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

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

How often are flights from Cancún to Chicago delayed?

Historically, on average around 7% of flights between Cancún and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 135 minutes.

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

As of November 2025, 4 flights take off from Cancún and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.

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

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 7% of their flights experiencing any sort of delay.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening 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. Saturday has historically seen more delays on average compared to the rest of the week.

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

Prices for flights from Cancun Airport to Chicago Midway Airport refresh daily.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cancun Airport to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$144 Cheap Flights from Cancún to Chicago Midway Airport in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

1:45 pm - 4:30 pmCUN-MDW

3h 45mnonstop

9:15 am - 1:55 pmMDW-CUN

3h 40mnonstop

$265Southwest

Find Deal

jue., ene. 22 - lun., ene. 26

1:33 pm - 11:47 pmCUN-MDW

11h 14m1 stop

12:50 pm - 9:20 pmMDW-CUN

7h 30m1 stop

$274Aeromexico

Find Deal

vie., dic. 5 - mar., dic. 9

1:32 pm - 11:40 pmCUN-MDW

11h 08m1 stop

6:00 am - 3:34 pmMDW-CUN

8h 34m1 stop

$276Delta

Find Deal

vie., nov. 14 - lun., nov. 17

1:00 pm - 6:55 pmCUN-MDW

6h 55m1 stop

11:25 am - 7:45 pmMDW-CUN

7h 20m1 stop

$306Southwest

Find Deal

sáb., nov. 15 - lun., nov. 17

8:00 am - 9:46 pmCUN-MDW

14h 46m1 stop

6:00 am - 9:10 pmMDW-CUN

14h 10m1 stop

$326Delta

Find Deal

vie., feb. 13 - mar., feb. 17

2:30 pm - 10:11 pmCUN-MDW

8h 41m1 stop

8:41 pm - 10:38 amMDW-CUN

12h 57m1 stop

$358Frontier

Find Deal

lun., nov. 17 - jue., nov. 20

8:00 am - 4:39 pmCUN-MDW

9h 39m1 stop

6:00 am - 9:10 pmMDW-CUN

14h 10m2 stops

$385Multiple Airlines

Find Deal

lun., nov. 24 - mié., dic. 31

2:33 pm - 10:12 pmCUN-MDW

8h 39m1 stop

6:15 am - 1:58 pmMDW-CUN

6h 43m1 stop

$405Frontier

Find Deal

vie., dic. 12 - dom., dic. 14

10:53 am - 6:40 pmCUN-MDW

7h 47m1 stop

8:09 pm - 9:48 amMDW-CUN

13h 39m1 stop

$474Volaris

Find Deal

vie., abr. 17 - lun., abr. 27

11:09 am - 11:47 pmCUN-MDW

13h 38m1 stop

6:12 am - 1:40 pmMDW-CUN

6h 28m1 stop

$494Multiple Airlines

Find Deal

jue., dic. 18 - jue., dic. 25

Southwest flights from Cancún to Chicago Midway Airport

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

Southwest

Jan 22

CUN1:45 pmCancun

3h 45m

MDW4:30 pmChicago Midway

Jan 26

MDW9:15 amChicago Midway

3h 40m

CUN1:55 pmCancun

$265

Find similar

Southwest

Nov 8

CUN2:50 pmCancun

6h 45m

1 stop

MDW8:35 pmChicago Midway

Nov 15

MDW3:40 pmChicago Midway

3h 45m

CUN8:25 pmCancun

$296

Find similar

Southwest

Nov 8

CUN2:55 pmCancun

8h 40m

1 stop

MDW10:35 pmChicago Midway

Nov 10

MDW10:40 amChicago Midway

3h 45m

CUN3:25 pmCancun

$302

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Delta flights from Cancún to Chicago Midway Airport

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

Delta

Nov 14

CUN1:32 pmCancun

11h 08m

1 stop

MDW11:40 pmChicago Midway

Nov 17

MDW6:00 amChicago Midway

8h 34m

1 stop

CUN3:34 pmCancun

$276

Find similar

Delta

Feb 13

CUN8:00 amCancun

14h 46m

1 stop

MDW9:46 pmChicago Midway

Feb 17

MDW6:00 amChicago Midway

14h 10m

1 stop

CUN9:10 pmCancun

$326

Find similar

Delta

Feb 19

CUN5:30 pmCancun

6h 14m

1 stop

MDW10:44 pmChicago Midway

Feb 23

MDW6:00 amChicago Midway

9h 31m

1 stop

CUN4:31 pmCancun

$328

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momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/22

