$107+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Mar 10 — Mar 171
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 February, booked 57 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 February 8, 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 February 8, 2026.
This Super.com deal was found by Cheapflights users on 2/8. 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/8![Frontier logo]()
$245
This Trip.com deal was found by Cheapflights users on 2/7. 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 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/7![Frontier logo]()
$258
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$261
This Priceline deal was found by Cheapflights users on 2/7. 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.
Wed 3/47:15 am
MDW
- CUN
1 stop24h 36m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/7![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 2/8. 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 3/116:05 am
MDW
- CUN
1 stop8h 54m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/8![Frontier logo]()
$285
This Super.com deal was found by Cheapflights users on 2/6. 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 2/277:53 pm
MDW
- CUN
1 stop12h 13m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/6![Frontier logo]()
$287
This Expedia deal was found by Cheapflights users on 2/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
MDW
- CUN
1 stop6h 37m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/8![Frontier logo]()
$288
This Gotogate deal was found by Cheapflights users on 2/5. 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 3/87:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$289
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 February 8, 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 February 8, 2026.
This Southwest deal was found by Cheapflights users on 2/6. 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 3/94:05 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Fri 3/138:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/6![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 2/6. 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 2/2811:06 am
MDW
- CUN
1 stop9h 05m
Delta
Thu 3/511:00 am
CUN
- MDW
1 stop7h 45m
Delta
Deal found 2/6![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 2/5. 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 3/108:05 am
MDW
- CUN
Nonstop3h 45m
Southwest
Tue 3/178:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/5![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 2/7. 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 2/216:00 am
MDW
- CUN
1 stop9h 45m
Delta
Wed 2/258:00 am
CUN
- MDW
1 stop10h 45m
Delta
Deal found 2/7![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 2/7. 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 3/101:10 pm
MDW
- CUN
2 stops7h 10m
Delta
Tue 3/173:25 pm
CUN
- MDW
2 stops21h 04m
Delta
Deal found 2/7![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 2/4. 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 2/2111:45 am
MDW
- CUN
Nonstop3h 40m
Southwest
Wed 2/252:45 pm
CUN
- MDW
1 stop7h 15m
Southwest
Deal found 2/4![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 2/6. 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 3/171:10 pm
MDW
- CUN
2 stops7h 10m
Delta
Wed 3/2510:00 am
CUN
- MDW
1 stop12h 31m
Delta
Deal found 2/6![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 2/6. 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 3/54:05 pm
MDW
- CUN
Nonstop3h 40m
Southwest
Tue 3/1012:55 pm
CUN
- MDW
1 stop9h 00m
Southwest
Deal found 2/6![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 2/8. 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 3/71:25 pm
MDW
- CUN
Nonstop3h 35m
Southwest
Tue 3/108:40 am
CUN
- MDW
2 stops11h 05m
Southwest
Deal found 2/8![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 2/6. 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 4/96:34 pm
MDW
- CUN
1 stop15h 16m
Delta
Thu 4/1610:00 am
CUN
- MDW
1 stop6h 29m
Delta
Deal found 2/6![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 2/5. 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.
Wed 3/1812:25 pm
MDW
- CUN
1 stop7h 35m
Southwest
Tue 3/248:30 am
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 2/5![Southwest logo]()
$386
Last-minute flights from Midway to CancúnDiscover last-minute flight deals from Midway to Cancún. Data last updated February 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cancún. Data last updated February 8, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 2/6. 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 2/277:53 pm
MDW
- CUN
1 stop12h 13m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/6![Frontier logo]()
$287
This Trip.com deal was found by Cheapflights users on 2/7. 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 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/7![Frontier logo]()
$258
This Expedia deal was found by Cheapflights users on 2/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
MDW
- CUN
1 stop6h 37m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/8![Frontier logo]()
$288
This Priceline deal was found by Cheapflights users on 2/7. 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.
