Cheap Flights from San Jose to Chicago, IL from $141
Return flight: Chicago – San Jose
On Cheapflightsplus.com you will find 157 connecting flights from San Jose to Chicago. You can compare airfare deals from 11 airlines and multiple travel sites from $141, book and save on cheap plane tickets and last minute offers. Also check out SJO-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip San Jose to Chicago Flight Deals
To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights».
To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight.
Cheapest flights in November: $141 (one-way), $242 (round-trip).
Direct flights
Check prices for return flight
Best Flights from San Jose to Chicago Today
Take a look at the list of non stop flights and flights with layovers from San Jose to Chicago with the lowest price of $141. Take a look at the list of flights with layovers from San Jose to Chicago from $141. There’re no direct flights. The fastest connecting flight – 7h 45m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $165 | 13:54 San Jose Juan Santamaria Intl | 23:35 Chicago O'Hare International | 8h 41m layover 1h 38m - Panama City | Compania Panamena de Aviacion | CM796 CM235 |
| from $169 | 12:45 San Jose Juan Santamaria Intl | 00:19 Chicago O'Hare International | 10h 34m layover 4h 29m - Miami | Spirit Airlines | NK338 NK1 |
| from $171 | 12:41 San Jose Juan Santamaria Intl | 22:03 Chicago O'Hare International | 8h 22m layover 1h 48m - Miami | American Airlines | AA1600 AA2457 |
| from $179 | 11:00 San Jose Juan Santamaria Intl | 20:26 Chicago O'Hare International | 8h 26m layover 2h 2m - Orlando | Spirit Airlines | NK674 NK910 |
| from $186 | 14:10 San Jose Juan Santamaria Intl | 00:49 Chicago O'Hare International | 9h 39m layover 2h 59m - Miami | American Airlines | AA2202 F91422 |
| from $195 | 12:44 San Jose Juan Santamaria Intl | 00:05 Chicago Midway | 10h 21m layover 4h 11m - Miami | JetBlue | B638 WN543 |
| from $141 | 06:20 San Jose Juan Santamaria Intl | 19:49 Chicago O'Hare International | 12h 29m layover 3h 8m - Panama City 1h 46m - Miami | Compania Panamena de Aviacion | CM465 CM265 NK6 |
| from $155 | 08:36 San Jose Juan Santamaria Intl | 00:19 Chicago O'Hare International | 14h 43m layover 0h 52m - Panama City 6h 34m - Miami | Compania Panamena de Aviacion | CM392 CM265 NK1 |
| from $164 | 12:06 San Jose Juan Santamaria Intl | 00:49 Chicago O'Hare International | 11h 43m layover 1h 46m - Panama City 2h 26m - Miami | Compania Panamena de Aviacion | CM796 CM341 F91422 |
| from $169 | 08:36 San Jose Juan Santamaria Intl | 19:49 Chicago O'Hare International | 10h 13m layover 0h 52m - Panama City 1h 46m - Miami | Compania Panamena de Aviacion | CM392 CM265 NK6 |
| from $180 | 08:36 San Jose Juan Santamaria Intl | 23:05 Chicago O'Hare International | 13h 29m layover 0h 52m - Panama City 5h 16m - Miami | Compania Panamena de Aviacion | CM392 CM265 B6566 |
| from $194 | 08:36 San Jose Juan Santamaria Intl | 21:39 Chicago O'Hare International | 12h 3m layover 0h 52m - Panama City 3h 41m - Miami | Compania Panamena de Aviacion | CM392 CM265 UA628 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 24, 2024
Flight Schedule San Jose to Chicago (Illinois)
Full flight schedule will help you in detecting at what time planes fly from San Jose to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
| Departure | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
07:01 — 23:35
|
07:01 — 09:18
CM459
Compania Panamena de Aviacion
San Jose — Panama City
8h 38m stop
17:56 — 23:35
CM235
Compania Panamena de Aviacion
Panama City — Chicago
|
15h 34m including layover |
Find flight
from$165 |
|
|
11:00 — 20:26
|
11:00 — 16:17
NK674
Spirit Airlines
San Jose — Orlando
2h 2m stop
18:19 — 20:26
NK910
Spirit Airlines
Orlando — Chicago
