Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Cancún?

With an average price of $574 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Cancún with. Instead, for the lowest price, our data suggests flying with United Airlines, where a return flight costs $490 on average.

Does Southwest fly direct to Cancún from Chicago Midway Airport?

Yes, Southwest does offer direct flights for the route, with around 5 flights per week.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Cancún with Southwest?

On average, the cheapest day of the week to fly from Chicago Midway Airport to Cancún with Southwest is Monday, when prices are around $109. The most expensive day is generally Tuesday, where the average price is around $336.

What’s the cheapest month to fly from Chicago Midway Airport to Cancún with Southwest?

The cheapest month for Southwest flights to Cancún from Chicago Midway Airport is generally July, where plane tickets cost $123 on average. If possible, try to avoid the most expensive months of May and December, where tickets cost $426 and $447 respectively.

$115 Cheap Southwest Flights from Chicago Midway Airport to Cancún

MDW - CUN

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Flight Deals

Cheap Southwest Flight Deals from Chicago Midway Airport to Cancún

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Chicago Midway Airport to Cancún that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Chicago Midway Airport to Cancún

Sun, Nov 16 - Fri, Nov 21

10:40 am - 3:25 pmMDW-CUN

3h 45mnonstop

2:15 pm - 5:00 pmCUN-MDW

3h 45mnonstop

$252Southwest

Find Deal

Sat, Nov 8 - Fri, Nov 14

3:40 pm - 8:25 pmMDW-CUN

3h 45mnonstop

2:15 pm - 5:00 pmCUN-MDW

3h 45mnonstop

$257Southwest

Find Deal

Mon, Nov 17 - Wed, Nov 19

8:40 am - 1:25 pmMDW-CUN

3h 45mnonstop

1:45 pm - 4:30 pmCUN-MDW

3h 45mnonstop

$262Southwest

Find Deal

Sat, Nov 8 - Sat, Nov 15

3:40 pm - 8:25 pmMDW-CUN

3h 45mnonstop

1:00 pm - 6:55 pmCUN-MDW

6h 55m1 stop

$282Southwest

Find Deal

Mon, Oct 27 - Sat, Nov 1

9:40 am - 1:15 pmMDW-CUN

3h 35mnonstop

1:20 pm - 7:05 pmCUN-MDW

5h 45m1 stop

$287Southwest

Find Deal

Sat, Dec 13 - Wed, Dec 17

5:05 am - 2:00 pmMDW-CUN

7h 55m1 stop

1:45 pm - 4:30 pmCUN-MDW

3h 45mnonstop

$301Southwest

Find Deal

Tue, Nov 11 - Thu, Nov 13

8:40 am - 1:25 pmMDW-CUN

3h 45mnonstop

2:15 pm - 5:00 pmCUN-MDW

3h 45mnonstop

$302Southwest

Find Deal

Sat, Nov 1 - Sat, Nov 15

8:20 am - 7:50 pmMDW-CUN

11h 30m2 stops

8:40 am - 4:45 pmCUN-MDW

9h 05m1 stop

$306Southwest

Find Deal

Sat, Nov 8 - Thu, Nov 13

3:40 pm - 8:25 pmMDW-CUN

3h 45mnonstop

6:55 pm - 12:10 amCUN-MDW

6h 15m1 stop

$307Southwest

Find Deal

Sat, Dec 13 - Sat, Dec 20

5:05 am - 2:00 pmMDW-CUN

7h 55m1 stop

4:25 pm - 7:10 pmCUN-MDW

3h 45mnonstop

$311Southwest

Find Deal

Useful Info

Low season	August
High season	January
Cheapest flight	$115
Average price round-trip	$506
Good deal one-way	$139

Best time to beat the crowds with an average 7% drop in price.

Most popular time to fly with an average 21% increase in price.

