Compare live prices for ORD to SJO on
Thu, 16 Apr 2026. Use the search panel
to change origin, destination, passengers, cabin and trip type instantly.
ORD → SJO16 Apr 2026Live inventory
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Showing 25
of 159
live flights
aircanada
AC-8900
07:55
04/16/2026
ORD
13h 40m
1 Stop
⏱ YYZ · 7h 39m
21:35
04/16/2026
SJO
₹18,811
per person
✕ Non-refundable🔥 Last 2 seats4 fare options
aircanada
AC-4986
07:04
04/16/2026
ORD
14h 31m
1 Stop
⏱ YYZ · 8h 16m
21:35
04/16/2026
SJO
₹18,835
per person
✕ Non-refundable🔥 Last 2 seats3 fare options
Southwest Airlines
WN-3684
06:00
04/16/2026
ORD
6h 10m
1 Stop
⏱ MCO · 1h 25m
12:10
04/16/2026
SJO
₹20,986
per person
✕ Non-refundable8 fare options
Southwest Airlines Dallas
WN-4071
19:35
04/16/2026
ORD
16h 35m
1 Stop
⏱ MCO · 11h 45m
12:10
04/17/2026
+1
SJO
₹20,986
per person
✕ Non-refundable7 fare options
Southwest Airlines
WN-3310
20:35
04/16/2026
MDW
15h 35m
1 Stop
⏱ MCO · 10h 55m
12:10
04/17/2026
+1
SJO
₹22,160
per person
✓ Refundable🔥 Last 3 seats4 fare options
Southwest Airlines
WN-3685
15:05
04/16/2026
ORD
21h 5m
1 Stop
⏱ MCO · 16h 5m
12:10
04/17/2026
+1
SJO
₹22,510
per person
✕ Non-refundable🔥 Last 1 seats4 fare options
Southwest Airlines
WN-3682
16:15
04/16/2026
ORD
19h 55m
2 Stops
⏱ DAL · 2h 25m⏱ MCO · 10h 25m
12:10
04/17/2026
+1
SJO
₹23,984
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3838
05:35
04/16/2026
MDW
6h 35m
1 Stop
⏱ MCO · 2h 0m
12:10
04/16/2026
SJO
₹24,898
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-3964
12:10
04/16/2026
MDW
6h 50m
1 Stop
⏱ HOU · 1h 50m
19:00
04/16/2026
SJO
₹24,898
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-667
07:30
04/16/2026
MDW
11h 30m
2 Stops
⏱ AUS · 2h 30m⏱ HOU · 2h 55m
19:00
04/16/2026
SJO
₹24,960
per person
✓ Refundable4 fare options
Spirit Airlines
NK-2209
19:15
04/16/2026
ORD
16h 18m
1 Stop
⏱ FLL · 11h 19m
11:33
04/17/2026
+1
SJO
₹27,586
per person
✕ Non-refundable2 fare optionsLCC
Spirit Airlines
NK-1986
05:05
04/16/2026
ORD
6h 28m
1 Stop
⏱ FLL · 1h 33m
11:33
04/16/2026
SJO
₹27,586
per person
✕ Non-refundable2 fare optionsLCC
Southwest Airlines
WN-3683
18:15
04/16/2026
ORD
17h 55m
2 Stops
⏱ DEN · 3h 45m⏱ MCO · 5h 35m
12:10
04/17/2026
+1
SJO
₹28,973
per person
✕ Non-refundable4 fare options
aircanada
AC-522
12:50
04/16/2026
ORD
9h 20m
1 Stop
⏱ YUL · 2h 5m
22:10
04/16/2026
SJO
₹29,177
per person
✕ Non-refundable🔥 Last 1 seats12 fare options
aircanada
AC-506
14:00
04/16/2026
ORD
7h 35m
1 Stop
⏱ YYZ · 1h 27m
21:35
04/16/2026
SJO
₹29,621
per person
✕ Non-refundable🔥 Last 3 seats13 fare options
Southwest Airlines
WN-3414
10:15
04/16/2026
MDW
8h 45m
1 Stop
⏱ HOU · 3h 40m
19:00
04/16/2026
SJO
₹29,900
per person
✓ Refundable4 fare options
Southwest Airlines
WN-455
06:55
04/16/2026
MDW
12h 5m
1 Stop
⏱ HOU · 7h 5m
19:00
04/16/2026
SJO
₹29,900
per person
✓ Refundable4 fare options
Southwest Airlines
WN-1433
10:00
04/16/2026
MDW
9h 0m
2 Stops
⏱ MEM · 0h 40m⏱ HOU · 2h 40m
19:00
04/16/2026
SJO
₹29,900
per person
✓ Refundable4 fare options
Southwest Airlines
WN-2644
07:50
04/16/2026
MDW
11h 10m
3 Stops
⏱ MCI · 0h 35m⏱ AUS · 0h 45m⏱ HOU · 2h 55m
19:00
04/16/2026
SJO
₹29,900
per person
✓ Refundable4 fare options
Southwest Airlines
WN-833
07:45
04/16/2026
MDW
11h 15m
2 Stops
⏱ SDF · 0h 45m⏱ HOU · 4h 25m
19:00
04/16/2026
SJO
₹29,900
per person
✓ Refundable4 fare options
Southwest Airlines
WN-7
05:30
04/16/2026
MDW
13h 30m
2 Stops
⏱ DAL · 0h 35m⏱ HOU · 6h 50m
19:00
04/16/2026
SJO
₹29,900
per person
✓ Refundable4 fare options
Southwest Airlines
WN-4646
06:15
04/16/2026
ORD
12h 45m
2 Stops
⏱ LAS · 1h 25m⏱ HOU · 1h 55m
19:00
04/16/2026
SJO
₹30,856
per person
✕ Non-refundable🔥 Last 3 seats4 fare options
aircanada
AC-4081
07:13
04/16/2026
ORD
14h 22m
2 Stops
⏱ YUL · 1h 20m⏱ YYZ · 4h 46m
21:35
04/16/2026
SJO
₹32,834
per person
✕ Non-refundable🔥 Last 1 seats2 fare options
aircanada
AC-4081
07:13
04/16/2026
ORD
14h 57m
1 Stop
⏱ YUL · 7h 30m
22:10
04/16/2026
SJO
₹33,827
per person
✕ Non-refundable🔥 Last 3 seats17 fare options
aircanada
AC-8478
08:40
04/16/2026
ORD
13h 30m
1 Stop
⏱ YUL · 6h 19m
22:10
04/16/2026
SJO
₹33,932
per person
✕ Non-refundable🔥 Last 1 seats16 fare options
😕 No flights match your filters.
Chicago (ORD)
San Jose (SJO)
📅 Results on this page are loaded for 16 Apr 2026. Click View all flights for the complete live search.
Chicago to San Jose — what to expect when booking
The ORD–SJO route is served by multiple carriers throughout the year.
Fares on this route can move quickly — a price available now may not be there 30 minutes later.
If your dates are flexible, try shifting your departure by a day or two using the date strip above.
Mid-week departures often show lower base fares compared to weekend starts on many routes.
Before you book
Compare nearby dates
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❓ Frequently asked questions — Chicago to San Jose flights
Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.
The straight-line distance between Chicago,USA (ORD) and San Jose,Costa Rica (SJO) is approximately shown in the route details above. Actual flying distance may vary slightly depending on routing.
Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.
Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.