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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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$275
(Delta)

One-way from

$148
(Southwest)

Popular in

August

Cheapest in

June

Average price

$248

Good one-way deal

$236 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 junio 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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.
jue. 9/251:45 pmCUN - MDW
1 stop7h 59mDelta
mar. 9/301:05 pmMDW - CUN
1 stop6h 57mDelta
Deal found 6/10$275
This Priceline deal was found by Cheapflights users on 6/12. 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.
sáb. 7/129:09 amCUN - MDW
1 stop11h 13mFrontier
lun. 7/146:20 amMDW - CUN
1 stop6h 07mFrontier
Deal found 6/12$290
This Southwest deal was found by Cheapflights users on 6/11. 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.
vie. 7/118:30 amCUN - MDW
Nonstop3h 35mSouthwest
lun. 7/144:35 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 6/11$361
This Aeromexico deal was found by Cheapflights users on 6/10. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/1311:10 amCUN - MDW
1 stop10h 34mAeromexico
sáb. 9/2010:35 amMDW - CUN
1 stop9h 27mAeromexico
Deal found 6/10$367
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
sáb. 7/1912:26 pmCUN - MDW
2 stops10h 09mMultiple Airlines
sáb. 8/29:12 pmMDW - CUN
1 stop11h 05mMultiple Airlines
Deal found 6/9$505
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
jue. 7/38:00 amCUN - MDW
1 stop11h 16mVolaris
lun. 7/78:39 pmMDW - CUN
1 stop13h 09mVolaris
Deal found 6/11$636

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 junio 12, 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

jue. 9/25

1:45 pm-9:44 pm

1 stop7h 59m

Chicago Midway

mar. 9/30

1:05 pm-8:02 pm

1 stop6h 57m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 7/12

9:09 am-8:22 pm

1 stop11h 13m

Chicago Midway

lun. 7/14

6:20 am-12:27 pm

1 stop6h 07m

$290

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 7/11

8:30 am-12:05 pm

Nonstop3h 35m

Chicago Midway

lun. 7/14

4:35 pm-8:10 pm

Nonstop3h 35m

$361

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 9/13

11:10 am-9:44 pm

1 stop10h 34m

Chicago Midway

sáb. 9/20

10:35 am-8:02 pm

1 stop9h 27m

$367

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 7/19

12:26 pm-10:35 pm

2 stops10h 09m

Chicago Midway

sáb. 8/2

9:12 pm-8:17 am

1 stop11h 05m

$505

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 7/3

8:00 am-7:16 pm

1 stop11h 16m

Chicago Midway

lun. 7/7

8:39 pm-9:48 am

1 stop13h 09m

$636

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 7/12

8:30 am-12:05 pm

Nonstop3h 35m

$148

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 10/11

1:41 pm-11:09 pm

1 stop9h 28m

$164

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 11/1

11:10 am-9:44 pm

1 stop10h 34m

$175

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 9/25

11:15 am-11:25 pm

2 stops12h 10m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 12 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 junio 12, 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 junio 12, 2025.

The most flights from CUN to MDW are scheduled on a Monday (2 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 junio 12, 2025.
Read through reviews of airlines operating flights from Cancún to Chicago, such as Southwest, Delta and Air Transat. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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.
Air Transat
7.8
Good
396 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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
1,706 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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 1 outbound flight 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, Delta ($275), Frontier ($290), and Southwest ($361) offers the cheapest pricing from Cancún to Chicago Midway Airport. You may be able to fly from Cancún to Chicago Midway Airport for 25% 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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