What are the cheapest airlines to fly from Chicago Midway Airport to Playa del Carmen one-way?

To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $111. Aeromexico flights start at $135 while deals on Frontier start at $142 one-way.

What is the cheapest day to fly from Chicago Midway Airport to Playa del Carmen?

Travelers seeking maximum savings on their Chicago Midway Airport to Playa del Carmen flight should consider departing on Friday at noon when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Chicago Midway Airport to Playa del Carmen?

Looking at all options, your cheapest flight can be booked for $110. While the most popular route (Chicago Midway - Cancun) can be booked for $308 on average our data indicates $500 when flying from Chicago Midway Airport to Playa del Carmen.

What are the most popular airlines that fly from Chicago Midway Airport to Playa del Carmen?

Before booking your flight from Chicago Midway Airport to Playa del Carmen check out the most popular airlines for this route: Aeromexico, Delta or Frontier.

What is the cheapest month to fly from Chicago Midway Airport to Playa del Carmen?

September is one of the best times of the year to fly to Playa del Carmen from Chicago Midway Airport. Prices for September average $400 per person but you can even find prices for as low as $104. The most expensive prices can be found in the month of March. Opting for a September flight can save you 28% on your journey compared to booking in March

Can I find deals for flights from Midway to Playa del Carmen that include hotel bookings?

Yes. In addition to deals on Midway to Playa del Carmen flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Midway to Playa del Carmen?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Playa del Carmen.

Can I find deals for business class flights from Midway to Playa del Carmen?

Yes. Cheapflights offers flight deals from Midway to Playa del Carmen by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$111+ Flights from Chicago Midway Airport to Playa del Carmen

Q: How far in advance should I book a flight from Chicago Midway Airport to Playa del Carmen?

To save on the cost of your flight from Chicago Midway Airport to Playa del Carmen, book at least 60 days before your planned departure. Booking around this time can save you about 2% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $320 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $332.

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Find cheap flights from Midway to Playa del Carmen with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago Midway to Playa del Carmen are usually found in September or April, booked 57 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap flight deals from Midway to Playa del Carmen

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$301 (Trip.com)
One-way from	$111 (Southwest)
Popular in	December
Cheapest in	September
Average price	$474

Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.

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Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.

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From Chicago Midway to Playa del Carmen

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One-way flight from Chicago Midway to Playa del Carmen

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Highest demand for flights based on searches. 15% potential increase in price ($109 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).

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Average for round-trip flights in April 2025

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Find flight deals from Midway to Playa del Carmen

Cheapest flights from Midway to Playa del Carmen
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 April 1, 2025.

Wed 7/94:30 pmMDW - CUN

Nonstop3h 35mSouthwest

Wed 7/168:30 amCUN - MDW

Nonstop3h 35mSouthwest

Deal found 3/31

$246

Mon 4/1412:48 pmMDW - CUN

1 stop7h 14mAeromexico

Fri 6/2011:00 amCUN - MDW

1 stop10h 38mAeromexico

Deal found 3/31

$306

Mon 5/1212:48 pmMDW - CUN

1 stop7h 32mDelta

Tue 5/208:00 amCUN - MDW

1 stop7h 20mDelta

Deal found 3/31

$321

Fri 5/162:45 pmMDW - CUN

1 stop18h 52mMultiple Airlines

Mon 5/191:45 pmCUN - MDW

1 stop6h 48mMultiple Airlines

Deal found 3/30

$359

Thu 5/152:45 pmMDW - CUN

1 stop19h 13mFrontier

Sun 5/1811:09 amCUN - MDW

1 stop9h 24mFrontier

Deal found 3/31

$406

Best flights from Midway to Playa del Carmen
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 April 1, 2025.

Wed 5/712:48 pmMDW - CUN

1 stop7h 32mAeromexico

Wed 5/1412:35 pmCUN - MDW

1 stop8h 53mAeromexico

Deal found 3/29

$301

Mon 5/1212:48 pmMDW - CUN

1 stop7h 32mDelta

Wed 5/1411:00 amCUN - MDW

1 stop10h 28mDelta

Deal found 3/31

$321

Sun 4/64:30 pmMDW - CUN

Nonstop3h 55mSouthwest

Thu 4/103:55 pmCUN - MDW

1 stop6h 45mSouthwest

Deal found 3/31

$341

Mon 5/512:48 pmMDW - CUN

1 stop7h 14mMultiple Airlines

Sat 5/108:00 amCUN - MDW

1 stop11h 06mMultiple Airlines

Deal found 3/30

$352

Thu 5/152:45 pmMDW - CUN

1 stop19h 13mFrontier

Sun 5/1811:09 amCUN - MDW

1 stop9h 24mFrontier

Deal found 3/31

$406

Last-minute flights from Midway to Playa del Carmen
Discover last-minute flight deals from Midway to Playa del Carmen. Data last updated April 1, 2025 and is based on user searches.

