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$138+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Southwest)

One-way from

$138
(Kiwi.com)

Popular in

June

Cheapest in

March

Average price

$132

Good one-way deal

$376 or less
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. 14% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/69:20 amCUN - MDW
Nonstop3h 40mSouthwest
Mon 3/104:30 pmMDW - CUN
Nonstop3h 55mSouthwest
Deal found 2/20$249
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/53:49 pmCUN - MDW
1 stop9h 28mFrontier
Wed 3/125:58 pmMDW - CUN
1 stop14h 18mFrontier
Deal found 2/19$276
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/281:12 pmCUN - MDW
1 stop7h 07mMultiple Airlines
Wed 3/51:16 pmMDW - CUN
2 stops22h 04mMultiple Airlines
Deal found 2/19$314
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 2/278:00 amCUN - MDW
1 stop9h 20mDelta
Wed 3/510:57 amMDW - CUN
1 stop9h 08mDelta
Deal found 2/20$347
This Aeromexico deal was found by Cheapflights users on 2/20. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/153:11 pmCUN - MDW
1 stop7h 15mAeromexico
Fri 4/186:04 amMDW - CUN
1 stop5h 21mAeromexico
Deal found 2/20$378
This eDestinos deal was found by Cheapflights users on 2/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/218:00 amCUN - MDW
1 stop11h 10mVolaris
Fri 3/288:39 pmMDW - CUN
1 stop13h 16mVolaris
Deal found 2/19$470
This WestJet deal was found by Cheapflights users on 2/20. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/152:00 pmCUN - MDW
2 stops24h 22mWestJet
Fri 4/181:16 pmMDW - CUN
2 stops29h 54mWestJet
Deal found 2/20$1,297

Find flights from Cancún to Midway within your budget

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 February 20, 2025.

Fly from

Cancún

Fly to

Midway

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/6

9:20 am-12:00 pm

Nonstop3h 40m

Chicago Midway

Mon 3/10

4:30 pm-8:25 pm

Nonstop3h 55m

$249

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 3/5

3:49 pm-12:17 am

1 stop9h 28m

Chicago Midway

Wed 3/12

5:58 pm-8:16 am

1 stop14h 18m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 3/19

11:05 am-6:02 pm

1 stop6h 57m

Chicago Midway

Wed 3/26

9:54 am-8:00 pm

1 stop10h 06m

$347

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/22

9:49 am-8:41 pm

1 stop10h 52m

Chicago Midway

Fri 5/30

9:12 pm-10:11 am

1 stop12h 59m

$361

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 4/15

3:11 pm-10:26 pm

1 stop7h 15m

Chicago Midway

Fri 4/18

6:04 am-11:25 am

1 stop5h 21m

$378

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 3/21

8:00 am-7:10 pm

1 stop11h 10m

Chicago Midway

Fri 3/28

8:39 pm-9:55 am

1 stop13h 16m

$470

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 4/15

2:00 pm-2:22 pm

2 stops24h 22m

Chicago Midway

Fri 4/18

1:16 pm-7:10 pm

2 stops29h 54m

$1,297

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 4/23

1:20 am-10:26 pm

2 stops21h 06m

Chicago Midway

Sun 4/27

4:59 pm-2:15 pm

2 stops21h 16m

$2,212

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 4/15

12:40 pm-7:45 pm

1 stop7h 05m

$138

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 3/18

12:25 pm-3:46 pm

2 stops27h 21m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 13 results
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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*2 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 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.

Travel insights for flights from Cancún to Midway

Get recent, data-driven insights about flights from Cancún to Midway including ideal travel times, pricing trends, and more.

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 February 20, 2025.

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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated February 20, 2025.
Read through reviews of airlines operating flights from Cancún to Chicago, such as Southwest, Delta and LATAM Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,771 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

  • What are the cheapest airlines flying from Cancún to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($249), Frontier ($276), and Delta ($347) offers the cheapest pricing from Cancún to Chicago Midway Airport. You may be able to fly from Cancún to Chicago Midway Airport for 29% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Cancún to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $138 on Frontier. Other airlines that offer cheap prices include Southwest from $158 and Volaris from $189 one-way.

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

    Looking at all options, your cheapest flight can be booked for $283. While the most popular route (Cancun - Chicago Midway) can be booked for $337 on average our data indicates $456 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 Cancún?

Book flights to Cancún if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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