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

Compare Cancun to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Cancun to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Cancun Airport to Chicago Midway Airport? If you want to travel next month, return fares start from £292. Find the lowest prices on one-way and return tickets right here.
Chicago.£150 per passenger.Departing Thu, 24 Sep.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Cancun on Thu, 24 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £150, select.
Chicago.£163 per passenger.Departing Fri, 23 Oct.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Cancun on Fri, 23 Oct, arriving in Chicago Midway.Price includes taxes and charges.From £163, select.
Chicago.£170 per passenger.Departing Wed, 19 Aug.One-way flight with Aeromexico.Outbound indirect flight with Aeromexico, departs from Cancun on Wed, 19 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £170, select.
Chicago.£170 per passenger.Departing Thu, 17 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Thu, 17 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £170, select.
Chicago.£170 per passenger.Departing Thu, 27 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Thu, 27 Aug, arriving in Chicago Midway.Price includes taxes and charges.From £170, select.
Chicago.£171 per passenger.Departing Thu, 3 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Thu, 3 Dec, arriving in Chicago Midway.Price includes taxes and charges.From £171, select.
Chicago.£174 per passenger.Departing Tue, 10 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Cancun on Tue, 10 Nov, arriving in Chicago Midway.Price includes taxes and charges.From £174, select.
Chicago.£175 per passenger.Departing Thu, 25 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Cancun on Thu, 25 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £175, select.
Chicago.£175 per passenger.Departing Thu, 5 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Thu, 5 Nov, arriving in Chicago Midway.Price includes taxes and charges.From £175, select.
Chicago.£176 per passenger.Departing Wed, 5 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Cancun on Wed, 5 May, arriving in Chicago Midway.Price includes taxes and charges.From £176, select.
Chicago.£178 per passenger.Departing Wed, 29 Jul.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Cancun on Wed, 29 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £178, select.
Chicago.£189 per passenger.Departing Thu, 25 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Thu, 25 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £189, select.
Chicago.£205 per passenger.Departing Sat, 25 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Sat, 25 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £205, select.
Chicago.£206 per passenger.Departing Sat, 3 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Sat, 3 Oct, arriving in Chicago Midway.Price includes taxes and charges.From £206, select.
Chicago.£245 per passenger.Departing Mon, 1 Mar.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Cancun on Mon, 1 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £245, select.
Chicago.£248 per passenger.Departing Fri, 8 Jan.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Cancun on Fri, 8 Jan, arriving in Chicago Midway.Price includes taxes and charges.From £248, select.

Find the cheapest month to fly from Cancun to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Cancun to Chicago Midway flights are currently cheapest in September.
Jul
from £178
Aug
from £170
Sep
from £150
Oct
from £163
Nov
from £174
Dec
from £171
Jan
from £248
Feb
from £175
Mar
from £245
Apr
from £307
May
from £176
Jun
Find prices

Direct flights from Cancun to Chicago Midway

Cancun to Chicago Midway: Alternative routes

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

Chicago Midway

9 miles from central Chicago
Closest
from £150
Search flights

Chicago O'Hare International

16 miles from central Chicago
Cheapest
from £119
Search flights

Chicago Rockford

79 miles from central Chicago
from £175
Search flights

Cancun to Chicago: Flight information

The things to know before you go.
Cheapest flight found£150
Cheapest month to flySeptember
Average flight time3 hrs, 38 mins
Most popular airlineSouthwest Airlines
Average flights per week10

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

The best price we found for a return flight from Cancun to Chicago Midway is £287. 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 38 minutes is the average flight time from Cancun to Chicago Midway.
Southwest Airlines flies direct from Cancun to Chicago Midway.
As of July 2026, there are 10 flights per week flying from Cancun to Chicago Midway.
The cheapest month to fly from Cancun to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Cancun Airport to Chicago Midway Airport on Friday, 18 September 2026.
Yes – the average flight time is 3 hours and 38 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 Chicago Midway 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Delta and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

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

  • The average length of a direct flight from Cancun Airport to Chicago Midway Airport is 3 hours 35 minutes.

  • The timezone in Chicago is UTC-6, which is one hour behind Cancun.

  • Pack your bags and choose from five weekly Cancun Airport to Chicago Midway Airport flights.

  • To ensure you catch your CUN to MDW flight, leave plenty of time to check in and find your gate. Turning up two hours before international departures and one hour before domestic flights is the standard rule.

  • Be prepared for bigger queues in popular months such as April. Arriving up to four hours ahead of international flights and two hours for domestic departures will help ensure a smooth travel experience.

  • Southwest Airlines has direct flights from Cancun Airport to Chicago Midway Airport. Book with this popular carrier, then get ready to discover the sights in Chicago — and maybe even more of the United States if your schedule allows.

  • The airline most travellers fly with on this route is Southwest Airlines.

  • With a dependable 82.86% of services arriving on schedule, Southwest Airlines has the best on-time performance for CUN to MDW flights.

  • Think about adding a stopover when booking your ticket from Cancun Airport to Chicago Midway Airport. Just deselect 'Direct flights only' to break up your trip, or even explore someplace new along the way. Here are some options between CUN and MDW:

    • Atlanta Hartsfield-Jackson Airport

    • Orlando International Airport

    • St Louis Airport

Handy information about Cancun Airport (CUN)

  • Cancun Airport gets top marks for its on-time performance. 80% of flights that depart CUN land on time.

  • Central Cancun to Cancun Airport is approximately 16 kms (10 miles). Depending on traffic, it'll take about 25 minutes to get there if you're ride-sharing, catching a taxi or driving.

  • Planning to catch public transport? You can expect a journey time of around 35 minutes.

  • Have an early flight from Cancun Airport to Chicago Midway Airport? Avoid the stress of rushing to the terminal (and catch some extra z's) by picking one of these hotels close to CUN:

Arriving at Chicago Midway Airport (MDW)

  • The last thing you want is a long trip to your hotel if you're arriving on a late Cancun Airport to Chicago Midway Airport flight. Check in to one of these accommodation options near MDW instead:

  • Get your adventure underway by picking up a Chicago Midway Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's usual tourist stops.

  • Lock in the best deal by booking your ride from Chicago Midway Airport about four weeks ahead of your trip.

Getting from Chicago Midway Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway Airport to the centre of Chicago has a drive time of about 25 minutes. It's approximately 16 kms (10 miles) away.

  • Travelling on public transport takes roughly 30 minutes.

When to fly to Chicago Midway Airport (MDW)

  • It's time to work out your dates for your flight from Cancun Airport to Chicago Midway Airport. July is the most popular month to head to Chicago. If you prefer a more relaxed vibe, go in December.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC and 28ºC. Book your flights from Cancun Airport to Chicago Midway Airport in this month if this is the type of weather you like.

  • Search for cheap tickets from CUN to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

Explore more of the United States

  • You've done Chicago, now it's time to discover other corners of the United States. Travel about 451 kms (280 miles) south-east to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, your itinerary will be busy.

  • Around 257 kms (160 miles) south-east of Chicago, Indianapolis is another essential stop in the United States. No visit is complete without checking out Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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