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Cheap flights from Chicago Midway Airport to Cancún from $107

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 2/6. 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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0 bags

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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.
Frontier Logo
6:25 am - 3:22 pm
MDW
-
CUN
7h 57m
1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$254Frontier
Sat, Feb 28 - Sat, Mar 7
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
3:07 pm - 7:13 pm
CUN
-
MDW
4h 06mnonstop
$264Frontier
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:19 pm
CUN
-
MDW
8h 54m
1 stop
$272Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
1:47 pm - 8:54 pm
CUN
-
MDW
7h 07m
1 stop
$276Frontier
Sat, Mar 7 - Tue, Mar 10
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:19 pm
CUN
-
MDW
8h 54m
1 stop
$277Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
11:30 am - 10:21 pm
CUN
-
MDW
10h 51m
1 stop
$278Frontier
Sat, Apr 11 - Thu, Apr 16
Frontier Logo
6:25 am - 3:22 pm
MDW
-
CUN
7h 57m
1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$285Frontier
Sat, Feb 28 - Sat, Mar 7
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
4:09 pm - 7:31 pm
CUN
-
MDW
27h 22m
1 stop
$290Frontier
Sat, Apr 11 - Wed, Apr 15
Southwest Logo
10:35 am - 3:15 pm
MDW
-
CUN
3h 40mnonstop
Southwest Logo
1:40 pm - 4:25 pm
CUN
-
MDW
3h 45mnonstop
$291Southwest
Mon, Feb 23 - Wed, Mar 4
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
3:07 pm - 7:13 pm
CUN
-
MDW
4h 06mnonstop
$293Frontier
Sat, Mar 7 - Sat, Mar 14

Frontier flights from Chicago Midway Airport to Cancún

Our best Frontier deals on Chicago Midway Airport to Cancún flight tickets
Frontier
Feb 28
MDW6:25 amChicago Midway
7h 57m
1 stop
CUN3:22 pmCancun
Mar 7
CUN3:07 pmCancun
4h 06m
MDW6:13 pmChicago Midway
$254
Frontier
Mar 7
MDW9:00 amChicago Midway
4h 02m
CUN2:02 pmCancun
Mar 14
CUN3:07 pmCancun
4h 06m
MDW7:13 pmChicago Midway
$264
Frontier
Mar 7
MDW9:00 amChicago Midway
4h 02m
CUN2:02 pmCancun
Mar 10
CUN1:47 pmCancun
7h 07m
1 stop
MDW8:54 pmChicago Midway
$276

Southwest flights from Chicago Midway Airport to Cancún

Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets
Southwest
Feb 23
MDW10:35 amChicago Midway
3h 40m
CUN3:15 pmCancun
Mar 4
CUN1:40 pmCancun
3h 45m
MDW4:25 pmChicago Midway
$291
Southwest
Mar 6
MDW4:05 pmChicago Midway
3h 40m
CUN8:45 pmCancun
Mar 12
CUN2:05 pmCancun
3h 45m
MDW5:50 pmChicago Midway
$296
Southwest
Mar 12
MDW4:05 pmChicago Midway
3h 40m
CUN7:45 pmCancun
Mar 16
CUN2:05 pmCancun
3h 45m
MDW5:50 pmChicago Midway
$301

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 January 27, 2026.
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

Sat 2/28

6:25 am-3:22 pm

1 stop7h 57m

Cancun

Sat 3/7

3:07 pm-6:13 pm

Nonstop4h 06m

$254

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$264

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/11

8:30 am-12:20 pm

Nonstop3h 50m

Cancun

Sat 4/18

1:25 pm-10:19 pm

1 stop8h 54m

$272

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Tue 3/10

1:47 pm-8:54 pm

1 stop7h 07m

$276

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/11

8:30 am-12:20 pm

Nonstop3h 50m

Cancun

Sat 4/18

1:25 pm-10:19 pm

1 stop8h 54m

$277

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/11

8:30 am-12:20 pm

Nonstop3h 50m

Cancun

Thu 4/16

11:30 am-10:21 pm

1 stop10h 51m

$278

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/28

6:25 am-3:22 pm

1 stop7h 57m

Cancun

Sat 3/7

3:07 pm-6:13 pm

Nonstop4h 06m

$285

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/11

8:30 am-12:20 pm

Nonstop3h 50m

Cancun

Wed 4/15

4:09 pm-7:31 pm

1 stop27h 22m

$290

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/23

10:35 am-3:15 pm

Nonstop3h 40m

Cancun

Wed 3/4

1:40 pm-4:25 pm

Nonstop3h 45m

$291

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

3:07 pm-7:13 pm

Nonstop4h 06m

$293

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 April to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $450.

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 $423. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $508. 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 afternoon. Flights from Chicago Midway Airport to Cancún during this time can be as low as $457. 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 $358 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

$144

Fastest flight time

3h 30m

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 $144. The best round-trip flight deal from Chicago Midway Airport to Cancún found on momondo in the last 72 hours is $441.
The fastest flight from Chicago Midway Airport to Cancún takes 3h 30m
Direct flights go from Chicago Midway Airport to Cancún every day.
There is 1 airport in Cancún. From Chicago Midway Airport there are direct flights to 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 30m 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
SouthwestPriceFrom $295Free CancellationRating
8.0
4,268 reviews
Search Southwest flights
AeromexicoPriceFrom $309Free CancellationRating
7.4
1,589 reviews
Search Aeromexico flights
DeltaPriceFrom $358Free CancellationRating
7.9
8,123 reviews
Search Delta flights
FrontierPriceFrom $362Free CancellationRating
5.7
3,056 reviews
Search Frontier 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 $524, but momondo users have found Southwest deals from Chicago Midway Airport to Cancún from as low as $295 round-trip. Southwest has been scored 8.0/10 in 4,268 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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