Flight from Chicago Midway Airport to Cancun

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from Chicago Midway Airport to Cancún

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Cancún?
With an average price of $574 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Cancún with. Instead, for the lowest price, our data suggests flying with United Airlines, where a return flight costs $490 on average.
What is the cheapest Southwest flight from Chicago Midway Airport to Cancún?
In the last 3 days, the lowest price for a flight with Southwest from Chicago Midway Airport to Cancún was $265 for a return flight and $124 for a one-way flight.
Does Southwest fly direct to Cancún from Chicago Midway Airport?
Yes, Southwest does offer direct flights for the route, with around 5 flights per week.
What’s the cheapest day of the week to fly from Chicago Midway Airport to Cancún with Southwest?
On average, the cheapest day of the week to fly from Chicago Midway Airport to Cancún with Southwest is Monday, when prices are around $109. The most expensive day is generally Tuesday, where the average price is around $336.
What’s the cheapest month to fly from Chicago Midway Airport to Cancún with Southwest?
The cheapest month for Southwest flights to Cancún from Chicago Midway Airport is generally July, where plane tickets cost $123 on average. If possible, try to avoid the most expensive months of May and December, where tickets cost $426 and $447 respectively.

8.0

Very good4,238 verified ratings

7.5Entertainment

7.0Food

8.0Comfort

8.6Crew

8.1Boarding

Pros +

Cons -

Show reviews that mention

6.0 Okay

Thomas, Oct 2025

DAL-SAT

Late again.

6.0 Okay

Thomas, Oct 2025

CMH-DAL

Just the usual delays

2.0 Poor

TODD, Oct 2025

CMH-MDW

2.5 hours late but no one said why.

10.0 Wonderful

Aleksandar, Oct 2025

OAK-SAN

On time, and it was not full flight

4.0 Mediocre

Annette, Oct 2025

LGA-MCI

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

10.0 Wonderful

Gerald, Oct 2025

SJC-PDX

Boarding quick & efficient. Crew was friendly. Arrived early

6.0 Okay

Hung, Oct 2025

PHX-ABQ

mandatory demand customer to check their carry on because not enough people check bags.

8.0 Very good

Annette, Oct 2025

MCI-LGA

Good non stop is always good

10.0 Wonderful

Gabriel, Sep 2025

DEN-SMF

Connecting flight is on time and boarding was a breeze!

10.0 Wonderful

Gabriel, Sep 2025

LGA-DEN

Easy boarding process. No delays!

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

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Cabin class types available on flights to Cancún

First Class flights from Chicago Midway Airport to Cancún

Business Class flights from Chicago Midway Airport to Cancún

Prem Econ Class flights from Chicago Midway Airport to Cancún

Economy Class flights from Chicago Midway Airport to Cancún

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MDW - CUN

$115 Find Cheap Southwest Flights from Chicago Midway Airport to Cancún

Search hundreds of travel sites at once for deals on Southwest flights from Chicago Midway Airport to Cancún

Cheap Southwest Flight Deals from Chicago Midway Airport to Cancún

Recent round-trip Southwest flight deals from Chicago Midway Airport to Cancún

Recent one-way Southwest flight deals from Chicago Midway Airport to Cancún

Recent last minute Southwest flight deals from Chicago Midway Airport to Cancún

Recent direct Southwest flight deals from Chicago Midway Airport to Cancún

Good to know

When to Book Flights with Southwest from Chicago Midway Airport to Cancún

FAQs for flying to Cancún with Southwest

Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Cancún?

What is the cheapest Southwest flight from Chicago Midway Airport to Cancún?

Does Southwest fly direct to Cancún from Chicago Midway Airport?

What’s the cheapest day of the week to fly from Chicago Midway Airport to Cancún with Southwest?

What’s the cheapest month to fly from Chicago Midway Airport to Cancún with Southwest?

Southwest Customer Reviews

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

Cabin class types available on flights to Cancún

Cabin classes available on flights to Chicago Midway Airport. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Cancún with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Find deals for your return flight

Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.