
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Frontier) |
One-way from | $106 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $353 |
Good round-trip deal | $254 or less |
Good one-way deal | $91 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 4/21
6:00 am-2:01 pm
1 stop8h 01m
Cancun
Fri 4/24
3:15 pm-10:28 pm
1 stop7h 13m
ChicagoMorelia
MDW - MLM
MDWMLM
Chicago Midway
Sat 5/2
2:32 pm-5:41 pm
Nonstop4h 09m
Morelia
Sat 5/9
8:22 am-1:15 pm
Nonstop3h 53m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/9
6:10 am-9:45 am
Nonstop3h 35m
Cancun
Tue 5/12
3:15 pm-6:55 pm
Nonstop3h 40m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 5/7
6:23 am-8:16 pm
1 stop13h 53m
Cancun
Thu 5/14
3:02 pm-9:09 pm
1 stop6h 07m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 5/16
6:23 am-12:40 pm
1 stop6h 17m
Cancun
Tue 5/19
8:00 am-4:12 pm
1 stop8h 12m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 4/25
10:40 am-2:10 pm
Nonstop3h 30m
Cancun
Sat 5/2
4:00 pm-7:40 pm
Nonstop3h 40m
ChicagoDurango
MDW - DGO
MDWDGO
Chicago Midway
Sat 5/9
4:15 pm-7:14 pm
Nonstop3h 59m
Durango Guadalupe Victoria
Tue 5/19
10:26 am-2:51 pm
Nonstop3h 25m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 4/12
6:00 am-2:08 pm
1 stop8h 08m
Cancun
Wed 4/15
1:50 pm-10:28 pm
1 stop8h 38m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 4/16
9:35 am-1:10 pm
Nonstop3h 35m
Cancun
Thu 4/23
4:10 pm-7:50 pm
Nonstop3h 40m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 4/12
6:00 am-2:08 pm
1 stop8h 08m
Cancun
Mon 4/20
8:00 am-10:28 pm
1 stop14h 28m
Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $101). Flying from Chicago Midway Airport to Mexico in November is currently the most expensive (average of $243). 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.
One of the essential ways to save on airfare from Chicago Midway Airport to Mexico is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 24% on airfare.
About 16% of weekly flights between Chicago and Mexico have experienced delays in the past year, with the average delay time being 149 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Friday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 13% of flights being delayed.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$417 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$198 | Average$420 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$292 | Average$606 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$358 | Average$3,633 | FlexibilityNo cancel fee | On-timeN/A |