$101+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Apr 25 — May 21
Round-trip
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 October or February, booked 11 days in advance, depart on a Monday or Tuesday and return on a Thursday
Cheap flight deals from Midway to Cancún
Cheapest
Best
Last-minute
One-way
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 March 26, 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 March 26, 2026.
This Frontier deal was found by Cheapflights users on 3/22. 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 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Thu 4/1612:04 pm
CUN
- MDW
1 stop10h 18m
Frontier
Deal found 3/22![Frontier logo]()
$251
This Priceline deal was found by Cheapflights users on 3/25. 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.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Wed 4/154:07 pm
CUN
- MDW
1 stop27h 24m
Frontier
Deal found 3/25![Frontier logo]()
$252
This Orbitz deal was found by Cheapflights users on 3/24. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/115:17 pm
CUN
- MDW
1 stop7h 20m
Frontier
Deal found 3/24![Frontier logo]()
$257
This Travelocity deal was found by Cheapflights users on 3/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 3/23![Frontier logo]()
$261
This Trip.com deal was found by Cheapflights users on 3/25. 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.
Thu 4/96:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/111:20 pm
CUN
- MDW
Nonstop3h 45m
Frontier
Deal found 3/25![Frontier logo]()
$262
This Frontier deal was found by Cheapflights users on 3/26. 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.
Mon 4/136:00 am
MDW
- CUN
1 stop9h 05m
Frontier
Wed 4/224:07 pm
CUN
- MDW
1 stop27h 24m
Frontier
Deal found 3/26![Frontier logo]()
$263
This FlightHub deal was found by Cheapflights users on 3/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- CUN
1 stop9h 05m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/22![Frontier logo]()
$265
This Frontier deal was found by Cheapflights users on 3/25. 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.
Wed 4/86:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/25![Frontier logo]()
$271
Best flights from Midway to CancúnDiscover carefully curated flight deals from Midway to Cancún that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 26, 2026.
Discover carefully curated flight deals from Midway to Cancún that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 26, 2026.
This Southwest deal was found by Cheapflights users on 3/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:30 am
MDW
- CUN
Nonstop3h 30m
Southwest
Tue 5/123:15 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/21![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 3/25. 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.
Sun 5/106:23 am
MDW
- CUN
1 stop7h 39m
Delta
Wed 5/138:00 am
CUN
- MDW
1 stop8h 12m
Delta
Deal found 3/25![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 3/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:35 am
MDW
- CUN
Nonstop3h 35m
Southwest
Sun 5/104:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/21![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 3/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:22 am
MDW
- CUN
2 stops10h 54m
Delta
Thu 6/48:00 am
CUN
- MDW
2 stops10h 33m
Delta
Deal found 3/21![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 3/25. 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.
Thu 6/1111:05 am
MDW
- CUN
1 stop9h 20m
Delta
Tue 6/163:39 pm
CUN
- MDW
1 stop6h 38m
Delta
Deal found 3/25![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 3/22. 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.
Sat 5/166:10 am
MDW
- CUN
Nonstop3h 35m
Southwest
Fri 5/223:15 pm
CUN
- MDW
1 stop8h 40m
Southwest
Deal found 3/22![Southwest logo]()
$438
This Delta deal was found by Cheapflights users on 3/23. 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 5/239:22 am
MDW
- CUN
2 stops10h 54m
Delta
Thu 5/288:08 am
CUN
- MDW
2 stops13h 01m
Delta
Deal found 3/23![Delta logo]()
$429
This Southwest deal was found by Cheapflights users on 3/23. 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.
Fri 5/157:45 am
MDW
- CUN
2 stops7h 35m
Southwest
Sun 5/174:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 3/23![Southwest logo]()
$477
This Delta deal was found by Cheapflights users on 3/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:05 am
MDW
- CUN
1 stop9h 10m
Delta
Wed 7/158:00 am
CUN
- MDW
2 stops10h 25m
Delta
Deal found 3/21![Delta logo]()
$474
This Southwest deal was found by Cheapflights users on 3/23. 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 7/96:25 am
MDW
- CUN
Nonstop3h 35m
Southwest
Mon 7/134:10 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 3/23![Southwest logo]()
$485
This Delta deal was found by Cheapflights users on 3/25. 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.
Mon 6/156:05 am
MDW
- CUN
1 stop8h 34m
Delta
Thu 6/188:00 am
CUN
- MDW
1 stop8h 16m
Delta
Deal found 3/25![Delta logo]()
$484
This Southwest deal was found by Cheapflights users on 3/24. 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.
Sat 6/277:20 am
MDW
- CUN
1 stop8h 45m
Southwest
Thu 7/21:20 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 3/24![Southwest logo]()
$489
Last-minute flights from Midway to CancúnDiscover last-minute flight deals from Midway to Cancún. Data last updated March 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cancún. Data last updated March 26, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 3/24. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Sat 4/115:17 pm
CUN
- MDW
1 stop7h 20m
Frontier
Deal found 3/24![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 3/25. 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.
Wed 4/86:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/25![Frontier logo]()
$271
This Trip.com deal was found by Cheapflights users on 3/25. 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.
