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$209+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Cheap 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 July 28, 2026.

This Kissandfly.com deal was found by Cheapflights users on 7/24. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Sun 9/138:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Deal found 7/24$385
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Fri 8/288:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Deal found 7/24$391
This Delta deal was found by Cheapflights users on 7/27. 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.
Thu 9/173:20 pm
CUN
-
MDW
1 stop7h 25m
Delta
Tue 9/221:00 pm
MDW
-
CUN
1 stop6h 50m
Delta
Deal found 7/27$402
This Frontier deal was found by Cheapflights users on 7/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:51 pm
CUN
-
MDW
1 stop9h 53m
Frontier
Mon 9/286:25 am
MDW
-
CUN
1 stop6h 12m
Frontier
Deal found 7/26$404
This Delta deal was found by Cheapflights users on 7/28. 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 11/138:00 am
CUN
-
MDW
1 stop15h 56m
Delta
Tue 11/249:30 am
MDW
-
CUN
2 stops10h 40m
Delta
Deal found 7/28$407
This Delta deal was found by Cheapflights users on 7/24. 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 10/278:00 am
CUN
-
MDW
1 stop8h 20m
Delta
Tue 11/39:29 am
MDW
-
CUN
2 stops10h 46m
Delta
Deal found 7/24$410
This Delta deal was found by Cheapflights users on 7/27. 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.
Tue 12/228:00 am
CUN
-
MDW
2 stops9h 22m
Delta
Sun 1/36:00 am
MDW
-
CUN
1 stop8h 30m
Delta
Deal found 7/27$412
This Aeromexico deal was found by Cheapflights users on 7/23. 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 9/168:05 am
CUN
-
MDW
1 stop14h 39m
Aeromexico
Sat 9/1911:35 am
MDW
-
CUN
1 stop8h 15m
Aeromexico
Deal found 7/23$422
This Delta deal was found by Cheapflights users on 7/23. 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 9/28:05 am
CUN
-
MDW
2 stops8h 54m
Delta
Thu 9/109:29 am
MDW
-
CUN
2 stops10h 21m
Delta
Deal found 7/23$423
This Delta deal was found by Cheapflights users on 7/27. 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.
Wed 9/99:20 am
CUN
-
MDW
2 stops13h 24m
Delta
Sat 9/199:29 am
MDW
-
CUN
2 stops10h 21m
Delta
Deal found 7/27$424
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 11/144:35 pm
CUN
-
MDW
1 stop7h 21m
Delta
Tue 11/249:30 am
MDW
-
CUN
2 stops10h 40m
Delta
Deal found 7/28$429

Find 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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$385
(Kissandfly.com)

One-way from

$209
(FlightHub)

Popular in

September

Cheapest in

April

Average price

$364

Good one-way deal

$299 or less
Provider with most accurate pricing for Cancun-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cancun-Chicago Midway flights.
Search Deals
From Cancun to Chicago Midway
Search Deals
One-way flight from Cancun to Chicago Midway
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a one-way flight from Cancun to Chicago Midway.
Search Deals

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 July 28, 2026.
Use the filters below to find and compare flights from Cancún to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 9/19

8:05 am-6:22 pm

2 stops10h 17m

Chicago Midway

Sat 9/26

9:29 am-7:50 pm

2 stops10h 21m

$446

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/25

9:20 am-10:44 pm

2 stops13h 24m

Chicago Midway

Mon 9/28

6:05 am-2:10 pm

1 stop8h 05m

$449
Quickest round-trip

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/17

1:05 pm-4:40 pm

Nonstop3h 35m

Chicago Midway

Tue 9/22

8:35 am-12:10 pm

Nonstop3h 35m

$452

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/24

1:05 pm-4:40 pm

Nonstop3h 35m

Chicago Midway

Sun 9/27

5:15 am-11:50 am

1 stop6h 35m

$457

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/25

1:05 pm-4:40 pm

Nonstop3h 35m

Chicago Midway

Sun 9/27

5:00 am-1:50 pm

1 stop8h 50m

$457

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/4

1:05 pm-4:40 pm

Nonstop3h 35m

Chicago Midway

Sun 9/13

6:05 am-2:50 pm

2 stops8h 45m

$487

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 10/14

9:11 am-10:25 pm

2 stops13h 14m

Chicago Midway

Wed 10/28

1:00 pm-8:15 pm

1 stop7h 15m

$514

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/8

11:40 am-8:35 pm

2 stops8h 55m

Chicago Midway

Mon 10/12

5:00 am-3:00 pm

1 stop10h 00m

$520

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 9/27

2:15 pm-10:30 pm

1 stop8h 15m

Chicago Midway

Mon 9/28

8:25 am-12:00 pm

Nonstop3h 35m

$526
Cheapest one-way

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 9/29

8:00 am-10:44 pm

2 stops14h 44m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust 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 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 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 July 28, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cancún to Chicago Midway Airport as you normally would.

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 1 outbound flight 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 $452, Delta can have you in Chicago Midway Airport from Cancún in 3h 35m. 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 $275. While the most popular route (Cancun - Chicago Midway) can be booked for $402 on average, our data indicates $346 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.

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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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