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$106+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
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The best prices from Chicago Midway to Cancun are usually found in February or April, booked 57 days in advance, depart on a Monday or Thursday 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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(Kiwi.com)

One-way from

$106
(Travelocity)

Popular in

December

Cheapest in

February

Average price

$388

Good round-trip deal

$601 or less

Good one-way deal

$111 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. 18% potential increase in price ($127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/12:45 pmMDW - CUN
1 stop21h 20mFrontier
Tue 4/810:40 amCUN - MDW
1 stop9h 11mFrontier
Deal found 2/19$247
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/14:40 pmMDW - CUN
1 stop15h 33mMultiple Airlines
Thu 4/1010:30 amCUN - MDW
1 stop11h 57mMultiple Airlines
Deal found 2/19$266
This Southwest deal was found by Cheapflights users on 2/20. 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 5/78:45 amMDW - CUN
1 stop6h 05mSouthwest
Wed 5/149:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 2/20$307
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 2/256:00 amMDW - CUN
1 stop8h 15mDelta
Sat 3/111:19 amCUN - MDW
2 stops12h 01mDelta
Deal found 2/20$390
This Kiwi.com deal was found by Cheapflights users on 2/21. 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.
Sun 3/168:39 pmMDW - CUN
1 stop12h 25mVolaris
Thu 3/208:00 amCUN - MDW
1 stop11h 10mVolaris
Deal found 2/21$394
This Aeromexico deal was found by Cheapflights users on 2/20. 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.
Tue 3/2512:51 pmMDW - CUN
2 stops12h 07mAeromexico
Wed 3/268:00 amCUN - MDW
1 stop8h 14mAeromexico
Deal found 2/20$407

Find flights from Midway to Cancún within your budget

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 February 21, 2025.

Fly from

Midway

Fly to

Cancún

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

2:45 pm-12:05 pm

1 stop21h 20m

Cancun

Tue 4/8

10:40 am-7:51 pm

1 stop9h 11m

$247

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

4:40 pm-8:13 am

1 stop15h 33m

Cancun

Thu 4/10

10:30 am-10:27 pm

1 stop11h 57m

$266

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 5/7

8:45 am-2:50 pm

1 stop6h 05m

Cancun

Wed 5/14

9:00 am-12:40 pm

Nonstop3h 40m

$307

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/3

6:00 am-6:35 pm

2 stops11h 35m

Cancun

Thu 3/6

8:00 am-4:20 pm

1 stop9h 20m

$390

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/16

8:39 pm-9:04 am

1 stop12h 25m

Cancun

Thu 3/20

8:00 am-7:10 pm

1 stop11h 10m

$394

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 3/12

9:25 am-8:00 pm

2 stops10h 35m

Cancun

Wed 3/19

10:00 am-4:14 pm

1 stop6h 14m

$395

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/5

8:03 pm-2:10 pm

1 stop18h 07m

$106

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 4/6

4:30 pm-8:25 pm

Nonstop3h 55m

$110

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

4:40 pm-8:13 am

1 stop15h 33m

$133

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/22

6:04 am-5:32 pm

2 stops11h 28m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 12 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
CheapTicketsDealPrice Accuracy3 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 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.

Travel insights for flights from Midway to Cancún

Get recent, data-driven insights about flights from Midway to Cancún including ideal travel times, pricing trends, and more.

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 February 14, 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 February 21, 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.

What is the cheapest day to fly from Chicago Midway Airport to Cancún?

Use this chart to determine the cheapest time to fly round-trip from Midway to Cancún. Price data was last updated on February 16, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Cancún flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 21, 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
8.1
Very good
4,406 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,406 reviews
Southwest
8.1
Very good
4,406 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,217 reviews
Southwest
8.1
Very good
4,406 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,771 reviews
Southwest
8.1
Very good
4,406 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Volaris
6.7
Okay
1,208 reviews
Southwest
8.1
Very good
4,406 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,354 reviews
Southwest
8.1
Very good
4,406 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 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 $247. Other airlines that can offer you cheap pricing are Southwest, from $307, and Aeromexico, from $390. These flights start at 56% 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 Frontier, which is currently one of the cheapest options available, starting at $106. Southwest flights start at $110 while deals on Delta start at $180 one-way.

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

    On average you can expect to pay $473 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 $332.

  • 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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$175Average$393FlexibilityNo cancel feeOn-time69%
FrontierCheapest$177Average$338FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$183Average$409FlexibilityNo cancel feeOn-time65%
DeltaCheapest$380Average$537FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$382Average$567FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$460Average$704FlexibilityNo cancel feeOn-time63%
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%
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