Airlines with flights from San Jose to Chicago
There are 9 airlines with scheduled flights between SJO and ORD. United is the only airline with non-stop flights from Juan Santamaria International to Chicago O'Hare and the flight time is 5 hours and 33 minutes.
There are 9 airlines with scheduled flights between SJO and ORD. United is the only airline with non-stop flights from Juan Santamaria International to Chicago O'Hare and the flight time is 5 hours and 33 minutes. Choose airline
Direct
Non-stop
5h 33min
Via Miami
7h 57min
Via Atlanta
7h 59min
Via Houston
8h 6min
Via Panama City
8h 12min
Via Orlando
8h 25min
Via Dallas
8h 31min
Via Fort Lauderdale
8h 47min
Via Toronto
8h 48min
Via Charlotte
8h 54min
Via Dulles
9h 8min
Via Mexico City
9h 28min
NEW
Via Guatemala City
7h 20min
Via San Salvador
9h 50min
Schedules
Non-stop with United Airlines
-
Total flight time: 5 hours and 33 minutes
-
Chicago is a United Airlines hub (Largest hub ).
-
1 flight per week
-
Boeing 737MAX 8 Passenger
-
First class available
SJO
Direct
ORD
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
UA1952
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----
----
----
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13:00
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The timetable & schedule information was updated at 2026-04-21
Via Miami with American Airlines
-
Total flight time: 7h 57m - 11h 53m.
-
One World Alliance
-
Chicago is a American Airlines hub.
-
114 flights per week
SJO
Via MIA
ORD
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
AA498
AA2247
AA2247
06:00
07:00
07:00
06:00
06:00
06:00
06:00
AA1600
AA1881
AA1881
12:58
12:58
12:58
12:58
12:58
12:58
12:58
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
-
Total flight time: 7h 59m - 9h 48m.
-
Sky Team Alliance
-
39 flights per week
SJO
Via ATL
ORD
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
DL1756
DL1199
DL1199
13:16
13:16
13:16
13:16
13:16
13:16
13:16
The timetable & schedule information was updated at 2026-04-21
Via Houston with United Airlines
-
Total flight time: 8h 06m - 11h 20m.
-
Chicago is a United Airlines hub (Largest hub ).
-
91 flights per week
-
Boeing 737MAX 8 Passenger
SJO
Via IAH
ORD
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
UA1097
UA2182
UA2182
00:30
00:30
00:30
00:30
00:30
00:30
00:30
UA1447
UA699
UA699
07:55
07:55
07:55
07:55
07:55
07:55
07:55
UA1589
UA2197
UA2197
11:13
11:13
11:13
11:13
11:13
11:13
11:13
UA1099
UA1752
UA1752
13:25
13:25
13:25
13:25
13:25
13:25
13:25
The timetable & schedule information was updated at 2026-04-21
Via Panama City with Copa Airlines
-
Total flight time: 8h 12m - 12h 16m.
-
San Jose is a Copa Airlines focus city.
-
56 flights per week
SJO
Via PTY
ORD
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
CM461
CM228
CM228
04:08
04:08
04:08
04:08
04:08
04:08
04:08
CM193
CM773
CM773
----
12:06
----
----
12:06
11:00
----
CM145
CM773
CM773
----
13:37
----
----
----
----
----
CM343
CM844
CM844
14:48
14:48
14:48
----
----
CM343
CM773
CM773
----
14:48
----
----
14:48
14:48
----
CM343
CM235
CM235
----
----
----
----
----
----
14:48
CM115
CM844
CM844
17:55
17:55
17:55
17:55
17:55
----
----
CM839
CM844
CM844
18:17
18:17
18:17
18:17
18:17
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The timetable & schedule information was updated at 2026-04-21
Via Orlando with Southwest
Via Fort Lauderdale with Spirit
Via Toronto with Air Canada
Via Mexico City with Aeromexico
Via Guatemala City with AVIANCA