How long is the flight from Chicago Midway Airport to Cancún?

Airlines like Southwest and Delta fly from Chicago Midway Airport to Cancún in about 3h 45m. The time it takes to get you to your destination can typically vary by up to 5h 46m. There are 1434 mi between Chicago Midway Airport and Cancún. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Chicago Midway Airport to Cancún round-trip?

Cheapflights users have booked flights from Chicago Midway Airport to Cancún round-trip from $161. Other airlines that can offer you cheap pricing are Aeromexico, from $312, and Southwest, from $345. These flights start at 72% lower than the current average price 3 months from now.

What is the cheapest day to fly from Chicago Midway Airport to Cancún?

Travelers seeking maximum savings on their Chicago Midway Airport to Cancún 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.

In terms of precipitation, rainfall in Cancún 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 Cancún when rainfall is around 1.1 in.

If weather is an important factor for your trip to Cancún, 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).

What are the cheapest flights from Chicago Midway Airport to Cancún?

On average you can expect to pay $315 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $124 while the most popular route, (Chicago Midway - Cancun) is currently priced at $280.

What are the most popular airlines that fly from Chicago Midway Airport to Cancún?

The most popular airlines flying from Chicago Midway Airport to Cancún are Aeromexico, Delta and Frontier. Something to consider prior to booking your flight.

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.

What airport do you fly into for flights to Cancún from Chicago Midway?

Located just 8.9 mi from the city center, Cancun is the airport most travelers will use when flying to Cancún from Chicago Midway. Booking flights from Chicago Midway to Cancun (CUN) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 7 different airlines.

Can I find deals for flights from Midway to Cancún that include hotel bookings?

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

How can I find direct flights from Midway to Cancún?

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

Can I find deals for business class flights from Midway to Cancún?

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

$119+ Flights from Chicago Midway Airport to Cancún

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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

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

Cheap flight deals from Midway to Cancún

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$261 (Southwest)
One-way from	$119 (Southwest)
Popular in	December
Cheapest in	September
Average price	$430
Good round-trip deal	$396 or less
Good one-way deal	$134 or less

Provider with most accurate pricing for Chicago Midway-Cancun flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago Midway-Cancun flights.

Search Deals

From Chicago Midway to Cancun

Search Deals

One-way flight from Chicago Midway to Cancun

Search Deals

Highest demand for flights based on searches. 16% potential increase in price ($114 potential increase over avg. RT price).

Search Deals

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

Search Deals

Average for round-trip flights in September 2025

Search Deals

Price to beat on a round-trip flight from Chicago Midway to Cancun.

Search Deals

Price to beat on a one-way flight from Chicago Midway to Cancun.

Search Deals

Find flight deals from Midway to Cancún

Cheapest flights from Midway to Cancún
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 September 25, 2025.

