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Cheap flights from Chicago Midway Airport to Cancún from $115

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 12/1. 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

Enter your travel dates to find the best prices.
Southwest Logo
8:40 am - 1:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
$252Southwest
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mar., nov. 18 - vie., nov. 21
Southwest Logo
8:40 am - 1:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
$257Southwest
Find Deal
lun., nov. 17 - vie., nov. 21
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
4:25 pm - 7:10 pmCUN-MDW
3h 45mnonstop
$262Southwest
Find Deal
dom., nov. 16 - sáb., nov. 22
Southwest Logo
8:40 am - 1:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
4:25 pm - 7:10 pmCUN-MDW
3h 45mnonstop
$267Southwest
Find Deal
lun., nov. 17 - sáb., nov. 22
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
11:55 am - 2:45 pmCUN-MDW
3h 50mnonstop
$272Southwest
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dom., nov. 9 - sáb., nov. 15
Delta Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
Delta Logo
8:00 am - 4:38 pmCUN-MDW
9h 38m1 stop
$317Delta
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dom., nov. 9 - mar., nov. 18
Aeromexico Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
Aeromexico Logo
7:50 am - 11:47 pmCUN-MDW
16h 57m2 stops
$318Aeromexico
Find Deal
vie., dic. 5 - vie., dic. 12
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
dom., ene. 11 - vie., ene. 16
Multiple Airlines Logo
11:36 am - 9:13 amMDW-CUN
20h 37m1 stop
Multiple Airlines Logo
12:16 pm - 11:38 amCUN-MDW
24h 22m2 stops
$340Multiple Airlines
Find Deal
sáb., nov. 15 - lun., nov. 17
Aeromexico Logo
10:47 am - 9:20 pmMDW-CUN
9h 33m1 stop
Aeromexico Logo
8:00 am - 4:38 pmCUN-MDW
9h 38m1 stop
$341Aeromexico
Find Deal
mié., nov. 12 - mar., nov. 18

Aeromexico flights from Chicago Midway Airport to Cancún

Our best Aeromexico deals on Chicago Midway Airport to Cancún flight tickets
Aeromexico
Dec 5
MDW6:00 amChicago Midway
14h 20m
1 stop
CUN9:20 pmCancun
Dec 12
CUN7:50 amCancun
16h 57m
2 stops
MDW11:47 pmChicago Midway
$318
Find similar
Aeromexico
Nov 12
MDW10:47 amChicago Midway
9h 33m
1 stop
CUN9:20 pmCancun
Nov 18
CUN8:00 amCancun
9h 38m
1 stop
MDW4:38 pmChicago Midway
$341
Find similar
Aeromexico
Mar 10
MDW6:00 amChicago Midway
14h 00m
2 stops
CUN8:00 pmCancun
Mar 11
CUN11:10 amCancun
10h 36m
1 stop
MDW9:46 pmChicago Midway
$343
Find similar

Southwest flights from Chicago Midway Airport to Cancún

Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets
Southwest
Nov 18
MDW8:40 amChicago Midway
3h 45m
CUN1:25 pmCancun
Nov 21
CUN2:15 pmCancun
3h 45m
MDW5:00 pmChicago Midway
$252
Find similar
Southwest
Nov 17
MDW8:40 amChicago Midway
3h 45m
CUN1:25 pmCancun
Nov 21
CUN2:15 pmCancun
3h 45m
MDW5:00 pmChicago Midway
$257
Find similar
Southwest
Nov 16
MDW10:40 amChicago Midway
3h 45m
CUN3:25 pmCancun
Nov 22
CUN4:25 pmCancun
3h 45m
MDW7:10 pmChicago Midway
$262
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 octubre 23, 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

mar. 11/18

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

vie. 11/21

2:15 pm-5:00 pm

Nonstop3h 45m

$252

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 11/17

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

vie. 11/21

2:15 pm-5:00 pm

Nonstop3h 45m

$257

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 11/16

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

sáb. 11/22

4:25 pm-7:10 pm

Nonstop3h 45m

$262

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 11/17

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

sáb. 11/22

4:25 pm-7:10 pm

Nonstop3h 45m

$267

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 11/9

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

sáb. 11/15

11:55 am-2:45 pm

Nonstop3h 50m

$272

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 11/9

6:00 am-9:20 pm

1 stop14h 20m

Cancun

mar. 11/18

8:00 am-4:38 pm

1 stop9h 38m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

vie. 12/5

6:00 am-9:20 pm

1 stop14h 20m

Cancun

vie. 12/12

7:50 am-11:47 pm

2 stops16h 57m

$318

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 1/11

10:35 am-9:10 pm

1 stop9h 35m

Cancun

vie. 1/16

4:25 pm-9:46 pm

1 stop6h 21m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 11/15

11:36 am-9:13 am

1 stop20h 37m

Cancun

lun. 11/17

12:16 pm-11:38 am

2 stops24h 22m

$340

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mié. 11/12

10:47 am-9:20 pm

1 stop9h 33m

Cancun

mar. 11/18

8:00 am-4:38 pm

1 stop9h 38m

$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 $401. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $525. 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 $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 $571 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

$194

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 $194. The best round-trip flight deal from Chicago Midway Airport to Cancún found on momondo in the last 72 hours is $271.
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 40m 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
8,992 reviews
Search United Airlines flights
AeromexicoPriceFrom $312Free CancellationRating
7.4
1,681 reviews
Search Aeromexico flights
SouthwestPriceFrom $345Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
FrontierPriceFrom $362Free CancellationRating
5.8
3,127 reviews
Search Frontier flights
DeltaPriceFrom $380Free CancellationRating
7.9
7,981 reviews
Search Delta flights
VolarisPriceFrom $486Free CancellationRating
6.7
1,152 reviews
Search Volaris flights
LATAM AirlinesPriceFrom $3,369Free CancellationRating
7.5
1,871 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 $574, 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 4,236 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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