Cheap flights from Chicago Midway Airport to Cancún from $181
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 1/26. 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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Not ready to book? to track prices.Frontier flights from Chicago Midway Airport to Cancún
Our best Frontier deals on Chicago Midway Airport to Cancún flight tickets
Southwest flights from Chicago Midway Airport to Cancún
Our best Southwest deals on Chicago Midway Airport to Cancún flight tickets
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Fly from
Fly to
Route
Depart
Return
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sun 11/1
6:16 am-1:41 pm
1 stop6h 25m
Cancun
Thu 11/5
2:51 pm-11:47 pm
1 stop9h 56m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sun 11/1
6:16 am-1:41 pm
1 stop6h 25m
Cancun
Fri 11/6
2:51 pm-11:47 pm
1 stop9h 56m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Fri 11/6
6:17 pm-9:41 am
1 stop14h 24m
Cancun
Fri 11/13
2:51 pm-11:47 pm
1 stop9h 56m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 10/26
9:05 am-12:40 pm
Nonstop3h 35m
Cancun
Wed 11/4
6:00 pm-8:35 pm
Nonstop3h 35m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 11/28
3:45 pm-8:25 pm
Nonstop3h 40m
Cancun
Fri 12/4
6:00 pm-8:35 pm
Nonstop3h 35m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/30
1:05 pm-8:55 pm
1 stop6h 50m
Cancun
Thu 12/3
4:10 pm-10:54 pm
1 stop7h 44m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 10/26
6:04 am-7:55 pm
1 stop13h 51m
Cancun
Wed 11/4
8:00 am-3:17 pm
1 stop8h 17m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Mon 11/2
6:04 am-8:55 pm
1 stop13h 51m
Cancun
Wed 11/11
4:06 pm-10:54 pm
1 stop7h 48m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 12/5
6:00 am-9:08 pm
1 stop14h 08m
Cancun
Sat 12/12
5:48 pm-10:54 pm
2 stops30h 06m
ChicagoCancún
MDW Chicago Midway - CUN Cancun
MDWCUN
Chicago Midway
Sat 10/24
3:30 pm-8:45 am
1 stop17h 15m
Cancun
Fri 10/30
1:51 pm-11:47 pm
1 stop9h 56m
See travel insights to Cancún from
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 typical price of a round-trip flight between Chicago Midway Airport and Cancún?
Prices are currently low for flights on this route.
Typical prices usually range from $453 to $743.The lowest price recently found on this route was $403.
What is the cheapest month to fly to Cancún?
If you don’t want to visit Cancún in February, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $458.
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 Sunday when prices can be found for as low as $472. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $555. 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 morning. Flights from Chicago Midway Airport to Cancún during this time can be as low as $515. Flights to Cancún are more costly at noon, with an average ticket price of $664. 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 from Chicago Midway Airport 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 $556 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 $491 on momondo.
What cabin class options are available on Chicago Midway Airport to Cancún flights?
There are 2 cabin classes available to choose from on Chicago Midway Airport to Cancún 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?
Southwest and Delta are the most popular carriers operating from Chicago Midway to Cancun
What airlines fly to Cancún?
Southwest, Frontier and Aeromexico 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 72% of people opting to fly with this airline when traveling to Cancún. Keep in mind that there are 4 different airlines that fly to Cancún on a routine basis, so you have a few additional options to choose from.
How often are flights from Chicago to Cancún delayed?
Historically, on average around 25% of flights between Chicago and Cancún have experienced a delay on any given week. The average delay length over the past 12 months has been 117 minutes.
What is the most punctual flight time for Chicago to Cancún flights?
Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.
What day of the week experiences the fewest flight delays on this route?
Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.
Which airline has the best punctuality record on Chicago to Cancún flights?
According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 24% of their flights experiencing any sort of delay.
Which airport is the most popular layover for flights between Chicago Midway Airport and Cancún?
Atlanta (ATL) was the most common stop: 75% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from Chicago Midway Airport to Cancún?
Flights via Guadalajara (GDL) offer the lowest average round-trip price of $345.
Which layover airport has the shortest travel time from Chicago Midway Airport to Cancún?
Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 30m.
Which layover airport has the shortest connection time from Chicago Midway Airport to Cancún?
Atlanta (ATL) has the shortest average layover time for this route: 1h 51m.
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
Frequently asked questions about flying 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 October 2026, there are 4 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 A321neo, making up 14.50% of the total bookings. Other popular models include Airbus A321 (sharklets) with 14.17%, Airbus A321-100/200 with 11.86%, and Boeing 737-800 with 10.54%.
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 (72% of total bookings). The next most popular airlines are Frontier (18%), Aeromexico (6%), and Delta (4%).
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 $194 | Free Cancellation | Rating 7.5 1,442 reviews | |||
| PriceFrom $198 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $327 | Free Cancellation | Rating 7.8 8,641 reviews | |||
| PriceFrom $356 | Free Cancellation | Rating 7.9 4,221 reviews |
Southwest Flights From Chicago Midway Airport to Cancún
Southwest operates around 5 flights from Chicago Midway Airport to Cancún every week. The average price of these flights found in the last 72 hours has been $555, but momondo users have found Southwest deals from Chicago Midway Airport to Cancún from as low as $356 round-trip. Southwest has been scored 7.9/10 in 4,220 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.