Cheap Flights from San Jose, CA to Chicago, IL from $71

Return flight: Chicago – San Jose

On Cheapflightsplus.com you will find 1 direct and 332 connecting flights from San Jose to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $71, 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: $71 (one-way), $122 (round-trip).
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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$183
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$80
06:00 — 10:50
+1 day
06:00 — 07:30 NK2385 Spirit Airlines
San Jose — Las Vegas
21h 45m stop
05:15 — 10:55 NK2619 Spirit Airlines
Las Vegas — Chicago
26h 50m
including layover
Find flight
from$80
09:19 — 23:43
09:19 — 10:47 NK1371 Spirit Airlines
San Jose — Las Vegas
7h 9m stop
17:56 — 23:43 NK184 Spirit Airlines
Las Vegas — Chicago
12h 24m
including layover
Find flight
from$119
10:03 — 23:59
10:03 — 12:14 HA7065 Hawaiian Airlines
San Jose — Seattle
5h 40m stop
17:54 — 23:59 HA6819 Hawaiian Airlines
Seattle — Chicago
11h 56m
including layover
Find flight
from$123
10:03 — 05:40
+1 day
10:03 — 12:14 HA7065 Hawaiian Airlines
San Jose — Seattle
11h 26m stop
23:40 — 05:40 HA6815 Hawaiian Airlines
Seattle — Chicago
17h 37m
including layover
Find flight
from$123
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$80
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$80
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$119
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$83
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$103
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$88
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$87
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$77
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$71
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$96
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$102
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$124
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$103
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$82
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$82
*Departure and arrival times - local. Updated on May 20, 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 22m.

  • The fastest flight 4h 22m
  • Average flight time 4h 22m
  • The earliest flight 06:00
  • The latest flight 21:46
  • Distance 1840 ml

The cheapest months to travel to Chicago are june (from 95 $), july (from 103 $), may (from 118 $).

The most expensive months are november (from 486 $), december (from 299 $), february (from 241 $).

What is the lowest airfare San Jose to Chicago?

The cheapest plane ticket found by our users is $71. This airfare is for economy class on one-way NK2183 flight by Spirit Airlines for June 5, 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
$71
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Business class
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First class
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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 - 101 departures per week at the price of from $ 126 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 5568.

Direct flights

There are 1 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 $183.

  • UA - United Airlines
    from $183
    Find
See more direct flights

Connecting Flights

There are 332 flights with layovers on the route. The fastest connecting flight is UA720 by United Airlines takes 6h 3m and the cheapest is NK2183 by Spirit Airlines for $71.

  • AS - Alaska Airlines
    from $126
    Find
  • F9 - Frontier Airlines
    from $83
    Find
  • HA - Hawaiian Airlines
    from $119
    Find
  • UA - United Airlines
    from $197
    Find
  • NK - Spirit Airlines
    from $71
    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 $71
    Find
  • Reid-Hillview-RHV
    Find

Chicago airports

  • O'Hare International-ORD
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  • 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.

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