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$120+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 Tuesday and return on a Monday

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 November 6, 2025.

This Aeromexico deal was found by Cheapflights users on 11/5. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amMDW - CUN
1 stop14h 20mAeromexico
Sat 12/1311:17 amCUN - MDW
2 stops13h 30mAeromexico
Deal found 11/5$316
This Aeromexico deal was found by Cheapflights users on 11/6. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/112:47 pmMDW - CUN
1 stop7h 33mAeromexico
Wed 12/108:00 amCUN - MDW
1 stop9h 34mAeromexico
Deal found 11/6$317
This Aeromexico deal was found by Cheapflights users on 11/5. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amMDW - CUN
1 stop14h 20mAeromexico
Wed 11/128:00 amCUN - MDW
1 stop9h 39mAeromexico
Deal found 11/5$327
This Delta deal was found by Cheapflights users on 11/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/129:34 amMDW - CUN
2 stops10h 46mDelta
Tue 12/168:00 amCUN - MDW
2 stops11h 00mDelta
Deal found 11/5$331
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/17:10 pmMDW - CUN
1 stop14h 18mFrontier
Sat 12/62:48 pmCUN - MDW
2 stops49h 04mFrontier
Deal found 11/6$332
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/912:50 pmMDW - CUN
1 stop7h 30mAeromexico
Fri 12/128:00 amCUN - MDW
1 stop9h 18mAeromexico
Deal found 11/6$335
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:42 pmMDW - CUN
1 stop15h 56mFrontier
Mon 12/82:58 pmCUN - MDW
1 stop18h 48mFrontier
Deal found 11/5$337
This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/188:40 amMDW - CUN
Nonstop3h 45mSouthwest
Tue 11/252:30 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/5$342
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amMDW - CUN
2 stops30h 13mMultiple Airlines
Sat 12/2010:12 amCUN - MDW
1 stop11h 52mMultiple Airlines
Deal found 11/6$343
This Delta deal was found by Cheapflights users on 11/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amMDW - CUN
1 stop8h 34mDelta
Sat 12/66:00 amCUN - MDW
2 stops10h 44mDelta
Deal found 11/5$345
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:29 pmMDW - CUN
2 stops16h 06mMultiple Airlines
Mon 11/2412:11 pmCUN - MDW
1 stop13h 02mMultiple Airlines
Deal found 11/5$346

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$302
(SmartFares)

One-way from

$120
(Southwest)

Popular in

March

Cheapest in

September

Average price

$656

Good round-trip deal

$281 or less

Good one-way deal

$124 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. 5% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 6, 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 1/9

6:45 am-3:30 pm

1 stop7h 45m

Cancun

Tue 1/13

8:00 am-4:31 pm

1 stop9h 31m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/23

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Wed 1/28

12:15 pm-5:32 pm

1 stop6h 17m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/29

12:48 pm-9:11 pm

1 stop7h 23m

Cancun

Mon 2/2

8:00 am-5:32 pm

1 stop10h 32m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/5

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Fri 1/9

12:05 pm-10:09 pm

2 stops11h 04m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/19

6:00 am-6:47 pm

2 stops11h 47m

Cancun

Mon 1/26

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 12/12

10:49 am-9:20 pm

1 stop9h 31m

Cancun

Tue 12/16

8:00 am-4:44 pm

1 stop9h 44m

$345

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 12/9

9:25 am-7:45 pm

1 stop9h 20m

Cancun

Thu 12/11

1:45 pm-4:30 pm

Nonstop3h 45m

$353

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/17

5:25 am-3:25 pm

1 stop9h 00m

Cancun

Mon 12/22

2:30 pm-5:15 pm

Nonstop3h 45m

$353

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/2

6:00 am-12:30 pm

1 stop5h 30m

Cancun

Fri 1/9

8:00 am-4:31 pm

1 stop9h 31m

$392

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/1

3:29 pm-12:03 pm

2 stops19h 34m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 19 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Cancún flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 31, 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $245). Flying from Chicago Midway Airport to Cancún in January is currently the most expensive (average of $430). 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 November 6, 2025.

It’s typically best to fly out from Chicago Midway Airport to Cancún in the evening. Doing so could potentially save you 41% 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 November 6, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cancún, such as Southwest, Delta, and LATAM Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
LATAM Airlines
7.5
Good
1,872 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Aeromexico
7.4
Good
1,672 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.7
Okay
1,151 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 7 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 7h 45m. 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 $161. Other airlines that can offer you cheap pricing are Aeromexico, from $312, and Southwest, from $345. These flights start at 71% 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 $324 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $114 while the most popular route, (Chicago Midway - Cancun) is currently priced at $327.

  • 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $245). Flying from Chicago Midway Airport to Cancún in January is currently the most expensive (average of $430). 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

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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 7 airlines flying from Midway to Cancún

Discover the top 7 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$510FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$572FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$567FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$618FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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