Cheap flights from Chicago Midway Airport to Cancún from $110
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Cancún departing on 9/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Frontier flights from Chicago Midway Airport to Cancún
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Delta flights from Chicago Midway Airport to Cancún
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How to get the cheapest flight ticket from Chicago Midway Airport to Cancún
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Cancún?
If you don’t want to visit Cancún in September, then you should wait until July to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $457.
What is the cheapest day to depart on your flight to Cancún?
The cheapest day to depart from Chicago Midway Airport to Cancún is on a Monday when prices can be found for as low as $370. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $528. These prices are subject to change though, so be sure to set up a Price Alert for flights to Cancún.
What is the cheapest time of day to depart on your flight to Cancún?
Our most recent data shows that the best time of day to fly to Cancún is in the evening. Flights from Chicago Midway Airport to Cancún during this time can be as low as $405. Flights to Cancún are more costly at noon, with an average ticket price of $713. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago Midway to Cancun flight route?
Fly from Chicago Midway to Cancun for the best Chicago Midway - Cancun flight prices
How far in advance should I book a flight to Cancún?
You are more likely to see cheaper flights to Cancún from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Cancún for around $587 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cancún from Chicago Midway Airport for as low as $440 on momondo.
What cabin class options are available on Chicago Midway to Cancun flights?
There are 1 cabin classes available to choose from on Chicago Midway to Cancun flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago Midway to Cancun?
Frontier, Southwest, and Aeromexico are the most popular carriers operating from Chicago Midway to Cancun
What airlines fly to Cancún?
Southwest, Delta and Volaris are the top three most popular airlines that fly to Cancún from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 77% of people opting to fly with this airline when traveling to Cancún. Keep in mind that there are 8 different airlines that fly to Cancún on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Cancún on average per day?
1 flights are operational daily from Chicago Midway Airport to Cancún as of July 2025. The most popular departure time for this route is 9:00AM, with 58% of flights per day taking off at noon.
How many flights depart from Chicago Midway Airport to Cancún on average per week?
As of July 2025, 9 flights take off from Chicago Midway Airport and land in Cancún each week. The most common flight departure day for this route is Mon, with 22% of weekly flights taking off on this day.
When to book flights from Chicago Midway Airport to Cancún
Cheap Chicago Midway Airport to Cancún (MDW to CUN) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Cancún
How far is Chicago Midway to Cancun by plane?
Chicago Midway and Cancun are 1425.4 mi apart from one another. Typically, this will take 3h 35m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Cancun Airport?
Prices for flights from Chicago Midway Airport to Cancun Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Cancun Airport?
As of July 2025, there are 8 operators available to choose from for flights from Chicago Midway Airport to Cancun Airport.
How old do you have to be to fly from Chicago Midway Airport to Cancun Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Cancun Airport.
What documentation or ID do you need to fly to Cancun Airport?
The travel and health documents you'll need for your trip to Cancun Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cancun Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Cancún?
Based on momondo bookings for flights between Chicago Midway Airport and Cancún, the leading plane model is Airbus A320neo, making up 21.66% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 21.51%, Boeing 737 MAX 8 with 16.73%, and Boeing 737-900 with 10.63%.
What is the most popular airline from Chicago Midway Airport to Cancún?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Cancún is Southwest (74% of total bookings). The next most popular airlines are Delta (15%), Volaris (4%), and Aeromexico (3%).
Best airlines flying from Chicago Midway Airport to Cancún
Compare and see reviews for airlines that fly from Chicago Midway Airport to Cancún with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $161 | Free Cancellation | Rating 7.4 8,861 reviews | |||
| PriceFrom $198 | Free Cancellation | Rating 5.9 3,286 reviews | |||
| PriceFrom $241 | Free Cancellation | Rating 6.3 8,086 reviews | |||
| PriceFrom $319 | Free Cancellation | Rating 7.5 1,718 reviews | |||
| PriceFrom $345 | Free Cancellation | Rating 8.0 4,266 reviews | |||
| PriceFrom $380 | Free Cancellation | Rating 8.0 7,982 reviews | |||
| PriceFrom $486 | Free Cancellation | Rating 6.7 1,171 reviews | |||
| PriceFrom $3,369 | Free Cancellation | Rating 7.5 1,805 reviews |
Southwest Flights From Chicago Midway Airport to Cancún
Southwest operates around 9 flights from Chicago Midway Airport to Cancún every week. The average price of these flights found in the last 72 hours has been $580, but momondo users have found Southwest deals from Chicago Midway Airport to Cancún from as low as $345 round-trip. Southwest has been scored 8.0/10 in 4,266 reviews.
Traveling to a place near Cancún?
Book flights to Cancún if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Cancún?
Finding the right flight to Cancún from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Cancún quick and easy, saving you time and money.
Can I find flights from Chicago to Cancún with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to Cancún flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Cancún?
momondo provides multiple filters to help you find the best flight to Cancún from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Cancún right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Cancún from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.