$218 Cheap Flights from Cancun (CUN) to Chicago (MDW)
Popular airlines from Cancun Intl. Airport (CUN) to Chicago Midway Airport (MDW)
DeltaDelta
Southwest AirlinesSouthwest Airlines
AeromexicoAeromexico
Frontier AirlinesFrontier Airlines
VolarisVolaris
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Cheap Flights from Cancun to Chicago (CUN-MDW)
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
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Cancun (CUN) to Chicago (MDW) at a glance
Travel from Cancun (CUN) to Chicago (MDW) with a selection of airlines catering to this international short-haul route. You can compare a range of options from full-service to budget carriers, allowing you to find flights from Cancun that align with your budget and schedule. As you plan your visit, get ready to explore the iconic sights and vibrant neighborhoods of Chicago while securing cheap fares from Cancun for your journey.
- Fastest flight duration: around 3h 45m non-stop
- Route distance: roughly 1,400 miles (2,250 km)
- Flights per week: around 11 departures on average
- Typical fares (one-way): economy tickets often range from $135–$495, depending on seasonality and how far ahead you book
Flights from Cancun International Airport (CUN) to Midway International Airport (MDW)
Based on the latest traveler bookings, here are the top airlines favored for flights from Cancun to Chicago, featuring both non-stop and one-stop options. Popular layover locations include Hartsfield-Jackson Atlanta International Airport (ATL) with an approximate layover of 3 hours and 30 minutes, William P. Hobby Airport (HOU) at about 2 hours and 15 minutes, and Detroit Metropolitan Wayne County Airport (DTW) with a layover of around 1 hour and 45 minutes. This variety allows you to tailor your itinerary by balancing price, total travel time, and cabin class.
- Southwest Airlines: This budget-friendly airline provides both non-stop and one-stop flights, with one-way ticket prices generally ranging from $135 to $505. It operates about 74% of the departures on this route, typically taking around 3 hours and 45 minutes for direct flights.
- Frontier Airlines: A low-cost option that offers both non-stop and one-stop services, Frontier's one-way fares usually fall between $135 and $445. It makes up approximately 11% of departures on this route, with one-stop flights averaging 5 hours of air time and a total travel duration of about 7 hours and 30 minutes.
- Delta: As a full-service airline, Delta provides one-stop service with one-way fares typically ranging from $180 to $465. It represents around 9% of departures on this route, featuring an in-flight time of 5 hours, leading to a total journey time of roughly 7 hours and 30 minutes including layovers.
- Volaris: This budget airline specializes in one-stop flights, with one-way fares usually between $200 and $520. It accounts for about 4% of the departures on this route, offering an in-flight duration of 5 hours and an overall travel time of approximately 7 hours and 30 minutes, including layovers.
- Aeromexico: A full-service airline providing one-stop flights, Aeromexico's one-way ticket prices typically range from $180 to $680. It comprises about 3% of departures on this route, with an in-flight duration of 5 hours, resulting in a total travel time of around 7 hours and 30 minutes with layovers.
Best time to fly from Cancun (CUN) to Chicago (MDW)
The most popular months for travelers flying from Cancun to Chicago are January, March, and April, when peak temperatures in Chicago reach up to 46°F in April. If you prefer quieter travel, consider September, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 67.1°F. For better deals, July usually offers the lowest average one-way fare around $206. Flight availability peaks in March, with approximately 15 flights per week, making it easier to find convenient departure times. May has the fewest flights, with approximately 8 flights per week.
- Cheapest time to fly: July usually offers good deals with average one-way fare around $206, roughly 17% cheaper than the yearly average.
- More budget-friendly months to fly: June, September, and May typically offer average one-way fares roughly ranging from $210 to $221.
- Most flight options: March has the highest number of flights from Cancun to Chicago, with approximately 15 flights per week, giving you more flexibility in scheduling your trip.
| Month | Temperature | Demand | Weekly Flights | Average one-way Fare |
| January | 25.7°F (-3.5°C) | High | 13 | $341 |
| February | 27.0°F (-2.8°C) | Average | 9 | $263 |
| March | 37.0°F (2.8°C) | High | 15 | $274 |
| April | 46.0°F (7.8°C) | High | 11 | $300 |
| May | 57.0°F (13.9°C) | Average | 8 | $221 |
| June | 67.3°F (19.6°C) | Average | 12 | $210 |
| July | 73.4°F (23.0°C) | Average | 13 | $206 |
| August | 73.0°F (22.8°C) | Average | 10 | $251 |
| September | 67.1°F (19.5°C) | Low | 9 | $214 |
| October | 54.9°F (12.7°C) | Low | 9 | $244 |
| November | 42.3°F (5.7°C) | Average | 10 | $255 |
| December | 33.1°F (0.6°C) | Low | 9 | $231 |
*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.
