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$124+ Cheap flights from Midway (MDW) to Cancún (CUN)

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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Cancun are usually found in September or July, booked 57 days in advance, depart on a Monday or Sunday and return on a Tuesday

Cheap flight deals from Midway to Cancún

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Cancún (CUN). 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 July 28, 2025.

Round-trip from

$270
(Southwest)

One-way from

$124
(Southwest)

Popular in

December

Cheapest in

September

Average price

$457

Good round-trip deal

$309 or less

Good one-way deal

$122 or less
From Chicago Midway to Cancun
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One-way flight from Chicago Midway to Cancun
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Highest demand for flights based on searches. 15% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago Midway to Cancun.
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Price to beat on a one-way flight from Chicago Midway to Cancun.
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Find flight deals from Midway to Cancún

Cheapest flights from Midway to Cancún
Explore the most affordable flight options available from Midway to Cancún. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

This Southwest deal was found by Cheapflights users on 7/26. 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.
Mon 8/259:55 amMDW - CUN
Nonstop3h 35mSouthwest
Wed 8/273:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 7/26$270
This eDestinos deal was found by Cheapflights users on 7/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1010:31 amMDW - CUN
1 stop9h 49mAeromexico
Wed 9/178:00 amCUN - MDW
1 stop9h 35mAeromexico
Deal found 7/27$295
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3010:35 amMDW - CUN
1 stop9h 40mDelta
Sat 10/48:00 amCUN - MDW
1 stop7h 26mDelta
Deal found 7/28$324
This Frontier deal was found by Cheapflights users on 7/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:20 amMDW - CUN
1 stop6h 07mFrontier
Sat 8/231:54 pmCUN - MDW
1 stop9h 14mFrontier
Deal found 7/26$332
This CheapOair deal was found by Cheapflights users on 7/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:10 amMDW - CUN
1 stop6h 29mMultiple Airlines
Sat 9/68:00 amCUN - MDW
1 stop13h 12mMultiple Airlines
Deal found 7/26$341

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Cancún 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 July 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Cancún that are best for you.

Fly from

Midway

Fly to

Cancún

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 8/25

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Wed 8/27

3:10 pm-6:50 pm

Nonstop3h 40m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 9/10

10:31 am-8:20 pm

1 stop9h 49m

Cancun

Wed 9/17

8:00 am-5:35 pm

1 stop9h 35m

$295

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/30

10:35 am-8:15 pm

1 stop9h 40m

Cancun

Sat 10/4

8:00 am-3:26 pm

1 stop7h 26m

$324

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/16

6:20 am-12:27 pm

1 stop6h 07m

Cancun

Sat 8/23

1:54 pm-11:08 pm

1 stop9h 14m

$332

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/30

6:10 am-12:39 pm

1 stop6h 29m

Cancun

Sat 9/6

8:00 am-9:12 pm

1 stop13h 12m

$341

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 8/3

5:25 pm-9:00 pm

Nonstop3h 35m

$124

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/9

6:00 am-12:50 pm

1 stop6h 50m

$133

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 10/21

8:00 am-8:55 am

1 stop24h 55m

$142

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/25

6:10 am-12:26 pm

1 stop6h 16m

$146

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/9

6:00 am-5:45 pm

2 stops11h 45m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from Midway to Cancún

Have a flexible travel schedule? Discover the best time to fly to Cancún from Midway 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 Chicago Midway Airport to Cancún

How far ahead should I book a flight from Chicago Midway Airport to Cancún?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Cancún. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Cancún, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport to Cancún?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $360). Flying from Chicago Midway Airport to Cancún in March is currently the most expensive (average of $492). 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.

What is the cheapest time of day to fly from MDW to CUN?

Find hourly flight availability from Midway to Cancún. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2025.

It’s typically best to fly out from Chicago Midway Airport to Cancún in the evening. Doing so could potentially save you 47% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Chicago Midway Airport to Cancún

Explore weekly flight availability from Midway to Cancún. 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 July 28, 2025.

The most flights from MDW to CUN are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Cancún

Get insights into the airlines that provide service to Cancún. 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 Cancún. Reviews last updated July 28, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cancún, such as Southwest, Delta, and Aeromexico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,719 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Midway to Cancún. 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 into for flights to Cancún from Chicago Midway?

    Located just 8.9 mi from the city center, Cancun is the airport most travelers will use when flying to Cancún from Chicago Midway. Booking flights from Chicago Midway to Cancun (CUN) should be relatively easy as there is 1 daily inbound flight from Chicago Midway from 8 different airlines.

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

    Cheapflights users have booked flights from Chicago Midway Airport to Cancún round-trip from $270. Other airlines that can offer you cheap pricing are Aeromexico, from $295, and Delta, from $324. These flights start at 54% lower than the current average price 3 months from now.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $124. Aeromexico flights start at $144 while deals on Frontier start at $146 one-way.

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

    On average you can expect to pay $271 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $122 while the most popular route, (Chicago Midway - Cancun) is currently priced at $285.

  • Can I find deals for flights from Midway to Cancún that include hotel bookings?

    Yes. In addition to deals on Midway to Cancún flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Cancún?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Cancún.

  • Can I find deals for business class flights from Midway to Cancún?

    Yes. Cheapflights offers flight deals from Midway to Cancún 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 Chicago Midway Airport to Cancún?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $360). Flying from Chicago Midway Airport to Cancún in March is currently the most expensive (average of $492). 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
Puerto Aventuras
Holbox
Punta Sam

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Alternative routes for Midway to Cancún

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Cozumel flights
Midway to Cozumel flights
O'Hare Intl to Chetumal flights

Top 8 airlines flying from Midway to Cancún

Discover the top 8 airlines that operate flights from Midway to Cancún. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$445FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$312Average$514FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$346Average$579FlexibilityNo cancel feeOn-time63%
DeltaCheapest$380Average$610FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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