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Cheap flights from Chicago Midway Airport to Cancún from $116

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.
1 adult
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 57m1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$291Frontier
Sat, Feb 28 - Sat, Mar 7
Frontier Logo
6:25 am - 3:22 pm
MDW
-
CUN
7h 57m1 stop
Frontier Logo
3:07 pm - 6:13 pm
CUN
-
MDW
4h 06mnonstop
$293Frontier
Sat, Feb 28 - Sat, Mar 7
Aeromexico Logo
12:46 pm - 9:11 pm
MDW
-
CUN
7h 25m1 stop
Aeromexico Logo
8:00 am - 3:21 pm
CUN
-
MDW
8h 21m1 stop
$296Aeromexico
Tue, Feb 10 - Sat, Feb 14
Volaris Logo
7:54 pm - 9:48 am
MDW
-
CUN
13h 54m1 stop
Volaris Logo
10:39 am - 6:34 pm
CUN
-
MDW
7h 55m1 stop
$299Volaris
Sun, Mar 15 - Fri, Mar 20
Volaris Logo
7:54 pm - 9:48 am
MDW
-
CUN
13h 54m1 stop
Volaris Logo
10:39 am - 6:34 pm
CUN
-
MDW
7h 55m1 stop
$300Volaris
Sun, Mar 15 - Fri, Mar 20
Frontier Logo
1:20 pm - 1:47 pm
MDW
-
CUN
23h 27m1 stop
Frontier Logo
4:30 pm - 11:45 am
CUN
-
MDW
20h 15m1 stop
$302Frontier
Wed, Jan 28 - Sat, Jan 31
Multiple Airlines Logo
9:22 pm - 9:18 am
MDW
-
CUN
10h 56m1 stop
Multiple Airlines Logo
10:13 am - 2:26 pm
CUN
-
MDW
29h 13m1 stop
$304Multiple Airlines
Mon, Feb 16 - Wed, Feb 25
Frontier Logo
6:00 am - 4:36 pm
MDW
-
CUN
9h 36m1 stop
Frontier Logo
10:16 am - 9:39 pm
CUN
-
MDW
12h 23m1 stop
$306Frontier
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
7:30 am - 9:18 am
MDW
-
CUN
24h 48m1 stop
Multiple Airlines Logo
11:48 am - 2:29 pm
CUN
-
MDW
27h 41m1 stop
$308Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
1:00 pm - 9:13 am
MDW
-
CUN
19h 13m1 stop
Multiple Airlines Logo
2:49 pm - 10:34 pm
CUN
-
MDW
8h 45m1 stop
$310Multiple Airlines
Sun, Feb 8 - Thu, Feb 12

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
$293
Find similar
Frontier
Jan 28
MDW1:20 pmChicago Midway
23h 27m
1 stop
CUN1:47 pmCancun
Jan 31
CUN4:30 pmCancun
20h 15m
1 stop
MDW11:45 amChicago Midway
$302
Find similar
Frontier
Feb 21
MDW6:00 amChicago Midway
9h 36m
1 stop
CUN4:36 pmCancun
Feb 28
CUN10:16 amCancun
12h 23m
1 stop
MDW9:39 pmChicago Midway
$306
Find similar

Delta flights from Chicago Midway Airport to Cancún

Our best Delta deals on Chicago Midway Airport to Cancún flight tickets
Delta
Jan 8
MDW6:45 amChicago Midway
7h 45m
1 stop
CUN3:30 pmCancun
Jan 15
CUN1:40 pmCancun
9h 27m
1 stop
MDW10:07 pmChicago Midway
$325
Find similar
Delta
Feb 7
MDW6:25 amChicago Midway
12h 37m
2 stops
CUN8:02 pmCancun
Feb 14
CUN8:00 amCancun
8h 21m
1 stop
MDW3:21 pmChicago Midway
$333
Find similar
Delta
Mar 19
MDW9:35 amChicago Midway
10h 45m
2 stops
CUN8:20 pmCancun
Mar 27
CUN8:00 amCancun
8h 55m
1 stop
MDW4:55 pmChicago Midway
$338
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 December 28, 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

Sat 2/28

6:25 am-3:22 pm

1 stop7h 57m

Cancun

Sat 3/7

3:07 pm-6:13 pm

Nonstop4h 06m

$291

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

$293

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 2/10

12:46 pm-9:11 pm

1 stop7h 25m

Cancun

Sat 2/14

8:00 am-3:21 pm

1 stop8h 21m

$296

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/15

7:54 pm-9:48 am

1 stop13h 54m

Cancun

Fri 3/20

10:39 am-6:34 pm

1 stop7h 55m

$299

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/15

7:54 pm-9:48 am

1 stop13h 54m

Cancun

Fri 3/20

10:39 am-6:34 pm

1 stop7h 55m

$300

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 1/28

1:20 pm-1:47 pm

1 stop23h 27m

Cancun

Sat 1/31

4:30 pm-11:45 am

1 stop20h 15m

$302

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/16

9:22 pm-9:18 am

1 stop10h 56m

Cancun

Wed 2/25

10:13 am-2:26 pm

1 stop29h 13m

$304

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/21

6:00 am-4:36 pm

1 stop9h 36m

Cancun

Sat 2/28

10:16 am-9:39 pm

1 stop12h 23m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 2/19

7:30 am-9:18 am

1 stop24h 48m

Cancun

Sun 2/22

11:48 am-2:29 pm

1 stop27h 41m

$308

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 2/8

1:00 pm-9:13 am

1 stop19h 13m

Cancun

Thu 2/12

2:49 pm-10:34 pm

1 stop8h 45m

$310

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 $414. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $514. 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 morning. Flights from Chicago Midway Airport to Cancún during this time can be as low as $465. 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 $549 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 $385 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

$165

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 $165. The best round-trip flight deal from Chicago Midway Airport to Cancún found on momondo in the last 72 hours is $433.
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
United AirlinesPriceFrom $161Free CancellationRating
7.4
9,114 reviews
Search United Airlines flights
AeromexicoPriceFrom $309Free CancellationRating
7.4
1,622 reviews
Search Aeromexico flights
SouthwestPriceFrom $312Free CancellationRating
8.0
4,256 reviews
Search Southwest flights
FrontierPriceFrom $362Free CancellationRating
5.7
3,064 reviews
Search Frontier flights
DeltaPriceFrom $375Free CancellationRating
7.9
8,017 reviews
Search Delta flights
American AirlinesPriceFrom $506Free CancellationRating
7.2
11,070 reviews
Search American 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 $546, but momondo users have found Southwest deals from Chicago Midway Airport to Cancún from as low as $312 round-trip. Southwest has been scored 8.0/10 in 4,256 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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