Cheap Flights from San Jose, CA to Chicago, IL from $97
Return flight: Chicago – San Jose
On Cheapflightsplus.com you will find 2 direct and 479 connecting flights from San Jose to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $97, book and save on cheap plane tickets and last minute offers. Also check out SJC-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: $97 (one-way), $166 (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 $97. The fastest direct flight takes 4h 22m and the fastest connecting – 5h 58m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $236 | 06:30 San Jose San Jose Municipal | 12:55 Chicago O'Hare International | 4h 25m | United Airlines | UA356 |
| from $97 | 16:33 San Jose San Jose Municipal | 05:25+1 день Chicago O'Hare International | 10h 52m layover 5h 48m - Las Vegas | Spirit Airlines | NK2183 NK2186 |
| from $98 | 10:19 San Jose San Jose Municipal | 23:43 Chicago O'Hare International | 11h 24m layover 6h 10m - Las Vegas | Spirit Airlines | NK1371 NK184 |
| from $110 | 11:00 San Jose San Jose Municipal | 05:25+1 день Chicago O'Hare International | 16h 25m layover 11h 15m - Las Vegas | Spirit Airlines | NK2387 NK2186 |
| from $110 | 06:00 San Jose San Jose Municipal | 05:25+1 день Chicago O'Hare International | 21h 25m layover 16h 16m - Las Vegas | Spirit Airlines | NK2385 NK2186 |
| from $110 | 11:01 San Jose San Jose Municipal | 10:50+1 день Chicago O'Hare International | 21h 49m layover 16h 43m - Las Vegas | Spirit Airlines | NK2387 NK2619 |
| from $110 | 06:00 San Jose San Jose Municipal | 10:50+1 день Chicago O'Hare International | 26h 50m layover 21h 45m - Las Vegas | Spirit Airlines | NK2385 NK2619 |
| from $114 | 12:18 San Jose San Jose Municipal | 00:10+1 день Chicago O'Hare International | 9h 52m layover 4h 27m - Denver | Frontier Airlines | F94918 F93172 |
| from $118 | 16:25 San Jose San Jose Municipal | 14:46+1 день Chicago O'Hare International | 20h 21m layover 15h 8m - Las Vegas | Spirit Airlines | NK1141 NK1269 |
| from $118 | 06:30 San Jose San Jose Municipal | 06:03+1 день Chicago O'Hare International | 21h 33m layover 16h 34m - Las Vegas | Spirit Airlines | NK1646 NK1053 |
| from $120 | 14:35 San Jose San Jose Municipal | 14:56+1 день Chicago Midway | 22h 21m layover 17h 13m - Las Vegas | Frontier Airlines | F94104 F92330 |
| from $113 | 15:23 San Jose San Jose Municipal | 05:25+1 день Chicago O'Hare International | 12h 2m layover 0h 58m - San Diego 4h 45m - Las Vegas | Spirit Airlines | NK2506 NK2507 NK2186 |
| from $118 | 11:00 San Jose San Jose Municipal | 11:36+1 день Chicago O'Hare International | 22h 36m layover 7h 25m - Las Vegas 8h 15m - Los Angeles | Spirit Airlines | NK2387 NK2508 NK2192 |
| from $118 | 06:00 San Jose San Jose Municipal | 11:36+1 день Chicago O'Hare International | 27h 36m layover 5h 12m - Las Vegas 15h 24m - Los Angeles | Spirit Airlines | NK2385 NK2686 NK2192 |
| from $118 | 06:00 San Jose San Jose Municipal | 11:36+1 день Chicago O'Hare International | 27h 36m layover 0h 44m - Las Vegas 19h 55m - Los Angeles | Spirit Airlines | NK2385 NK2684 NK2192 |
| from $130 | 06:00 San Jose San Jose Municipal | 23:31 Chicago O'Hare International | 15h 31m layover 2h 14m - Las Vegas 6h 21m - Los Angeles | Spirit Airlines | NK436 NK711 NK3010 |
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on August 17, 2025
Flight Schedule San Jose (California) 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 |
|---|---|---|---|---|
|
06:20 — 12:42
|
06:20 — 12:42
UA374
United Airlines
San Jose — Chicago