|
8h 26m including layover |
Find flight
from$179 |
|
|
12:45 — 00:19
|
12:45 — 17:39
NK338
Spirit Airlines
San Jose — Miami
4h 29m stop
22:08 — 00:19
NK1
Spirit Airlines
Miami — Chicago
|
10h 34m including layover |
Find flight
from$169 |
|
|
13:40 — 21:17
+1 day
|
13:40 — 18:57
NK924
Spirit Airlines
San Jose — Orlando
24h 11m stop
19:08 — 21:17
NK912
Spirit Airlines
Orlando — Chicago
|
30h 37m including layover |
Find flight
from$157 |
|
|
13:54 — 23:35
|
13:54 — 16:18
CM796
Compania Panamena de Aviacion
San Jose — Panama City
1h 38m stop
17:56 — 23:35
CM235
Compania Panamena de Aviacion
Panama City — Chicago
|
8h 41m including layover |
Find flight
from$165 |
|
|
14:10 — 00:49
|
14:10 — 19:20
AA2202
American Airlines
San Jose — Miami
2h 59m stop
22:19 — 00:49
F91422
Frontier Airlines
Miami — Chicago
|
9h 39m including layover |
Find flight
from$186 |
|
|
17:33 — 14:22
+1 day
|
17:33 — 20:48
Y45614
Volaris
San Jose — Cancun
13h 39m stop
10:27 — 14:22
NK105
Spirit Airlines
Cancun — Chicago
|
19h 49m including layover |
Find flight
from$238 |
|
|
00:44 — 18:25
|
00:44 — 06:06
AA696
American Airlines
San Jose — Dallas
2h 49m stop
08:55 — 10:29
AA2603
American Airlines
Dallas — New Orleans
5h 36m stop
16:05 — 18:25
WN1300
Southwest Airlines
New Orleans — Chicago
|
16h 41m including layover |
Find flight
from$341 |
|
|
00:44 — 18:12
|
00:44 — 06:06
AA696
American Airlines
San Jose — Dallas
2h 44m stop
08:50 — 12:58
AA1276
American Airlines
Dallas — Miami
2h 47m stop
15:45 — 18:12
UA715
United Airlines
Miami — Chicago
|
16h 28m including layover |
Find flight
from$344 |
|
|
06:20 — 19:49
|
06:20 — 08:28
CM465
Compania Panamena de Aviacion
San Jose — Panama City
3h 8m stop
11:36 — 15:34
CM265
Compania Panamena de Aviacion
Panama City — Miami
1h 46m stop
17:20 — 19:49
NK6
Spirit Airlines
Miami — Chicago
|
12h 29m including layover |
Find flight
from$141 |
|
|
06:20 — 00:19
|
06:20 — 08:28
CM465
Compania Panamena de Aviacion
San Jose — Panama City
3h 8m stop
11:36 — 15:34
CM265
Compania Panamena de Aviacion
Panama City — Miami
6h 34m stop
22:08 — 00:19
NK1
Spirit Airlines
Miami — Chicago
|
16h 59m including layover |
Find flight
from$141 |
|
|
08:36 — 00:19
|
08:36 — 10:44
CM392
Compania Panamena de Aviacion
San Jose — Panama City
52m stop
11:36 — 15:34
CM265
Compania Panamena de Aviacion
Panama City — Miami
6h 34m stop
22:08 — 00:19
NK1
Spirit Airlines
Miami — Chicago
|
14h 43m including layover |
Find flight
from$155 |
|
|
08:36 — 19:49
|
08:36 — 10:44
CM392
Compania Panamena de Aviacion
San Jose — Panama City
52m stop
11:36 — 15:34
CM265
Compania Panamena de Aviacion
Panama City — Miami
1h 46m stop
17:20 — 19:49
NK6
Spirit Airlines
Miami — Chicago
|
10h 13m including layover |
Find flight
from$169 |
|
|
11:00 — 00:19
|
11:00 — 16:17
NK674
Spirit Airlines
San Jose — Orlando
3h 42m stop
19:59 — 21:08
NK675
Spirit Airlines
Orlando — Miami
1h stop
22:08 — 00:19
NK1
Spirit Airlines
Miami — Chicago
|
12h 19m including layover |
Find flight
from$251 |
|
|
12:06 — 00:49
|
12:06 — 14:14
CM796
Compania Panamena de Aviacion
San Jose — Panama City
1h 46m stop
16:00 — 19:53
CM341
Compania Panamena de Aviacion
Panama City — Miami
2h 26m stop
22:19 — 00:49
F91422
Frontier Airlines
Miami — Chicago
|
11h 43m including layover |
Find flight
from$164 |
|
|
14:22 — 00:49
+1 day
|
14:22 — 20:55
AA1706
American Airlines
San Jose — Charlotte
12h 11m stop
09:06 — 11:18
AA1697
American Airlines
Charlotte — Miami
11h 1m stop
22:19 — 00:49
F91422
Frontier Airlines
Miami — Chicago
|
33h 27m including layover |
Find flight
from$188 |
|
|
15:14 — 09:39
+1 day
|
15:14 — 17:22
CM145
Compania Panamena de Aviacion
San Jose — Panama City
42m stop
18:04 — 21:59
CM268
Compania Panamena de Aviacion
Panama City — Miami
9h 16m stop
07:15 — 09:39
NK478
Spirit Airlines
