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 270 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 to choose departure date Check to choose departure date
Check prices for return flight
Find flights
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
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$124
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$161
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$141
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
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
*Departure and arrival times - local. Updated on July 6, 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 $), june (from 109 $).

The most expensive months are november (from 497 $), december (from 305 $), february (from 246 $).

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
Find
Business class
?
Find
First class
?
Find

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 - 84 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 Airlines
    from $235
    Find
See more direct flights

Connecting Flights

There are 270 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 Airlines
    from $169
    Find
  • F9 - Frontier Airlines
    from $114
    Find
  • HA - Hawaiian Airlines
    from $161
    Find
  • UA - United Airlines
    from $249
    Find
  • NK - Spirit Airlines
    from $97
    Find
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-SJC
    from $97
    Find
  • Reid-Hillview-RHV
    Find

Chicago airports

  • O'Hare International-ORD
    Find
  • Midway-MDW
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air 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.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

Back