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Cheap flights from Chicago Midway Airport to Cancún from $119

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 10/27. 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

Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$261Southwest
Find Deal
Sun, Nov 16 - Wed, Nov 19
Southwest Logo
3:40 pm - 8:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$266Southwest
Find Deal
Sat, Nov 15 - Wed, Nov 19
Aeromexico Logo
6:00 am - 3:33 pmMDW-CUN
8h 33m1 stop
Aeromexico Logo
4:29 pm - 10:16 pmCUN-MDW
6h 47m1 stop
$303Aeromexico
Find Deal
Sun, Dec 14 - Sat, Dec 20
Multiple Airlines Logo
5:20 pm - 8:47 amMDW-CUN
15h 27m1 stop
Multiple Airlines Logo
11:16 am - 11:20 pmCUN-MDW
12h 04m1 stop
$313Multiple Airlines
Find Deal
Thu, Oct 23 - Mon, Oct 27
Aeromexico Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
Aeromexico Logo
8:00 am - 11:32 pmCUN-MDW
16h 32m1 stop
$319Aeromexico
Find Deal
Fri, Nov 28 - Wed, Dec 3
Multiple Airlines Logo
3:27 pm - 9:10 amMDW-CUN
16h 43m1 stop
Multiple Airlines Logo
12:16 pm - 5:59 pmCUN-MDW
6h 43m1 stop
$324Multiple Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
10:35 am - 9:10 pmMDW-CUN
9h 35m1 stop
Delta Logo
4:25 pm - 9:46 pmCUN-MDW
6h 21m1 stop
$326Delta
Find Deal
Sat, Jan 17 - Sat, Jan 24
Delta Logo
10:35 am - 9:10 pmMDW-CUN
9h 35m1 stop
Delta Logo
12:05 pm - 9:46 pmCUN-MDW
10h 41m2 stops
$330Delta
Find Deal
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
12:28 pm - 2:31 pmMDW-CUN
26h 03m1 stop
Frontier Logo
4:14 pm - 9:31 amCUN-MDW
17h 17m1 stop
$335Frontier
Find Deal
Fri, Oct 10 - Sun, Oct 12
Frontier Logo
6:15 am - 12:31 pmMDW-CUN
6h 16m1 stop
Frontier Logo
11:16 am - 11:20 pmCUN-MDW
12h 04m1 stop
$341Frontier
Find Deal
Sat, Oct 25 - Mon, Oct 27

Southwest flights from Chicago Midway Airport to Cancún

Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets
Southwest
Nov 16
MDW10:40 amChicago Midway
3h 45m
CUN3:25 pmCancun
Nov 19
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$261
Find similar
Southwest
Nov 15
MDW3:40 pmChicago Midway
3h 45m
CUN8:25 pmCancun
Nov 19
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$266
Find similar
Southwest
Nov 15
MDW3:40 pmChicago Midway
3h 45m
CUN8:25 pmCancun
Nov 20
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$271
Find similar

Aeromexico flights from Chicago Midway Airport to Cancún

Our best Aeromexico deals on Chicago Midway Airport to Cancún flight tickets
Aeromexico
Dec 14
MDW6:00 amChicago Midway
8h 33m
1 stop
CUN3:33 pmCancun
Dec 20
CUN4:29 pmCancun
6h 47m
1 stop
MDW10:16 pmChicago Midway
$303
Find similar
Aeromexico
Nov 28
MDW6:00 amChicago Midway
14h 20m
1 stop
CUN9:20 pmCancun
Dec 3
CUN8:00 amCancun
16h 32m
1 stop
MDW11:32 pmChicago Midway
$319
Find similar
Aeromexico
Sep 30
MDW12:43 pmChicago Midway
7h 32m
1 stop
CUN8:15 pmCancun
Dec 11
CUN3:07 pmCancun
9h 25m
1 stop
MDW11:32 pmChicago Midway
$328
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Cancún that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 17, 2025.
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

Sun 11/16

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

Wed 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$261

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Wed 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$266

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 12/14

6:00 am-3:33 pm

1 stop8h 33m

Cancun

Sat 12/20

4:29 pm-10:16 pm

1 stop6h 47m

$303

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 10/23

5:20 pm-8:47 am

1 stop15h 27m

Cancun

Mon 10/27

11:16 am-11:20 pm

1 stop12h 04m

$313

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 11/28

6:00 am-9:20 pm

1 stop14h 20m

Cancun

Wed 12/3

8:00 am-11:32 pm

1 stop16h 32m

$319

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 11/14

3:27 pm-9:10 am

1 stop16h 43m

Cancun

Mon 11/17

12:16 pm-5:59 pm

1 stop6h 43m

$324

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Sat 1/24

4:25 pm-9:46 pm

1 stop6h 21m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Sat 1/24

12:05 pm-9:46 pm

2 stops10h 41m

$330

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 10/10

12:28 pm-2:31 pm

1 stop26h 03m

Cancun

Sun 10/12

4:14 pm-9:31 am

1 stop17h 17m

$335

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/25

6:15 am-12:31 pm

1 stop6h 16m

Cancun

Mon 10/27

11:16 am-11:20 pm

1 stop12h 04m

$341

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

The cheapest day to depart from Chicago Midway Airport to Cancún is on a Monday when prices can be found for as low as $395. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $532. 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 evening. Flights from Chicago Midway Airport to Cancún during this time can be as low as $405. Flights to Cancún are more costly at noon, with an average ticket price of $713. 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 $585 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 $425 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 35m

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 $386.
The fastest flight from Chicago Midway Airport to Cancún takes 3h 35m
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 35m 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
United AirlinesPriceFrom $161Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
AeromexicoPriceFrom $312Free CancellationRating
7.4
1,696 reviews
Search Aeromexico flights
SouthwestPriceFrom $345Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
FrontierPriceFrom $362Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
DeltaPriceFrom $380Free CancellationRating
7.9
7,961 reviews
Search Delta flights
VolarisPriceFrom $486Free CancellationRating
6.6
1,154 reviews
Search Volaris flights
LATAM AirlinesPriceFrom $3,369Free CancellationRating
7.5
1,849 reviews
Search LATAM Airlines flights

  • Southwest Flights From Chicago Midway Airport to Cancún

    Southwest operates around 5 flights from Chicago Midway Airport to Cancún every week. The average price of these flights found in the last 72 hours has been $577, 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 4,242 reviews.

Traveling to a place near Cancún?

Book flights to Cancún if you plan to visit one of these locations
Playa del Carmen
Isla Mujeres
Holbox
Puerto Morelos
Akumal
Puerto Aventuras
Valladolid
Punta Sam

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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