|
4h 22m |
Find flight
from$252 |
|
|
06:30 — 12:55
|
06:30 — 12:55
UA356
United Airlines
San Jose — Chicago
|
4h 25m |
Find flight
from$236 |
|
|
06:00 — 14:16
|
06:00 — 07:28
NK436
Spirit Airlines
San Jose — Las Vegas
1h 4m stop
08:32 — 14:16
NK187
Spirit Airlines
Las Vegas — Chicago
|
6h 16m including layover |
Find flight
from$98 |
|
|
06:00 — 05:25
+1 day
|
06:00 — 07:30
NK2385
Spirit Airlines
San Jose — Las Vegas
16h 16m stop
23:46 — 05:25
NK2186
Spirit Airlines
Las Vegas — Chicago
|
21h 25m including layover |
Find flight
from$110 |
|
|
09:00 — 19:48
|
09:00 — 11:18
HA7029
Hawaiian Airlines
San Jose — Seattle
2h 21m stop
13:39 — 19:48
HA6817
Hawaiian Airlines
Seattle — Chicago
|
8h 48m including layover |
Find flight
from$162 |
|
|
10:19 — 23:43
|
09:19 — 10:47
NK1371
Spirit Airlines
San Jose — Las Vegas
6h 10m stop
17:56 — 23:43
NK184
Spirit Airlines
Las Vegas — Chicago
|
11h 24m including layover |
Find flight
from$98 |
|
|
11:00 — 05:25
+1 day
|
11:00 — 12:31
NK2387
Spirit Airlines
San Jose — Las Vegas
11h 15m stop
23:46 — 05:25
NK2186
Spirit Airlines
Las Vegas — Chicago
|
16h 25m including layover |
Find flight
from$110 |
|
|
11:01 — 10:50
+1 day
|
11:00 — 12:31
NK2387
Spirit Airlines
San Jose — Las Vegas
16h 43m stop
05:15 — 10:55
NK2619
Spirit Airlines
Las Vegas — Chicago
|
21h 49m including layover |
Find flight
from$110 |
|
|
12:18 — 00:10
+1 day
|
12:18 — 16:04
F94918
Frontier Airlines
San Jose — Denver
4h 27m stop
20:31 — 00:10
F93172
Frontier Airlines
Denver — Chicago
|
9h 52m including layover |
Find flight
from$114 |
|
|
12:46 — 23:59
|
12:46 — 14:54
HA6780
Hawaiian Airlines
San Jose — Seattle
2h 56m stop
17:50 — 23:59
HA6819
Hawaiian Airlines
Seattle — Chicago
|
9h 13m including layover |
Find flight
from$162 |
|
|
13:10 — 17:10
+1 day
|
13:10 — 18:50
NK1846
Spirit Airlines
San Jose — Dallas
20h 6m stop
14:56 — 17:10
NK1634
Spirit Airlines
Dallas — Chicago
|
26h including layover |
Find flight
from$142 |
|
|
14:33 — 20:53
+1 day
|
14:33 — 16:05
F94104
Frontier Airlines
San Jose — Las Vegas
22h 58m stop
15:03 — 20:53
F92146
Frontier Airlines
Las Vegas — Chicago
|
28h 20m including layover |
Find flight
from$121 |
|
|
14:35 — 14:56
+1 day
|
14:33 — 16:05
F94104
Frontier Airlines
San Jose — Las Vegas
17h 13m stop
09:25 — 15:00
F92330
Frontier Airlines
Las Vegas — Chicago
|
22h 21m including layover |
Find flight
from$120 |
|
|
16:25 — 06:03
+1 day
|
16:25 — 17:56
NK1141
Spirit Airlines
San Jose — Las Vegas
6h 38m stop
00:34 — 06:03
NK1053
Spirit Airlines
Las Vegas — Chicago
|
11h 38m including layover |
Find flight
from$105 |
|
|
16:33 — 05:25
+1 day
|
16:33 — 17:58
NK2183
Spirit Airlines
San Jose — Las Vegas
5h 48m stop
23:46 — 05:25
NK2186
Spirit Airlines
Las Vegas — Chicago
|
10h 52m including layover |
Find flight
from$97 |
|
|
19:00 — 14:56
+1 day
|
19:00 — 20:31
F91590
Frontier Airlines
San Jose — Las Vegas
12h 48m stop
09:19 — 14:56
F92330
Frontier Airlines
Las Vegas — Chicago
|
17h 56m including layover |
Find flight
from$132 |
|
|
19:00 — 20:56
+1 day
|
19:00 — 20:31
F91590
Frontier Airlines
San Jose — Las Vegas
18h 29m stop
15:00 — 20:56
F92146
Frontier Airlines
Las Vegas — Chicago
|
23h 56m including layover |
Find flight
from$140 |
|
|
09:19 — 22:28
|
09:19 — 10:47
NK1371
Spirit Airlines
San Jose — Las Vegas
39m stop
11:26 — 18:24
NK1203
Spirit Airlines
Las Vegas — Atlanta
2h 55m stop
21:19 — 22:28
NK1200
Spirit Airlines
Atlanta — Chicago
|
11h 9m including layover |
Find flight
from$154 |
|
|
10:19 — 23:31
+1 day
|
10:19 — 11:46
