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$137+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$249
(Southwest)

One-way from

$137
(Southwest)

Popular in

June

Cheapest in

January

Average price

$226

Good one-way deal

$147 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. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/29. 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 7/318:15 amCUN - MDW
Nonstop3h 35mSouthwest
Sun 8/35:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 4/29$249
This Delta deal was found by Cheapflights users on 4/30. 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 5/38:15 amCUN - MDW
1 stop9h 44mDelta
Fri 5/99:16 amMDW - CUN
2 stops11h 04mDelta
Deal found 4/30$274
This eDestinos deal was found by Cheapflights users on 4/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1411:00 amCUN - MDW
1 stop10h 28mAeromexico
Tue 5/206:00 amMDW - CUN
1 stop6h 45mAeromexico
Deal found 4/28$325
This Frontier deal was found by Cheapflights users on 4/29. 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.
Tue 5/272:20 pmCUN - MDW
1 stop7h 54mFrontier
Tue 6/36:40 amMDW - CUN
1 stop6h 20mFrontier
Deal found 4/29$391
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/78:00 amCUN - MDW
1 stop11h 16mVolaris
Fri 8/88:39 pmMDW - CUN
1 stop14h 24mVolaris
Deal found 4/29$575
This eDestinos deal was found by Cheapflights users on 4/29. 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.
Wed 7/93:05 pmCUN - MDW
2 stops28h 11mMultiple Airlines
Thu 7/312:44 pmMDW - CUN
3 stops41h 09mMultiple Airlines
Deal found 4/29$757
This WestJet deal was found by Cheapflights users on 4/30. 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.
Sun 5/42:20 pmCUN - MDW
2 stops27h 39mWestJet
Sat 5/106:30 pmMDW - CUN
2 stops48h 15mWestJet
Deal found 4/30$2,903

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 May 1, 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

Thu 7/31

8:15 am-11:50 am

Nonstop3h 35m

Chicago Midway

Sun 8/3

5:25 pm-9:00 pm

Nonstop3h 35m

$249

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/14

9:55 am-6:45 pm

2 stops8h 50m

Chicago Midway

Tue 5/20

6:00 am-11:25 am

1 stop5h 25m

$274

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/14

11:00 am-9:28 pm

1 stop10h 28m

Chicago Midway

Tue 5/20

6:00 am-12:45 pm

1 stop6h 45m

$325

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 5/27

2:20 pm-10:14 pm

1 stop7h 54m

Chicago Midway

Tue 6/3

6:40 am-1:00 pm

1 stop6h 20m

$391

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 8/7

8:00 am-7:16 pm

1 stop11h 16m

Chicago Midway

Fri 8/8

8:39 pm-11:03 am

1 stop14h 24m

$575

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 7/9

3:05 pm-7:16 pm

2 stops28h 11m

Chicago Midway

Thu 7/31

2:44 pm-7:53 am

3 stops41h 09m

$757

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 6/5

3:20 pm-6:55 pm

Nonstop3h 35m

$137

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 6/28

9:28 am-9:45 pm

2 stops12h 17m

$174

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 5/31

9:20 am-8:17 pm

1 stop10h 57m

$176

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 6/18

11:00 am-9:45 pm

1 stop10h 45m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Cancún-Chicago Midway Airport flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 May 1, 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 May 1, 2025.

The most flights from CUN to MDW are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, 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 May 1, 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
4,294 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Volaris
6.7
Okay
1,174 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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, Southwest ($249), Delta ($274), and Aeromexico ($325) offers the cheapest pricing from Cancún to Chicago Midway Airport.

  • 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 $137 on Southwest. Other airlines that offer cheap prices include Delta from $174 and Frontier from $176 one-way.

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

    Looking at all options, your cheapest flight can be booked for $136. While the most popular route (Cancun - Chicago Midway) can be booked for $249 on average our data indicates $286 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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