How many flights depart from Chicago Midway Airport to Cancún on average per week?

As of November 2025, 6 flights take off from Chicago Midway Airport and land in Cancún each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

What is the most punctual flight time for Chicago to Cancún flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

What is the cheapest airline that flies from Chicago Midway to Cancun?

Southwest, Frontier, and Aeromexico are the most popular carriers operating from Chicago Midway to Cancun

Which airline has the best punctuality record on Chicago to Cancún flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

What airlines fly to Cancún?

Southwest, Delta and Volaris are the top three most popular airlines that fly to Cancún from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 77% of people opting to fly with this airline when traveling to Cancún. Keep in mind that there are 7 different airlines that fly to Cancún on a routine basis, so you have a few additional options to choose from.

How often are flights from Chicago to Cancún delayed?

Historically, on average around 11% of flights between Chicago and Cancún have experienced a delay on any given week. The average delay length over the past 12 months has been 150 minutes.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

When did momondo last update prices for flights from Chicago Midway Airport to Cancun Airport?

Prices for flights from Chicago Midway Airport to Cancun Airport are updated daily.

How many operators does momondo search for flights from Chicago Midway Airport to Cancun Airport?

As of November 2025, there are 7 operators available to choose from for flights from Chicago Midway Airport to Cancun Airport.

How old do you have to be to fly from Chicago Midway Airport to Cancun Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Cancun Airport.

What documentation or ID do you need to fly to Cancun Airport?

The travel and health documents you'll need for your trip to Cancun Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cancun Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$120 Cheap Flights from Chicago Midway Airport to Cancún in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Cancún