Wed 3/47:15 am
MDW
- CUN
1 stop24h 36m
Frontier
Sat 3/73:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/7![Frontier logo]()
$279
This Super.com deal was found by Cheapflights users on 2/8. 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 3/79:00 am
MDW
- CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/8![Frontier logo]()
$245
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Sat 3/76:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$261
This Gotogate deal was found by Cheapflights users on 2/5. 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 3/87:54 pm
MDW
- CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$289
This Frontier deal was found by Cheapflights users on 2/8. 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 3/116:05 am
MDW
- CUN
1 stop8h 54m
Frontier
Sat 3/143:07 pm
CUN
- MDW
Nonstop4h 06m
Frontier
Deal found 2/8![Frontier logo]()
$285
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 February 8, 2026.
Search for one-way flight options from Midway to Cancún. Find affordable one-way fares based on user searches. Data last updated February 8, 2026.
This FlightHub deal was found by Cheapflights users on 2/7. 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.
Thu 3/56:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/7![Volaris logo]()
$107
This FlightHub deal was found by Cheapflights users on 2/5. 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 2/236:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/5![Volaris logo]()
$108
This Expedia deal was found by Cheapflights users on 2/8. 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 Expedia 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 2/8![Frontier logo]()
$110
This FlightHub deal was found by Cheapflights users on 2/5. 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.
Wed 2/256:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/5![Volaris logo]()
$114
This FlightHub deal was found by Cheapflights users on 2/7. 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 3/237:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/7![Volaris logo]()
$115
This FlightHub deal was found by Cheapflights users on 2/8. 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.
Fri 2/276:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/8![Volaris logo]()
$116
This FlightHub deal was found by Cheapflights users on 2/8. 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.
Wed 3/46:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/8![Volaris logo]()
$117
This FlightHub deal was found by Cheapflights users on 2/6. 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.
Fri 6/58:09 pm
MDW
- CUN
1 stop13h 39m
Volaris
Deal found 2/6![Volaris logo]()
$118
This FlightHub deal was found by Cheapflights users on 2/5. 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 3/26:54 pm
MDW
- CUN
1 stop13h 54m
Volaris
Deal found 2/5![Volaris logo]()
$123
This FlightHub deal was found by Cheapflights users on 2/8. 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.
Fri 5/18:09 pm
MDW
- CUN
1 stop13h 39m
Volaris
Deal found 2/8![Volaris logo]()
$125
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 February 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (Frontier) |
One-way from | $107 (FlightHub) |
Popular in | January |
Cheapest in | September |
Average price | $425 |
Good round-trip deal | $411 or less |
Good one-way deal | $301 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 February 8, 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
Mon 3/9
4:05 pm-7:45 pm
Nonstop3h 40m
Cancun
Fri 3/13
8:30 am-12:10 pm
Nonstop3h 40m
$293
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 3/10
8:05 am-11:50 am
Nonstop3h 45m
Cancun
Tue 3/17
8:30 am-12:10 pm
Nonstop3h 40m
$293
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 2/28
11:06 am-9:11 pm
1 stop9h 05m
Cancun
Thu 3/5
11:00 am-5:45 pm
1 stop7h 45m
$338
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 2/21
6:00 am-4:45 pm
1 stop9h 45m
Cancun
Wed 2/25
8:00 am-5:45 pm
1 stop10h 45m
$338
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 3/10
1:10 pm-8:20 pm
2 stops7h 10m
Cancun
Tue 3/17
3:25 pm-12:29 pm
2 stops21h 04m
$342
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 3/17
1:10 pm-8:20 pm
2 stops7h 10m
Cancun
Wed 3/25
10:00 am-10:31 pm
1 stop12h 31m
$342
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 2/21
11:45 am-4:25 pm
Nonstop3h 40m
Cancun
Wed 2/25
2:45 pm-9:00 pm
1 stop7h 15m
$346
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 3/5
4:05 pm-8:45 pm
Nonstop3h 40m
Cancun
Tue 3/10
12:55 pm-9:55 pm
1 stop9h 00m
$352
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 3/7
1:25 pm-6:00 pm
Nonstop3h 35m
Cancun
Tue 3/10
8:40 am-7:45 pm
2 stops11h 05m
$352
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 4/9
6:34 pm-9:50 am
1 stop15h 16m
Cancun
Thu 4/16
10:00 am-4:29 pm
1 stop6h 29m
$367
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars |
- 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 January 30, 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, 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 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 February 8, 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 13% 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 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 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 February 8, 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.
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
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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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 February 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$198 | Average$445 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$293 | Average$520 | 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 |