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$149+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
feb. 26 — mar. 51
jue. 2/26
jue. 3/5
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 enero 27, 2026.

This Delta deal was found by Cheapflights users on 1/26. 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.
vie. 1/3012:15 pm
CUN
-
MDW
1 stop6h 14m
Delta
lun. 2/29:33 am
MDW
-
CUN
2 stops10h 38m
Delta
Deal found 1/26$282
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/2311:30 am
CUN
-
MDW
1 stop10h 51m
Frontier
lun. 4/276:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Deal found 1/27$283
This Southwest deal was found by Cheapflights users on 1/26. 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.
vie. 2/133:40 pm
CUN
-
MDW
Nonstop3h 40m
Southwest
lun. 2/1610:15 pm
MDW
-
CUN
1 stop15h 20m
Southwest
Deal found 1/26$287
This Southwest deal was found by Cheapflights users on 1/26. 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.
jue. 3/52:55 pm
CUN
-
MDW
Nonstop3h 45m
Southwest
lun. 3/94:05 pm
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/26$295
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/1911:48 am
CUN
-
MDW
1 stop10h 24m
Frontier
lun. 2/236:00 am
MDW
-
CUN
1 stop6h 37m
Frontier
Deal found 1/27$305
This Southwest deal was found by Cheapflights users on 1/27. 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.
vie. 1/301:45 pm
CUN
-
MDW
Nonstop3h 45m
Southwest
lun. 2/29:15 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/27$306
This Frontier deal was found by Cheapflights users on 1/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/2611:48 am
CUN
-
MDW
1 stop10h 24m
Frontier
dom. 3/19:04 pm
MDW
-
CUN
2 stops19h 13m
Frontier
Deal found 1/25$310
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/1610:34 am
CUN
-
MDW
2 stops21h 30m
Frontier
mar. 4/216:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Deal found 1/27$317
This Southwest deal was found by Cheapflights users on 1/26. 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.
mié. 2/252:55 pm
CUN
-
MDW
1 stop9h 00m
Southwest
mié. 3/49:15 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/26$335
This Expedia deal was found by Cheapflights users on 1/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/2610:01 am
CUN
-
MDW
1 stop7h 15m
Multiple Airlines
mar. 3/36:00 am
MDW
-
CUN
1 stop7h 03m
Multiple Airlines
Deal found 1/25$339
This Delta deal was found by Cheapflights users on 1/26. 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.
jue. 4/238:05 am
CUN
-
MDW
2 stops14h 23m
Delta
lun. 4/276:00 am
MDW
-
CUN
2 stops10h 40m
Delta
Deal found 1/26$341

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 enero 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Delta)

One-way from

$149
(Southwest)

Popular in

March

Cheapest in

June

Average price

$363

Good one-way deal

$348 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. 9% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 enero 27, 2026.
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

mié. 3/11

8:00 am-5:22 pm

1 stop9h 22m

Chicago Midway

mié. 3/18

12:47 pm-8:20 pm

1 stop7h 33m

$282

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 2/25

4:45 pm-10:31 pm

1 stop6h 46m

Chicago Midway

mié. 3/4

6:00 am-4:45 pm

1 stop9h 45m

$282

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 2/13

11:00 am-5:45 pm

1 stop7h 45m

Chicago Midway

lun. 2/16

6:00 am-4:45 pm

1 stop9h 45m

$282

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 3/5

8:00 am-5:45 pm

1 stop10h 45m

Chicago Midway

mar. 3/10

6:00 am-3:45 pm

1 stop9h 45m

$282

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 3/5

8:00 am-5:45 pm

1 stop10h 45m

Chicago Midway

lun. 3/9

1:10 pm-8:20 pm

2 stops7h 10m

$282

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 2/12

11:00 am-5:45 pm

1 stop7h 45m

Chicago Midway

mar. 2/17

10:49 am-9:11 pm

1 stop9h 22m

$282

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 4/16

11:30 am-10:21 pm

1 stop10h 51m

Chicago Midway

mar. 4/21

6:00 am-2:56 pm

1 stop8h 56m

$283

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 2/19

11:48 am-9:12 pm

1 stop10h 24m

Chicago Midway

lun. 2/23

6:00 am-1:37 pm

1 stop6h 37m

$283

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 4/23

11:30 am-10:21 pm

1 stop10h 51m

Chicago Midway

lun. 4/27

6:00 am-2:56 pm

1 stop8h 56m

$283

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 2/13

3:40 pm-6:20 pm

Nonstop3h 40m

Chicago Midway

lun. 2/16

10:15 pm-2:35 pm

1 stop15h 20m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 22 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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 enero 27, 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 $282, Delta can have you in Chicago Midway Airport from Cancún in 9h 22m. The distance between Cancún and Chicago Midway Airport is about 1434 mi.

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

    Looking at all options, your cheapest flight can be booked for $253. While the most popular route (Cancun - Chicago Midway) can be booked for $282 on average, our data indicates $370 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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