
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $344 (Kiwi.com) |
One-way from | $84 (Priceline) |
Popular in | December |
Cheapest in | October |
Average price | $712 |
Good round-trip deal | $445 or less |
Good one-way deal | $258 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 2/12
2:22 pm-9:52 pm
1 stop7h 30m
San José Juan Santamaria Intl
Mon 2/16
11:01 am-12:04 am
1 stop13h 03m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 2/13
2:22 pm-7:06 am
1 stop16h 44m
San José Juan Santamaria Intl
Fri 2/27
5:50 am-12:04 am
1 stop18h 14m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 2/15
2:22 pm-7:06 am
1 stop16h 44m
San José Juan Santamaria Intl
Sun 2/22
6:08 pm-12:31 pm
1 stop18h 23m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 2/3
2:22 pm-9:52 pm
1 stop7h 30m
San José Juan Santamaria Intl
Tue 2/10
5:50 am-12:04 am
1 stop18h 14m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 2/13
2:22 pm-7:06 am
1 stop16h 44m
San José Juan Santamaria Intl
Tue 2/17
5:50 am-12:04 am
1 stop18h 14m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 2/10
7:34 am-9:52 pm
1 stop14h 18m
San José Juan Santamaria Intl
Tue 2/17
2:54 pm-12:04 am
1 stop9h 10m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 1/18
2:13 pm-8:21 am
1 stop18h 08m
San José Juan Santamaria Intl
Sun 1/25
8:11 am-12:24 am
1 stop16h 13m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 2/2
5:30 am-1:00 pm
1 stop7h 30m
San José Juan Santamaria Intl
Fri 2/13
7:00 am-4:49 pm
1 stop9h 49m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 1/19
6:50 am-10:15 pm
2 stops15h 25m
San José Juan Santamaria Intl
Fri 1/23
7:00 am-6:45 pm
2 stops11h 45m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 1/19
7:39 am-12:56 pm
Nonstop5h 17m
San José Juan Santamaria Intl
Mon 1/26
2:05 pm-7:35 pm
Nonstop5h 30m
| 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*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*1 star |
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to San José, you should look to book at least 5 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, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San José (average of $248). Flying from Chicago O'Hare Intl Airport to San José in March is currently the most expensive (average of $380). 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.
When flying from Chicago O'Hare Intl Airport to San José, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
About 9% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 174 minutes.
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Monday 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, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
Panama City (PTY) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago O'Hare Intl Airport to San José on Cheapflights.
Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $371.
Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 7h 06m.
Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 29m.
Overall
Entertainment
Comfort
Boarding
Crew
Food
Reviews
Maria,Dec 2025
PTY - SLA
Overall
Entertainment
Comfort
Boarding
Crew
Food
Reviews
Maria,Dec 2025
PTY - SLA
Overall
Entertainment
Comfort
Boarding
Crew
Food
Reviews
Maria,Dec 2025
PTY - SLA
Overall
Entertainment
Comfort
Boarding
Crew
Food
Reviews
Maria,Dec 2025
PTY - SLA
Overall
Entertainment
Comfort
Boarding
Crew
Food
Reviews
Maria,Dec 2025
PTY - SLA
Overall
Entertainment
Comfort
Boarding
Crew
Food
Reviews
Maria,Dec 2025
PTY - SLA
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$221 | Average$645 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$381 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$307 | Average$454 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$309 | Average$507 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$345 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$349 | Average$590 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$423 | Average$642 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$441 | Average$627 | FlexibilityNo cancel fee | On-time63% |