Round-trip from | $184 (Cheapflightsfares) |
---|---|
One-way from | $106 (Cheapflightsfares) |
Popular in | June |
Cheapest in | November |
Average price | $446 |
Good round-trip deal | $395 or less |
Good one-way deal | $224 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 10/1
12:19 pm-10:48 pm
1 stop9h 29m
Chicago O'Hare Intl
Mon 10/6
7:51 pm-11:30 am
2 stops16h 39m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 9/30
5:54 pm-1:41 pm
1 stop18h 47m
Chicago O'Hare Intl
Tue 10/7
7:59 am-6:58 pm
1 stop11h 59m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 10/1
10:58 am-12:21 am
1 stop12h 23m
Chicago O'Hare Intl
Fri 10/17
3:07 pm-8:19 am
1 stop18h 12m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 11/12
4:08 am-12:46 pm
1 stop8h 38m
Chicago O'Hare Intl
Tue 11/18
2:07 pm-8:19 am
1 stop18h 12m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 10/2
10:08 am-12:21 am
1 stop13h 13m
Chicago O'Hare Intl
Thu 10/9
3:07 pm-4:52 pm
3 stops26h 45m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 10/4
2:54 pm-12:21 am
1 stop8h 27m
Chicago O'Hare Intl
Sun 10/12
3:07 pm-4:52 pm
3 stops26h 45m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 10/21
5:57 am-12:21 am
1 stop17h 24m
Chicago O'Hare Intl
Thu 10/23
3:07 pm-4:52 pm
3 stops26h 45m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 11/7
5:49 am-12:05 am
1 stop18h 16m
Chicago O'Hare Intl
Sun 11/16
2:07 pm-4:50 pm
3 stops26h 43m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 11/5
11:00 am-12:05 am
1 stop13h 05m
Chicago O'Hare Intl
Thu 11/6
2:07 pm-4:50 pm
3 stops26h 43m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 10/24
1:30 pm-12:45 am
1 stop10h 15m
Chicago Midway
Tue 10/28
5:15 am-11:50 am
1 stop7h 35m
The price you pay for your flight from San José, San José Province to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, August is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $245). Flying from San José, San José Province to Chicago in March is currently the most expensive (average of $321). 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 San José, San José Province to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 42% on airfare.
Guatemala City (GUA) – chosen by Cheapflights users on 50% of 1-stop itineraries from San José, San José Province to Chicago on Cheapflights.
Guatemala City (GUA) is the most affordable 1-stop option, with an average round-trip price of $391.
Flights via Guatemala City (GUA) have the shortest average one-way travel time for 1-stop routes: 7h 40m.
Flights via Bogotá (BOG) offer the fastest connection on this route, with an average layover time of 1h 55m.
Crew
Entertainment
Overall
Boarding
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Boarding
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Boarding
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Boarding
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Boarding
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Overall
Boarding
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$249 | Average$485 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$264 | Average$417 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$314 | Average$478 | FlexibilityNo cancel fee | On-time70% | |
Cheapest$377 | Average$560 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$425 | Average$527 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$437 | Average$620 | FlexibilityNo cancel fee | On-time69% |