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$113+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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The best prices from Chicago Midway to Cancun are usually found in January or February, booked 62 days in advance, depart on a Friday or Wednesday 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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

January

Round-trip from

$326
(Expedia)

One-way from

$113
(Orbitz)
Provider with most accurate pricing for Chicago Midway-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Cancun flights.
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High demand for flights, 40% potential price rise
Search Deals
Best time to find cheap flights, 63% potential price drop
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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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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 21, 2024.

This Expedia deal was found by Cheapflights users on 11/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/212:43 pmMDW - CUN
1 stop7h 20mMultiple Airlines
Fri 12/611:43 amCUN - MDW
1 stop13h 37mMultiple Airlines
Deal found 11/20$326
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1212:36 pmMDW - CUN
1 stop20h 52mFrontier
Tue 12/179:53 amCUN - MDW
1 stop9h 01mFrontier
Deal found 11/19$333
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/73:00 pmMDW - CUN
Nonstop3h 45mSouthwest
Tue 12/107:10 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 11/19$343
This Delta deal was found by Cheapflights users on 11/20. 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 12/36:00 amMDW - CUN
1 stop8h 15mDelta
Tue 12/105:54 amCUN - MDW
2 stops11h 18mDelta
Deal found 11/20$392
This Trip.com deal was found by Cheapflights users on 11/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/36:00 amMDW - CUN
1 stop6h 46mAeromexico
Thu 12/58:10 amCUN - MDW
1 stop9h 05mAeromexico
Deal found 11/20$415
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/268:42 pmMDW - CUN
1 stop12h 25mVolaris
Tue 12/39:45 pmCUN - MDW
1 stop12h 00mVolaris
Deal found 11/20$550

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 2,629,791 searches. Data last updated November 21, 2024.

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Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 12/2

12:43 pm-9:03 pm

1 stop7h 20m

Cancun

Fri 12/6

11:43 am-12:20 am

1 stop13h 37m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 1/22

8:01 pm-9:01 am

1 stop12h 00m

Cancun

Sun 1/26

2:25 pm-9:32 pm

1 stop8h 07m

$332

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 12/7

3:00 pm-7:45 pm

Nonstop3h 45m

Cancun

Tue 12/10

7:10 am-9:45 am

Nonstop3h 35m

$343

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/19

6:00 am-6:31 pm

2 stops11h 31m

Cancun

Wed 1/22

12:15 pm-6:14 pm

1 stop6h 59m

$392

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/3

10:57 am-9:05 pm

1 stop9h 08m

Cancun

Fri 2/7

4:25 pm-10:20 pm

1 stop6h 55m

$405

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/10

8:39 pm-9:04 am

1 stop12h 25m

Cancun

Sun 3/16

7:39 am-4:54 pm

1 stop9h 15m

$463

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 3/4

7:05 am-2:34 pm

1 stop30h 29m

$113

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 2/16

10:35 pm-2:00 pm

1 stop14h 25m

$119

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/9

4:08 pm-9:13 am

2 stops16h 05m

$153

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/4

10:08 am-4:30 pm

1 stop5h 22m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 12 results
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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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
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 November 15, 2024.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Cancún, you should look to book at least 62 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 $358). Flying from Chicago Midway Airport to Cancún in June is currently the most expensive (average of $463). 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 21, 2024.

It’s typically best to fly out from Chicago Midway Airport to Cancún at noon. Doing so could potentially save you 64% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 November 21, 2024.
Read through reviews of airlines operating flights from Chicago to Cancún, such as Frontier, Southwest and Delta. 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
5,015 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,759 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Aeromexico
7.5
Good
2,004 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 6 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 $332. Other airlines that can offer you cheap pricing are Southwest, from $343, and Delta, from $392. These flights start at 27% 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 $113. Southwest flights start at $119 while deals on Aeromexico start at $168 one-way.

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

    On average you can expect to pay $520 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $146 while the most popular route, (Chicago Midway - Cancun) is currently priced at $359.

  • 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 $358). Flying from Chicago Midway Airport to Cancún in June is currently the most expensive (average of $463). 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

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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 6 airlines flying from Midway to Cancún

Discover the top 6 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$160Average$242FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$183Average$407FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$311Average$381FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$342Average$669FlexibilityNo cancel feeOn-time63%
DeltaCheapest$376Average$542FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$399Average$583FlexibilityNo cancel feeOn-timeN/A
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