Sun 10/268:25 amMDW - CUN

Nonstop3h 40mSouthwest

Thu 10/303:20 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$261

Sat 10/259:40 amMDW - CUN

Nonstop3h 35mSouthwest

Fri 10/313:15 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$266

Sun 12/1410:40 amMDW - CUN

Nonstop3h 45mSouthwest

Mon 12/222:30 pmCUN - MDW

Nonstop3h 45mSouthwest

Deal found 9/23

$270

Sat 12/63:40 pmMDW - CUN

Nonstop3h 45mSouthwest

Sat 12/133:10 pmCUN - MDW

Nonstop3h 45mSouthwest

Deal found 9/25

$271

Sat 10/256:30 amMDW - CUN

1 stop7h 10mSouthwest

Thu 10/303:20 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$280

Mon 10/69:40 amMDW - CUN

Nonstop3h 35mSouthwest

Thu 10/93:20 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$281

Sat 10/257:00 amMDW - CUN

1 stop6h 10mSouthwest

Sat 11/12:00 pmCUN - MDW

Nonstop3h 45mSouthwest

Deal found 9/25

$285

Tue 11/118:40 amMDW - CUN

Nonstop3h 45mSouthwest

Sat 11/1511:20 amCUN - MDW

2 stops8h 45mSouthwest

Deal found 9/25

$286

Mon 9/299:55 amMDW - CUN

Nonstop3h 35mSouthwest

Wed 10/13:10 pmCUN - MDW

Nonstop3h 40mSouthwest

Deal found 9/25

$301

Fri 10/245:28 pmMDW - CUN

1 stop16h 58mFrontier

Fri 11/72:30 pmCUN - MDW

1 stop8h 38mFrontier

Deal found 9/24

$302

Best flights from Midway to Cancún
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 September 25, 2025.

Tue 11/118:40 amMDW - CUN

Nonstop3h 45mSouthwest

Sat 11/158:40 amCUN - MDW

1 stop9h 05mSouthwest

Deal found 9/24

$301

Sat 1/176:00 amMDW - CUN

1 stop9h 31mDelta

Wed 1/213:03 pmCUN - MDW

1 stop7h 43mDelta

Deal found 9/25

$326

Sun 2/86:00 amMDW - CUN

1 stop6h 36mFrontier

Sat 2/142:51 pmCUN - MDW

1 stop9h 34mFrontier

Deal found 9/25

$374

Wed 12/39:34 amMDW - CUN

2 stops10h 46mDelta

Wed 12/178:00 amCUN - MDW

2 stops11h 00mDelta

Deal found 9/24

$330

Wed 12/39:20 amMDW - CUN

1 stop10h 05mSouthwest

Wed 12/172:15 pmCUN - MDW

1 stop9h 40mSouthwest

Deal found 9/24

$356

Sun 1/116:00 amMDW - CUN

1 stop9h 31mDelta

Fri 1/1612:15 pmCUN - MDW

1 stop7h 19mDelta

Deal found 9/24

$341

Sat 11/84:23 pmMDW - CUN

2 stops19h 12mDelta

Fri 11/148:00 amCUN - MDW

1 stop9h 38mDelta

Deal found 9/25

$345

Mon 11/109:34 amMDW - CUN

2 stops10h 46mDelta

Fri 11/148:00 amCUN - MDW

2 stops11h 08mDelta

Deal found 9/24

$345

Mon 1/1210:35 amMDW - CUN

1 stop9h 35mDelta

Mon 1/264:25 pmCUN - MDW

1 stop6h 21mDelta

Deal found 9/24

$381

Mon 11/1710:47 amMDW - CUN

1 stop9h 33mDelta

Sat 11/226:00 amCUN - MDW

2 stops10h 43mDelta

Deal found 9/24

$386

Last-minute flights from Midway to Cancún
Discover last-minute flight deals from Midway to Cancún. Data last updated September 25, 2025 and is based on user searches.

