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Cheap Flights from Chicago (MDW) to Cancun (CUN)

Compare Chicago Midway to Cancun flight deals

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

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Flight deals from Chicago Midway to Cancun

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Cancun Airport? If you want to travel next month, return fares start from $633. Find the lowest prices on one-way and return tickets right here.
Cancun.$518 per passenger.Departing Mon, 17 Aug, returning Wed, 26 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 17 Aug, arriving in Cancun.Inbound direct flight with Southwest Airlines departs from Cancun on Wed, 26 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $518, select.
Cancun.$526 per passenger.Departing Tue, 20 Oct, returning Wed, 28 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 20 Oct, arriving in Cancun.Inbound indirect flight with Southwest Airlines, departs from Cancun on Wed, 28 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $526, select.
Cancun.$526 per passenger.Departing Wed, 26 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 26 Aug, arriving in Cancun.Inbound indirect flight with Southwest Airlines, departs from Cancun on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $526, select.
Cancun.$571 per passenger.Departing Tue, 25 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 25 Aug, arriving in Cancun.Inbound direct flight with Southwest Airlines departs from Cancun on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $571, select.
Cancun.$615 per passenger.Departing Mon, 14 Sep, returning Thu, 17 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 14 Sep, arriving in Cancun.Inbound direct flight with Southwest Airlines departs from Cancun on Thu, 17 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $615, select.
Cancun.$619 per passenger.Departing Mon, 26 Oct, returning Thu, 29 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 26 Oct, arriving in Cancun.Inbound direct flight with Southwest Airlines departs from Cancun on Thu, 29 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $619, select.
Cancun.$625 per passenger.Departing Mon, 9 Nov, returning Thu, 12 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 9 Nov, arriving in Cancun.Inbound indirect flight with Southwest Airlines, departs from Cancun on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $625, select.
Cancun.$627 per passenger.Departing Sun, 27 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 27 Sep, arriving in Cancun.Inbound direct flight with Southwest Airlines departs from Cancun on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $627, select.
Cancun.$627 per passenger.Departing Tue, 27 Oct, returning Tue, 3 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 27 Oct, arriving in Cancun.Inbound indirect flight with Southwest Airlines, departs from Cancun on Tue, 3 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $627, select.
Cancun.$633 per passenger.Departing Wed, 10 Mar, returning Wed, 17 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 10 Mar, arriving in Cancun.Inbound indirect flight with Delta, departs from Cancun on Wed, 17 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $633, select.
Cancun.$633 per passenger.Departing Mon, 27 Jul, returning Thu, 30 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 27 Jul, arriving in Cancun.Inbound indirect flight with Southwest Airlines, departs from Cancun on Thu, 30 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $633, select.
Cancun.$635 per passenger.Departing Tue, 19 Jan, returning Fri, 5 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 19 Jan, arriving in Cancun.Inbound indirect flight with Delta, departs from Cancun on Fri, 5 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $635, select.
Cancun.$637 per passenger.Departing Fri, 31 Jul, returning Thu, 6 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 31 Jul, arriving in Cancun.Inbound indirect flight with Frontier Airlines, departs from Cancun on Thu, 6 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $637, select.
Cancun.$640 per passenger.Departing Tue, 8 Dec, returning Tue, 15 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 8 Dec, arriving in Cancun.Inbound indirect flight with Delta, departs from Cancun on Tue, 15 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $640, select.
Cancun.$641 per passenger.Departing Mon, 18 Jan, returning Wed, 20 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 18 Jan, arriving in Cancun.Inbound indirect flight with Delta, departs from Cancun on Wed, 20 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $641, select.
Cancun.$642 per passenger.Departing Tue, 4 May, returning Tue, 11 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 4 May, arriving in Cancun.Inbound indirect flight with Delta, departs from Cancun on Tue, 11 May, arriving in Chicago Midway.Price includes taxes and charges.From $642, 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 August.
Jun
from $875
Jul
from $633
Aug
from $518
Sep
from $615
Oct
from $526
Nov
from $625
Dec
from $640
Jan
from $641
Feb
from $646
Mar
from $633
Apr
from $839
May
from $642

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.

Cancun

14km from central Cancun
ClosestCheapest
from $518
Search flights

Chicago to Cancun: Flight information

The things to know before you go.
Cheapest flight found$518
Cheapest month to flyAugust
Average flight time3 hrs, 41 mins
Most popular airlineSouthwest Airlines
Average flights per week8

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 $518. 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 41 minutes is the average flight time from Chicago Midway to Cancun.
Southwest Airlines flies direct from Chicago Midway to Cancun.
As of June 2026, there are 8 flights per week flying from Chicago Midway to Cancun.
The cheapest month to fly from Chicago Midway to Cancun is usually August.
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 Monday, 17 August 2026.
Yes – the average flight time is 3 hours and 41 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 Airport (MDW) to Cancun Airport (CUN): what you need to know

  • Around 3 hours 35 minutes is how long you can expect to be travelling on a direct flight from Chicago Midway Airport to Cancun Airport.

  • Cancun is one hour ahead of Chicago and is in the UTC-5 timezone.

  • Every week, there are five Chicago Midway Airport to Cancun Airport flights.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are tried-and-true travel tips. Be at the airport on time to catch your MDW to CUN flight.

  • You'll likely experience longer queues during popular months like July. Arriving up to four hours in advance for international flights and two hours for a domestic departure will give you ample time for security and boarding.

  • Southwest Airlines offers direct flights from Chicago Midway Airport to Cancun Airport. Book with this popular airline, then get ready to discover the sights in Cancun — and maybe even more of Mexico if time allows.

  • The airline with the highest number of bookings on this route is Southwest Airlines.

  • The most punctual carrier offering MDW to CUN flights is Southwest Airlines. Its services land as planned 69.01% of the time.

  • If you'd like to split up your journey, simply uncheck 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Cancun Airport. These are the top stopovers between MDW and CUN:

    • Atlanta Hartsfield-Jackson Airport

    • Nashville Airport

    • St Louis Airport

Handy information about Chicago Midway Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • 76% of flights departing from Chicago Midway Airport reach their destination on time.

  • Chicago Midway Airport is around 16 kilometres from central Chicago. If you're driving, catching a taxi or ride-sharing from the centre, it'll take you 25 minutes or so to get there, depending on the traffic.

  • The journey when using public transport will take about 30 minutes.

  • Have an early flight from Chicago Midway Airport to Cancun Airport? Avoid the last-minute rush to the terminal (and get some extra shut-eye) by choosing one of these hotels close to MDW:

Arriving at Cancun Airport (CUN)

  • If you're landing on a late Chicago Midway Airport to Cancun Airport flight, nothing tops the convenience of being near the terminal. Grab your suitcases from the carousel and then be showered and relaxing soon after at one of these hotels near CUN:

  • Travel at your own pace with a Cancun Airport rental car. Pick up your wheels from MEX, America or Europcar and experience more of Cancun and beyond.

  • To get the best deal, reserve your ride from Cancun Airport about three weeks before travelling.

When to fly to Cancun Airport (CUN)

  • The quietest month for a flight from Chicago Midway Airport to Cancun Airport is March, while April is the busiest. Pick the best time to go to Cancun based on whether you prefer a faster pace or a more relaxed vibe.

  • The warmest month in Cancun is August, with the temperature ranging between 26ºC (79ºF) and 32ºC (90ºF). Book your flights from Chicago Midway Airport to Cancun Airport in this month if this is the type of weather you like.

  • January has average temperatures of between 20ºC (68ºF) and 27ºC (81ºF). Search for cheap tickets from MDW to CUN sometime then if you want to travel when it's cooler.

Explore more of Mexico

  • You've seen Cancun, now it's time to explore other corners of Mexico. Journey about 290 kilometres west to Merida to check off its must-visit sights. From Chichen Itza, cenotes y pueblos magicos to Chichen-itza Park and Nva. Chichen Itza Park, there's plenty to keep you on the go.

  • Around 418 kilometres west of Cancun, Campeche is another essential stop in Mexico. Get a taste of what this destination has to offer at Zona Arquelogica Edzna, Old City Wall and Plaza de la Independencia.

Plan the rest of your trip from Chicago to Cancun

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.