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Cancún

$115+ Cheap flights from Midway (MDW) to Cancún (CUN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Find cheap flights from Midway to Cancún with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago Midway to Cancun are usually found in October or February, booked 11 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap flight deals from Midway to Cancún

Cheapest flights from Midway to Cancún
Explore the most affordable flight options available from Midway to Cancún. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 7, 2026.

This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1711:00 am
MDW
-
CUN
Nonstop3h 35m
Southwest
Fri 5/224:10 pm
CUN
-
MDW
Nonstop3h 40m
Southwest
Deal found 5/3$334
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1710:59 am
MDW
-
CUN
1 stop9h 17m
Delta
Wed 5/2011:10 am
CUN
-
MDW
1 stop9h 59m
Delta
Deal found 5/3$348
This FlightHub deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:49 pm
MDW
-
CUN
1 stop13h 06m
Volaris
Sun 6/2810:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/6$353
This Justfly.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/7$358
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1711:00 am
MDW
-
CUN
Nonstop3h 35m
Southwest
Sat 5/2310:35 am
CUN
-
MDW
Nonstop3h 40m
Southwest
Deal found 5/2$359
This FlightHub deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Fri 6/1210:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/5$362
This FlightHub deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/58:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Mon 7/133:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/6$364
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1710:59 am
MDW
-
CUN
1 stop9h 17m
Delta
Sat 5/2312:45 pm
CUN
-
MDW
1 stop8h 24m
Delta
Deal found 5/2$366
This Frontier deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
MDW
-
CUN
1 stop7h 44m
Frontier
Tue 7/213:01 pm
CUN
-
MDW
1 stop7h 07m
Frontier
Deal found 5/5$368
This FlightHub deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Sat 6/1310:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/6$369
This Justfly.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Tue 7/213:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/5$372
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1812:53 pm
MDW
-
CUN
1 stop7h 23m
Delta
Sat 5/238:00 am
CUN
-
MDW
1 stop13h 09m
Delta
Deal found 5/2$373

Find flight deals from Midway to Cancún

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Cancún (CUN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(Southwest)

One-way from

$115
(Frontier)

Popular in

December

Cheapest in

October

Average price

$618

Good round-trip deal

$382 or less

Good one-way deal

$150 or less
Provider with most accurate pricing for Chicago Midway-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Cancun flights.
Search Deals
From Chicago Midway to Cancun
Search Deals
One-way flight from Chicago Midway to Cancun
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Cancun.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Cancun.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Cancún that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 7, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Cancún that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 7/14

6:00 am-11:20 am

1 stop5h 20m

Cancun

Wed 7/15

2:10 pm-10:15 pm

1 stop8h 05m

$398

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 7/31

6:00 am-1:00 pm

1 stop7h 00m

Cancun

Tue 8/4

8:05 am-6:33 pm

2 stops10h 28m

$448

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/23

11:05 am-8:15 pm

1 stop9h 10m

Cancun

Tue 7/28

8:00 am-4:15 pm

1 stop8h 15m

$453

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/11

6:23 am-12:40 pm

1 stop6h 17m

Cancun

Tue 5/19

8:00 am-4:12 pm

1 stop8h 12m

$465

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 5/13

6:23 am-6:35 pm

2 stops12h 12m

Cancun

Wed 5/20

8:00 am-9:09 pm

1 stop13h 09m

$483
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/1

10:15 am-1:50 pm

Nonstop3h 35m

Cancun

Sat 8/8

1:30 pm-7:20 pm

1 stop5h 50m

$504

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/2

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Sun 7/5

10:55 am-5:35 pm

1 stop6h 40m

$534

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 6/15

6:40 am-4:10 pm

2 stops9h 30m

Cancun

Wed 6/24

11:05 am-11:20 pm

1 stop12h 15m

$548

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 6/4

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Thu 6/11

8:00 am-10:17 pm

1 stop14h 17m

$563

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/20

6:00 am-2:39 pm

1 stop8h 39m

Cancun

Wed 6/24

8:00 am-10:17 pm

1 stop14h 17m

$563

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 23 resultsSorted by cheapest first
1
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3

Compare providers for flights from Midway to Cancún

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Cancún in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Cancún flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Cancún flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Cancún flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Cancún flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Cancún flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Cancún

Have a flexible travel schedule? Discover the best time to fly to Cancún from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Cancún

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

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Cancún, you should look to book at least 10 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport to Cancún?

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $313). Flying from Chicago Midway Airport to Cancún in December is currently the most expensive (average of $659). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to CUN?

Find hourly flight availability from Midway to Cancún. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 7, 2026.

When flying from Chicago Midway Airport to Cancún, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Chicago Midway Airport to Cancún?

Reviews of airlines servicing Cancún

Get insights into the airlines that provide service to Cancún. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cancún. Reviews last updated May 7, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cancún, such as Southwest,Delta, andAeromexico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,301 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,459 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Aeromexico
7.4
Good
1,517 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,964 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Midway to Cancún. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Cancún from Chicago Midway?

    Located just 8.9 mi from the city center, Cancun is the airport most travelers will use when flying to Cancún from Chicago Midway. Booking flights from Chicago Midway to Cancun (CUN) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 4 different airlines.

  • How long is the flight from Chicago Midway Airport to Cancún?

    Airlines like Delta fly from Chicago Midway Airport to Cancún in about 5h 20m. The time it takes to get you to your destination can typically vary by up to . There are 1434 mi between Chicago Midway Airport and Cancún.

  • What are the cheapest airlines flying from Chicago Midway Airport to Cancún round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to Cancún round-trip from $198. Other airlines that can offer you cheap pricing are Southwest, from $296, and Aeromexico, from $309. These flights start at 58% lower than the current average price 3 months from now.

  • What are the most reliable airlines from Chicago Midway Airport to Cancún?

    Before booking your flight to Cancún from Chicago Midway Airport, check out the most reliable airlines to get you to your destination on time: Southwest (64%), Frontier (17%), Volaris( 17%).

  • What are the cheapest flights from Chicago Midway Airport to Cancún?

    On average you can expect to pay $306 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $107 while the most popular route, (Chicago Midway - Cancun) is currently priced at $364.

  • Can I find deals for flights from Midway to Cancún that include hotel bookings?

    Yes. In addition to deals on Midway to Cancún flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Cancún?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Cancún.

  • Can I find deals for business class flights from Midway to Cancún?

    Yes. Cheapflights offers flight deals from Midway to Cancún by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Cancún?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $313). Flying from Chicago Midway Airport to Cancún in December is currently the most expensive (average of $659). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Cancún?

Book flights to Cancún if you plan to visit one of these locations
Puerto Aventuras
Punta Sam
Holbox

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Alternative routes for Midway to Cancún

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Cozumel flights

Top 4 airlines flying from Midway to Cancún

Discover the top 4 airlines that operate flights from Midway to Cancún. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$198Average$515FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$296Average$508FlexibilityNo cancel feeOn-time63%
AeromexicoCheapest$309Average$401FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$375Average$3,633FlexibilityNo cancel feeOn-timeN/A

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