
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $407 (Frontier) |
One-way from | $151 (Priceline) |
Popular in | March |
Cheapest in | January |
Average price | $515 |
Fly from
Fly to
Route
Depart
Return
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 5/5
1:10 pm-11:05 pm
1 stop8h 55m
Chicago Midway
Tue 5/12
12:15 pm-7:00 pm
1 stop7h 45m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 9/11
9:00 am-9:00 pm
2 stops11h 00m
Chicago Midway
Tue 9/15
7:40 am-6:40 pm
2 stops12h 00m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 8/26
9:00 am-9:50 pm
2 stops11h 50m
Chicago Midway
Wed 9/2
7:40 am-6:40 pm
2 stops12h 00m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 9/17
1:25 pm-9:46 pm
1 stop7h 21m
Chicago Midway
Tue 9/22
6:00 am-11:54 am
1 stop6h 54m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 5/5
1:21 pm-10:28 pm
1 stop8h 07m
Chicago Midway
Sat 5/9
6:23 am-1:15 pm
1 stop7h 52m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 6/4
8:45 am-6:55 pm
2 stops9h 10m
Chicago Midway
Sun 6/7
5:05 am-11:35 am
1 stop7h 30m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 5/14
9:00 am-10:45 pm
2 stops12h 45m
Chicago Midway
Tue 5/19
6:00 am-12:10 pm
1 stop7h 10m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 7/28
8:45 am-7:50 pm
2 stops10h 05m
Chicago Midway
Tue 8/4
10:10 am-6:40 pm
2 stops9h 30m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 7/23
1:40 pm-11:00 pm
1 stop8h 20m
Chicago Midway
Wed 8/5
6:15 am-12:45 pm
1 stop7h 30m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 7/31
8:45 am-9:55 pm
2 stops12h 10m
Chicago Midway
Thu 8/6
9:20 am-6:40 pm
2 stops10h 20m
About 0% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
Overall
Boarding
Entertainment
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Boarding
Entertainment
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |