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Cheap flights from Chicago Midway Airport to Cancún from $113

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 2/25. 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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Find the cheapest flights from Chicago Midway Airport to Cancún

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Cancún that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Cancún.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Cancún? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Cancún, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Cancún

Find recent round-trip train or bus tickets from Chicago Midway Airport to Cancún.

All round-trip flight deals to Cancún

The cheapest plane tickets to Cancún found on KAYAK recently.
7:15 am - 9:01 amMDW-CUN
24h 46m1 stop
2:25 pm - 11:29 pmCUN-MDW
10h 04m1 stop
$274Frontier
Find Deal
Sat, Feb 1 - Sat, Feb 8
3:00 pm - 7:45 pmMDW-CUN
3h 45mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$278Southwest
Find Deal
Sat, Dec 7 - Wed, Dec 11
7:15 am - 9:01 amMDW-CUN
24h 46m1 stop
2:25 pm - 11:29 pmCUN-MDW
10h 04m1 stop
$279Frontier
Find Deal
Sat, Feb 1 - Sat, Feb 8
10:41 am - 9:03 pmMDW-CUN
9h 22m1 stop
4:25 pm - 10:06 pmCUN-MDW
6h 41m1 stop
$343Aeromexico
Find Deal
Tue, Dec 3 - Sat, Dec 7
6:00 am - 3:15 pmMDW-CUN
8h 15m1 stop
8:10 am - 4:12 pmCUN-MDW
9h 02m1 stop
$345Aeromexico
Find Deal
Tue, Dec 10 - Wed, Dec 18
1:35 pm - 9:00 pmMDW-CUN
6h 25m1 stop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$352Southwest
Find Deal
Fri, Dec 13 - Tue, Dec 17
6:00 am - 12:34 pmMDW-CUN
5h 34m1 stop
8:10 am - 5:01 pmCUN-MDW
9h 51m2 stops
$387Delta
Find Deal
Sat, Dec 7 - Tue, Dec 10
6:00 am - 4:25 pmMDW-CUN
9h 25m1 stop
3:03 pm - 10:20 pmCUN-MDW
8h 17m1 stop
$402Delta
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Sun, Jan 19 - Thu, Jan 23
8:39 pm - 9:04 amMDW-CUN
12h 25m1 stop
7:57 am - 7:14 pmCUN-MDW
11h 17m1 stop
$420Volaris
Find Deal
Wed, Mar 26 - Tue, Apr 1
10:14 pm - 9:37 amMDW-CUN
11h 23m1 stop
7:57 am - 7:14 pmCUN-MDW
11h 17m1 stop
$424Volaris
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Sun, Apr 6 - Tue, Apr 15
10:59 am - 10:50 amMDW-CUN
22h 51m1 stop
$113Frontier
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Tue, Feb 25
7:10 am - 4:05 pmMDW-CUN
7h 55m1 stop
$114Southwest
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Mon, Feb 24
7:59 pm - 10:50 amMDW-CUN
13h 51m1 stop
$115Frontier
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Sun, Feb 23
10:35 pm - 2:00 pmMDW-CUN
14h 25m1 stop
$124Southwest
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Sun, Feb 16
12:43 pm - 9:03 pmMDW-CUN
7h 20m1 stop
$174Aeromexico
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Tue, Nov 19
6:00 am - 11:28 pmMDW-CUN
16h 28m2 stops
$187Aeromexico
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Sun, Mar 2
6:00 am - 6:36 pmMDW-CUN
12h 36m2 stops
$189Delta
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Mon, Mar 10
7:55 pm - 1:03 pmMDW-CUN
16h 08m2 stops
$207Volaris
Find Deal
Wed, Jan 15
8:39 pm - 9:04 amMDW-CUN
12h 25m1 stop
$223Volaris
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Mon, Mar 24
9:30 am - 8:05 pmMDW-CUN
10h 35m2 stops
$239Delta
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Thu, Mar 13
3:00 pm - 7:45 pmMDW-CUN
3h 45mnonstop
8:10 am - 10:50 amCUN-MDW
3h 40mnonstop
$288Southwest
Find Deal
Sat, Nov 16 - Sat, Nov 23
6:00 am - 3:15 pmMDW-CUN
8h 15m1 stop
12:03 pm - 7:20 amCUN-MDW
20h 17m1 stop
Sun, Nov 17 - Fri, Nov 22
6:00 am - 12:25 pmMDW-CUN
5h 25m1 stop
12:10 pm - 6:02 pmCUN-MDW
6h 52m1 stop
$382Aeromexico
Find Deal
Sun, Nov 17 - Mon, Nov 25
6:00 am - 3:15 pmMDW-CUN
8h 15m1 stop
8:10 am - 2:34 pmCUN-MDW
7h 24m1 stop
$392Delta
Find Deal
Sat, Nov 16 - Wed, Nov 20
6:00 am - 1:46 pmMDW-CUN
6h 46m1 stop
8:10 am - 5:02 pmCUN-MDW
9h 52m2 stops
$397Delta
Find Deal
Sun, Nov 17 - Mon, Nov 25
6:00 am - 9:59 pmMDW-CUN
14h 59m2 stops
8:10 am - 2:34 pmCUN-MDW
7h 24m1 stop
$437Aeromexico
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Sun, Nov 17 - Tue, Nov 19
10:41 pm - 12:46 pmMDW-CUN
13h 05m1 stop
7:39 am - 6:40 pmCUN-MDW
12h 01m1 stop
$787Volaris
Find Deal
Sat, Nov 16 - Wed, Nov 20
10:41 pm - 12:46 pmMDW-CUN
13h 05m1 stop
7:39 am - 6:40 pmCUN-MDW
12h 01m1 stop
$822Volaris
Find Deal
Mon, Nov 18 - Fri, Nov 22
9:30 am - 8:18 pmMDW-CUN
33h 48m2 stops
7:40 pm - 6:02 pmCUN-MDW
47h 22m2 stops
$1,844WestJet
Find Deal
Sun, Nov 17 - Sat, Nov 23
12:43 pm - 8:18 pmMDW-CUN
30h 35m2 stops
7:40 pm - 9:32 amCUN-MDW
38h 52m2 stops
$1,976WestJet
Find Deal
Sun, Nov 17 - Thu, Nov 21
3:00 pm - 7:45 pmMDW-CUN
3h 45mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$278Southwest
Find Deal
Sat, Dec 7 - Wed, Dec 11
3:00 pm - 7:45 pmMDW-CUN
3h 45mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$323Southwest
Find Deal
Sat, Dec 14 - Thu, Dec 19
3:00 pm - 7:45 pmMDW-CUN
3h 45mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$333Southwest
Find Deal
Sat, Dec 7 - Tue, Dec 10
3:00 pm - 7:45 pmMDW-CUN
3h 45mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$343Southwest
Find Deal
Sat, Dec 14 - Wed, Dec 18
9:25 am - 2:15 pmMDW-CUN
3h 50mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$348Southwest
Find Deal
Mon, Nov 18 - Wed, Nov 20
3:00 pm - 7:45 pmMDW-CUN
3h 45mnonstop
8:10 am - 10:50 amCUN-MDW
3h 40mnonstop
$358Southwest
Find Deal
Sat, Dec 7 - Sat, Dec 14
10:15 am - 3:05 pmMDW-CUN
3h 50mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$363Southwest
Find Deal
Sun, Dec 15 - Thu, Dec 19
9:25 am - 2:15 pmMDW-CUN
3h 50mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$368Southwest
Find Deal
Mon, Nov 18 - Thu, Nov 21
9:25 am - 2:15 pmMDW-CUN
3h 50mnonstop
7:10 am - 9:45 amCUN-MDW
3h 35mnonstop
$383Southwest
Find Deal
Sun, Nov 17 - Tue, Nov 19
9:25 am - 2:15 pmMDW-CUN
3h 50mnonstop
8:10 am - 10:50 amCUN-MDW
3h 40mnonstop
$393Southwest
Find Deal
Sun, Nov 17 - Sat, Nov 23

Frontier flights from Chicago Midway Airport to Cancún

Our best Frontier deals on Chicago Midway Airport to Cancún flight tickets
Frontier
Feb 1
MDW7:15 amChicago Midway
24h 46m
1 stop
CUN9:01 amCancun
Feb 8
CUN2:25 pmCancun
10h 04m
1 stop
MDW11:29 pmChicago Midway
Frontier
Feb 1
MDW7:15 amChicago Midway
24h 46m
1 stop
CUN9:01 amCancun
Feb 8
CUN2:25 pmCancun
10h 04m
1 stop
MDW11:29 pmChicago Midway
Frontier
Feb 25
MDW9:44 pmChicago Midway
10h 03m
1 stop
CUN8:47 amCancun
Feb 28
CUN12:10 pmCancun
8h 03m
1 stop
MDW7:13 pmChicago Midway

Southwest flights from Chicago Midway Airport to Cancún

Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets
Southwest
Dec 7
MDW3:00 pmChicago Midway
3h 45m
CUN7:45 pmCancun
Dec 11
CUN7:10 amCancun
3h 35m
MDW9:45 amChicago Midway
Southwest
Dec 13
MDW1:35 pmChicago Midway
6h 25m
1 stop
CUN9:00 pmCancun
Dec 17
CUN7:10 amCancun
3h 35m
MDW9:45 amChicago Midway
Southwest
Dec 15
MDW10:15 amChicago Midway
3h 50m
CUN3:05 pmCancun
Dec 19
CUN7:10 amCancun
3h 35m
MDW9:45 amChicago Midway

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 typical price of a round-trip flight between Chicago Midway Airport and Cancún?

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

January. The cheapest time of year to fly to Cancún from Chicago Midway Airport is January. Most expensive is March

What is the cheapest day to depart Chicago Midway Airport for Cancún?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Saturday

When is the cheapest time to fly from Chicago Midway Airport to Cancún?

At noon. Chicago Midway Airport to Cancún flights are approximately 75% more expensive in the afternoon than at noon

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

Frontier. Frontier, United Airlines, and Spirit Airlines are the most popular carriers operating from Chicago Midway Airport to Cancún

How far in advance should you book Chicago Midway Airport to Cancún flights?

33 days before. The cheapest time to buy a flight from Chicago Midway Airport to Cancún is approximately 33 days to departure

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

As of November 2024, 6 flights take off from Chicago Midway Airport and land in Cancún each week. The most common flight departure day for this route is Sunday, with 17% of weekly flights taking off on this day.

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

You could potentially save up to 12% on your flight if you consider stops on a Chicago Midway Airport to Cancún flight.

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

$113

Fastest flight time

3h 45m

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 $113. The best round-trip flight deal from Chicago Midway Airport to Cancún found on momondo in the last 72 hours is $274.
The fastest flight from Chicago Midway Airport to Cancún takes 3h 45m
Direct flights go from Chicago Midway Airport to Cancún every day.
There is 1 airport near Cancún: Cancun (CUN)

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $160Free CancellationRating
6.1
3,551 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $183Free CancellationRating
6.3
8,167 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $311Free CancellationRating
7.4
9,194 reviews
Search United Airlines flights
SouthwestPriceFrom $331Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
DeltaPriceFrom $376Free CancellationRating
8.0
8,788 reviews
Search Delta flights
AeromexicoPriceFrom $399Free CancellationRating
7.5
2,018 reviews
Search Aeromexico 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 $673, but momondo users have found Southwest deals from Chicago Midway Airport to Cancún from as low as $331 round-trip. Southwest has been scored 8.1/10 in 5,045 reviews.


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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