1:45 pm-4:30 pm

Nonstop3h 45m

Chicago Midway

lun. 1/26

9:15 am-1:55 pm

Nonstop3h 40m

$265

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 12/5

1:33 pm-11:47 pm

1 stop11h 14m

Chicago Midway

mar. 12/9

12:50 pm-9:20 pm

1 stop7h 30m

$274

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 11/14

1:32 pm-11:40 pm

1 stop11h 08m

Chicago Midway

lun. 11/17

6:00 am-3:34 pm

1 stop8h 34m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 11/15

1:00 pm-6:55 pm

1 stop6h 55m

Chicago Midway

lun. 11/17

11:25 am-7:45 pm

1 stop7h 20m

$306

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 2/13

8:00 am-9:46 pm

1 stop14h 46m

Chicago Midway

mar. 2/17

6:00 am-9:10 pm

1 stop14h 10m

$326

CancúnChicago

CUN - MDW

CUNMDW

Cancun

lun. 11/17

2:30 pm-10:11 pm

1 stop8h 41m

Chicago Midway

jue. 11/20

8:41 pm-10:38 am

1 stop12h 57m

$358

CancúnChicago

CUN - MDW

CUNMDW

Cancun

lun. 11/24

8:00 am-4:39 pm

1 stop9h 39m

Chicago Midway

mié. 12/31

6:00 am-9:10 pm

2 stops14h 10m

$385

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 12/12

2:33 pm-10:12 pm

1 stop8h 39m

Chicago Midway

dom. 12/14

6:15 am-1:58 pm

1 stop6h 43m

$405

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 4/17

10:53 am-6:40 pm

1 stop7h 47m

Chicago Midway

lun. 4/27

8:09 pm-9:48 am

1 stop13h 39m

$474

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 12/18

11:09 am-11:47 pm

1 stop13h 38m

Chicago Midway

jue. 12/25

6:12 am-1:40 pm

1 stop6h 28m

$494

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 Cancún to Chicago Midway Airport

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Cancún. The lowest ticket price found for a Monday departure recently was $539. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Cancún because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $552.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Cancún in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $455 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $461. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Cancun to Chicago Midway flight route?

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

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

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

Can stopping save me money on Cancún to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Cancún to Chicago Midway Airport.

How have Cancún to Chicago Midway Airport flight prices changed over time?

As of November 2025, prices for Cancún to Chicago Midway Airport flights are approximately 206% more expensive when compared to flights at the same time last year.

When to book flights from Cancún to Chicago Midway Airport

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

Estimated round-trip price

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

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

Fastest flight time	3h 40m
Direct flights	Every day

The fastest flight from Cancún to Chicago Midway Airport takes 3h 40m

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

Search flight deals

How far is Cancun to Chicago Midway by plane?
Chicago Midway is 1425.4 mi away from Cancun. Flights usually cover this in 3h 40m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Cancun Airport to Chicago Midway Airport?
Prices for flights from Cancun Airport to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Cancun Airport to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cancun Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Cancún to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Cancún to Chicago Midway Airport is Boeing 737-900, representing 42.11% of all bookings. The subsequent popular models are Airbus A321-100/200 at 12.28%, Airbus A320neo at 8.77%, and Airbus A320-100/200 at 8.77%.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find Cancún to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

momondo does allow users to show only those flights to Chicago from Cancún which offer a flexible booking policy as well as other useful filters and features.

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

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

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

Yes. momondo can track prices for Cancún to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Chicago Midway Airport 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.

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mié. 12/3

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Cheap flights from Cancún to Chicago from $144

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cancún to Chicago departing on 2/5. 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

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Filter for what you want

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Southwest flights from Cancún to Chicago Midway Airport

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

Delta flights from Cancún to Chicago Midway Airport

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

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

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

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 day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest Cancun to Chicago Midway flight route?

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

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

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

Can stopping save me money on Cancún to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Cancún to Chicago Midway Airport.

How have Cancún to Chicago Midway Airport flight prices changed over time?

As of November 2025, prices for Cancún to Chicago Midway Airport flights are approximately 206% more expensive when compared to flights at the same time last year.

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

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

How often are flights from Cancún to Chicago delayed?

Historically, on average around 7% of flights between Cancún and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 135 minutes.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening 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. Saturday has historically seen more delays on average compared to the rest of the week.

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

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 7% of their flights experiencing any sort of delay.

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

As of November 2025, 4 flights take off from Cancún and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.

When to book flights from Cancún to Chicago Midway Airport

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

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

Fastest flight time

Direct flights

How far is Cancun to Chicago Midway by plane?

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

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

What documentation or ID do you need to fly to Chicago Midway Airport?

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

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago Midway Airport 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 Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo