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Cheap Flights from Chicago Midway to Cancun

Compare Chicago Midway to Cancun flight deals

Find the cheapest month or even day of the year to fly to Cancun

Book the best Cancun fare with no extra fees

Flight deals from Chicago Midway to Cancun

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to Cancun? Find the lowest prices on one-way and return tickets right here.
Cancun.Rs32,068 per passenger.Departing Sun, 30 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 30 Nov, arriving in Cancun.Price includes taxes and charges.From Rs32,068, select.
Cancun.Rs32,068 per passenger.Departing Tue, 13 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 13 Jan, arriving in Cancun.Price includes taxes and charges.From Rs32,068, select.
Cancun.Rs32,275 per passenger.Departing Tue, 28 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Oct, arriving in Cancun.Price includes taxes and charges.From Rs32,275, select.
Cancun.Rs35,093 per passenger.Departing Sat, 6 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 6 Dec, arriving in Cancun.Price includes taxes and charges.From Rs35,093, select.
Cancun.Rs41,726 per passenger.Departing Tue, 17 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 17 Mar, arriving in Cancun.Price includes taxes and charges.From Rs41,726, select.
Cancun.Rs41,726 per passenger.Departing Mon, 13 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 13 Apr, arriving in Cancun.Price includes taxes and charges.From Rs41,726, select.
Cancun.Rs41,726 per passenger.Departing Wed, 4 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 4 Feb, arriving in Cancun.Price includes taxes and charges.From Rs41,726, select.
Cancun.Rs55,024 per passenger.Departing Mon, 2 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Feb, arriving in Cancun.Price includes taxes and charges.From Rs55,024, select.

Find the cheapest month to fly from Chicago Midway to Cancun

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Cancun flights are currently cheapest in November.
Oct
from Rs32,275
Nov
from Rs32,068
Dec
from Rs35,093
Jan
from Rs32,068
Feb
from Rs41,726
Mar
from Rs41,726
Apr
from Rs41,726
May
from Rs105,316
Jun
from Rs67,612
Jul
from Rs105,997
Aug
from Rs55,843
Sep
Find prices

Direct flights from Chicago Midway to Cancun

Chicago Midway to Cancun: Alternative routes

Compare routes from Chicago Midway to Cancun below. You may find an airport to fly into that's cheaper, faster, or easier than Cancun.

Chicago to Cancun: Flight information

The things to know before you go.
Cheapest flight foundRs32,068
Cheapest month to flyJanuary
Average flight time3 hrs, 40 mins
Most popular airlineSouthwest Airlines
Average flights per week10

Finding cheap flights from Chicago Midway to Cancun: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Cancun is Rs70,871. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 40 minutes is the average flight time from Chicago Midway to Cancun.
Southwest Airlines flies direct from Chicago Midway to Cancun.
As of October 2025, there are 10 flights per week flying from Chicago Midway to Cancun.
The cheapest month to fly from Chicago Midway to Cancun is usually November.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Cancun Airport on Sunday, 16 November 2025.
Yes – the average flight time is 3 hours and 40 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Cancun but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Cancun is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Cancun.

Travelling from Chicago Midway International Airport (MDW) to Cancun International Airport (CUN): what you need to know

  • Around 3 hours 45 minutes is how long you can expect to be in the air on a direct flight from Chicago Midway International Airport to Cancun International Airport.

  • Chicago and Cancun share the UTC-5 timezone. This means there's no time difference to consider.

  • Flights from MDW to CUN start from 06:15 — the first with Southwest Airlines. The latest departure is at 15:00 with Southwest Airlines. In total, you can choose from six weekly Chicago Midway International Airport to Cancun International Airport flights.

  • To ensure you catch your MDW to CUN flight, leave plenty of time to navigate the airport and find your gate. Turning up two hours before international departures and an hour before domestic flights is the general travel rule.

  • You'll likely experience longer lines during popular months such as July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a wise move.

  • Travelling to Cancun (and then exploring more of Mexico!) is a breeze with Southwest Airlines. This popular airline has direct flights from Chicago Midway International Airport to Cancun International Airport.

  • The airline with the highest booking volume on this route is Southwest Airlines.

  • With 71.01% of services arriving as planned, Southwest Airlines is the most punctual carrier offering MDW to CUN flights.

  • We make it a breeze to book a flight with a stopover. To see your options for tickets from Chicago Midway International Airport to Cancun International Airport, deselect 'Direct flights only.' Then, choose a flight offering a stop long enough to visit the city of your choice. Worthwhile stopovers between MDW and CUN include:

    • Hartsfield-Jackson Atlanta International Airport

    • Nashville International Airport

    • Kansas City International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Cancun International Airport (CUN)

  • At the moment, Rs32,068 is the lowest price we've seen for a one-way Chicago Midway International Airport to Cancun International Airport flight. The best price for a return ticket is Rs70,871. Keep in mind that fares could change due to availability at the time of booking.

  • To score cheap tickets from MDW to CUN, reserve your trip six months ahead of your departure date.

  • Schedule your trip for May. That's the cheapest month for flights from Chicago Midway International Airport to Cancun International Airport. If you're flexible with your dates, use the 'Whole month' tool to see the cheapest price across every month.

  • You won't have to check back in every day to see if fares have gone down when you set up a Price Alert. We'll let you know the moment there's a change in price on cheap flights from MDW to CUN.

  • Secure the ideal flight for you with the help of the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Chicago Midway International Airport to Cancun International Airport, use the 'Sort by' function. You can also filter results by airline, departure and arrival times, and journey duration.

Handy information about Chicago Midway International Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • 77.88% of flights leaving from Chicago Midway International Airport land at their destination on schedule.

  • To get to Chicago Midway International Airport from central Chicago, it'll take about 20 minutes if you're planning to drive. This depends on traffic though. It's approximately 19 kilometres from the airport to the city centre.

  • The trip when using public transport will take about 45 minutes.

  • Get your travels off to a hassle-free start by staying near MDW. Whether you're catching an early flight from Chicago Midway International Airport to Cancun International Airport or just don't want to be rushed, these stays are perfect:

Arriving at Cancun International Airport (CUN)

  • The last thing you need is a lengthy trip to your hotel if you're arriving on a late Chicago Midway International Airport to Cancun International Airport flight. Stay at one of these accommodation options near CUN instead:

  • Grab a Cancun International Airport rental car and explore Cancun and beyond with your own wheels. MEX, America and Europcar are popular outlets to choose from here.

  • Reserving your ride from Cancun International Airport about three weeks in advance gives you the best shot at securing a great deal.

Getting from Cancun International Airport (CUN) to central Cancun

  • Cancun International Airport is roughly 19 kilometres from the centre of Cancun. The drive time takes about 25 minutes.

When to fly to Cancun International Airport (CUN)

  • The quietest month for a flight from Chicago Midway International Airport to Cancun International Airport is May, while July is the most popular. Pick the best time to visit Cancun based on whether you prefer a faster pace or a more relaxed vibe.

  • When booking your flight from Chicago Midway International Airport to Cancun International Airport, think about the kind of weather you enjoy. August is the warmest month in Cancun, with the temperature ranging from 26ºC to 32ºC.

  • Search for cheap tickets from MDW to CUN in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between 20ºC and 27ºC on average.

Explore more of Mexico

  • You've seen Cancun, now it's time to explore other parts of Mexico. Travel about 290 kilometres west to Merida to tick off its leading sights. From P. ANDADOR NVA. CHICHEN ITZA to Pre Hispanic Town Of Uxmal and El Palacio de Gobierno, you've got a jam-packed schedule ahead.

  • Campeche is another must-experience destination in Mexico and is around 418 kilometres west of Cancun. No journey is complete without a visit to Campeche Waterfront Promenade, Zona Arquelogica Edzna and Centro Historico de San Francisco de Campeche.

Plan the rest of your trip from Chicago to Cancun

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.