Cheap Flights from Cancun to Chicago

Compare Cancun to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Cancun to Chicago Midway

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

Chicago.$568 per passenger.Departing Mon, 3 Feb, returning Mon, 10 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Cancun on Mon, 3 Feb, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 10 Feb, arriving in Cancun.Price includes taxes and charges.From $568, select.

Chicago.$920 per passenger.Departing Thu, 26 Dec, returning Mon, 6 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Cancun on Thu, 26 Dec, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 6 Jan, arriving in Cancun.Price includes taxes and charges.From $920, select.

Chicago.$1,277 per passenger.Departing Fri, 13 Dec, returning Thu, 19 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Cancun on Fri, 13 Dec, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Thu, 19 Dec, arriving in Cancun.Price includes taxes and charges.From $1,277, select.

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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 February.

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Direct flights from Cancun to Chicago Midway

Southwest Airlines

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 found	$568
Cheapest month to fly	February
Average flight time	3 hrs, 41 mins
Most popular airline	Southwest Airlines
Average flights per week	9

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 $568. 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.
: As of April 2024, there are 9 flights per week flying from Cancun to Chicago Midway.
: The cheapest month to fly from Cancun to Chicago Midway is usually February.
: 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 Monday, 3 February 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 Midway is around 40 days in advance, so don’t leave your flight to the last minute.
: Currently, Delta offers the cheapest flight tickets to Chicago Midway.

How to find cheap flights to Chicago (MDW) from Cancun (CUN) in 2024

Looking for cheap tickets from Cancun to Chicago Midway? Return tickets start from $568 and one-way flights to Chicago Midway from Cancun start from $282

Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Cancun to Chicago Midway. And with us there are no hidden fees - what you see is what you pay.
Compare flight deals to Chicago from Cancun from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from $282 one-way.
Flex your dates to find the best CUN-MDW ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago Midway from Cancun.
Set up a Price Alert. You can easily track the fare of your cheap Cancun-Chicago Midway flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
Fly without stops. Only interested in direct flights between Cancun and Chicago Midway? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results. Airlines that fly direct include: Southwest Airlines
Flexible on when you travel? The cheapest month to fly from Cancun to Chicago Midway is February.
Find the cheapest Business class flights from Cancun and Chicago Midway. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for Cancun to Chicago Midway flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Cancun and Chicago Midway whenever you want.

Combine your flight to Chicago Midway from Cancun with hotels and car hire

Once you've secured your cheap flight ticket from Cancun to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.

Plan the rest of your trip from Cancun to Chicago

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