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 237 connecting flights from San Jose to Chicago. You can compare airfare deals from 4 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
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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 $235 | 06:30 San Jose San Jose Municipal | 12:55 Chicago O'Hare International | 4h 25m | United Airlines | UA356 |
| from $97 | 06:00 San Jose San Jose Municipal | 14:16 Chicago O'Hare International | 6h 16m layover 1h 4m - Las Vegas | Spirit Airlines | NK436 NK187 |
| 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 $152 | 10:19 San Jose San Jose Municipal | 14:16+1 день Chicago O'Hare International | 25h 57m layover 20h 46m - Las Vegas | Spirit Airlines | NK1371 NK187 |
| from $161 | 12:46 San Jose San Jose Municipal | 23:59 Chicago O'Hare International | 9h 13m layover 2h 56m - Seattle | Hawaiian Airlines | HA6780 HA6819 |
| from $129 | 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 |
| from $141 | 11:32 San Jose San Jose Municipal | 06:03+1 день Chicago O'Hare International | 16h 31m layover 5h 43m - San Diego 4h 21m - Las Vegas | Spirit Airlines | NK1826 NK1151 NK1053 |
| from $141 | 11:32 San Jose San Jose Municipal | 06:03+1 день Chicago O'Hare International | 16h 31m layover 3h 50m - San Diego 6h 15m - Las Vegas | Spirit Airlines | NK1826 NK1157 NK1053 |
| from $141 | 13:10 San Jose San Jose Municipal | 14:46+1 день Chicago O'Hare International | 23h 36m layover 3h 36m - Dallas 9h 36m - Las Vegas | Spirit Airlines | NK1846 NK1381 NK1269 |
| from $141 | 11:32 San Jose San Jose Municipal | 14:46+1 день Chicago O'Hare International | 25h 14m layover 5h 43m - San Diego 12h 51m - Las Vegas | Spirit Airlines | NK1826 NK1151 NK1269 |
| from $141 | 11:32 San Jose San Jose Municipal | 14:46+1 день Chicago O'Hare International | 25h 14m layover 3h 50m - San Diego 14h 45m - Las Vegas | Spirit Airlines | NK1826 NK1157 NK1269 |
| from $145 | 13:10 San Jose San Jose Municipal | 06:03+1 день Chicago O'Hare International | 14h 53m layover 3h 36m - Dallas 1h 6m - Las Vegas | Spirit Airlines | NK1846 NK1381 NK1053 |
| from $153 | 09:19 San Jose San Jose Municipal | 22:28 Chicago O'Hare International | 11h 9m layover 0h 39m - Las Vegas 2h 55m - Atlanta | Spirit Airlines | NK1371 NK1203 NK1200 |
| from $155 | 06:30 San Jose San Jose Municipal | 16:46+1 день Chicago O'Hare International | 32h 16m layover 13h 37m - Las Vegas 11h 46m - Los Angeles | Spirit Airlines | NK1646 NK1657 NK1105 |
| from $161 | 06:30 San Jose San Jose Municipal | 16:46+1 день Chicago O'Hare International | 32h 16m layover 10h 59m - Las Vegas 14h 20m - Los Angeles | Spirit Airlines | NK1646 NK1551 NK1105 |
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 14, 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$251 |
|
|
06:30 — 12:55
|
06:30 — 12:55
UA356
United Airlines
San Jose — Chicago
|
4h 25m |
Find flight
from$235 |
|
|
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$97 |
|
|
06:30 — 06:03
+1 day
|
06:30 — 08:00
NK1646
Spirit Airlines
San Jose — Las Vegas
16h 34m stop
00:34 — 06:03
NK1053
Spirit Airlines
Las Vegas — Chicago
|
21h 33m including layover |
Find flight
from$118 |
|
|
08:00 — 23:59
|
06:45 — 09:02
HA7063
Hawaiian Airlines
San Jose — Seattle
7h 35m stop
17:55 — 23:59
HA6819
Hawaiian Airlines
Seattle — Chicago
|
13h 59m including layover |
Find flight
from$167 |
|
|
08:00 — 23:59
|
07:03 — 09:15
AS1193
Alaska Airlines
San Jose — Seattle
7h 35m stop
17:54 — 23:59
AS538
Alaska Airlines
Seattle — Chicago
|
13h 59m including layover |
Find flight
from$176 |
|
|
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$97 |
|
|
