$192+ Cheap flights from Midway (MDW) to Cancún (CUN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Dec 4 — Dec 111
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 February or January, booked 11 days in advance, depart on a Monday or Tuesday and return on a Wednesday
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 November 4, 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 November 4, 2026.
This FlightHub deal was found by Cheapflights users on 10/31. 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.
Sun 12/135:02 pm -
1 stop16h 16m
Sat 12/194:24 pm -
1 stop8h 37m
Deal found 10/31![Frontier logo]()
$431
This FlightHub deal was found by Cheapflights users on 11/2. 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.
Sun 12/65:02 pm -
1 stop16h 16m
Fri 12/1111:28 am -
1 stop25h 05m
Deal found 11/2![Frontier logo]()
$434
This Justfly.com deal was found by Cheapflights users on 11/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:02 pm -
1 stop15h 51m
Thu 12/1012:32 pm -
1 stop22h 33m
Deal found 11/3![Frontier logo]()
$435
This FlightHub deal was found by Cheapflights users on 11/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1210:40 am -
1 stop23h 42m
Thu 12/174:28 pm -
1 stop7h 49m
Deal found 11/4![Frontier logo]()
$436
This FlightHub deal was found by Cheapflights users on 10/31. 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 12/45:02 pm -
1 stop15h 53m
Thu 12/1012:32 pm -
1 stop22h 33m
Deal found 10/31![Frontier logo]()
$440
This FlightHub deal was found by Cheapflights users on 11/3. 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.
Tue 11/249:09 am -
1 stop24h 25m
Thu 11/2611:44 am -
1 stop25h 50m
Deal found 11/3![Frontier logo]()
$444
This FlightHub deal was found by Cheapflights users on 11/1. 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 12/512:28 pm -
1 stop20h 50m
Thu 12/1012:32 pm -
1 stop22h 33m
Deal found 11/1![Frontier logo]()
$445
This FlightHub deal was found by Cheapflights users on 11/1. 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 12/115:02 pm -
1 stop15h 53m
Fri 12/184:28 pm -
1 stop8h 33m
Deal found 11/1![Frontier logo]()
$448
This FlightHub deal was found by Cheapflights users on 10/31. 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 12/105:02 pm -
1 stop16h 16m
Thu 12/314:28 pm -
1 stop8h 33m
Deal found 10/31![Frontier logo]()
$452
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 November 4, 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 November 4, 2026.
This Delta deal was found by Cheapflights users on 11/1. 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 1/1610:47 am -
1 stop9h 43m
Sat 2/65:45 pm -
1 stop7h 10m
Deal found 11/1![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 10/31. 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 12/99:55 am -
2 stops8h 50m
Tue 12/1512:35 pm -
1 stop7h 20m
Deal found 10/31![Southwest logo]()
$495
This Delta deal was found by Cheapflights users on 11/3. 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 12/511:28 am -
1 stop8h 40m
Wed 12/912:13 pm -
1 stop11h 41m
Deal found 11/3![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 11/3. 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 2/26:00 am -
1 stop9h 35m
Sun 2/74:30 pm -
1 stop8h 25m
Deal found 11/3![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 11/3. 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 1/87:45 am -
2 stops11h 00m
Wed 1/139:40 am -
2 stops11h 30m
Deal found 11/3![Southwest logo]()
$553
This Delta deal was found by Cheapflights users on 11/1. 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 1/236:00 am -
1 stop5h 37m
Thu 1/284:30 pm -
1 stop8h 25m
Deal found 11/1![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 10/31. 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 12/811:28 am -
1 stop8h 40m
Tue 12/298:15 am -
1 stop15h 07m
Deal found 10/31![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 11/3. 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 1/86:00 am -
1 stop5h 37m
Wed 1/138:00 am -
2 stops11h 00m
Deal found 11/3![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 10/30. 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 2/16:00 am -
1 stop9h 35m
Sat 2/611:50 am -
2 stops13h 05m
Deal found 10/30![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 11/3. 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 1/56:00 am -
1 stop8h 17m
Sun 1/101:50 pm -
1 stop9h 27m
Deal found 11/3![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 11/2. 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.
Wed 12/235:05 pm -
1 stop16h 15m
Sun 12/278:15 am -
1 stop15h 07m
Deal found 11/2![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 10/31. 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.
Wed 1/610:47 am -
1 stop9h 43m
Mon 1/1112:15 pm -
1 stop11h 02m
Deal found 10/31![Delta logo]()
$544
Last-minute flights from Midway to CancúnDiscover last-minute flight deals from Midway to Cancún. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cancún. Data last updated November 4, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 11/3. 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.
