Cheap flights from Cancun to Chicago Midway

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Flight deals from Cancun to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Cancun to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.

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 June.

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.

Cancun to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$376
Cheapest month to flyJuly
Average flight time3 hrs, 41 mins
Most popular airlineSouthwest Airlines
Average flights per week11

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

The best price we found for a round-trip flight from Cancun to Chicago Midway is C$376. 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 Cancun to Chicago Midway.
Southwest Airlines flies direct from Cancun to Chicago Midway.
There are 11 flights per week flying from Cancun to Chicago Midway, as of May 2025.
The cheapest month to fly from Cancun to Chicago Midway is usually May 2025.
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 Thursday, July 10, 2025.
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 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, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

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

  • Jump on a direct flight from Cancun International Airport to Chicago Midway International Airport and you'll be in the air for an average of 3 hours 40 minutes.

  • Cancun and Chicago are in the UTC-5 timezone. That means you won't have to change your watch on arrival.

  • Flights from CUN to MDW start at 08:10 — the earliest with Southwest Airlines. The last departure is at 19:15 with Southwest Airlines. In total, you can take your pick of six weekly Cancun International Airport to Chicago Midway International Airport flights.

  • Your CUN to MDW flight won't wait if you're running late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • During popular months like July, you'll want to get to the airport earlier than normal. Plan to arrive two hours before domestic departures and four hours ahead of international flights when you travel during a peak period in general.

  • Southwest Airlines is your gateway to discovering Chicago (and perhaps some other great corners of United States!). Browse the direct flights from Cancun International Airport to Chicago Midway International Airport offered by this popular airline.

  • The airline that serves the most passengers on this route is Southwest Airlines.

  • With a reliable 88.41% of services landing on schedule, Southwest Airlines is the most punctual carrier operating CUN to MDW flights.

  • If you want to break up your flight, simply deselect 'Direct flights only' when searching for your ticket from Cancun International Airport to Chicago Midway International Airport. These are the most popular stopovers between CUN and MDW:

    • Hartsfield-Jackson Atlanta International Airport

    • Lambert-St. Louis International Airport

    • Orlando International Airport

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

  • Currently, C$206 is the lowest price we've seen for a one-way Cancun International Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is C$376. Bear in mind that fares can change due to demand when booking.

  • Book six months before flying. After crunching the numbers on our calendar, this is how far you should book ahead to secure cheap tickets from CUN to MDW.

  • May is the cheapest month for flights from Cancun International Airport to Chicago Midway International Airport. If you'd like to fly at a different time of year, the 'Whole month' tool will give you the lowest airfares for each month.

  • You won't have to check back in every day to find out if fares have gone down when you set up a Price Alert. We'll notify you as soon as there's a better deal on cheap flights from CUN to MDW.

  • Select your preferred departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to get the best deals on flights from Cancun International Airport to Chicago Midway International Airport.

Handy information about Cancun International Airport (CUN)

  • When it comes to Cancun International Airport's on-time performance, 72.87% of flights arrive within the scheduled timeframe.

  • Central Cancun to Cancun International Airport is approximately 19 kilometres. Depending on traffic, it'll take you about 25 minutes to get there if you're driving, ride-sharing or catching a cab.

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

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The street address for MDW is 5700 South Cicero.

  • Chicago Midway International Airport is roughly 19 kilometres from the centre of Chicago. Driving there takes about 20 minutes.

  • If you're travelling by public transport, expect a journey time of roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to pick your dates for your flight from Cancun International Airport to Chicago Midway International Airport. July is the busiest month to head to Chicago. If you like a more laid-back vibe, go in May.

  • Lock in your flight from Cancun International Airport to Chicago Midway International Airport for July if you want to visit Chicago during its warmest month. Expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

  • If you want to travel in cooler conditions, search for a cheap ticket from CUN to MDW in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of United States

  • You've done Chicago, now it's time to explore more of United States. Journey around 451 kilometres south-east to Columbus to tick off its top sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you on the go.

  • Indianapolis is another sought-after destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without visiting The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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