
Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 9, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $439 (American Airlines) |
One-way from | $302 (Avianca) |
Popular in | December |
Cheapest in | July |
Average price | $742 |
Fly from
Fly to
Route
Depart
Return
MadisonSan Jos é
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Wed 2/17
6:39 pm-12:15 pm
1 stop17h 36m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Tue 3/23
7:00 am-9:24 pm
2 stops15h 24m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Thu 2/18
6:00 am-7:53 pm
1 stop13h 53m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Sun 3/21
7:55 pm-9:24 pm
2 stops26h 29m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Mon 3/22
11:00 am-11:55 am
2 stops25h 55m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Mon 3/22
6:39 pm-11:15 am
1 stop17h 36m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Fri 3/26
12:33 pm-12:22 pm
2 stops24h 49m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Sat 3/20
6:30 am-11:15 am
1 stop29h 45m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Wed 11/25
5:30 am-1:12 pm
1 stop7h 42m
San José Juan Santamaria Intl
Wed 12/2
7:00 am-10:52 pm
1 stop15h 52m
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Tue 2/2
6:36 am-6:16 pm
2 stops11h 40m
San José Juan Santamaria Intl
Tue 2/9
9:05 am-9:38 pm
1 stop12h 33m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
Everything you need to know about your flight from Madison to San José
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
Ellen,Oct 2026
GRR - ATL
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
Ellen,Oct 2026
GRR - ATL
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
Ellen,Oct 2026
GRR - ATL
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
Ellen,Oct 2026
GRR - ATL
Find useful and relevant information for your journey from Madison to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$382 | Average$702 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$476 | Average$712 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$539 | Average$959 | FlexibilityNo cancel fee | On-timeN/A |