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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 Airport to Chicago? If you want to travel next month, return fares start from R 2,361. Find the lowest prices on one-way and return tickets right here.
Chicago.R 1,753 per passenger.Departing Thu, 7 May.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Thu, 7 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,753, select.
Chicago.R 1,755 per passenger.Departing Wed, 3 Jun.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Wed, 3 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,755, select.
Chicago.R 1,786 per passenger.Departing Wed, 29 Apr.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Wed, 29 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,786, select.
Chicago.R 1,855 per passenger.Departing Wed, 1 Jul.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Wed, 1 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,855, select.
Chicago.R 2,155 per passenger.Departing Sun, 17 Jan.One-way flight with Viva.Outbound indirect flight with Viva, departs from Cancun on Sun, 17 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,155, select.
Chicago.R 2,204 per passenger.Departing Wed, 5 Aug.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Cancun on Wed, 5 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,204, select.
Chicago.R 2,253 per passenger.Departing Fri, 19 Feb.One-way flight with Viva.Outbound indirect flight with Viva, departs from Cancun on Fri, 19 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,253, select.
Chicago.R 2,928 per passenger.Departing Fri, 25 Sep.One-way flight with Viva.Outbound indirect flight with Viva, departs from Cancun on Fri, 25 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,928, select.
Chicago.R 3,015 per passenger.Departing Thu, 5 Nov.One-way flight with Viva.Outbound indirect flight with Viva, departs from Cancun on Thu, 5 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,015, select.
Chicago.R 3,018 per passenger.Departing Thu, 3 Dec.One-way flight with Viva.Outbound indirect flight with Viva, departs from Cancun on Thu, 3 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,018, select.
Chicago.R 3,026 per passenger.Departing Thu, 29 Oct.One-way flight with Viva.Outbound indirect flight with Viva, departs from Cancun on Thu, 29 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,026, select.
Chicago.R 4,161 per passenger.Departing Wed, 9 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Wed, 9 Sep, arriving in Chicago Midway.Price includes taxes and charges.From R 4,161, select.
Chicago.R 4,421 per passenger.Departing Thu, 1 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cancun on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 4,421, select.
Chicago.R 4,448 per passenger.Departing Tue, 17 Nov.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Cancun on Tue, 17 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 4,448, select.
Chicago.R 5,188 per passenger.Departing Mon, 1 Feb.One-way flight with United.Outbound direct flight with United departs from Cancun on Mon, 1 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 5,188, select.
Chicago.R 5,222 per passenger.Departing Mon, 1 Mar.One-way flight with United.Outbound direct flight with United departs from Cancun on Mon, 1 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 5,222, 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.
Apr
from R 1,786
May
from R 1,753
Jun
from R 1,755
Jul
from R 1,855
Aug
from R 2,204
Sep
from R 2,928
Oct
from R 3,026
Nov
from R 3,015
Dec
from R 3,018
Jan
from R 2,155
Feb
from R 2,253
Mar
from R 5,222

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.

Chicago Midway

14km from central Chicago
Closest
from R 2,474
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from R 1,753
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from R 3,131
Search flights

Cancun to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,753
Cheapest month to flyMay
Average flight time3 hrs, 51 mins
Most popular airlineUnited
Average flights per week174

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 R 2,361. 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 50 minutes is the average flight time from Cancun to Chicago.
United, Emirates and American Airlines fly direct from Cancun to Chicago.
As of April 2026, there are 98 flights per week flying from Cancun to Chicago.
The cheapest month to fly from Cancun to Chicago is usually May.
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 R 2,361.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Cancun Airport to Chicago on Thursday, 7 May 2026.
Yes – the average flight time is 3 hours and 50 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 April, the average temperature is usually around 8°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

  • Approximately 3 hours 50 minutes is how long you can expect to be travelling on a direct flight from Cancun International Airport to Chicago.

  • Chicago is one hour behind Cancun, where Cancun International Airport is located. Chicago follows the UTC-6 timezone.

  • Cancun International Airport (CUN) to Chicago O'Hare International Airport (ORD) is the most traveled route, with 41 flights a week to pick from. If you have things to do before leaving, the last flight from CUN to ORD is with United Airlines at 16:40. Choose the first departure with United Airlines at 08:15 if you want to fly out earlier.

