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$121+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
May 24 — May 311
Sat 5/24
Sat 5/31
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Cancun are usually found in September or May, booked 57 days in advance, depart on a Monday or Tuesday and return on a Monday

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 May 19, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$267
(Southwest)

One-way from

$121
(Southwest)

Popular in

December

Cheapest in

September

Average price

$462

Good round-trip deal

$345 or less

Good one-way deal

$121 or less
Provider with most accurate pricing for Chicago Midway-Cancun flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Cancun flights.
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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. 16% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
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 May 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 May 19, 2025.

This Southwest deal was found by Cheapflights users on 5/17. 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.
Tue 5/209:35 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 5/229:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 5/17$267
This Flightnetwork deal was found by Cheapflights users on 5/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/32:44 pmMDW - CUN
1 stop25h 38mFrontier
Thu 7/101:49 pmCUN - MDW
1 stop9h 28mFrontier
Deal found 5/19$312
This Aeromexico deal was found by Cheapflights users on 5/19. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:00 amMDW - CUN
1 stop5h 17mAeromexico
Tue 9/1612:25 pmCUN - MDW
1 stop9h 19mAeromexico
Deal found 5/19$316
This Delta deal was found by Cheapflights users on 5/18. 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.
Fri 5/3012:48 pmMDW - CUN
2 stops11h 42mDelta
Thu 6/58:00 amCUN - MDW
1 stop9h 36mDelta
Deal found 5/18$322
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/29:12 pmMDW - CUN
1 stop11h 04mMultiple Airlines
Fri 6/612:39 pmCUN - MDW
1 stop9h 39mMultiple Airlines
Deal found 5/18$407

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 19, 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

Fri 6/6

4:35 pm-8:10 pm

Nonstop3h 35m

Cancun

Mon 6/9

8:30 am-12:05 pm

Nonstop3h 35m

$267

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/3

2:44 pm-4:22 pm

1 stop25h 38m

Cancun

Thu 7/10

1:49 pm-11:17 pm

1 stop9h 28m

$312

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 9/12

6:00 am-11:17 am

1 stop5h 17m

Cancun

Tue 9/16

12:25 pm-9:44 pm

1 stop9h 19m

$316

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 9/18

1:05 pm-12:03 am

2 stops10h 58m

Cancun

Tue 9/23

7:52 am-9:44 pm

2 stops13h 52m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 6/2

9:12 pm-8:16 am

1 stop11h 04m

Cancun

Fri 6/6

12:39 pm-10:18 pm

1 stop9h 39m

$407

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/23

9:15 am-12:50 pm

Nonstop3h 35m

$121

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/14

6:20 am-12:32 pm

1 stop6h 12m

$122

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/16

6:00 am-2:10 pm

1 stop8h 10m

$133

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 6/4

12:48 pm-12:27 am

2 stops11h 39m

$146

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 7/7

8:35 am-8:12 am

1 stop23h 37m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

Showing 1-10 of 11 results
1
2

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*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars

*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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Cancún flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Cancún. Price data was last updated on May 16, 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 May 19, 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.

Weekly flight availability from Chicago Midway Airport to Cancún

Explore weekly flight availability from Midway to Cancún. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 19, 2025.

The most flights from MDW to CUN are scheduled on a Saturday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Cancún by month

Plan your trip to Cancún by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Cancún ranges from 1.1 - 11.1 inches per month. October is typically the wettest month, when rainfall can reach 11.1 in. April is typically the driest time to visit Cancún when rainfall is around 1.1 in.

Temperature in Cancún by month

Plan your trip to Cancún by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Cancún, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 86.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

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 19, 2025.
Read through reviews of airlines operating flights from Chicago to Cancún, such as Southwest, Delta and Aeromexico. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,291 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,291 reviews
Southwest
8.0
Very good
4,291 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,951 reviews
Southwest
8.0
Very good
4,291 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,699 reviews
Southwest
8.0
Very good
4,291 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,845 reviews
Southwest
8.0
Very good
4,291 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Volaris
6.7
Okay
1,174 reviews
Southwest
8.0
Very good
4,291 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 is 1 daily inbound flight from Chicago Midway from 8 different airlines.

  • 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 $267. Other airlines that can offer you cheap pricing are Aeromexico, from $302, and Frontier, from $312. These flights start at 54% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Cancún one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $121. Frontier flights start at $122 while deals on Aeromexico start at $133 one-way.

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

    On average you can expect to pay $319 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $111 while the most popular route, (Chicago Midway - Cancun) is currently priced at $267.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport 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
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 May 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$450FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$341FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$320Average$526FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$375Average$657FlexibilityNo cancel feeOn-time63%
DeltaCheapest$380Average$532FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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