Thu 4/39:52 amMDW - CUN

1 stop10h 08mDelta

Mon 4/711:05 amCUN - MDW

1 stop6h 57mDelta

Deal found 3/31

$321

Sat 4/59:23 amMDW - CUN

1 stop5h 42mDelta

Tue 4/811:05 amCUN - MDW

1 stop6h 57mDelta

Deal found 3/31

$321

Sat 4/59:52 amMDW - CUN

1 stop10h 08mAeromexico

Tue 4/88:03 amCUN - MDW

2 stops14h 23mAeromexico

Deal found 3/31

$490

Sat 4/54:00 pmMDW - CUN

2 stops22h 15mLATAM Airlines

Tue 4/83:45 pmCUN - MDW

2 stops20h 18mLATAM Airlines

Deal found 3/31

$2,149

Sun 4/64:30 pmMDW - CUN

Nonstop3h 55mSouthwest

Thu 4/103:55 pmCUN - MDW

1 stop6h 45mSouthwest

Deal found 3/31

$341

Mon 4/79:52 amMDW - CUN

1 stop5h 32mMultiple Airlines

Sat 4/1212:15 pmCUN - MDW

1 stop21h 09mMultiple Airlines

Deal found 3/31

$389

Mon 4/710:41 pmMDW - CUN

1 stop14h 21mVolaris

Mon 4/148:00 amCUN - MDW

1 stop11h 06mVolaris

Deal found 3/31

$647

Thu 4/104:31 pmMDW - CUN

1 stop17h 09mFrontier

Thu 4/1712:00 pmCUN - MDW

1 stop7h 35mFrontier

Deal found 3/30

$417

Fri 4/114:36 pmMDW - CUN

1 stop16h 24mMultiple Airlines

Mon 4/148:15 amCUN - MDW

1 stop7h 57mMultiple Airlines

Deal found 3/31

$376

Sat 4/126:00 amMDW - CUN

1 stop27h 25mFrontier

Fri 4/182:33 pmCUN - MDW

1 stop9h 48mFrontier

Deal found 3/31

$413

Mon 4/1412:48 pmMDW - CUN

1 stop7h 14mAeromexico

Fri 6/2011:00 amCUN - MDW

1 stop10h 38mAeromexico

Deal found 3/31

$306

Wed 4/306:45 amMDW - CUN

1 stop6h 05mSouthwest

Fri 5/29:00 amCUN - MDW

Nonstop3h 40mSouthwest

Deal found 3/31

$336

One-way flights from Midway to Playa del Carmen
Search for one-way flight options from Midway to Playa del Carmen. Find affordable one-way fares based on user searches. Data last updated April 1, 2025.

Sun 4/64:30 pmMDW - CUN

Nonstop3h 55mSouthwest

Deal found 3/31

$111

Wed 5/1410:25 amMDW - CUN

1 stop9h 55mAeromexico

Deal found 3/30

$135

Mon 5/58:03 pmMDW - CUN

1 stop18h 07mFrontier

Deal found 3/31

$142

Thu 5/82:45 pmMDW - CUN

2 stops18h 36mMultiple Airlines

Deal found 3/31

$146

Sun 5/186:00 amMDW - CUN

2 stops11h 28mDelta

Deal found 3/31

$184

Wed 6/49:59 pmMDW - CUN

1 stop13h 48mVolaris

Deal found 3/30

$241

Wed 6/189:21 amMDW - CUN

3 stops33h 24mWestJet

Deal found 3/31

$348

Cheapflights Fare Finder

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

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 4/14

12:48 pm-8:02 pm

1 stop7h 14m

Cancun

Fri 6/20

11:00 am-9:38 pm

1 stop10h 38m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Tue 5/20

8:00 am-3:20 pm

1 stop7h 20m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 4/30

6:45 am-12:50 pm

1 stop6h 05m

Cancun

Fri 5/2

9:00 am-12:40 pm

Nonstop3h 40m

$336

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/16

2:45 pm-9:37 am

1 stop18h 52m

Cancun

Mon 5/19

1:45 pm-8:33 pm

1 stop6h 48m

$359

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/15

2:45 pm-9:58 am

1 stop19h 13m

Cancun

Sun 5/18

11:09 am-8:33 pm

1 stop9h 24m

$406

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 4/6

4:30 pm-8:25 pm

Nonstop3h 55m

$111

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/15

6:04 am-12:50 pm

1 stop6h 46m

$134

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/5

8:03 pm-2:10 pm

1 stop18h 07m

$142

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 4/3

9:23 am-8:00 pm

2 stops10h 37m

$145

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/8

2:45 pm-9:21 am

2 stops18h 36m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 12 results

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.

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

How far ahead should I book a flight from Chicago Midway Airport to Playa del Carmen?

