Round-trip from | $251 (Kiwi.com) |
---|---|
One-way from | $82 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $340 |
Good round-trip deal | $562 or less |
Good one-way deal | $217 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 10/8
7:59 am-4:34 pm
1 stop9h 35m
San José Juan Santamaria Intl
Mon 10/13
5:55 pm-1:41 pm
1 stop18h 46m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 11/6
2:07 pm-8:19 am
1 stop18h 12m
San José Juan Santamaria Intl
Mon 11/10
4:08 am-12:46 pm
1 stop8h 38m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 11/11
6:56 am-4:40 pm
1 stop9h 44m
San José Juan Santamaria Intl
Tue 11/18
4:08 am-12:46 pm
1 stop8h 38m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 11/1
3:07 pm-7:33 am
1 stop17h 26m
San José Juan Santamaria Intl
Wed 11/5
4:08 am-12:46 pm
1 stop8h 38m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 11/18
6:56 am-6:55 pm
1 stop11h 59m
San José Juan Santamaria Intl
Mon 11/24
11:00 am-12:05 am
1 stop13h 05m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 11/3
2:07 pm-7:33 am
1 stop17h 26m
San José Juan Santamaria Intl
Sun 11/9
4:08 am-12:46 pm
1 stop8h 38m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 11/13
2:07 pm-8:19 am
1 stop18h 12m
San José Juan Santamaria Intl
Mon 11/17
4:08 am-12:46 pm
1 stop8h 38m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 11/4
6:56 am-6:55 pm
1 stop11h 59m
San José Juan Santamaria Intl
Tue 11/25
10:08 am-12:05 am
1 stop13h 57m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 10/21
6:00 am-11:58 am
1 stop6h 58m
San José Juan Santamaria Intl
Fri 10/24
1:23 pm-10:14 pm
1 stop7h 51m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 11/11
7:00 am-8:30 pm
1 stop13h 30m
San José Juan Santamaria Intl
Fri 11/21
2:10 pm-12:10 am
1 stop10h 00m
The best time to book flights from Chicago to San José, San José Province is 23 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, September is the cheapest month in which you can book a flight from Chicago to San José, San José Province (average of $398). Flying from Chicago to San José, San José Province in March is currently the most expensive (average of $554). 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 to San José, San José Province is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 41% on airfare.
Travelers seeking maximum savings on their Chicago to San José, San José Province flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Orlando (MCO) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to San José, San José Province 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 Fort Lauderdale (FLL) offer the fastest connection on this route, with an average layover time of 2h 41m.
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$263 | Average$445 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$307 | Average$460 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$314 | Average$559 | FlexibilityNo cancel fee | On-time70% | |
Cheapest$345 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$394 | Average$618 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$432 | Average$635 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$442 | Average$680 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$442 | Average$657 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$467 | Average$731 | FlexibilityNo cancel fee | On-time69% |