Tue 11/249:09 am -
1 stop24h 25m
Thu 11/2611:44 am -
1 stop25h 50m
Deal found 11/3![Frontier logo]()
$444
This Justfly.com deal was found by Cheapflights users on 11/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:02 pm -
1 stop15h 51m
Thu 12/1012:32 pm -
1 stop22h 33m
Deal found 11/3![Frontier logo]()
$435
This FlightHub deal was found by Cheapflights users on 10/31. 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 12/45:02 pm -
1 stop15h 53m
Thu 12/1012:32 pm -
1 stop22h 33m
Deal found 10/31![Frontier logo]()
$440
This FlightHub deal was found by Cheapflights users on 11/1. 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 12/512:28 pm -
1 stop20h 50m
Thu 12/1012:32 pm -
1 stop22h 33m
Deal found 11/1![Frontier logo]()
$445
This FlightHub deal was found by Cheapflights users on 11/2. 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.
Sun 12/65:02 pm -
1 stop16h 16m
Fri 12/1111:28 am -
1 stop25h 05m
Deal found 11/2![Frontier logo]()
$434
This FlightHub deal was found by Cheapflights users on 10/31. 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 12/105:02 pm -
1 stop16h 16m
Thu 12/314:28 pm -
1 stop8h 33m
Deal found 10/31![Frontier logo]()
$452
This FlightHub deal was found by Cheapflights users on 11/1. 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 12/115:02 pm -
1 stop15h 53m
Fri 12/184:28 pm -
1 stop8h 33m
Deal found 11/1![Frontier logo]()
$448
This FlightHub deal was found by Cheapflights users on 11/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1210:40 am -
1 stop23h 42m
Thu 12/174:28 pm -
1 stop7h 49m
Deal found 11/4![Frontier logo]()
$436
This FlightHub deal was found by Cheapflights users on 10/31. 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.
Sun 12/135:02 pm -
1 stop16h 16m
Sat 12/194:24 pm -
1 stop8h 37m
Deal found 10/31![Frontier logo]()
$431
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 November 4, 2026.
Search for one-way flight options from Midway to Cancún. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This FlightHub deal was found by Cheapflights users on 11/2. 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.
Sun 12/135:02 pm -
1 stop16h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$192
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Sun 1/246:20 pm -
1 stop14h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Volaris logo]()
$193
This FlightHub deal was found by Cheapflights users on 11/2. 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 1/226:17 pm -
1 stop14h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Volaris logo]()
$195
This Super.com deal was found by Cheapflights users on 11/3. 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.
Sun 1/316:17 pm -
1 stop14h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Volaris logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Mon 1/186:17 pm -
1 stop16h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Volaris logo]()
$199
This Orbitz deal was found by Cheapflights users on 10/31. 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.
Sun 12/65:02 pm -
1 stop16h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Mon 1/256:17 pm -
2 stops38h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Volaris logo]()
$201
This WAYA deal was found by Cheapflights users on 11/2. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/196:20 pm -
1 stop14h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Volaris logo]()
$205
This Justfly.com deal was found by Cheapflights users on 11/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:18 pm -
1 stop25h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$206
This FlightHub deal was found by Cheapflights users on 11/2. 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 1/65:21 pm -
1 stop17h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$207
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $431 (FlightHub) |
One-way from | $192 (FlightHub) |
Popular in | October |
Cheapest in | February |
Average price | $569 |
Good round-trip deal | $669 or less |
Good one-way deal | $345 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 7,457,451 searches. Data last updated November 4, 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
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 11/28
6:00 am-3:06 pm
1 stop8h 06m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Tue 12/8
11:28 am-9:08 pm
1 stop8h 40m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Tue 1/12
8:50 am-1:45 pm
Nonstop3h 55m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$236
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Tue 12/1
9:55 am-7:45 pm
2 stops8h 50m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$241
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Fri 11/13
9:30 am-8:55 pm
2 stops10h 25m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/9
7:50 am-5:55 pm
2 stops9h 05m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sun 11/8
7:20 am-7:45 pm
2 stops11h 25m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$256
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Tue 12/15
6:40 am-7:45 pm
1 stop12h 05m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$261
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sun 11/29
5:10 am-4:00 pm
2 stops9h 50m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$275
Quickest round-trip
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 11/14
6:00 am-10:45 am
Nonstop3h 45m
Cancun
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$276
Showing 1-10 of 22 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | 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?
To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Cancún, you should look to book at least 10 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 $318). Flying from Chicago Midway Airport to Cancún in October is currently the most expensive (average of $736). 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 November 4, 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 25% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 117 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?
Tuesday 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 24% 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 November 4, 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.
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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
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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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$194 | Average$425 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$515 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$327 | Average$469 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$358 | Average$561 | FlexibilityNo cancel fee | On-time63% |