
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $302 (SmartFares) |
One-way from | $120 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $656 |
Good round-trip deal | $281 or less |
Good one-way deal | $124 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 1/9
6:45 am-3:30 pm
1 stop7h 45m
Cancun
Tue 1/13
8:00 am-4:31 pm
1 stop9h 31m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 1/23
6:00 am-4:45 pm
1 stop9h 45m
Cancun
Wed 1/28
12:15 pm-5:32 pm
1 stop6h 17m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 1/29
12:48 pm-9:11 pm
1 stop7h 23m
Cancun
Mon 2/2
8:00 am-5:32 pm
1 stop10h 32m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 1/5
6:45 am-9:11 pm
1 stop13h 26m
Cancun
Fri 1/9
12:05 pm-10:09 pm
2 stops11h 04m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 1/19
6:00 am-6:47 pm
2 stops11h 47m
Cancun
Mon 1/26
12:05 pm-10:26 pm
2 stops11h 21m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 12/12
10:49 am-9:20 pm
1 stop9h 31m
Cancun
Tue 12/16
8:00 am-4:44 pm
1 stop9h 44m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 12/9
9:25 am-7:45 pm
1 stop9h 20m
Cancun
Thu 12/11
1:45 pm-4:30 pm
Nonstop3h 45m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 12/17
5:25 am-3:25 pm
1 stop9h 00m
Cancun
Mon 12/22
2:30 pm-5:15 pm
Nonstop3h 45m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 1/2
6:00 am-12:30 pm
1 stop5h 30m
Cancun
Fri 1/9
8:00 am-4:31 pm
1 stop9h 31m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 1/1
3:29 pm-12:03 pm
2 stops19h 34m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Cancún, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Cancún (average of $245). Flying from Chicago Midway Airport to Cancún in January is currently the most expensive (average of $430). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s typically best to fly out from Chicago Midway Airport to Cancún in the evening. Doing so could potentially save you 41% on the flight price compared to flying at noon, which is usually more expensive.
About 11% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 150 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Wednesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Frontier have had the lowest number of delays on this route, with no flights being classified as delayed.
Crew
Entertainment
Overall
Comfort
Food
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Comfort
Food
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Comfort
Food
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Comfort
Food
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Comfort
Food
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Comfort
Food
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$161 | Average$490 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$510 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$345 | Average$572 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$362 | Average$567 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$380 | Average$618 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$486 | Average$872 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$3,369 | Average$3,369 | FlexibilityNo cancel fee | On-time81% |