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Cheap flights from Chicago Midway Airport to Cancún from $125

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 8/23. 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
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$271Southwest
Find Deal
Tue, Oct 28 - Tue, Nov 4
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$276Southwest
Find Deal
Sun, Nov 16 - Wed, Nov 19
Aeromexico Logo
6:00 am - 2:10 pmMDW-CUN
8h 10m1 stop
Aeromexico Logo
8:00 am - 3:26 pmCUN-MDW
7h 26m1 stop
$303Aeromexico
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
10:35 am - 9:02 pmMDW-CUN
9h 27m1 stop
Delta Logo
4:24 pm - 9:44 pmCUN-MDW
6h 20m1 stop
$326Delta
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Wed, Nov 12 - Thu, Nov 20
Delta Logo
9:35 am - 8:15 pmMDW-CUN
10h 40m2 stops
Delta Logo
8:00 am - 9:36 pmCUN-MDW
13h 36m1 stop
$330Delta
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Sat, Sep 13 - Fri, Sep 19
Logo
5:28 pm - 8:04 amMDW-CUN
14h 36m1 stop
Logo
9:09 am - 4:20 pmCUN-MDW
7h 11m1 stop
$332
Find Deal
Fri, Oct 17 - Fri, Oct 24
Logo
8:19 am - 8:04 amMDW-CUN
23h 45m1 stop
Logo
9:09 am - 4:20 pmCUN-MDW
7h 11m1 stop
$342
Find Deal
Mon, Oct 6 - Fri, Oct 10
Aeromexico Logo
12:43 pm - 8:15 pmMDW-CUN
7h 32m1 stop
Aeromexico Logo
8:00 am - 9:36 pmCUN-MDW
13h 36m1 stop
$347Aeromexico
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Thu, Sep 11 - Wed, Sep 17
Frontier Logo
6:20 am - 12:31 pmMDW-CUN
6h 11m1 stop
Frontier Logo
11:16 am - 11:20 pmCUN-MDW
12h 04m1 stop
$360Frontier
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Thu, Oct 16 - Mon, Oct 27
Frontier Logo
6:20 am - 12:40 pmMDW-CUN
6h 20m1 stop
Frontier Logo
1:55 pm - 11:20 pmCUN-MDW
9h 25m1 stop
$363Frontier
Find Deal
Thu, Sep 4 - Sun, Sep 7

Southwest flights from Chicago Midway Airport to Cancún

Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets
Southwest
Oct 28
MDW9:40 amChicago Midway
3h 35m
CUN1:15 pmCancun
Nov 4
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$271
Find similar
Southwest
Nov 16
MDW10:40 amChicago Midway
3h 45m
CUN3:25 pmCancun
Nov 19
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$276
Find similar
Southwest
Sep 14
MDW10:35 amChicago Midway
3h 35m
CUN2:10 pmCancun
Sep 18
CUN3:10 pmCancun
3h 40m
MDW6:50 pmChicago Midway
$281
Find similar

Aeromexico flights from Chicago Midway Airport to Cancún

Our best Aeromexico deals on Chicago Midway Airport to Cancún flight tickets
Aeromexico
Sep 6
MDW6:00 amChicago Midway
8h 10m
1 stop
CUN2:10 pmCancun
Sep 13
CUN8:00 amCancun
7h 26m
1 stop
MDW3:26 pmChicago Midway
$303
Find similar
Aeromexico
Sep 11
MDW12:43 pmChicago Midway
7h 32m
1 stop
CUN8:15 pmCancun
Sep 17
CUN8:00 amCancun
13h 36m
1 stop
MDW9:36 pmChicago Midway
$347
Find similar
Aeromexico
Oct 2
MDW6:00 amChicago Midway
11h 45m
2 stops
CUN5:45 pmCancun
Oct 9
CUN3:20 pmCancun
6h 54m
1 stop
MDW10:14 pmChicago Midway
$348
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 August 19, 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

Tue 10/28

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

Tue 11/4

1:45 pm-4:30 pm

Nonstop3h 45m

$271

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

$276

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

6:00 am-2:10 pm

1 stop8h 10m

Cancun

Sat 9/13

8:00 am-3:26 pm

1 stop7h 26m

$303

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 11/12

10:35 am-9:02 pm

1 stop9h 27m

Cancun

Thu 11/20

4:24 pm-9:44 pm

1 stop6h 20m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/13

9:35 am-8:15 pm

2 stops10h 40m

Cancun

Fri 9/19

8:00 am-9:36 pm

1 stop13h 36m

$330

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 10/17

5:28 pm-8:04 am

1 stop14h 36m

Cancun

Fri 10/24

9:09 am-4:20 pm

1 stop7h 11m

$332

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 10/6

8:19 am-8:04 am

1 stop23h 45m

Cancun

Fri 10/10

9:09 am-4:20 pm

1 stop7h 11m

$342

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 9/11

12:43 pm-8:15 pm

1 stop7h 32m

Cancun

Wed 9/17

8:00 am-9:36 pm

1 stop13h 36m

$347

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 10/16

6:20 am-12:31 pm

1 stop6h 11m

Cancun

Mon 10/27

11:16 am-11:20 pm

1 stop12h 04m

$360

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 9/4

6:20 am-12:40 pm

1 stop6h 20m

Cancun

Sun 9/7

1:55 pm-11:20 pm

1 stop9h 25m

$363

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 $386. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $534. 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 $582 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 $405 on momondo.

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

There are 1 cabin classes 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

$125

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 $125. 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 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
8,922 reviews
Search United Airlines flights
FrontierPriceFrom $198Free CancellationRating
5.8
3,211 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $241Free CancellationRating
6.3
8,037 reviews
Search Spirit Airlines flights
AeromexicoPriceFrom $312Free CancellationRating
7.5
1,718 reviews
Search Aeromexico flights
SouthwestPriceFrom $345Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $380Free CancellationRating
7.9
7,981 reviews
Search Delta flights
VolarisPriceFrom $486Free CancellationRating
6.6
1,161 reviews
Search Volaris flights
LATAM AirlinesPriceFrom $3,369Free CancellationRating
7.5
1,844 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 4,246 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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