$97+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Feb 20 — Feb 271
1 adult, Economy
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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.Cheapflights Tip: The best prices from Chicago Midway to Cancun are usually found in September or April, booked 57 days in advance, depart on a Monday or Tuesday and return on a Thursday
Cheap flight deals from Midway to Cancún
Cheapest flights from Midway to CancúnExplore 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 21, 2026.
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 21, 2026.
This Super.com deal was found by Cheapflights users on 1/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
- CUN
1 stop7h 57m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 1/20![Frontier logo]()
$252
This Gotogate deal was found by Cheapflights users on 1/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 1/19![Multiple Airlines logo]()
$260
This CheapOair deal was found by Cheapflights users on 1/21. 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 1/21![Frontier logo]()
$261
This Mytrip deal was found by Cheapflights users on 1/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/142:07 pm
CUN
- MDW
Nonstop4h 07m
Multiple Airlines
Deal found 1/19![Multiple Airlines logo]()
$266
This Mytrip deal was found by Cheapflights users on 1/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/142:07 pm
CUN
- MDW
Nonstop4h 07m
Multiple Airlines
Deal found 1/19![Multiple Airlines logo]()
$278
This Frontier deal was found by Cheapflights users on 1/19. 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.
Mon 2/236:00 am
MDW
- CUN
1 stop6h 37m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 1/19![Frontier logo]()
$280
This Gotogate deal was found by Cheapflights users on 1/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/26:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Thu 2/52:57 pm
CUN
- MDW
1 stop8h 22m
Multiple Airlines
Deal found 1/19![Multiple Airlines logo]()
$284
This Booking.com deal was found by Cheapflights users on 1/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:15 am
MDW
- CUN
1 stop24h 23m
Frontier
Sat 2/2810:16 am
CUN
- MDW
1 stop12h 23m
Frontier
Deal found 1/19![Frontier logo]()
$285
This Gotogate deal was found by Cheapflights users on 1/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/26:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 2/74:30 pm
CUN
- MDW
1 stop20h 15m
Multiple Airlines
Deal found 1/19![Multiple Airlines logo]()
$287
This Trip.com deal was found by Cheapflights users on 1/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
- CUN
1 stop7h 57m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 1/21![Frontier logo]()
$290
Find 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 21, 2026.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $252 (CheapOair) |
One-way from | $97 (Mytrip) |
Popular in | January |
Cheapest in | September |
Average price | $1,078 |
Good round-trip deal | $425 or less |
Good one-way deal | $144 or less |
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 January 21, 2026.
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
Sat 1/31
6:25 am-2:03 pm
1 stop6h 38m
Cancun
Mon 2/9
5:25 pm-9:08 am
1 stop16h 43m
$336
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 3/2
6:00 am-3:35 pm
1 stop8h 35m
Cancun
Mon 3/9
8:00 am-4:55 pm
1 stop8h 55m
$336
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 1/26
6:00 am-2:03 pm
1 stop7h 03m
Cancun
Fri 1/30
8:00 am-5:29 pm
1 stop10h 29m
$336
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 1/26
6:00 am-2:03 pm
1 stop7h 03m
Cancun
Tue 2/3
8:00 am-5:29 pm
1 stop10h 29m
$336
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 1/24
6:25 am-3:30 pm
1 stop8h 05m
Cancun
Mon 1/26
8:00 am-5:29 pm
1 stop10h 29m
$336
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 2/18
9:34 am-9:11 pm
2 stops10h 37m
Cancun
Wed 2/25
4:45 pm-10:31 pm
1 stop6h 46m
$341
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 2/2
12:46 pm-9:11 pm
1 stop7h 25m
Cancun
Fri 2/6
12:05 pm-10:22 pm
2 stops11h 17m
$341
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 2/28
11:06 am-9:11 pm
1 stop9h 05m
Cancun
Wed 3/4
12:05 pm-10:31 pm
2 stops11h 26m
$341
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 1/26
6:00 am-3:30 pm
1 stop8h 30m
Cancun
Wed 2/4
8:00 am-5:55 pm
2 stops10h 55m
$341
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 3/7
9:34 am-9:11 pm
2 stops10h 37m
Cancun
Wed 3/11
8:00 am-4:55 pm
1 stop8h 55m
$376
Showing 1-10 of 20 results
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.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Cancún flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago Midway Airport-Cancún flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Cancún
Prices
Delays
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 16, 2026.
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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $260). Flying from Chicago Midway Airport to Cancún in January is currently the most expensive (average of $391). 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 21, 2026.
When flying from Chicago Midway Airport to Cancún, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Chicago to Cancún delayed?
About 12% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 143 minutes.
What is the most punctual flight time for Chicago to Cancún flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Cancún flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 12% of flights being delayed.
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 21, 2026.
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.
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Traveling to a place near Cancún?
Book flights to Cancún if you plan to visit one of these locationsPuerto 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.
Top 5 airlines flying from Midway to Cancún
Discover the top 5 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$295 | Average$523 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$309 | Average$398 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$358 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$362 | Average$476 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$506 | Average$635 | FlexibilityNo cancel fee | On-time71% |