The best time to book flights from Chicago Midway Airport to Playa del Carmen is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to Playa del Carmen?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $360). Flying from Chicago Midway Airport to Playa del Carmen in March is currently the most expensive (average of $492). 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 PL9?

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.

Rainfall in Playa del Carmen by month

In terms of precipitation, rainfall in Playa del Carmen ranges from 1.1 - 11.1 inches per month. October is typically the wettest month, when rainfall can reach 11.1 in. April is typically the driest time to visit Playa del Carmen when rainfall is around 1.1 in.

Temperature in Playa del Carmen by month

If weather is an important factor for your trip to Playa del Carmen, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 86.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

Reviews of airlines servicing Playa del Carmen

See what other customers who have flown with Southwest, Delta and Aeromexico from Chicago to Playa del Carmen have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,276 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest

8.0

Very good

4,276 reviews

Southwest

8.0

Very good

4,276 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta

8.0

Very good

7,899 reviews

Southwest

8.0

Very good

4,276 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Aeromexico

7.5

Good

1,700 reviews

Southwest

8.0

Very good

4,276 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

WestJet

7.2

Good

2,789 reviews

Southwest

8.0

Very good

4,276 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Volaris

6.7

Okay

1,171 reviews

Southwest

8.0

Very good

4,276 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

What are the cheapest airlines to fly from Chicago Midway Airport to Playa del Carmen one-way?
To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $111. Aeromexico flights start at $135 while deals on Frontier start at $142 one-way.
What are the cheapest flights from Chicago Midway Airport to Playa del Carmen?
Looking at all options, your cheapest flight can be booked for $110. While the most popular route (Chicago Midway - Cancun) can be booked for $308 on average our data indicates $500 when flying from Chicago Midway Airport to Playa del Carmen.
Can I find deals for flights from Midway to Playa del Carmen that include hotel bookings?
Yes. In addition to deals on Midway to Playa del Carmen flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to Playa del Carmen?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Playa del Carmen.
Can I find deals for business class flights from Midway to Playa del Carmen?
Yes. Cheapflights offers flight deals from Midway to Playa del Carmen by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago Midway Airport to Playa del Carmen?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $360). Flying from Chicago Midway Airport to Playa del Carmen in March is currently the most expensive (average of $492). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Midway to Playa del Carmen

O'Hare Intl to Cancún flights

Midway to Cancún flights

O'Hare Intl to Cozumel flights

Midway to Cozumel flights

O'Hare Intl to Chetumal flights

Top 8 airlines flying from Midway to Playa del Carmen

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$175	Average$393	FlexibilityNo cancel fee	On-time69%
Spirit Airlines	Cheapest$183	Average$333	FlexibilityNo cancel fee	On-time65%
Frontier	Cheapest$198	Average$443	FlexibilityNo cancel fee	On-time62%
Aeromexico	Cheapest$368	Average$537	FlexibilityNo cancel fee	On-timeN/A
Delta	Cheapest$380	Average$538	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$433	Average$693	FlexibilityNo cancel fee	On-time63%
Volaris	Cheapest$486	Average$872	FlexibilityNo cancel fee	On-time79%
LATAM Airlines	Cheapest$3,369	Average$3,369	FlexibilityNo cancel fee	On-time81%

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$111+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Playa del Carmen with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago Midway to Playa del Carmen are usually found in September or April, booked 57 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap 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 April 1, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Midway to Playa del Carmen

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 April 1, 2025.

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 April 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Playa del Carmen that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Playa del Carmen

How far ahead should I book a flight from Chicago Midway Airport to Playa del Carmen?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Playa del Carmen. Price data was last updated on March 28, 2025.

What is the cheapest month to book a flight from Chicago Midway Airport to Playa del Carmen?

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 April 1, 2025.

Rainfall in Playa del Carmen by month

Plan your trip to Playa del Carmen by taking into account the average rainfall totals by month.

Temperature in Playa del Carmen by month

Plan your trip to Playa del Carmen by taking into account the average temperature totals by month.

Reviews of airlines servicing Playa del Carmen

See what other customers who have flown with Southwest, Delta and Aeromexico from Chicago to Playa del Carmen have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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.

What are the cheapest airlines to fly from Chicago Midway Airport to Playa del Carmen one-way?

What are the cheapest flights from Chicago Midway Airport to Playa del Carmen?

Can I find deals for flights from Midway to Playa del Carmen that include hotel bookings?

How can I find direct flights from Midway to Playa del Carmen?

Can I find deals for business class flights from Midway to Playa del Carmen?

What is the cheapest month to book a flight from Chicago Midway Airport to Playa del Carmen?

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 for Midway to Playa del Carmen

See prices for flight routes from nearby airports that may be better suited for you.

Top 8 airlines flying from Midway to Playa del Carmen

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Cheapest flights from Midway to Playa del Carmen
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 April 1, 2025.