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$148+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$259
(Priceline)

One-way from

$148
(Southwest)

Popular in

August

Cheapest in

June

Average price

$248

Good one-way deal

$163 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. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Priceline deal was found by Cheapflights users on 6/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1112:35 pmCUN - MDW
1 stop11h 16mFrontier
Sat 7/128:05 amMDW - CUN
1 stop7h 51mFrontier
Deal found 6/13$259
This Southwest deal was found by Cheapflights users on 6/16. 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 6/268:30 amCUN - MDW
Nonstop3h 35mSouthwest
Sun 6/295:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 6/16$272
This Delta deal was found by Cheapflights users on 6/14. 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 8/168:00 amCUN - MDW
1 stop7h 28mDelta
Wed 8/206:04 amMDW - CUN
1 stop8h 06mDelta
Deal found 6/14$275
This Aeromexico deal was found by Cheapflights users on 6/16. 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.
Thu 8/143:10 pmCUN - MDW
1 stop6h 39mAeromexico
Tue 8/196:04 amMDW - CUN
1 stop8h 06mAeromexico
Deal found 6/16$340
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/139:54 amCUN - MDW
1 stop7h 09mMultiple Airlines
Mon 8/186:40 pmMDW - CUN
2 stops17h 57mMultiple Airlines
Deal found 6/16$424

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 June 16, 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 7/11

12:35 pm-11:51 pm

1 stop11h 16m

Chicago Midway

Sat 7/12

8:05 am-3:56 pm

1 stop7h 51m

$259

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 6/26

8:30 am-12:05 pm

Nonstop3h 35m

Chicago Midway

Sun 6/29

5:25 pm-9:00 pm

Nonstop3h 35m

$272

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 8/16

8:00 am-3:28 pm

1 stop7h 28m

Chicago Midway

Wed 8/20

6:04 am-2:10 pm

1 stop8h 06m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 8/14

3:10 pm-9:49 pm

1 stop6h 39m

Chicago Midway

Tue 8/19

6:04 am-2:10 pm

1 stop8h 06m

$340

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 8/13

9:54 am-5:03 pm

1 stop7h 09m

Chicago Midway

Mon 8/18

6:40 pm-12:37 pm

2 stops17h 57m

$424

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 7/16

8:30 am-12:05 pm

Nonstop3h 35m

$148

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 7/12

9:09 am-8:22 pm

1 stop11h 13m

$164

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 8/16

8:00 am-3:28 pm

1 stop7h 28m

$175

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 8/7

12:26 pm-12:21 pm

2 stops23h 55m

$215

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 8/20

7:00 am-9:49 pm

2 stops14h 49m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 11 results
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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 June 16, 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.

Weekly flight availability from Cancún to Chicago Midway Airport

Explore weekly flight availability from Cancún to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 16, 2025.

The most flights from CUN to MDW are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 June 16, 2025.
Read through reviews of airlines operating flights from Cancún to Chicago, such as Southwest, Delta and Aeromexico. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,711 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Volaris
6.7
Okay
1,170 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,296 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 2 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, Frontier ($259), Southwest ($272), and Delta ($275) offers the cheapest pricing from Cancún to Chicago Midway Airport. You may be able to fly from Cancún to Chicago Midway Airport for 30% 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 $148 on Southwest. Other airlines that offer cheap prices include Frontier from $164 and Delta from $175 one-way.

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

    Looking at all options, your cheapest flight can be booked for $147. While the most popular route (Cancun - Chicago Midway) can be booked for $272 on average our data indicates $288 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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