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

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Compare Cancun to Chicago flight deals

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

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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.$279 per passenger.Departing Fri, 9 May, returning Sat, 10 May.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Fri, 9 May, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 10 May, arriving in Cancun.Price includes taxes and charges.From $279, select.
Chicago.$279 per passenger.Departing Wed, 9 Jul, returning Tue, 15 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Wed, 9 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 15 Jul, arriving in Cancun.Price includes taxes and charges.From $279, select.
Chicago.$281 per passenger.Departing Wed, 30 Jul, returning Tue, 5 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Wed, 30 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 5 Aug, arriving in Cancun.Price includes taxes and charges.From $281, select.
Chicago.$281 per passenger.Departing Wed, 25 Jun, returning Tue, 1 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Wed, 25 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 1 Jul, arriving in Cancun.Price includes taxes and charges.From $281, select.
Chicago.$284 per passenger.Departing Thu, 15 May, returning Sat, 16 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Thu, 15 May, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 16 Aug, arriving in Cancun.Price includes taxes and charges.From $284, select.
Chicago.$317 per passenger.Departing Fri, 8 Aug, returning Fri, 15 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Fri, 8 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Fri, 15 Aug, arriving in Cancun.Price includes taxes and charges.From $317, select.
Chicago.$324 per passenger.Departing Thu, 29 May, returning Mon, 2 Jun.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cancun on Thu, 29 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 2 Jun, arriving in Cancun.Price includes taxes and charges.From $324, select.
Chicago.$341 per passenger.Departing Sat, 7 Jun, returning Tue, 10 Jun.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cancun on Sat, 7 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 10 Jun, arriving in Cancun.Price includes taxes and charges.From $341, 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 May.
May
from $279
Jun
from $341
Jul
from $279
Aug
from $317
Sep
from $386
Oct
from $434
Nov
from $439
Dec
from $500
Jan
from $448
Feb
from $445
Mar
from $772
Apr
from $1,191

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$280
Cheapest month to flyMay
Average flight time3 hrs, 52 mins
Most popular airlineAmerican Airlines
Average flights per week89

Finding cheap flights from Cancun to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Cancun to Chicago is $279. 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 52 minutes is the average flight time from Cancun to Chicago.
American Airlines, Qatar Airways and United fly direct from Cancun to Chicago.
As of May 2025, there are 89 flights per week flying from Cancun to Chicago.
The cheapest month to fly from Cancun to Chicago is usually May 2025.
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 $279.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Cancun Airport to Chicago on Friday, 9 May 2025.
Yes – the average flight time is 3 hours and 52 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 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.
In May, the average temperature is usually around 13°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.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago.

Travelling from Cancun International Airport (CUN) to Chicago: what you need to know

  • Book a direct flight from Cancun International Airport to Chicago and you'll be in the air for around 3 hours 46 minutes.

  • Cancun (the location of Cancun International Airport) and Chicago are in the same timezone — UTC-5.

  • The busiest route is from Cancun International Airport (CUN) to O'Hare International Airport (ORD). Take your pick of 52 services every week between these two airports. If you'd like to take off as soon as possible, the earliest flight from CUN to ORD is the 07:15 United option. If you'd rather fly out later on, the final departure is at 19:41 with United.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to catch your flight from CUN to Chicago.

  • You'll likely experience longer queues during popular months such as July and other peak seasons. Arriving up to fours hours ahead of an international flight and two hours for domestic departures is a smart move.

  • Direct flights from Cancun International Airport (CUN) to Chicago are available for booking. O'Hare International Airport (ORD) will be where your journey ends.

  • These are some of the most popular carriers operating direct flights from Cancun International Airport to Chicago:

  • Stopovers are the ideal opportunity to break up your journey — and possibly even explore a different city. When browsing flights from CUN to Chicago, deselect the 'Direct flights only' box to see where you can stop along the way. Some popular options include:

    • Los Angeles International Airport (LAX)

    • Nashville International Airport (BNA)

    • Lambert-St. Louis International Airport (STL)

  • If you have a passport from Mexico, you will need an embassy visa to enter United States. This applies when booking a cheap ticket from Cancun International Airport to Chicago for tourism purposes. The rules may differ if you're travelling for work or other reasons. Always check official visa guidelines ahead of booking and definitely before you fly.

  • CUN is around 19 kilometres from central Cancun. If you're driving, catching a cab or ride-sharing from the centre, it'll take 26 minutes or so to get there, depending on traffic conditions.

  • After a leisurely start to your journey? Stay near CUN. Whether you've booked an early flight from Cancun International Airport to Chicago or just don't like being rushed, these hotels are the answer:

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

  • $167 is the best price for a one-way ticket from Cancun International Airport to Chicago. A return flight starts from $279. These fares may change depending on availability.

  • To secure cheap tickets from CUN to Chicago, reserve your journey 9 months ahead of your departure date.

  • The cheapest month for tickets from Cancun International Airport to Chicago is May. Compare prices using the 'Whole month' tool to find the dates with the lowest fares.

  • Locking in a cheap ticket from CUN to Chicago couldn't be easier with Price Alerts. Simply create one of these automatic alerts and we'll let you know as soon as there's a better deal.

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

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month to catch a flight from Cancun International Airport to Chicago while February is the quietest. To work out the ideal time to go to Chicago, consider whether you like a lively atmosphere or a quieter vibe.

  • When booking your flight from Cancun International Airport to Chicago, think about the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • January sees average temperatures of between -12ºC and 3ºC. Search for cheap flights from CUN to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

  • After locking in your flight from Cancun International Airport to Chicago, think about where you want to stay in this city. Make one of these accommodation options your base for exploring Chicago:

  • Millennium Park and Art Institute of Chicago are just a couple of the major attractions to put on your Chicago travel itinerary. Keep the adventure rolling by checking out LandShark Beer Garden at Navy Pier.

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from Cancun International Airport to Chicago isn't our only cool trick. Check out our car rentals in Chicago and see the sights your way. We find deals from trusted car rental providers and put them all in one place. Instantly compare rates and then book with no fees.

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.