Cheap Flights from Cancun to Chicago

Compare Cancun to Chicago flight deals

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

Book the best Chicago fare with no extra fees

Flight deals from Cancun to Chicago

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

Chicago.$2,342 per passenger.Departing Thu, 24 Apr.One-way flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Cancun on Thu, 24 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $2,342, select.

Chicago.$2,649 per passenger.Departing Thu, 6 Nov.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Cancun on Thu, 6 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $2,649, select.

Chicago.$2,750 per passenger.Departing Wed, 25 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Wed, 25 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $2,750, select.

Chicago.$2,757 per passenger.Departing Thu, 8 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Thu, 8 May, arriving in Chicago Midway.Price includes taxes and charges.From $2,757, select.

Chicago.$2,884 per passenger.Departing Fri, 5 Sep.One-way flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Cancun on Fri, 5 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $2,884, select.

Chicago.$3,209 per passenger.Departing Mon, 18 Aug.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Cancun on Mon, 18 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $3,209, select.

Chicago.$3,323 per passenger.Departing Thu, 10 Jul.One-way flight with Aeromexico.Outbound indirect flight with Aeromexico, departs from Cancun on Thu, 10 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $3,323, select.

Chicago.$3,407 per passenger.Departing Wed, 15 Oct.One-way flight with Viva Aerobus.Outbound indirect flight with Viva Aerobus, departs from Cancun on Wed, 15 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $3,407, select.

Find the cheapest month to fly from Cancun to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Cancun to Chicago flights are currently cheapest in April.

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Direct flights from Cancun to Chicago

Alternative Cancun to Chicago routes

Looking for the cheapest, fastest or easiest route from Cancun to Chicago? You could fly into the following airports instead.

Cancun to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$2,342
Cheapest month to fly	April
Average flight time	3 hrs, 53 mins
Most popular airline	Qatar Airways
Average flights per week	118

Finding cheap flights from Cancun to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Cancun to Chicago?

The best price we found for a return flight from Cancun to Chicago is $4,214. 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.

How long does it take to fly from Cancun to Chicago?

3 hours and 53 minutes is the average flight time from Cancun to Chicago.

Which airlines fly direct from Cancun to Chicago?

Qatar Airways, American Airlines and United fly direct from Cancun to Chicago.

How many flights are there a week from Cancun to Chicago?

As of March 2025, there are 118 flights per week flying from Cancun to Chicago.

When is the cheapest time to fly from Cancun to Chicago?

The cheapest month to fly from Cancun to Chicago is usually April.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Cancun Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $4,214.

Which upcoming date is cheapest to fly from Cancun Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Cancun Airport to Chicago on Thursday, 24 April 2025.

Can I get a direct flight from Cancun Airport to Chicago?

Yes – the average flight time is 3 hours and 53 minutes.

How can I get the best flight deal from Cancun Airport to Chicago?

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 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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Cancun Airport to Chicago with?

Currently, Spirit Airlines offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Cancun

Looking for cheap tickets from Cancun to Chicago? 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. 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.
Flex your dates to find the best Cancun-Chicago 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 from Cancun.
Set up a Price Alert. You can easily track the fare of your cheap Cancun-Chicago 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? 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.
Find the cheapest Business class flights from Cancun and Chicago. 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 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.

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

Once you've secured your cheap flight ticket from Cancun to Chicago, 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.