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$144+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$274
(Kiwi.com)

One-way from

$144
(Southwest)

Popular in

November

Cheapest in

June

Average price

$334

Good round-trip deal

$445 or less

Good one-way deal

$329 or less
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. 10% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Cancun to Chicago Midway.
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Price to beat on a one-way flight from Cancun to Chicago Midway.
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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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/312:06 pmCUN - MDW
1 stop6h 43mFrontier
Fri 11/146:29 pmMDW - CUN
1 stop15h 13mFrontier
Deal found 9/11$274
This Southwest deal was found by Cheapflights users on 9/11. 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 12/2711:20 amCUN - MDW
Nonstop3h 40mSouthwest
Mon 1/510:40 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 9/11$275
This Delta deal was found by Cheapflights users on 9/10. 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 11/128:00 amCUN - MDW
1 stop9h 39mDelta
Mon 11/176:00 amMDW - CUN
1 stop8h 34mDelta
Deal found 9/10$276
This Aeromexico deal was found by Cheapflights users on 9/11. 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 9/208:00 amCUN - MDW
1 stop13h 10mAeromexico
Tue 9/2312:43 pmMDW - CUN
1 stop7h 32mAeromexico
Deal found 9/11$277
This Southwest deal was found by Cheapflights users on 9/11. 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 9/202:25 pmCUN - MDW
Nonstop3h 40mSouthwest
Tue 9/239:55 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 9/11$290
This Southwest deal was found by Cheapflights users on 9/11. 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 11/41:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Tue 11/1111:25 amMDW - CUN
1 stop7h 20mSouthwest
Deal found 9/11$293
This Southwest deal was found by Cheapflights users on 9/10. 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 10/153:15 pmCUN - MDW
Nonstop3h 35mSouthwest
Mon 10/209:40 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 9/10$295
This Southwest deal was found by Cheapflights users on 9/10. 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 10/412:00 pmCUN - MDW
Nonstop3h 35mSouthwest
Tue 10/75:35 amMDW - CUN
1 stop6h 30mSouthwest
Deal found 9/10$298
This Southwest deal was found by Cheapflights users on 9/10. 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 12/2512:55 pmCUN - MDW
1 stop9h 10mSouthwest
Mon 1/510:40 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 9/10$303
This Southwest deal was found by Cheapflights users on 9/11. 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 9/183:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Mon 9/229:55 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 9/11$306
This Southwest deal was found by Cheapflights users on 9/10. 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 9/1310:45 amCUN - MDW
1 stop6h 35mSouthwest
Tue 9/169:55 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 9/10$311

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 September 11, 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

Sat 12/27

11:20 am-2:00 pm

Nonstop3h 40m

Chicago Midway

Mon 1/5

10:40 am-3:25 pm

Nonstop3h 45m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 12/17

8:00 am-4:36 pm

1 stop9h 36m

Chicago Midway

Tue 1/6

6:00 am-12:30 pm

1 stop5h 30m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 11/12

8:00 am-4:39 pm

1 stop9h 39m

Chicago Midway

Tue 11/18

6:00 am-1:55 pm

1 stop6h 55m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 12/21

4:30 pm-10:16 pm

1 stop6h 46m

Chicago Midway

Mon 1/5

6:00 am-1:55 pm

1 stop6h 55m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 12/22

8:00 am-4:15 pm

1 stop9h 15m

Chicago Midway

Fri 1/2

12:43 pm-9:20 pm

1 stop7h 37m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 11/27

4:15 pm-9:01 am

1 stop17h 46m

Chicago Midway

Wed 12/3

6:00 am-9:20 pm

1 stop14h 20m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

4:25 pm-9:46 pm

1 stop6h 21m

Chicago Midway

Mon 1/26

6:00 am-3:17 pm

1 stop8h 17m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 12/17

4:34 pm-11:32 pm

1 stop7h 58m

Chicago Midway

Wed 12/31

9:54 am-4:26 pm

1 stop5h 32m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 11/26

6:00 am-11:32 pm

2 stops18h 32m

Chicago Midway

Wed 12/3

6:00 am-9:20 pm

1 stop14h 20m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 12/17

4:34 pm-11:32 pm

1 stop7h 58m

Chicago Midway

Thu 1/1

9:54 am-4:26 pm

1 stop5h 32m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 20 results
1
2

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 September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from Cancún to Chicago Midway Airport in the morning. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight at noon.

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 $275, Southwest can have you in Chicago Midway Airport from Cancún in 3h 40m. The distance between Cancún and Chicago Midway Airport is about 1434 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Looking at all options, your cheapest flight can be booked for $277. While the most popular route (Cancun - Chicago Midway) can be booked for $276 on average, our data indicates $489 when flying from Cancún to Chicago Midway Airport.

  • 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.

  • What is the cheapest month to book a flight from Cancún to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Cancún to Chicago Midway Airport (average of $160). Flying from Cancún to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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