$124+ Cheap flights from Midway (MDW) to Playa del Carmen, Mexico
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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Aug 2 — Aug 91
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Playa del Carmen 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 Playa del Carmen are usually found in October or February, booked 11 days in advance, depart on a Tuesday or Monday and return on a Thursday
Cheap flight deals from Midway to Playa del Carmen
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to Playa del CarmenExplore the most affordable flight options available from Midway to Playa del Carmen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2026.
Explore the most affordable flight options available from Midway to Playa del Carmen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2026.
This CheapOair deal was found by Cheapflights users on 7/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/2410:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/3![Volaris logo]()
$335
This FlightHub deal was found by Cheapflights users on 6/28. 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 7/68:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 7/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/28![Volaris logo]()
$349
This FlightHub deal was found by Cheapflights users on 7/1. 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 7/188:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 7/1![Volaris logo]()
$350
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/30![Volaris logo]()
$351
This Super.com deal was found by Cheapflights users on 7/3. 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.
Mon 8/248:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/3110:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/3![Volaris logo]()
$353
This Super.com deal was found by Cheapflights users on 7/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Mon 7/2010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/2![Volaris logo]()
$354
This FlightHub deal was found by Cheapflights users on 7/3. 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.
Wed 9/98:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Sun 9/1310:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/3![Volaris logo]()
$360
This FlightHub deal was found by Cheapflights users on 6/29. 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 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 7/810:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/29![Volaris logo]()
$362
This Super.com deal was found by Cheapflights users on 6/28. 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 7/18:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 7/810:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/28![Volaris logo]()
$372
This Super.com deal was found by Cheapflights users on 6/29. 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 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 7/911:10 am
CUN
- MDW
1 stop9h 22m
Volaris
Deal found 6/29![Volaris logo]()
$373
This FlightHub deal was found by Cheapflights users on 7/3. 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.
Wed 9/98:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 9/1610:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/3![Volaris logo]()
$374
Best flights from Midway to Playa del CarmenDiscover carefully curated flight deals from Midway to Playa del Carmen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2026.
Discover carefully curated flight deals from Midway to Playa del Carmen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2026.
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:30 am
MDW
- CUN
2 stops7h 10m
Southwest
Wed 8/262:10 pm
CUN
- MDW
1 stop9h 00m
Southwest
Deal found 6/30![Southwest logo]()
$457
This Delta deal was found by Cheapflights users on 7/1. 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.
Wed 11/41:00 pm
MDW
- CUN
1 stop7h 15m
Delta
Tue 11/104:35 pm
CUN
- MDW
1 stop6h 35m
Delta
Deal found 7/1![Delta logo]()
$486
This Volaris deal was found by Cheapflights users on 6/30. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 8/1210:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/30![Volaris logo]()
$516
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:20 pm
MDW
- CUN
2 stops14h 40m
Southwest
Fri 10/91:05 pm
CUN
- MDW
1 stop8h 55m
Southwest
Deal found 7/1![Southwest logo]()
$461
This Delta deal was found by Cheapflights users on 7/1. 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.
Tue 9/226:05 am
MDW
- CUN
2 stops12h 34m
Delta
Mon 9/288:05 am
CUN
- MDW
1 stop8h 11m
Delta
Deal found 7/1![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 6/28. 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 7/209:55 am
MDW
- CUN
Nonstop3h 35m
Southwest
Wed 7/293:05 pm
CUN
- MDW
1 stop7h 35m
Southwest
Deal found 6/28![Southwest logo]()
$488
This Delta deal was found by Cheapflights users on 7/2. 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.
Sun 10/111:00 pm
MDW
- CUN
1 stop7h 15m
Delta
Sat 10/178:00 am
CUN
- MDW
1 stop14h 25m
Delta
Deal found 7/2![Delta logo]()
$492
This Delta deal was found by Cheapflights users on 6/30. 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.
Sat 9/266:05 am
MDW
- CUN
1 stop5h 20m
Delta
Wed 9/308:05 am
CUN
- MDW
1 stop8h 11m
Delta
Deal found 6/30![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:05 am
MDW
- CUN
2 stops10h 40m
Southwest
Mon 12/78:20 am
CUN
- MDW
2 stops8h 15m
Southwest
Deal found 7/2![Southwest logo]()
$520
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 10/319:29 am
MDW
- CUN
2 stops10h 46m
Delta
Wed 11/48:00 am
CUN
- MDW
2 stops11h 05m
Delta
Deal found 7/2![Delta logo]()
$496
This Delta deal was found by Cheapflights users on 6/29. 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 10/109:29 am
MDW
- CUN
2 stops10h 46m
Delta
Fri 10/168:00 am
CUN
- MDW
1 stop14h 25m
Delta
Deal found 6/29![Delta logo]()
$497
Last-minute flights from Midway to Playa del CarmenDiscover last-minute flight deals from Midway to Playa del Carmen. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Playa del Carmen. Data last updated July 3, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 6/29. 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 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Wed 7/810:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/29![Volaris logo]()
$362
This Super.com deal was found by Cheapflights users on 6/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 7/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/30![Volaris logo]()
$372
This Super.com deal was found by Cheapflights users on 6/29. 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 7/38:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Thu 7/911:10 am
CUN
- MDW
1 stop9h 22m
Volaris
Deal found 6/29![Volaris logo]()
$373
This FlightHub deal was found by Cheapflights users on 6/28. 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 7/68:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 7/1010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 6/28![Volaris logo]()
$349
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 6/30![Volaris logo]()
$351
This Super.com deal was found by Cheapflights users on 7/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Mon 7/2010:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/2![Volaris logo]()
$354
This FlightHub deal was found by Cheapflights users on 7/1. 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 7/188:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Tue 7/2110:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 7/1![Volaris logo]()
$350
This Expedia deal was found by Cheapflights users on 7/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:05 am
MDW
- CUN
1 stop7h 41m
Frontier
Wed 8/53:06 pm
CUN
- MDW
1 stop18h 45m
Frontier
Deal found 7/1![Frontier logo]()
$377
This Super.com deal was found by Cheapflights users on 7/3. 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.