Miami — Chicago
|
17h 25m including layover |
Find flight
from$155 |
|
|
15:14 — 12:00
+1 day
|
15:14 — 17:22
CM145
Compania Panamena de Aviacion
San Jose — Panama City
42m stop
18:04 — 21:59
CM268
Compania Panamena de Aviacion
Panama City — Miami
11h 46m stop
09:45 — 12:00
WN5346
Southwest Airlines
Miami — Chicago
|
19h 46m including layover |
Find flight
from$181 |
|
|
16:36 — 09:39
+2 days
|
16:36 — 19:43
P57085
Copa Airlines Colombia
San Jose — Bogota
18h 27m stop
14:10 — 19:15
NK400
Spirit Airlines
Bogota — Miami
12h stop
07:15 — 09:39
NK478
Spirit Airlines
Miami — Chicago
|
40h 3m including layover |
Find flight
from$292 |
|
|
16:50 — 07:40
+1 day
|
16:50 — 18:05
AV670
Avianca
San Jose — San Salvador
2h 35m stop
20:40 — 02:50
AV590
Avianca
San Salvador — Washington D.C.
3h 55m stop
06:45 — 07:40
WN4716
Southwest Airlines
Washington D.C. — Chicago
|
13h 50m including layover |
Find flight
from$325 |
|
|
17:33 — 13:12
+1 day
|
17:33 — 20:48
Y45614
Volaris
San Jose — Cancun
10h 12m stop
07:00 — 10:34
DL596
Delta Air Lines Inc.
Cancun — Atlanta
1h 36m stop
12:10 — 13:12
DL1792
Delta Air Lines Inc.
Atlanta — Chicago
|
18h 39m including layover |
Find flight
from$254 |
|
*Departure and arrival times - local. Updated on April 24, 2024
Flight Information
Below we will explain in detail what the flights cost on the destination from San Jose to Chicago depends on and how to choose the most interesting flight option for you.
Distance between San Jose and Chicago is 3562 miles. Time difference between the cities is 0h. Airplanes depart 00:44 to 23:21 from 2 San Jose airports and arrive 00:44 to 23:21 to 7 Chicago airports. Average flight time is 13h 29m.
- The fastest flight 7h 45m
- Average flight time 13h 29m
- The earliest flight 00:44
- The latest flight 23:21
- Distance 2214 ml
What is the lowest airfare San Jose to Chicago?
The cheapest plane ticket found by our users is $141. This airfare is for economy class on one-way CM465 flight by Compania Panamena de Aviacion for July 31, 2021 which leaves Juan Santamaria Intl in San Jose at 06:20 am and arrives at Chicago O'Hare International at 00:19.
Economy class
$141
Business class
?
First class
?
Popular Airlines on the Route
The flight San Jose — Chicago is served by 11 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by American Airlines - 27 departures per week at the price of from $ 171 . And the most expensive tickets are offered by Avianca airline - from $ 1158.
Direct flights
There’re no direct flights on this route. Try flights with stops.
Connecting Flights
There are 157 flights with layovers on the route. The fastest connecting flight is CM145 by Compania Panamena de Aviacion takes 7h 45m and the cheapest is CM465 by Compania Panamena de Aviacion for $141.
- AA - American Airlinesfrom $171Find
- B6 - JetBluefrom $194Find
- P5 - Copa Airlines Colombiafrom $292Find
- AV - Aviancafrom $299Find
- WN - Southwest Airlinesfrom $407Find
- DL - Delta Air Lines Inc.from $291Find
- CM - Compania Panamena de Aviacionfrom $141Find
- Y4 - Volarisfrom $238Find
- UA - United Airlinesfrom $339Find
- AM - Aeromexicofrom $389Find
- NK - Spirit Airlinesfrom $157Find
See more connecting flights
Airports
You can fly from San Jose to Chicago from 2 airports (Juan Santamaria Intl, Tobias Bolanos Intl).
San Jose airports
- Juan Santamaria Intl-SJOfrom $141Find
- Tobias Bolanos Intl-SYQFind
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from San Jose by 11 airlines that use 3 aircraft brands. They range from huge modern airplanes to small-sized.
- Boeing 737-800from $165Find
- Airbus A319from $171Find
- Airbus A320-100/200from $442Find
Top International Destinations from San Jose
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
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