Mon 9/299:55 amMDW - CUN

Nonstop3h 35mSouthwest

Wed 10/13:10 pmCUN - MDW

Nonstop3h 40mSouthwest

Deal found 9/25

$301

Tue 9/309:55 amMDW - CUN

Nonstop3h 35mSouthwest

Sat 10/42:00 pmCUN - MDW

Nonstop3h 45mSouthwest

Deal found 9/24

$286

Mon 10/69:40 amMDW - CUN

Nonstop3h 35mSouthwest

Thu 10/93:20 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$281

Mon 10/65:00 amMDW - CUN

1 stop7h 40mSouthwest

Sat 10/1112:00 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/24

$310

Fri 10/245:28 pmMDW - CUN

1 stop16h 58mFrontier

Fri 11/72:30 pmCUN - MDW

1 stop8h 38mFrontier

Deal found 9/24

$302

Sat 10/259:40 amMDW - CUN

Nonstop3h 35mSouthwest

Fri 10/313:15 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$266

Sat 10/259:40 amMDW - CUN

Nonstop3h 35mSouthwest

Sat 11/12:00 pmCUN - MDW

Nonstop3h 45mSouthwest

Deal found 9/25

$271

Sat 10/256:30 amMDW - CUN

1 stop7h 10mSouthwest

Thu 10/303:20 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$280

Sun 10/268:25 amMDW - CUN

Nonstop3h 40mSouthwest

Thu 10/303:20 pmCUN - MDW

Nonstop3h 35mSouthwest

Deal found 9/25

$261

One-way flights from Midway to Cancún
Search for one-way flight options from Midway to Cancún. Find affordable one-way fares based on user searches. Data last updated September 25, 2025.

Tue 10/149:40 amMDW - CUN

Nonstop3h 35mSouthwest

Deal found 9/25

$119

Sun 12/1410:40 amMDW - CUN

Nonstop3h 45mSouthwest

Deal found 9/23

$123

Sat 12/133:40 pmMDW - CUN

Nonstop3h 45mSouthwest

Deal found 9/25

$124

Sat 1/176:40 amMDW - CUN

1 stop9h 00mSouthwest

Deal found 9/25

$129

Tue 1/206:10 amMDW - CUN

1 stop6h 35mSouthwest

Deal found 9/25

$134

Sat 11/111:45 amMDW - CUN

1 stop8h 05mSouthwest

Deal found 9/24

$139

Fri 10/245:28 pmMDW - CUN

1 stop14h 36mMultiple Airlines

Deal found 9/24

$144

Fri 10/245:28 pmMDW - CUN

1 stop16h 58mFrontier

Deal found 9/25

$145

Sat 10/118:35 amMDW - CUN

1 stop23h 29mMultiple Airlines

Deal found 9/25

$148

Fri 1/29:29 amMDW - CUN

2 stops10h 51mDelta

Deal found 9/25

$149

Tue 10/215:20 pmMDW - CUN

1 stop15h 27mMultiple Airlines

Deal found 9/25

$150

Cheapflights Fare Finder

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

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/11

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

Sat 11/15

8:40 am-4:45 pm

1 stop9h 05m

$301

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

6:00 am-4:31 pm

1 stop9h 31m

Cancun

Wed 1/21

3:03 pm-9:46 pm

1 stop7h 43m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/3

9:34 am-9:20 pm

2 stops10h 46m

Cancun

Wed 12/17

8:00 am-6:00 pm

2 stops11h 00m

$330

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

6:00 am-4:31 pm

1 stop9h 31m

Cancun

Fri 1/16

12:15 pm-6:34 pm

1 stop7h 19m

$341

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/8

4:23 pm-12:35 pm

2 stops19h 12m

Cancun

Fri 11/14

8:00 am-4:38 pm

1 stop9h 38m

$345

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/10

9:34 am-9:20 pm

2 stops10h 46m

Cancun

Fri 11/14

8:00 am-6:08 pm

2 stops11h 08m

$345

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/3

9:20 am-8:25 pm

1 stop10h 05m

Cancun

Wed 12/17

2:15 pm-10:55 pm

1 stop9h 40m

$356

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 2/8

6:00 am-1:36 pm

1 stop6h 36m

Cancun

Sat 2/14

2:51 pm-11:25 pm

1 stop9h 34m

$374

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/12

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Mon 1/26

4:25 pm-9:46 pm

1 stop6h 21m

$381

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/17

10:47 am-9:20 pm

1 stop9h 33m

Cancun

Sat 11/22

6:00 am-3:43 pm

2 stops10h 43m

$386

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 22 results

Compare providers for flights from Midway to Cancún

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Cancún in September.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
AranGrant	Price Accuracy3 stars	Trust Score*3 stars
CheapTicketsDeal	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

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.

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

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 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $360). Flying from Chicago Midway Airport to Cancún 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 CUN?

