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$125+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Cancun are usually found in September or July, booked 57 days in advance, depart on a Monday or Sunday and return on a Tuesday

Cheap 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 August 7, 2025.

Round-trip from

$271
(Southwest)

One-way from

$125
(Southwest)

Popular in

December

Cheapest in

September

Average price

$542

Good round-trip deal

$379 or less

Good one-way deal

$123 or less
From Chicago Midway to Cancun
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One-way flight from Chicago Midway to Cancun
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Highest demand for flights based on searches. 15% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to Cancun.
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Price to beat on a one-way flight from Chicago Midway to Cancun.
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Find 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 August 7, 2025.

This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/910:40 amMDW - CUN
Nonstop3h 45mSouthwest
Thu 11/132:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 8/6$271
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/189:55 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 8/232:25 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/6$276
This Southwest deal was found by Cheapflights users on 8/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1410:35 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 9/183:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/7$281
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Tue 11/181:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 8/6$295
This SmartFares deal was found by Cheapflights users on 8/6. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/610:31 amMDW - CUN
1 stop9h 49mAeromexico
Sat 9/138:00 amCUN - MDW
1 stop7h 26mAeromexico
Deal found 8/6$301
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/209:10 amMDW - CUN
1 stop6h 50mSouthwest
Wed 8/273:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/6$306
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/317:55 amMDW - CUN
1 stop6h 05mSouthwest
Sat 9/61:15 pmCUN - MDW
1 stop7h 30mSouthwest
Deal found 8/6$310
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2410:35 amMDW - CUN
Nonstop3h 35mSouthwest
Fri 8/291:45 pmCUN - MDW
1 stop6h 40mSouthwest
Deal found 8/6$311
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/229:55 amMDW - CUN
Nonstop3h 35mSouthwest
Fri 8/292:20 pmCUN - MDW
1 stop7h 40mSouthwest
Deal found 8/6$316
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/110:35 amMDW - CUN
1 stop9h 45mDelta
Thu 11/612:05 pmCUN - MDW
1 stop11h 09mDelta
Deal found 8/7$326

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 August 7, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Cancún that are best for you.

Fly from

Midway

Fly to

Cancún

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/9

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

Thu 11/13

2:15 pm-5:00 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 8/18

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Sat 8/23

2:25 pm-6:05 pm

Nonstop3h 40m

$276

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/14

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

Thu 9/18

3:10 pm-6:50 pm

Nonstop3h 40m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Tue 11/18

1:45 pm-4:30 pm

Nonstop3h 45m

$295

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

10:31 am-8:20 pm

1 stop9h 49m

Cancun

Sat 9/13

8:00 am-3:26 pm

1 stop7h 26m

$301

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 8/20

9:10 am-4:00 pm

1 stop6h 50m

Cancun

Wed 8/27

3:10 pm-6:50 pm

Nonstop3h 40m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 8/31

7:55 am-2:00 pm

1 stop6h 05m

Cancun

Sat 9/6

1:15 pm-8:45 pm

1 stop7h 30m

$310

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 8/24

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

Fri 8/29

1:45 pm-8:25 pm

1 stop6h 40m

$311

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/13

6:00 am-12:30 pm

1 stop5h 30m

Cancun

Wed 1/21

8:00 am-4:25 pm

1 stop9h 25m

$313

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 8/22

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Fri 8/29

2:20 pm-10:00 pm

1 stop7h 40m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Showing 1-10 of 22 results
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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?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Cancún. Price data was last updated on August 1, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Cancún, you should look to book at least 57 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $360). Flying from Chicago Midway Airport to Cancún in March is currently the most expensive (average of $492). 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 August 7, 2025.

It’s typically best to fly out from Chicago Midway Airport to Cancún in the evening. Doing so could potentially save you 47% on the flight price compared to flying at noon, which is usually more expensive.

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 August 7, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cancún, such as Southwest, Delta, and Aeromexico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,721 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,230 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 8 different airlines.

  • What is the cheapest airline to fly from Chicago Midway Airport to Cancún round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to Cancún round-trip from $271. This flight start at 53% lower than the current average price 3 months from now.

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

    On average you can expect to pay $289 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $122 while the most popular route, (Chicago Midway - Cancun) is currently priced at $281.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $360). Flying from Chicago Midway Airport to Cancún in March is currently the most expensive (average of $492). 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
Holbox
Punta Sam

Browse thousands of different options on Cheapflights for your next trip

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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
Midway to Cozumel flights
O'Hare Intl to Chetumal flights

Top 8 airlines flying from Midway to Cancún

Discover the top 8 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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$565FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$312Average$514FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$578FlexibilityNo cancel feeOn-time63%
DeltaCheapest$380Average$610FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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