NK1371
Spirit Airlines
San Jose — Las Vegas
7h 1m stop
18:47 — 20:08
NK1495
Spirit Airlines
Las Vegas — Los Angeles
21h 16m stop
17:24 — 23:31
NK3010
Spirit Airlines
Los Angeles — Chicago
|
35h 12m including layover |
Find flight
from$130 |
|
|
13:10 — 14:46
+1 day
|
13:10 — 18:50
NK1846
Spirit Airlines
San Jose — Dallas
3h 36m stop
22:26 — 23:28
NK1381
Spirit Airlines
Dallas — Las Vegas
9h 36m stop
09:04 — 14:46
NK1269
Spirit Airlines
Las Vegas — Chicago
|
23h 36m including layover |
Find flight
from$142 |
|
|
15:23 — 05:25
+1 day
|
15:23 — 16:45
NK2506
Spirit Airlines
San Jose — San Diego
58m stop
17:43 — 19:01
NK2507
Spirit Airlines
San Diego — Las Vegas
4h 45m stop
23:46 — 05:25
NK2186
Spirit Airlines
Las Vegas — Chicago
|
12h 2m including layover |
Find flight
from$113 |
|
|
15:23 — 05:25
+1 day
|
15:23 — 16:45
NK2506
Spirit Airlines
San Jose — San Diego
2h 13m stop
18:58 — 20:17
NK2296
Spirit Airlines
San Diego — Las Vegas
3h 29m stop
23:46 — 05:25
NK2186
Spirit Airlines
Las Vegas — Chicago
|
12h 2m including layover |
Find flight
from$113 |
|
*Departure and arrival times - local. Updated on August 17, 2025
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 2960 miles. Time difference between the cities is 2h. Airplanes depart 06:00 to 21:46 from 2 San Jose airports and arrive 06:00 to 21:46 to 7 Chicago airports. Average flight time is 4h 24m.
- The fastest flight 4h 22m
- Average flight time 4h 24m
- The earliest flight 06:00
- The latest flight 21:46
- Distance 1840 ml
The cheapest months to travel to Chicago are june (from 97 $), august (from 98 $), july (from 105 $).
The most expensive months are november (from 499 $), december (from 307 $), february (from 247 $).
What is the lowest airfare San Jose to Chicago?
The cheapest plane ticket found by our users is $97. This airfare is for economy class on one-way NK2183 flight by Spirit Airlines for June 6, 2025 which leaves San Jose Municipal in San Jose at 16:33 am and arrives at Chicago O'Hare International at 05:25.
Economy class
$97
Business class
?
First class
?
Popular Airlines on the Route
The flight San Jose — Chicago is served by 5 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 156 departures per week at the price of from $ 170 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 7617.
Direct flights
There are 2 nonstop flights on the route. The fastest direct flight is UA374 by United Airlines takes 4h 22m and the cheapest is NK2183 by Spirit Airlines for $236.
- UA - United Airlinesfrom $236Find
See more direct flights
Connecting Flights
There are 479 flights with layovers on the route. The fastest connecting flight is UA1325 by United Airlines takes 5h 58m and the cheapest is NK2183 by Spirit Airlines for $97.
- AS - Alaska Airlinesfrom $170Find
- F9 - Frontier Airlinesfrom $114Find
- HA - Hawaiian Airlinesfrom $162Find
- UA - United Airlinesfrom $250Find
- NK - Spirit Airlinesfrom $97Find
See more connecting flights
Airports
You can fly from San Jose to Chicago from 2 airports (San Jose Municipal, Reid-Hillview).
San Jose airports
- San Jose Municipal-SJCfrom $97Find
- Reid-Hillview-RHVFind
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 5 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from San Jose
You may also consider searching for discounted plane tickets to some other popular places from San Jose within United States.
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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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