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

One way Round trip

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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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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 $71. The fastest direct flight takes 4h 22m and the fastest connecting – 6h 3m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $183 Find flight	06:20 San Jose San Jose Municipal	12:42 Chicago O'Hare International	4h 22m	United Airlines	UA374
from $71 Find flight	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 $80 Find flight	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 $80 Find flight	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 $80 Find flight	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 $80 Find flight	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 $83 Find flight	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 $86 Find flight	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 $86 Find flight	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 $87 Find flight	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 $82 Find flight	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 $86 Find flight	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 $86 Find flight	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 $86 Find flight	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 $87 Find flight	06:00 San Jose San Jose Municipal	11:36+1 день Chicago O'Hare International	27h 36m layover 12h 26m - Las Vegas 8h 15m - Los Angeles	Spirit Airlines	NK2385 NK2508 NK2192
from $96 Find flight	16:33 San Jose San Jose Municipal	08:55+1 день Chicago O'Hare International	14h 22m layover 5h 4m - Las Vegas 1h 48m - Atlanta	Spirit Airlines	NK2183 NK2573 NK2707

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 20, 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	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	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*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

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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

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F9 - Frontier Airlines

from $83

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HA - Hawaiian Airlines

from $119

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UA - United Airlines

from $197

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NK - Spirit Airlines

from $71

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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
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Reid-Hillview-RHV

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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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.

San Jose — San Diego

from $60

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San Jose — Dallas

from $75

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San Jose — Portland

from $78

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San Jose — Chicago

from $74

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San Jose — Burbank

from $76

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San Jose — Boston

from $74

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San Jose — Honolulu

from $73

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San Jose — Nashville

from $77

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San Jose — Boise

from $65

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San Jose — Detroit

from $71

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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.

San Jose — Guadalajara

from $75

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San Jose — Cancun

from $57

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San Jose — London

from $64

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San Jose — Puerto Vallarta

from $65

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San Jose — Paris

from $55

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San Jose — Manila

from $62

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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.
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.
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