12:02 — 23:59
|
12:02 — 14:10
HA7029
Hawaiian Airlines
San Jose — Seattle
3h 44m stop
17:54 — 23:59
HA6819
Hawaiian Airlines
Seattle — Chicago
|
9h 57m including layover |
Find flight
from$162 |
|
|
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$161 |
|
|
15:00 — 23:59
|
15:00 — 17:10
AS1088
Alaska Airlines
San Jose — Seattle
44m stop
17:54 — 23:59
AS538
Alaska Airlines
Seattle — Chicago
|
6h 59m including layover |
Find flight
from$171 |
|
|
15:24 — 12:07
+1 day
|
15:24 — 17:34
HA7062
Hawaiian Airlines
San Jose — Seattle
12h 26m stop
06:00 — 12:07
HA6816
Hawaiian Airlines
Seattle — Chicago
|
18h 43m including layover |
Find flight
from$170 |
|
|
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 |
|
|
16:25 — 14:46
+1 day
|
16:25 — 17:56
NK1141
Spirit Airlines
San Jose — Las Vegas
15h 8m stop
09:04 — 14:46
NK1269
Spirit Airlines
Las Vegas — Chicago
|
20h 21m including layover |
Find flight
from$118 |
|
|
21:46 — 12:07
+1 day
|
21:46 — 23:59
HA7064
Hawaiian Airlines
San Jose — Seattle
6h 1m stop
06:00 — 12:07
HA6816
Hawaiian Airlines
Seattle — Chicago
|
12h 21m including layover |
Find flight
from$169 |
|
|
21:46 — 12:07
+1 day
|
21:46 — 23:59
AS1201
Alaska Airlines
San Jose — Seattle
6h 1m stop
06:00 — 12:07
AS408
Alaska Airlines
Seattle — Chicago
|
12h 21m including layover |
Find flight
from$177 |
|
|
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$153 |
|
|
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$129 |
|
|
11:32 — 06:03
+1 day
|
11:32 — 13:07
NK1826
Spirit Airlines
San Jose — San Diego
5h 43m stop
18:50 — 20:13
NK1151
Spirit Airlines
San Diego — Las Vegas
4h 21m stop
00:34 — 06:03
NK1053
Spirit Airlines
Las Vegas — Chicago
|
16h 31m including layover |
Find flight
from$141 |
|
|
11:32 — 06:03
+1 day
|
11:32 — 13:07
NK1826
Spirit Airlines
San Jose — San Diego
3h 50m stop
16:57 — 18:19
NK1157
Spirit Airlines
San Diego — Las Vegas
6h 15m stop
00:34 — 06:03
NK1053
Spirit Airlines
Las Vegas — Chicago
|
16h 31m including layover |
Find flight
from$141 |
|
|
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$141 |
|
|
13:10 — 06:03
+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
1h 6m stop
00:34 — 06:03
NK1053
Spirit Airlines
Las Vegas — Chicago
|
14h 53m including layover |
Find flight
from$145 |
|
*Departure and arrival times - local. Updated on July 14, 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 august (from 97 $), july (from 105 $), october (from 129 $).
The most expensive months are november (from 497 $), december (from 305 $), may (from 257 $).
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 NK1371 flight by Spirit Airlines for August 27, 2025 which leaves San Jose Municipal in San Jose at 10:19 am and arrives at Chicago O'Hare International at 23:43.
Economy class
$97
Business class
?
First class
?
Popular Airlines on the Route
The flight San Jose — Chicago is served by 4 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by Alaska Airlines - 81 departures per week at the price of from $ 169 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 7527.
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 NK1371 by Spirit Airlines for $235.
- UA - United Airlinesfrom $235Find
See more direct flights
Connecting Flights
There are 237 flights with layovers on the route. The fastest connecting flight is UA1325 by United Airlines takes 5h 58m and the cheapest is NK1371 by Spirit Airlines for $97.
- AS - Alaska Airlinesfrom $169Find
- HA - Hawaiian Airlinesfrom $161Find
- UA - United Airlinesfrom $249Find
- 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 4 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?
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