HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cancún

$116+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Cancún with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$310
(Kiwi.com)

One-way from

$116
(Southwest)

Popular in

June

Cheapest in

February

Average price

$691
Provider with most accurate pricing for Chicago Midway-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Cancun flights.
Search Deals
From Chicago Midway to Cancun
Search Deals
One-way flight from Chicago Midway to Cancun
Search Deals
High demand for flights, 1% potential price rise
Search Deals
Best time to find cheap flights, 4% potential price drop
Search Deals
Average for round-trip flights in January 2025
Search Deals

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 January 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/16. 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 2/510:41 pmMDW - CUN
2 stops20h 14mMultiple Airlines
Wed 2/123:49 pmCUN - MDW
1 stop9h 28mMultiple Airlines
Deal found 1/16$310
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 2/58:01 pmMDW - CUN
1 stop12h 00mFrontier
Wed 2/123:49 pmCUN - MDW
1 stop9h 28mFrontier
Deal found 1/15$317
This Southwest deal was found by Cheapflights users on 1/16. 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.
Tue 2/256:10 amMDW - CUN
1 stop6h 45mSouthwest
Thu 2/275:10 pmCUN - MDW
1 stop6h 20mSouthwest
Deal found 1/16$351
This eDestinos deal was found by Cheapflights users on 1/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/312:44 pmMDW - CUN
1 stop7h 21mAeromexico
Thu 2/64:25 pmCUN - MDW
1 stop6h 55mAeromexico
Deal found 1/16$368
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 2/77:55 pmMDW - CUN
1 stop13h 08mVolaris
Mon 2/109:45 pmCUN - MDW
1 stop12h 00mVolaris
Deal found 1/15$382
This Delta deal was found by Cheapflights users on 1/15. 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.
Fri 4/256:00 amMDW - CUN
1 stop8h 12mDelta
Thu 5/13:29 pmCUN - MDW
1 stop7h 00mDelta
Deal found 1/15$394

Find flights from Midway to Cancún within your budget

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 January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 2/5

10:41 pm-7:55 pm

2 stops20h 14m

Cancun

Wed 2/12

3:49 pm-12:17 am

1 stop9h 28m

$310

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 2/5

8:01 pm-9:01 am

1 stop12h 00m

Cancun

Wed 2/12

3:49 pm-12:17 am

1 stop9h 28m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 2/25

6:10 am-1:55 pm

1 stop6h 45m

Cancun

Thu 2/27

5:10 pm-10:30 pm

1 stop6h 20m

$351

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/3

12:44 pm-9:05 pm

1 stop7h 21m

Cancun

Thu 2/6

4:25 pm-10:20 pm

1 stop6h 55m

$368

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/7

7:55 pm-10:03 am

1 stop13h 08m

Cancun

Mon 2/10

9:45 pm-8:45 am

1 stop12h 00m

$382

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 4/25

6:00 am-2:12 pm

1 stop8h 12m

Cancun

Thu 5/1

3:29 pm-10:29 pm

1 stop7h 00m

$394

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/10

4:30 pm-8:25 pm

Nonstop3h 55m

$116

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/1

5:10 am-9:56 am

1 stop27h 46m

$120

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 4/7

9:59 pm-9:22 am

1 stop11h 23m

$141

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 2/25

4:07 pm-1:04 pm

1 stop19h 57m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 12 results
1
2

Compare providers for flights from Midway to Cancún

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 Midway to Cancún in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 Chicago Midway Airport-Cancún flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Cancún flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Cancún flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Cancún 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 Chicago Midway Airport-Cancún 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 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.

Travel insights for flights from Midway to Cancún

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

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 January 10, 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 20 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 January 17, 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 in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to Cancún?

Use this chart to determine the cheapest time to fly round-trip from Midway to Cancún. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Cancún flight should consider departing on Friday at noon when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Cancún by month

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

In terms of precipitation, rainfall in Cancún ranges from 1.1 - 11.1 inches per month. October is typically the wettest month, when rainfall can reach 11.1 in. April is typically the driest time to visit Cancún when rainfall is around 1.1 in.

Temperature in Cancún by month

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

If weather is an important factor for your trip to Cancún, 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 86.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

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 January 17, 2025.
Read through reviews of airlines operating flights from Chicago to Cancún, such as Frontier, Aeromexico and Volaris. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,849 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Volaris
6.7
Okay
1,249 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,435 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 are 0 daily inbound flights 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 $317. Other airlines that can offer you cheap pricing are Southwest, from $351, and Aeromexico, from $368. These flights start at 43% 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 $116. Frontier flights start at $120 while deals on Volaris start at $141 one-way.

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

    On average you can expect to pay $553 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $268 while the most popular route, (Chicago Midway - Cancun) is currently priced at $358.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Puerto Aventuras
Punta Sam
Holbox

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 January 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$171Average$275FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$177Average$409FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$311Average$393FlexibilityNo cancel feeOn-time69%
DeltaCheapest$380Average$539FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$382Average$562FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$467Average$705FlexibilityNo cancel feeOn-time63%
VolarisCheapest$477Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.