Cheap Flight Tickets from Chicago (MDW) to Cancún (CUN), Starting at $175

Good to Know: Cheapest and Fastest MDW - CUN Flights

Useful information for finding best airline tickets from Chicago Midway International to Cancún International on your next trip.

Cheapest Round Trip Flight

$394

AM Aeromexico • 1 stop • 15h 11m

Aug 16 – Aug 22

The cheapest round trip flight from Chicago to Cancún (MDW-CUN-MDW) is currently $394

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Cheapest Direct Flight

$175

WN Southwest Airlines • nonstop • 5h 35m

Aug 16

The cheapest nonstop flight from Chicago to Cancún (MDW-CUN) is currently $175

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Fastest Flight

5h 35m

The fastest nonstop flight from Chicago to Cancún (MDW-CUN) takes 5h 35m

Top Airlines Flying from Chicago to Cancún

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Aeromexico Airline (AM)

Aeromexico

Latest Flight Deals from Chicago (MDW) to Cancún (CUN)

Compare and book low fare round-trip air tickets from Chicago to Cancún. Ideal for travelers with confirmed return itineraries.

Aug 16 - Aug 22, Economy
AM
Chicago → Cancún
15h 11m
10:54 AM - 8:05 PM • 1 stop
AM
Chicago → Cancún
23h 51m
8:05 AM - 10:36 PM • 1 stop
$394
Aeromexico
Aug 16 - Aug 22, Economy
DL
Chicago → Cancún
23h 20m
6:05 AM - 8:05 PM • 1 stop
DL
Chicago → Cancún
17h 8m
8:05 AM - 6:33 PM • 2 stops
$461
Delta Airlines
Aug 16 - Aug 22, Economy
Y4
Chicago → Cancún
20h 33m
9:27 PM - 10:00 AM • 1 stop
F9
Chicago → Cancún
12h 21m
3:06 PM - 10:47 PM • 1 stop
$560
Volaris Airline
Aug 16 - Aug 22, Economy
WN
Chicago → Cancún
15h
6:30 AM - 3:30 PM • 1 stop
WN
Chicago → Cancún
38h 45m
3:30 PM - 2:55 PM • 3 stops
$756
Southwest Airlines
Aug 16 - Aug 22, Economy
Y4
Chicago → Cancún
40h 40m
8:23 PM - 9:03 PM • 2 stops
Y4
Chicago → Cancún
35h 20m
3:55 PM - 1:15 PM • 1 stop
$820
Volaris Airline
Aug 16 - Aug 22, Economy
Y4
Chicago → Cancún
15h 11m
6:21 AM - 3:28 PM • 1 stop
Y4
Chicago → Cancún
25h 17m
2:21 PM - 5:38 AM • 2 stops
$1436
Volaris Airline

Fly from Chicago to Cancún with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Cancún? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Cancún Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to CUN?
The most popular airline flying from Chicago to Cancún are
Can I fly from MDW to CUN non-stop?
Yes, you can fly MDW to CUN non-stop on
Which airlines fly nonstop between Chicago and Cancún?
The non-stop flights between Chicago and Cancún are .
What’s the earliest departure time from MDW to CUN Airport?
The earliest flight leaves MDW at 6:05 am and lands in CUN - Cancún International
What are the airports in Cancún?
CUN
Can I make changes to my Chicago to Cancún flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to CUN?
Read the fare rules of the Chicago to Cancún air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Cancún?
operate flights between Chicago and Cancún
How long does a flight from Chicago to Cancún take?
It takes approximately 3 hour to fly non-stop from MDW to CUN, which is 1430.53 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Cancún (CUN) ?
In the past couple of days, the cheapest tickets to CUN from MDW were found on DL : USD 461
Do I need a passport to fly between MDW and CUN?
Yes
What’s the latest departure time from MDW to CUN ?
The last flight leaves MDW at 9:27 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to cun?
You can find affordable flights from Chicago Midway International Airport (mdw) to Cancún International Airport (cun) on Southwest Airlines. The airline offers a range of options, including First class with suites and fine dining. For round-trip flights with one stop, consider booking at least 28 days in advance for the best Low Fares. You can find cheap airfare deals on our website or through our travel agency partners.
What's the popular airline to fly from mdw to cun?
You can fly from Chicago Midway International Airport (mdw) to Cancún International Airport (cun) on Southwest Airlines. This luxury First cabin offers suites and fine dining, making it a popular choice among travelers. With 5 passengers traveling, you'll need to book at least one suite for your group. Booking in advance is recommended as the airline allows bookings up to 28 days prior to departure. For round-trip flights, Southwest Airlines is a great option.
What's the cheapest day of the week to fly from mdw to cun?
The cheapest day to fly from Chicago Midway International Airport (mdw) to Cancún International Airport (cun) is Thursday. Booking a flight on this day can help you secure a budget-friendly airfare.
What's the cheapest month to fly from mdw to cun?
The cheapest month to fly from Chicago Midway International (mdw) to Cancún International (cun) is November. This flight option offers a budget-friendly airfare, making it an ideal choice for travelers looking for affordable flights.
Which airline/airlines fly from mdw to cun?
The airlines that fly from Chicago Midway International Airport (mdw) to Cancún International Airport (cun) include WestJet Airlines, Viva Aerobus, Southwest Airlines, Allegiant, Air Transat, Porter Airline, Volaris Airline, Aeromexico, Arajet, and Sun Country Airlines.
What are the available flight options from Milwaukee to Cancún International Airport?
You can find flights from Milwaukee to Cancún International Airport with Southwest Airlines (WN) and other airlines such as WestJet Airlines (WS), Viva Aerobus (VB), Allegiant (G4), Air Transat (TS), Porter Airline (PD), Volaris Airline (Y4), Aeromexico (AM), Arajet (DM), Sun Country Airlines (SY).
How can I book my first class ticket on this route?
You can book your first class ticket on fareleaders.com website by searching for flights with Southwest Airlines (WN) and other airlines. Simply enter your travel dates, destinations, and preferred airline to get the best deals.
Can I get the cheapest airfare for my round trip journey from Chicago Midway International to Cancún International?
Yes, you can find the cheapest airfare for your round trip journey with Southwest Airlines (WN) or other airlines. The cheapest day to travel is Thursday and the cheapest month is November.
Are there any advance booking discounts for flights to Cancún?
Yes, there are advance booking discounts available for flights to Cancún. Book your flight at least 28 days in advance to get the best deals.
Is it possible to find the best airline deals for a July trip?
Yes, you can find the best airline deals for a July trip on fareleaders.com website. Simply search for flights with Southwest Airlines (WN) and other airlines during your preferred travel dates.
What is the process of searching and comparing airfares on fareleaders.com website?
To search and compare airfares, simply enter your travel dates, destinations, and preferred airline on fareleaders.com website. You can also filter your results by price, flight duration, and other factors to find the best deals.
Can I book my flight tickets online or do I need to visit an agency?
You can book your flight tickets online on fareleaders.com website. Simply search for flights, select your preferred airline and travel dates, and complete your booking process.

Chicago (MDW) to Cancún (CUN): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Cancún International , Cancún, MX
Distance 1431 miles

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