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Cheap round-trip flights

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9:07 pm - 3:53 pmMDW-CUN

17h 46m1 stop

2:31 pm - 11:25 pmCUN-MDW

9h 54m1 stop

$278Frontier

Find Deal

Fri, Jan 9 - Mon, Jan 12

11:21 am - 9:11 pmMDW-CUN

8h 50m1 stop

8:00 am - 4:31 pmCUN-MDW

9h 31m1 stop

$302Aeromexico

Find Deal

Wed, Jan 7 - Wed, Jan 14

8:55 am - 7:45 pmMDW-CUN

9h 50m1 stop

3:40 pm - 6:20 pmCUN-MDW

3h 40mnonstop

$312Southwest

Find Deal

Sun, Feb 8 - Thu, Feb 12

6:00 am - 9:20 pmMDW-CUN

14h 20m1 stop

11:17 am - 11:47 pmCUN-MDW

13h 30m2 stops

$316Aeromexico

Find Deal

Sat, Dec 6 - Sat, Dec 13

12:47 pm - 9:20 pmMDW-CUN

7h 33m1 stop

8:00 am - 4:34 pmCUN-MDW

9h 34m1 stop

$317Aeromexico

Find Deal

Mon, Dec 1 - Wed, Dec 10

2:01 pm - 9:13 amMDW-CUN

18h 12m2 stops

2:31 pm - 11:25 pmCUN-MDW

9h 54m1 stop

$320Multiple Airlines

Find Deal

Fri, Jan 9 - Mon, Jan 12

3:10 pm - 9:07 amMDW-CUN

16h 57m1 stop

2:00 pm - 8:45 pmCUN-MDW

7h 45m1 stop

$321Multiple Airlines

Find Deal

Fri, Jan 2 - Fri, Jan 9

6:45 am - 9:11 pmMDW-CUN

13h 26m1 stop

8:00 am - 3:40 pmCUN-MDW

8h 40m1 stop

$327Delta

Find Deal

Sat, Jan 17 - Sat, Jan 24

6:45 am - 9:11 pmMDW-CUN

13h 26m1 stop

12:05 pm - 10:26 pmCUN-MDW

11h 21m2 stops

$331Delta

Find Deal

Sat, Jan 17 - Wed, Jan 21

8:40 am - 1:25 pmMDW-CUN

3h 45mnonstop

4:25 pm - 7:10 pmCUN-MDW

3h 45mnonstop

$342Southwest

Find Deal

Tue, Nov 18 - Sat, Nov 22

Southwest flights from Chicago Midway Airport to Cancún

Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets

Southwest

Feb 8

MDW8:55 amChicago Midway

9h 50m

1 stop

CUN7:45 pmCancun

Feb 12

CUN3:40 pmCancun

3h 40m

MDW6:20 pmChicago Midway

$312

Find similar

Southwest

Nov 18

MDW8:40 amChicago Midway

3h 45m

CUN1:25 pmCancun

Nov 22

CUN4:25 pmCancun

3h 45m

MDW7:10 pmChicago Midway

$342

Find similar

Southwest

Nov 16

MDW10:40 amChicago Midway

3h 45m

CUN3:25 pmCancun

Nov 20

CUN5:05 pmCancun

6h 30m

1 stop

MDW10:35 pmChicago Midway

$352

Find similar

Frontier flights from Chicago Midway Airport to Cancún

Our best Frontier deals on Chicago Midway Airport to Cancún flight tickets

Frontier

Jan 9

MDW9:07 pmChicago Midway

17h 46m

1 stop

CUN3:53 pmCancun

Jan 12

CUN2:31 pmCancun

9h 54m

1 stop

MDW11:25 pmChicago Midway

$278

Find similar

Frontier

Jan 11

MDW9:07 pmChicago Midway

17h 46m

1 stop

CUN3:53 pmCancun

Jan 15

CUN2:31 pmCancun

9h 55m

1 stop

MDW11:26 pmChicago Midway

$319

Find similar

Frontier

Dec 1

MDW7:10 pmChicago Midway

14h 18m

1 stop

CUN10:28 amCancun

Dec 6

CUN2:48 pmCancun

49h 04m

2 stops

MDW2:52 pmChicago Midway

$332

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momondo 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

Fri 1/9

9:07 pm-3:53 pm

1 stop17h 46m

Cancun

Mon 1/12

2:31 pm-11:25 pm

1 stop9h 54m

$278

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 1/7

11:21 am-9:11 pm

1 stop8h 50m

Cancun

Wed 1/14

8:00 am-4:31 pm

1 stop9h 31m

$302

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 2/8

8:55 am-7:45 pm

1 stop9h 50m

Cancun

Thu 2/12

3:40 pm-6:20 pm

Nonstop3h 40m

$312

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 12/6

6:00 am-9:20 pm

1 stop14h 20m

Cancun

Sat 12/13

11:17 am-11:47 pm

2 stops13h 30m

$316

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 12/1

12:47 pm-9:20 pm

1 stop7h 33m

Cancun

Wed 12/10

8:00 am-4:34 pm

1 stop9h 34m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/9

2:01 pm-9:13 am

2 stops18h 12m

Cancun

Mon 1/12

2:31 pm-11:25 pm

1 stop9h 54m

$320

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/2

3:10 pm-9:07 am

1 stop16h 57m

Cancun

Fri 1/9

2:00 pm-8:45 pm

1 stop7h 45m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Sat 1/24

8:00 am-3:40 pm

1 stop8h 40m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Wed 1/21

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/18

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

Sat 11/22

4:25 pm-7:10 pm

Nonstop3h 45m

$342

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Cancún

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Cancún?

If you don’t want to visit Cancún in September, then you should wait until July to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $456.

What is the cheapest day to depart on your flight to Cancún?

The cheapest day to depart from Chicago Midway Airport to Cancún is on a Monday when prices can be found for as low as $405. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $527. These prices are subject to change though, so be sure to set up a Price Alert for flights to Cancún.

What is the cheapest time of day to depart on your flight to Cancún?

Our most recent data shows that the best time of day to fly to Cancún is in the morning. Flights from Chicago Midway Airport to Cancún during this time can be as low as $466. Flights to Cancún are more costly at noon, with an average ticket price of $653. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Cancun flight route?

Fly from Chicago Midway to Cancun for the best Chicago Midway - Cancun flight prices

How far in advance should I book a flight to Cancún?

You are more likely to see cheaper flights to Cancún from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Cancún for around $569 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cancún from Chicago Midway Airport for as low as $418 on momondo.

What cabin class options are available on Chicago Midway to Cancun flights?

There is only 1 cabin class available to choose from on Chicago Midway to Cancun flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Chicago Midway Airport to Cancún

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Cancún according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Cancún (MDW to CUN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Cancún

Best Price Found	$124
Fastest flight time	3h 30m
Direct flights	Every day
Airports in Cancún	1 airport

The best one-way flight to Cancún from Chicago Midway Airport in the past 72 hours is $124. The best round-trip flight deal from Chicago Midway Airport to Cancún found on momondo in the last 72 hours is $281.

The fastest flight from Chicago Midway Airport to Cancún takes 3h 30m

Direct flights go from Chicago Midway Airport to Cancún every day.

There is 1 airport near Cancún: Cancun (CUN)

Search flight deals

How far is Chicago Midway to Cancun by plane?
Chicago Midway and Cancun are 1425.4 mi apart from one another. Typically, this will take 3h 45m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Cancun Airport?
Prices for flights from Chicago Midway Airport to Cancun Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Cancun Airport?
As of November 2025, there are 7 operators available to choose from for flights from Chicago Midway Airport to Cancun Airport.
How old do you have to be to fly from Chicago Midway Airport to Cancun Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Cancun Airport.
What documentation or ID do you need to fly to Cancun Airport?
The travel and health documents you'll need for your trip to Cancun Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cancun Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Cancún?
Based on momondo bookings for flights between Chicago Midway Airport and Cancún, the leading plane model is Airbus A321-100/200, making up 14.13% of the total bookings. Other popular models include Boeing 777 with 11.93%, Boeing 737 MAX 8 with 11.56%, and Boeing 737-800 with 10.64%.
What is the most popular airline from Chicago Midway Airport to Cancún?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Cancún is Southwest (75% of total bookings). The next most popular airlines are Delta (14%), Volaris (4%), and Aeromexico (3%).