It’s typically best to fly out from Chicago Midway Airport to Cancún in the evening. Doing so could potentially save you 47% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Cancún

Read through reviews of airlines operating flights from Chicago Midway Airport to Cancún, such as Southwest, Delta, and LATAM Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Southwest

8.0

Very good

4,246 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Delta

8.0

Very good

7,973 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

LATAM Airlines

7.5

Good

1,855 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Aeromexico

7.5

Good

1,693 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Volaris

6.7

Okay

1,152 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

What airport do you fly into for flights to Cancún from Chicago Midway?
Located just 8.9 mi from the city center, Cancun is the airport most travelers will use when flying to Cancún from Chicago Midway. Booking flights from Chicago Midway to Cancun (CUN) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 7 different airlines.
How long is the flight from Chicago Midway Airport to Cancún?
Airlines like Southwest and Delta fly from Chicago Midway Airport to Cancún in about 3h 45m. The time it takes to get you to your destination can typically vary by up to 5h 46m. There are 1434 mi between Chicago Midway Airport and Cancún. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.
What are the cheapest airlines flying from Chicago Midway Airport to Cancún round-trip?
Cheapflights users have booked flights from Chicago Midway Airport to Cancún round-trip from $161. Other airlines that can offer you cheap pricing are Aeromexico, from $312, and Southwest, from $345. These flights start at 72% lower than the current average price 3 months from now.
What are the cheapest flights from Chicago Midway Airport to Cancún?
On average you can expect to pay $315 for a flight from Chicago Midway Airport to Cancún. The cheapest flight overall is $124 while the most popular route, (Chicago Midway - Cancun) is currently priced at $280.
Can I find deals for flights from Midway to Cancún that include hotel bookings?
Yes. In addition to deals on Midway to Cancún flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to Cancún?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Cancún.
Can I find deals for business class flights from Midway to Cancún?
Yes. Cheapflights offers flight deals from Midway to Cancún 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 Cancún?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $360). Flying from Chicago Midway Airport to Cancún 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

Puerto Aventuras

Holbox

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Alternative routes for Midway to Cancún

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Midway to Cozumel flights

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Other flights to Cancún

Top 7 airlines flying from Midway to Cancún

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$161	Average$419	FlexibilityNo cancel fee	On-time69%
Aeromexico	Cheapest$312	Average$494	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$345	Average$575	FlexibilityNo cancel fee	On-time63%
Frontier	Cheapest$362	Average$565	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$380	Average$609	FlexibilityNo cancel fee	On-timeN/A
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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$119+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Cancún 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 Cancun are usually found in September or July, booked 57 days in advance, depart on a Monday or Sunday and return on a Tuesday

Cheap flight deals from Midway to Cancún

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Midway to Cancún

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 September 25, 2025.

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 September 25, 2025.

Cheapflights Fare Finder

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

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 September.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Cancún

How far ahead should I book a flight from Chicago Midway Airport to Cancún?

What is the cheapest month to book a flight from Chicago Midway Airport to Cancún?

What is the cheapest time of day to fly from MDW to CUN?

Reviews of airlines servicing Cancún

Read through reviews of airlines operating flights from Chicago Midway Airport to Cancún, such as Southwest, Delta, and LATAM Airlines. Reviews also offer insight into each airline's 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 Cancún. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to Cancún from Chicago Midway?

How long is the flight from Chicago Midway Airport to Cancún?

What are the cheapest airlines flying from Chicago Midway Airport to Cancún round-trip?

What are the cheapest flights from Chicago Midway Airport to Cancún?

Can I find deals for flights from Midway to Cancún that include hotel bookings?

How can I find direct flights from Midway to Cancún?

Can I find deals for business class flights from Midway to Cancún?

What is the cheapest month to book a flight from Chicago Midway Airport to Cancún?

Traveling to a place near Cancún?

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Alternative routes for Midway to Cancún

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

Top 7 airlines flying from Midway to Cancún

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Cheapest flights from Midway to Cancún
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 September 25, 2025.