Alternative routes from Cancun (CUN) to Chicago (MDW)
- Cancun to Chicago (CUN-ORD): O'Hare International Airport (ORD) is located roughly 16 miles from Midway International Airport (MDW). One-way economy tickets on this route generally range from $130 to $520, influenced by the time of year and how far in advance you book. Travelers can choose between non-stop and one-stop flights. Major airlines operating on this route include American Airlines and United. Additionally, business class service is available for those looking for enhanced comfort.
- Cozumel to Chicago (CZM-ORD): Cozumel International Airport (CZM) is about 37 miles from Cancun International Airport (CUN), while O'Hare International Airport (ORD) is approximately 16 miles from Midway International Airport (MDW). One-way economy fares for this journey typically fall between $215 and $715, depending on factors like seasonality and booking lead time. This route offers both non-stop and one-stop flights, with common layover points at George Bush Intercontinental Airport (IAH) and Mexico City International Airport (MEX). American Airlines and United are the leading carriers for this route, and business class options are also offered.
How to find the best prices for flights from Cancun (CUN) to Chicago (MDW)
Getting some of the best deals on flights from Cancun to Chicago is all about timing and flexibility. Here are some key tips to help you save:
- Best times to book and fly: cheaper fares are usually found when booking 2 to 8 weeks in advance, which aligns with when most travelers make their reservations. Departures between 12 PM and 6 PM often offer lower prices and are also the most sought-after flight times. Additionally, flying on Saturday provides both affordable prices and is the most popular travel day.
- Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
- Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
- Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
- Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
- Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.
*Members only. Savings vary and are not available on all bundles. Select hotels.
Arriving at Midway International Airport from Cancun International Airport
Chicago welcomes travelers from Cancun with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:
- Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
- Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
- Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
- Public transportation: From Midway International Airport, travelers will find Midway Station (a metro station) just about 0.2 miles away on foot, while Chicago Ashburn Station (a train station) is located approximately 4.1 miles from the airport and is best accessed by car. Additionally, Lyons Seaport (a seaport) is around 7.2 miles away by car, providing further connectivity options.
Cancun to Chicago Flights
The cheapest times to fly from Cancun to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Cancun to Chicago are during the month of November. You can find some of the cheapest flights from Cancun to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Cancun to Chicago
Sunday is one of the best days to book for cheap flights from Cancun to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Cancun to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Cancun to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $218 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Cancun to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Cancun to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
Frequently Asked Questions
How much does a flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $218 and cheap return flights $359 Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights generally range between $242 and $931, and roundtrip flights usually range from $338 to $1234. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.
*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from CUN to MDW is November when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly direct from CUN to MDW on Frontier Airlines, with around 7 flights per week.
What is the cheapest airline that flies from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
Volaris is one of the cheapest airlines offering connecting flights from Cancun, Quintana Roo (CUN) to Chicago, IL (MDW), starting from around $383. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Cancun (CUN) to Chicago (MDW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. WN offers the most daily flights from CUN to MDW, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can find approximately 1 nonstop flights per day from Cancun Intl. (CUN) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Cancun, Quintana Roo (CUN) to Chicago, IL (MDW) typically departs at around 6:00 AM, operated by Aeromexico and Delta. This seasonal service is available in March, providing a great option for spring travelers. An early departure allows you to make the most of your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
For flights from Cancun Intl. (CUN) to Midway Intl. (MDW), the most popular departure times are in the late afternoon, from 3pm to 6pm. This accounts for around 41% of total traffic. Major carriers like Delta and Southwest Airlines offer flights during this window. Many travelers prefer this timing as it allows for a relaxed day at the beach before heading to the airport.
How long does it take to fly from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from CUN to MDW typically takes around 3 hours 50 minutes, covering approximately 1,435 miles. Connecting flights on this route usually add 3 hours 30 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
Business class seats are offered on the CUN to MDW route with Delta Air Lines and Aeromexico.
How do I earn miles on a Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.
*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Cancun Intl. (CUN)?
From Cancun Intl. (CUN), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Los Angeles Intl. (LAX), Seattle - Tacoma Intl. (SEA), San Francisco Intl. (SFO) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Cancun, Quintana Roo (CUN-Cancun Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.
Travel information
Origin airport | Cancun Intl. Airport |
|---|---|
Destination airport | Chicago Midway Airport |
Distance | 1,434 miles away |
Airlines serving | Delta, Southwest Airlines, Aeromexico, Frontier Airlines, Volaris |
Popular airline | Delta |
Roundtrip price | $359 |
Average flight time | 3 hours 39 mins |