Best airlines flying from Chicago Midway Airport to Cancún

Compare and see reviews for airlines that fly from Chicago Midway Airport to Cancún with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $161	Free Cancellation	Rating 7.4 9,007 reviews	Search United Airlines flights
Aeromexico	PriceFrom $312	Free Cancellation	Rating 7.4 1,672 reviews	Search Aeromexico flights
Southwest	PriceFrom $345	Free Cancellation	Rating 8.0 4,241 reviews	Search Southwest flights
Frontier	PriceFrom $362	Free Cancellation	Rating 5.8 3,116 reviews	Search Frontier flights
Delta	PriceFrom $380	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
Volaris	PriceFrom $486	Free Cancellation	Rating 6.7 1,151 reviews	Search Volaris flights
LATAM Airlines	PriceFrom $3,369	Free Cancellation	Rating 7.5 1,872 reviews	Search LATAM Airlines flights

Southwest Flights From Chicago Midway Airport to Cancún
Southwest operates around 6 flights from Chicago Midway Airport to Cancún every week. The average price of these flights found in the last 72 hours has been $572, but momondo users have found Southwest deals from Chicago Midway Airport to Cancún from as low as $345 round-trip. Southwest has been scored 8.0/10 in 4,241 reviews.

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cancún?

Finding the right flight to Cancún from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Cancún quick and easy, saving you time and money.

Can I find flights from Chicago to Cancún with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Cancún flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Cancún?

momondo provides multiple filters to help you find the best flight to Cancún from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Cancún right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Cancún from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Chicago Midway Airport to Cancún from $120

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Cancún departing on 1/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago Midway Airport to Cancún

Cheap round-trip flights

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Southwest flights from Chicago Midway Airport to Cancún

Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets

Frontier flights from Chicago Midway Airport to Cancún

Our best Frontier deals on Chicago Midway Airport to Cancún flight tickets

momondo Fare Finder

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

See travel insights to Cancún from

How to get the cheapest flight ticket from Chicago Midway Airport to Cancún

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Cancún?

If you don’t want to visit Cancún in September, then you should wait until July to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $456.

What is the cheapest day to depart on your flight to Cancún?

What is the cheapest time of day to depart on your flight to Cancún?

What is the cheapest Chicago Midway to Cancun flight route?

Fly from Chicago Midway to Cancun for the best Chicago Midway - Cancun flight prices

How far in advance should I book a flight to Cancún?

What cabin class options are available on Chicago Midway to Cancun flights?

There is only 1 cabin class available to choose from on Chicago Midway to Cancun flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest airline that flies from Chicago Midway to Cancun?

Southwest, Frontier, and Aeromexico are the most popular carriers operating from Chicago Midway to Cancun

What airlines fly to Cancún?

How often are flights from Chicago to Cancún delayed?

Historically, on average around 11% of flights between Chicago and Cancún have experienced a delay on any given week. The average delay length over the past 12 months has been 150 minutes.

What is the most punctual flight time for Chicago to Cancún flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Cancún flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

How many flights depart from Chicago Midway Airport to Cancún on average per week?

As of November 2025, 6 flights take off from Chicago Midway Airport and land in Cancún each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

When to book flights from Chicago Midway Airport to Cancún

Cheap Chicago Midway Airport to Cancún (MDW to CUN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Cancún

Best Price Found

Fastest flight time

Direct flights

Airports in Cancún

How far is Chicago Midway to Cancun by plane?

When did momondo last update prices for flights from Chicago Midway Airport to Cancun Airport?

How many operators does momondo search for flights from Chicago Midway Airport to Cancun Airport?

How old do you have to be to fly from Chicago Midway Airport to Cancun Airport?

What documentation or ID do you need to fly to Cancun Airport?

What is the most popular plane model from Chicago Midway Airport to Cancún?

What is the most popular airline from Chicago Midway Airport to Cancún?

Best airlines flying from Chicago Midway Airport to Cancún

Compare and see reviews for airlines that fly from Chicago Midway Airport to Cancún with momondo

Southwest Flights From Chicago Midway Airport to Cancún

Traveling to a place near Cancún?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cancún?

Can I find flights from Chicago to Cancún with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Cancún?

I’m not ready to book a flight from Chicago to Cancún right now. Can momondo alert me if prices change?

An easier way to manage your Cancún trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Mexico

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