good, the way the airline charges you for every service is ridiculous.

Plane never left the ground. Mech issues - entire trip was rerouted through united.

They didi not provide wheelchair though we had requested. We had to run around for 40 minutes and arrange it from the airport!

Everything was good except the check in. Could not do it online neither on the machines in the airport. Needed special assistance from the airline desk clerk

No entertainment but not expected. Unless you are referring to monitor that you can use. Then Al, was fine on all flights.

Friendly staff, It was the first flight out for our plane, so had to be deiced from the frost. Only delayed a few minutes,

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

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

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.

Better communication about delayed flight. I am thankful for a small credit for late flight.

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.

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

Stood inside the plane for more than an hour before take off

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.