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124 € Cheap Flights from Cancun (CUN) to Chicago (CHIA)

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.124 € per passenger.Departing Tue, 23 Dec, returning Fri, 2 Jan.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Tue, 23 Dec, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Fri, 2 Jan, arriving in Cancun.Price includes taxes and charges.From 124 €, select.
Chicago.124 € per passenger.Departing Fri, 13 Feb, returning Fri, 20 Feb.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Fri, 13 Feb, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Fri, 20 Feb, arriving in Cancun.Price includes taxes and charges.From 124 €, select.
Chicago.124 € per passenger.Departing Sat, 17 Jan, returning Tue, 20 Jan.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Sat, 17 Jan, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 20 Jan, arriving in Cancun.Price includes taxes and charges.From 124 €, select.
Chicago.124 € per passenger.Departing Thu, 4 Dec, returning Mon, 8 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Thu, 4 Dec, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 8 Dec, arriving in Cancun.Price includes taxes and charges.From 124 €, select.
Chicago.124 € per passenger.Departing Fri, 30 Jan, returning Sun, 1 Feb.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Fri, 30 Jan, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sun, 1 Feb, arriving in Cancun.Price includes taxes and charges.From 124 €, select.
Chicago.124 € per passenger.Departing Sat, 22 Nov, returning Fri, 28 Nov.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Sat, 22 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Fri, 28 Nov, arriving in Cancun.Price includes taxes and charges.From 124 €, select.
Chicago.124 € per passenger.Departing Tue, 25 Nov, returning Tue, 2 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Tue, 25 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 2 Dec, arriving in Cancun.Price includes taxes and charges.From 124 €, select.
Chicago.168 € per passenger.Departing Mon, 24 Nov, returning Sat, 3 Jan.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Mon, 24 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 3 Jan, arriving in Cancun.Price includes taxes and charges.From 168 €, 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 November.
Nov
from 124 €
Dec
from 124 €
Jan
from 124 €
Feb
from 124 €
Mar
from 202 €
Apr
from 225 €
May
from 218 €
Jun
from 277 €
Jul
from 274 €
Aug
from 241 €
Sep
from 322 €
Oct
Find prices

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 found124 €
Cheapest month to flyNovember
Average flight time3 hrs, 53 mins
Most popular airlineAmerican Airlines
Average flights per week97

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 124 €. 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 November 2025, there are 97 flights per week flying from Cancun to Chicago.
The cheapest month to fly from Cancun to Chicago is usually November.
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 124 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Cancun Airport to Chicago on Saturday, 22 November 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 November, the average temperature is usually around 5°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.

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

  • Expect to be in the air for 3 hours 50 minutes. That's the average journey time for a direct flight from Cancun International Airport to Chicago.

  • Chicago's timezone is UTC-5, which is the same as Cancun (the location of Cancun International Airport).

  • Cancun International Airport (CUN) to O'Hare International Airport (ORD) is the most popular route, with 37 weekly flights to pick from. If you have things to do before heading off, the last flight from CUN to ORD is with United Airlines at 16:40. Opt for the first departure with United Airlines at 08:15 if you want to get on your way earlier.

  • For a smooth journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to board your CUN to Chicago flight.

  • If you're heading away during a bank holiday or another peak period, give yourself extra time. A good rule is two hours before domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

  • You can book a direct Cancun International Airport to Chicago ticket. Start your journey at CUN and touch down at O'Hare International Airport (ORD).

  • Direct flights from Cancun International Airport to Chicago are offered by numerous airlines. Select your seat on any of these:

  • Think about adding a stopover to potentially save on your plane ticket from CUN to Chicago. All you need to do is deselect 'Direct flights only' during your search. Take a detour (and maybe pocket some savings) by stopping at one of these airports:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Los Angeles International Airport (LAX)

    • Orlando International Airport (MCO)

  • CUN is about 13 kilometres from central Cancun. If you're ride-sharing, catching a cab or driving from the centre, it'll take you 25 minutes or so to arrive, depending on traffic conditions.

  • Have an early flight from Cancun International Airport to Chicago? Avoid the hassle of rushing to the terminal (and get some extra shut-eye) by choosing one of these stays close to CUN:

  • 72.87% of flights that take off from Cancun International Airport reach their destination on time.

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

  • 92 € is the lowest price we've seen for a one-way Cancun International Airport to Chicago flight. A return ticket right now is 124 €. Depending on how early you book and the availability, these fares can change.

  • Get cheap flights from CUN to Chicago by booking one month ahead. Based on our research, that's the sweet spot for finding the biggest deals.

  • May is the best month for scoring an amazing deal on Cancun International Airport to Chicago tickets. If you're looking to travel at a different time of year, the 'Whole month' tool will give you the lowest prices across every month.

  • Save time searching for cheap flights from CUN to Chicago by setting up a Price Alert. You'll receive an email or notification through the app when a special offer becomes available.

  • Tailor your trip with filters. Pick your preferred departure and arrival times, airlines and total journey duration. You can also sort results by 'Cheapest,' 'Best' or 'Fastest' flights from Cancun International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're catching a cab or a ride-share, the drive takes about 35 minutes.

  • It typically takes 55 minutes to get there using public transport.

  • The last thing you want is a lengthy journey to your hotel if you're arriving on a late flight from Cancun International Airport to Chicago. Book one of these accommodation options near ORD instead:

  • Follow your own route with an O'Hare International Airport rental car. Book your wheels from Routes Car Rentals, Dollar or Budget and discover more of Chicago and beyond.

  • Lock in the best rate by reserving your ride from O'Hare International Airport about four weeks ahead of your flight from CUN to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is about 19 kilometres from central Chicago. Following your flight from Cancun International Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a ride-share or cab.

  • You can expect the trip to take roughly 45 minutes on public transport.

  • There are some great places to call home for the night near MDW. Settle in and get cosy after your CUN to Chicago flight at any of these well-located options:

  • Forget about inconvenient public transport schedules or waiting in a long cab line. Pick up a Chicago Midway International Airport rental car and blaze your own trail. Compare rates and availability from Dollar, Hertz and Budget.

  • Don't pay more than you need to. Securing your ride four weeks before your arrival at MDW can land you a better rate.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Cancun International Airport to Chicago and head for your hotel or start sightseeing right away. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to drive there.

  • If you travel by public transport, expect a journey of around 4 hours 15 minutes.

  • If you don't want to travel into the centre, head for a hotel near RFD. Make yourself comfy at one of these options after your CUN to Chicago flight:

  • Start your journey without worrying about how to get to where you're going with a Chicago Rockford International Airport rental car. Book your wheels with reliable companies here like Budget, Alamo and National.

  • Booking a couple of weeks ahead of your flight from Cancun International Airport to Chicago is a smart way to go. Along with better deals, you might find it easier to get the make and model you prefer at RFD.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your trip dates before booking your flight from Cancun International Airport to Chicago. The city comes alive in peak season, but prices are often higher and attractions can be crowded. Go to Chicago in the low season for a more relaxed vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Cancun International Airport to Chicago plane ticket then if that's your idea of comfortable weather.

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from CUN to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

  • After booking your flight from Cancun International Airport to Chicago, find a hotel that keeps you close to what you want to see. Make one of these options your base for exploring Chicago:

  • There are so many things to see and do in this city it can be hard to figure out where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top sights which should feature on any good Chicago itinerary.

Explore more of United States

  • Chicago has loads to offer, but there are so many other corners of United States you'll want to see. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep your itinerary packed. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another essential stop in United States and is around 257 kilometres south-east of Chicago. No journey is complete without a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

More travel options

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.