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$139+ Cheap flights from Cancún (CUN) to Midway (MDW)

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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Cancún to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Cancún (CUN) to Midway (MDW). 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 October 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$275
(Southwest)

One-way from

$139
(Southwest)

Popular in

December

Cheapest in

June

Average price

$454
Provider with most accurate pricing for Cancun-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Cancun-Chicago Midway flights.
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From Cancun to Chicago Midway
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One-way flight from Cancun to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Cancún to Midway

Cheapest flights from Cancún to Midway
Explore the most affordable flight options available from Cancún to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This Southwest deal was found by Cheapflights users on 10/26. 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 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Sat 11/295:55 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 10/26$275
This Delta deal was found by Cheapflights users on 10/27. 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 11/1411:50 amCUN - MDW
1 stop12h 50mDelta
Mon 11/176:00 amMDW - CUN
1 stop5h 22mDelta
Deal found 10/27$276
This Delta deal was found by Cheapflights users on 10/28. 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 12/512:00 pmCUN - MDW
1 stop12h 47mDelta
Tue 12/96:00 amMDW - CUN
1 stop8h 33mDelta
Deal found 10/28$277
This Southwest deal was found by Cheapflights users on 10/27. 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 11/142:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Mon 11/1711:25 amMDW - CUN
1 stop7h 20mSouthwest
Deal found 10/27$306
This Southwest deal was found by Cheapflights users on 10/27. 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.
Thu 12/412:55 pmCUN - MDW
1 stop9h 10mSouthwest
Sun 12/710:40 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 10/27$315
This Delta deal was found by Cheapflights users on 10/26. 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.
Wed 11/198:00 amCUN - MDW
2 stops11h 08mDelta
Mon 11/2410:47 amMDW - CUN
1 stop9h 33mDelta
Deal found 10/26$328
This Southwest deal was found by Cheapflights users on 10/27. 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 11/142:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Tue 11/189:20 amMDW - CUN
1 stop10h 05mSouthwest
Deal found 10/27$330
This Aeromexico deal was found by Cheapflights users on 10/25. 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.
Wed 11/128:00 amCUN - MDW
1 stop9h 39mAeromexico
Fri 11/146:00 amMDW - CUN
1 stop14h 20mAeromexico
Deal found 10/25$332
This Southwest deal was found by Cheapflights users on 10/27. 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 11/146:55 pmCUN - MDW
1 stop6h 15mSouthwest
Wed 11/197:00 amMDW - CUN
1 stop9h 00mSouthwest
Deal found 10/27$345

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cancún to Midway 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 October 28, 2025.
Use the filters below to find and compare flights from Cancún to Chicago Midway Airport that are best for you.

Fly from

Cancún

Fly to

Midway

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/14

11:50 am-11:40 pm

1 stop12h 50m

Chicago Midway

Mon 11/17

6:00 am-12:22 pm

1 stop5h 22m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

12:15 pm-5:32 pm

1 stop6h 17m

Chicago Midway

Mon 1/26

6:00 am-4:45 pm

1 stop9h 45m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/5

3:15 pm-11:47 pm

1 stop9h 32m

Chicago Midway

Tue 12/9

10:49 am-9:20 pm

1 stop9h 31m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/21

1:32 pm-11:40 pm

1 stop11h 08m

Chicago Midway

Sun 11/30

10:47 am-9:20 pm

1 stop9h 33m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/14

2:15 pm-5:00 pm

Nonstop3h 45m

Chicago Midway

Mon 11/17

8:40 am-1:25 pm

Nonstop3h 45m

$325

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 11/20

8:00 am-6:08 pm

2 stops11h 08m

Chicago Midway

Mon 11/24

10:47 am-9:20 pm

1 stop9h 33m

$328

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 11/19

8:00 am-6:08 pm

2 stops11h 08m

Chicago Midway

Mon 11/24

10:47 am-9:20 pm

1 stop9h 33m

$328

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 2/13

5:25 pm-8:54 am

1 stop16h 29m

Chicago Midway

Tue 2/17

6:00 am-4:31 pm

1 stop9h 31m

$328

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

3:40 pm-6:20 pm

Nonstop3h 40m

$139

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/12

8:30 am-12:10 pm

Nonstop3h 40m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 19 results
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Compare providers for flights from Cancún to Midway

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 Cancún to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
Kiwi.comPrice Accuracy3 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 Cancún-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cancún-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cancún-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cancún-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia 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 Cancún-Chicago Midway Airport 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 Cancún to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Cancún 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 Cancún to Chicago Midway Airport

What is the cheapest time of day to fly from CUN to MDW?

Find hourly flight availability from Cancún to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

A simple way to save on the total cost of your ticket is to fly from Cancún to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 62% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip from Cancún to Chicago Midway Airport?

Related info for your journey

Find useful and relevant information for your journey from Cancún to Midway. 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 from for flights from Cancún to Chicago Midway?

    For a flight from Cancún to Chicago Midway, you will be flying from Cancun. Cancun (CUN) is just 8.9 mi from the center of the city. Cancun is the only Cancún airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Cancun on a regular basis.

  • How long is the flight from Cancún to Chicago Midway Airport?

    For as low as $276, Delta can have you in Chicago Midway Airport from Cancún in 12h 50m. The distance between Cancún and Chicago Midway Airport is about 1434 mi.

  • Can I find deals for flights from Cancún to Midway that include hotel bookings?

    Yes. In addition to deals on Cancún to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cancún to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cancún to Midway.

  • Can I find deals for business class flights from Cancún to Midway?

    Yes. Cheapflights offers flight deals from Cancún to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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