Fri 8/218:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Fri 8/2810:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/3![Volaris logo]()
$335
This Super.com deal was found by Cheapflights users on 7/3. 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.
Mon 8/248:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Mon 8/3110:40 am
CUN
- MDW
1 stop8h 24m
Volaris
Deal found 7/3![Volaris logo]()
$353
One-way flights from Midway to Playa del CarmenSearch for one-way flight options from Midway to Playa del Carmen. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
Search for one-way flight options from Midway to Playa del Carmen. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This Super.com deal was found by Cheapflights users on 7/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Deal found 7/2![Volaris logo]()
$124
This FlightHub deal was found by Cheapflights users on 7/1. 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.
Sun 8/308:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/1![Volaris logo]()
$131
This Super.com deal was found by Cheapflights users on 6/28. 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.
Mon 7/138:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/28![Volaris logo]()
$135
This Super.com deal was found by Cheapflights users on 7/3. 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.
Sat 7/188:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Deal found 7/3![Volaris logo]()
$136
This CheapOair deal was found by Cheapflights users on 7/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/1![Volaris logo]()
$146
This Trip.com deal was found by Cheapflights users on 6/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:49 pm
MDW
- CUN
1 stop14h 06m
Volaris
Deal found 6/30![Volaris logo]()
$148
This Super.com deal was found by Cheapflights users on 7/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/2![Volaris logo]()
$153
This Super.com deal was found by Cheapflights users on 6/28. 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 7/108:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 6/28![Volaris logo]()
$154
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Wed 7/298:23 pm
MDW
- CUN
1 stop13h 32m
Volaris
Deal found 7/2![Volaris logo]()
$157
Find flight deals from Midway to Playa del Carmen
Keep the following information in mind while searching for Midway to Playa del Carmen flight deals. Data was last updated July 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $335 (Super.com) |
One-way from | $124 (Super.com) |
Popular in | March |
Cheapest in | October |
Average price | $528 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Playa del Carmen 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 July 3, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Playa del Carmen that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 8/17
5:30 am-12:40 pm
2 stops7h 10m
Cancun
Wed 8/26
2:10 pm-11:10 pm
1 stop9h 00m
$457
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 10/4
9:20 pm-12:00 pm
2 stops14h 40m
Cancun
Fri 10/9
1:05 pm-10:00 pm
1 stop8h 55m
$461
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 11/4
1:00 pm-9:15 pm
1 stop7h 15m
Cancun
Tue 11/10
4:35 pm-10:10 pm
1 stop6h 35m
$486
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 7/20
9:55 am-1:30 pm
Nonstop3h 35m
Cancun
Wed 7/29
3:05 pm-10:40 pm
1 stop7h 35m
$488
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 9/22
6:05 am-6:39 pm
2 stops12h 34m
Cancun
Mon 9/28
8:05 am-4:16 pm
1 stop8h 11m
$492
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 10/11
1:00 pm-8:15 pm
1 stop7h 15m
Cancun
Sat 10/17
8:00 am-10:25 pm
1 stop14h 25m
$492
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 9/26
6:05 am-11:25 am
1 stop5h 20m
Cancun
Wed 9/30
8:05 am-4:16 pm
1 stop8h 11m
$492
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 10/31
9:29 am-8:15 pm
2 stops10h 46m
Cancun
Wed 11/4
8:00 am-6:05 pm
2 stops11h 05m
$496
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 10/10
9:29 am-8:15 pm
2 stops10h 46m
Cancun
Fri 10/16
8:00 am-10:25 pm
1 stop14h 25m
$497
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 8/9
8:23 pm-9:55 am
1 stop13h 32m
Cancun
Wed 8/12
10:40 am-7:04 pm
1 stop8h 24m
$516
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from Midway to Playa del Carmen
Have a flexible travel schedule? Discover the best time to fly to Playa del Carmen 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 Playa del Carmen
MDW-PL9
MDW-CUN
What is the cheapest time of day to fly from MDW to PL9?
Find hourly flight availability from Midway to Playa del Carmen. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Playa del Carmen as you normally would.
How much does it cost to fly round-trip from Chicago Midway Airport to Playa del Carmen?
Reviews of airlines servicing Playa del Carmen
Get insights into the airlines that provide service to Playa del Carmen. 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 Playa del Carmen. Reviews last updated July 3, 2026.
See what other customers who have flown with Southwest,Delta, andAeromexico from Chicago Midway Airport to Playa del Carmen have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Playa del Carmen. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
Top destinations
Alternative routes for Midway to Playa del Carmen
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Playa del Carmen by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Playa del Carmen by cabin class
Find flights from Midway to Playa del Carmen, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Playa del Carmen flights
Browse other Midway and Playa del Carmen flight options. Last updated on July 3, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on July 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Playa del Carmen flights
Consider these flights traveling from Midway to Playa del Carmen.
Top 4 airlines flying from Midway to Playa del Carmen
Discover the top 4 airlines that operate flights from Midway to Playa del Carmen. 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 July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$194 | Average$425 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$489 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$534 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$327 | Average$449 | FlexibilityNo cancel fee | On-timeN/A |