  • To avoid missing your CUN to Chicago flight, leave plenty of time for things like check-in and baggage drop. Turning up two hours before international departures and an hour before domestic flights is the standard rule.

  • You can expect bigger queues during popular months like March. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a smart move.

  • Direct Cancun International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll step off the plane.

  • Numerous airlines operate direct flights from Cancun International Airport to Chicago. Some of the most popular are:

  • Consider adding a stopover to potentially unlock a cheaper plane ticket from CUN to Chicago. Simply uncheck 'Direct flights only' during your search. Take a detour (and maybe pocket some savings) by stopping at one of these airports:

    • Atlanta Hartsfield-Jackson International Airport (ATL)

    • Los Angeles International Airport (LAX)

    • Orlando International Airport (MCO)

  • CUN is about 13 kilometres from central Cancun. If you're catching a taxi, ride-sharing or driving from the centre, it'll take you 25 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the trip time to be around 35 minutes.

  • Searching for a hotel close to CUN? If you're catching an early flight from Cancun International Airport to Chicago, these accommodation options will put you moments from your departure gate:

  • Cancun International Airport maintains a strong on-time performance, reducing your chances of a delayed flight. Departures from CUN make it to their destination as scheduled 80% of the time.

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

  • The lowest price we've found for a one-way Cancun International Airport to Chicago flight is R 1,753. The cheapest price for a return flight is R 2,361. Keep in mind fares can change due to availability at the time of booking.

  • Don't leave things to the last minute. You're more likely to find cheap flights from CUN to Chicago if you book in advance. Airlines often offer some great early bird deals.

  • If you're flexible with your trip dates, check out the 'Whole month' search tool. It'll show you the lowest price across each month when searching for your Cancun International Airport to Chicago ticket.

  • Picking up a cheap flight from CUN to Chicago couldn't be easier with Price Alerts. Simply create one of these automatic notifications and we'll let you know as soon as a new discount appears.

  • Snag an affordable flight from Cancun International Airport to Chicago with the help of our filters. Choose your ideal duration, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is around 27 kilometres from the centre of Chicago. If you're grabbing a taxi or a ride-share, the drive takes roughly 30 minutes.

  • If you're using public transport, expect a journey time of around 45 minutes.

  • 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. Stay at one of these accommodation options near ORD instead:

  • Reserving your vehicle from Chicago O'Hare International Airport about four weeks in advance of your flight from CUN to Chicago can help you secure the lowest rate.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is located around 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Cancun International Airport to Chicago has hit the runway and you've navigated your way to arrivals, expect a drive of about 25 minutes.

  • If you're catching public transport, it'll take around 30 minutes.

  • After stepping off your CUN to Chicago flight, tuck yourself in at a hotel close to MDW. These are some great options that'll help you get into relaxation mode:

  • Get the pick of the lot. Securing your ride from MDW four weeks in advance often means more savings and a wider range of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Find your way to the city centre after your flight from Cancun International Airport to Chicago has landed. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to get to by car.

  • If you travel by public transport, the journey will take you about 2 hours.

  • If you don't want to make the trip into the centre, find a hotel close to RFD. Make yourself comfy at one of these options after your CUN to Chicago flight:

  • Booking a couple of weeks in advance of your flight from Cancun International Airport to Chicago is a smart way to go. Along with better prices, you'll likely have a better variety of makes and models to choose from at RFD.

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

Best time to go to Chicago

  • January is the quietest month for flights from Cancun International Airport to Chicago, while July is the busiest. Work out the best time to visit Chicago based on whether you like a laid-back vibe or a lively atmosphere.

  • When booking your Cancun International Airport to Chicago plane ticket, think about what kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from CUN to Chicago around that time if you like travelling in cooler conditions.

More about Chicago

Explore more of the United States

  • You've done Chicago, now it's time to explore other corners of the United States. Travel about 451 kilometres southeast to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, your itinerary will be busy.

  • If you want to check out another major destination in the United States, consider Indianapolis, about 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among the biggest draws.

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.