Thu 4/96:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Sat 4/111:20 pm
CUN
- MDW
Nonstop3h 45m
Frontier
Deal found 3/25![Frontier logo]()
$262
This Frontier deal was found by Cheapflights users on 3/22. 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 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Thu 4/1612:04 pm
CUN
- MDW
1 stop10h 18m
Frontier
Deal found 3/22![Frontier logo]()
$251
This Priceline deal was found by Cheapflights users on 3/25. 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.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Wed 4/154:07 pm
CUN
- MDW
1 stop27h 24m
Frontier
Deal found 3/25![Frontier logo]()
$252
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Fri 4/174:07 pm
CUN
- MDW
1 stop26h 30m
Frontier
Deal found 3/24![Frontier logo]()
$264
This Frontier deal was found by Cheapflights users on 3/26. 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.
Mon 4/136:00 am
MDW
- CUN
1 stop9h 05m
Frontier
Wed 4/224:07 pm
CUN
- MDW
1 stop27h 24m
Frontier
Deal found 3/26![Frontier logo]()
$263
This FlightHub deal was found by Cheapflights users on 3/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- CUN
1 stop9h 05m
Frontier
Sat 4/181:25 pm
CUN
- MDW
1 stop8h 49m
Frontier
Deal found 3/22![Frontier logo]()
$265
This Travelocity deal was found by Cheapflights users on 3/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Sat 5/22:09 pm
CUN
- MDW
1 stop8h 05m
Frontier
Deal found 3/23![Frontier logo]()
$261
One-way flights from Midway to CancúnSearch for one-way flight options from Midway to Cancún. Find affordable one-way fares based on user searches. Data last updated March 26, 2026.
Search for one-way flight options from Midway to Cancún. Find affordable one-way fares based on user searches. Data last updated March 26, 2026.
This FlightHub deal was found by Cheapflights users on 3/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Deal found 3/25![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 3/24. 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 4/48:30 am
MDW
- CUN
Nonstop3h 50m
Frontier
Deal found 3/24![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 3/23. 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 4/146:10 am
MDW
- CUN
1 stop8h 46m
Frontier
Deal found 3/23![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 3/25. 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 5/26:00 am
MDW
- CUN
1 stop6h 46m
Frontier
Deal found 3/25![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 3/25. 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.
Wed 4/226:15 am
MDW
- CUN
1 stop8h 41m
Frontier
Deal found 3/25![Frontier logo]()
$121
This Mytrip deal was found by Cheapflights users on 3/23. 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 4/108:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 3/23![Volaris logo]()
$126
This Super.com deal was found by Cheapflights users on 3/25. 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.
Wed 4/86:00 am
MDW
- CUN
1 stop8h 56m
Frontier
Deal found 3/25![Frontier logo]()
$129
This Super.com deal was found by Cheapflights users on 3/22. 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.
Fri 5/154:52 pm
MDW
- CUN
1 stop23h 05m
Frontier
Deal found 3/22![Frontier logo]()
$130
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 March 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Frontier) |
One-way from | $101 (FlightHub) |
Popular in | December |
Cheapest in | October |
Average price | $649 |
Good round-trip deal | $386 or less |
Good one-way deal | $184 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 March 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Cancún that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 5/5
10:30 am-2:00 pm
Nonstop3h 30m
Cancun
Tue 5/12
3:15 pm-6:55 pm
Nonstop3h 40m
$323
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 5/10
6:23 am-2:02 pm
1 stop7h 39m
Cancun
Wed 5/13
8:00 am-4:12 pm
1 stop8h 12m
$339
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 5/4
9:35 am-1:10 pm
Nonstop3h 35m
Cancun
Sun 5/10
4:10 pm-7:50 pm
Nonstop3h 40m
$344
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/29
9:22 am-8:16 pm
2 stops10h 54m
Cancun
Thu 6/4
8:00 am-6:33 pm
2 stops10h 33m
$384
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 6/11
11:05 am-8:25 pm
1 stop9h 20m
Cancun
Tue 6/16
3:39 pm-10:17 pm
1 stop6h 38m
$424
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/23
9:22 am-8:16 pm
2 stops10h 54m
Cancun
Thu 5/28
8:08 am-9:09 pm
2 stops13h 01m
$429
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/16
6:10 am-9:45 am
Nonstop3h 35m
Cancun
Fri 5/22
3:15 pm-11:55 pm
1 stop8h 40m
$438
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 7/9
11:05 am-8:15 pm
1 stop9h 10m
Cancun
Wed 7/15
8:00 am-6:25 pm
2 stops10h 25m
$474
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/15
7:45 am-3:20 pm
2 stops7h 35m
Cancun
Sun 5/17
4:10 pm-7:50 pm
Nonstop3h 40m
$477
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 6/15
6:05 am-2:39 pm
1 stop8h 34m
Cancun
Thu 6/18
8:00 am-4:16 pm
1 stop8h 16m
$484
Showing 1-10 of 23 resultsSorted by cheapest first
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 March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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.
MDW-CUN
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 March 13, 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 11 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $198). Flying from Chicago Midway Airport to Cancún in March is currently the most expensive (average of $402). 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 March 26, 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 14% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 142 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 Saturday 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 13% 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 March 26, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cancún, such as Southwest,Delta, andAeromexico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Punta Sam
Holbox
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Top 4 airlines flying from Midway to Cancún
Discover the top 4 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 March 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$198 | Average$515 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$292 | Average$511 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$308 | Average$340 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$358 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |