Cheap Flights from San Jose, CA to Chicago, IL from $77

One way Round trip

Adults

Children under 12

Infants under 2 without place

Economy

Business

First

done

Return flight: Chicago – San Jose

Page navigation

Price Calendar Cheap Flights Flights Schedule

On Cheapflightsplus.com you will find 5 direct and 408 connecting flights from San Jose to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $77, 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: $77 (one-way), $132 (round-trip).

Direct flights

Check to choose departure date Check to choose departure date

Check prices for return flight

Find flights

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 $77. The fastest direct flight takes 4h 15m and the fastest connecting – 5h 47m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $304 Find flight	08:00 San Jose San Jose Municipal	14:20 Chicago O'Hare International	4h 20m	United Airlines	UA1719
from $388 Find flight	06:30 San Jose San Jose Municipal	12:50 Chicago O'Hare International	4h 20m	United Airlines	UA528
from $77 Find flight	22:20 San Jose San Jose Municipal	06:33+1 день Chicago Midway	6h 13m layover 1h 9m - Las Vegas	Frontier Airlines	F94104 F92330
from $77 Find flight	19:08 San Jose San Jose Municipal	04:45+1 день Chicago O'Hare International	7h 37m layover 2h 42m - Las Vegas	Spirit Airlines	NK2901 NK182
from $92 Find flight	14:28 San Jose San Jose Municipal	00:13+1 день Chicago Midway	7h 45m layover 2h 47m - Denver	Frontier Airlines	F94918 F92210
from $117 Find flight	19:50 San Jose San Jose Municipal	05:30+1 день Chicago O'Hare International	7h 40m layover 2h 41m - Las Vegas	Spirit Airlines	NK1501 NK182
from $117 Find flight	15:08 San Jose San Jose Municipal	05:30+1 день Chicago O'Hare International	12h 22m layover 7h 22m - Las Vegas	Spirit Airlines	NK194 NK182
from $127 Find flight	19:59 San Jose San Jose Municipal	05:28+1 день Chicago O'Hare International	7h 29m layover 1h 42m - Portland	Alaska Airlines	AS1065 AS340
from $130 Find flight	21:24 San Jose San Jose Municipal	12:05+1 день Chicago O'Hare International	12h 41m layover 7h 11m - Los Angeles	Spirit Airlines	NK479 NK466
from $136 Find flight	15:28 San Jose San Jose Municipal	05:18+1 день Chicago O'Hare International	11h 50m layover 6h 26m - Los Angeles	Spirit Airlines	NK910 NK1679
from $149 Find flight	12:58 San Jose San Jose Municipal	01:13+1 день Chicago O'Hare International	10h 15m layover 4h 23m - Dallas	Spirit Airlines	NK1942 NK828
from $104 Find flight	11:50 San Jose San Jose Municipal	12:04+1 день Chicago O'Hare International	22h 14m layover 9h 47m - Los Angeles 6h 6m - Las Vegas	Spirit Airlines	NK469 NK473 NK187
from $127 Find flight	18:58 San Jose San Jose Municipal	17:40+1 день Chicago O'Hare International	20h 42m layover 9h 6m - Las Vegas 4h 57m - Dallas	Spirit Airlines	NK2901 NK2708 NK241
from $128 Find flight	14:58 San Jose San Jose Municipal	12:04+1 день Chicago O'Hare International	19h 6m layover 3h 50m - Burbank 9h 22m - Las Vegas	Spirit Airlines	NK2750 NK2381 NK187
from $128 Find flight	14:58 San Jose San Jose Municipal	12:04+1 день Chicago O'Hare International	19h 6m layover 5h 54m - Burbank 7h 19m - Las Vegas	Spirit Airlines	NK2750 NK2375 NK187
from $147 Find flight	14:58 San Jose San Jose Municipal	04:45+1 день Chicago O'Hare International	11h 47m layover 3h 50m - Burbank 2h 12m - Las Vegas	Spirit Airlines	NK2750 NK2381 NK182

Show all tickets

*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 01, 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 — 12:35	06:20 — 12:35 UA467 United Airlines San Jose — Chicago	4h 15m	Find flight from$316
06:30 — 12:50	06:30 — 12:50 UA1239 United Airlines San Jose — Chicago	4h 20m	Find flight from$311
06:30 — 12:50	06:30 — 12:50 UA528 United Airlines San Jose — Chicago	4h 20m	Find flight from$388
08:00 — 14:20	08:00 — 14:20 UA1719 United Airlines San Jose — Chicago	4h 20m	Find flight from$304
22:40 — 04:57 +1 day	22:40 — 04:57 UA1885 United Airlines San Jose — Chicago	4h 17m	Find flight from$311
06:00 — 00:33 +1 day	06:00 — 07:26 NK1654 Spirit Airlines San Jose — Los Angeles 11h 5m stop 18:31 — 00:33 NK517 Spirit Airlines Los Angeles — Chicago	16h 33m including layover	Find flight from$158
10:29 — 15:50 +1 day	10:29 — 14:10 F94918 Frontier Airlines San Jose — Denver 22h 18m stop 12:28 — 15:50 F91228 Frontier Airlines Denver — Chicago	27h 21m including layover	Find flight from$164
12:04 — 21:24	12:04 — 13:26 NK469 Spirit Airlines San Jose — Los Angeles 1h 49m stop 15:15 — 21:24 NK1486 Spirit Airlines Los Angeles — Chicago	7h 20m including layover	Find flight from$125
12:58 — 01:13 +1 day	12:58 — 18:36 NK1942 Spirit Airlines San Jose — Dallas 4h 23m stop 22:59 — 01:13 NK828 Spirit Airlines Dallas — Chicago	10h 15m including layover	Find flight from$149
13:11 — 00:48 +1 day	13:11 — 16:45 F94918 Frontier Airlines San Jose — Denver 4h 27m stop 21:12 — 00:48 F93174 Frontier Airlines Denver — Chicago	9h 37m including layover	Find flight from$118
13:45 — 23:42	13:45 — 15:11 NK1371 Spirit Airlines San Jose — Las Vegas 2h 44m stop 17:55 — 23:42 NK184 Spirit Airlines Las Vegas — Chicago	7h 57m including layover	Find flight from$192
14:28 — 00:13 +1 day	14:28 — 18:08 F94918 Frontier Airlines San Jose — Denver 2h 47m stop 20:55 — 00:13 F92210 Frontier Airlines Denver — Chicago	7h 45m including layover	Find flight from$92
14:28 — 00:35 +1 day	14:28 — 18:08 F94918 Frontier Airlines San Jose — Denver 2h 51m stop 20:59 — 00:35 F93172 Frontier Airlines Denver — Chicago	8h 7m including layover	Find flight from$92
15:08 — 05:30 +1 day	13:33 — 15:01 NK194 Spirit Airlines San Jose — Las Vegas 7h 22m stop 23:17 — 04:45 NK182 Spirit Airlines Las Vegas — Chicago	12h 22m including layover	Find flight from$117
15:28 — 05:18 +1 day	15:28 — 16:49 NK910 Spirit Airlines San Jose — Los Angeles 6h 26m stop 23:15 — 05:18 NK1679 Spirit Airlines Los Angeles — Chicago	11h 50m including layover	Find flight from$136
17:19 — 17:25 +1 day	17:08 — 18:31 F94104 Frontier Airlines San Jose — Las Vegas 16h 50m stop 13:39 — 19:30 F92146 Frontier Airlines Las Vegas — Chicago	22h 6m including layover	Find flight from$77
19:08 — 04:45 +1 day	19:08 — 20:35 NK2901 Spirit Airlines San Jose — Las Vegas 2h 42m stop 23:17 — 04:45 NK182 Spirit Airlines Las Vegas — Chicago	7h 37m including layover	Find flight from$77
19:08 — 12:04 +1 day	19:08 — 20:35 NK2901 Spirit Airlines San Jose — Las Vegas 9h 52m stop 06:27 — 12:04 NK187 Spirit Airlines Las Vegas — Chicago	14h 56m including layover	Find flight from$77
21:17 — 06:25 +1 day	21:17 — 22:43 NK479 Spirit Airlines San Jose — Los Angeles 1h 40m stop 00:23 — 06:25 NK486 Spirit Airlines Los Angeles — Chicago	7h 8m including layover	Find flight from$157
21:24 — 12:05 +1 day	21:20 — 22:45 NK479 Spirit Airlines San Jose — Los Angeles 7h 11m stop 06:00 — 12:05 NK466 Spirit Airlines Los Angeles — Chicago	12h 41m including layover	Find flight from$130
22:20 — 06:33 +1 day	17:08 — 18:31 F94104 Frontier Airlines San Jose — Las Vegas 1h 9m stop 06:11 — 11:48 F92330 Frontier Airlines Las Vegas — Chicago	6h 13m including layover	Find flight from$77
06:00 — 23:35	06:00 — 07:26 NK1654 Spirit Airlines San Jose — Los Angeles 5h 34m stop 13:00 — 18:15 NK307 Spirit Airlines Los Angeles — Houston 2h 36m stop 20:51 — 23:35 NK175 Spirit Airlines Houston — Chicago	15h 35m including layover	Find flight from$191
08:43 — 04:45 +1 day	08:43 — 10:05 NK428 Spirit Airlines San Jose — San Diego 2h 31m stop 12:36 — 13:58 NK1499 Spirit Airlines San Diego — Las Vegas 9h 19m stop 23:17 — 04:45 NK182 Spirit Airlines Las Vegas — Chicago	18h 2m including layover	Find flight from$180
10:28 — 04:45 +1 day	10:28 — 11:36 NK2912 Spirit Airlines San Jose — Burbank 3h 48m stop 15:24 — 16:37 NK2373 Spirit Airlines Burbank — Las Vegas 6h 40m stop 23:17 — 04:45 NK182 Spirit Airlines Las Vegas — Chicago	16h 17m including layover	Find flight from$172
11:50 — 12:04 +1 day	11:50 — 13:18 NK469 Spirit Airlines San Jose — Los Angeles 9h 47m stop 23:05 — 00:21 NK473 Spirit Airlines Los Angeles — Las Vegas 6h 6m stop 06:27 — 12:04 NK187 Spirit Airlines Las Vegas — Chicago	22h 14m including layover	Find flight from$104
11:50 — 12:04 +1 day	11:50 — 13:18 NK469 Spirit Airlines San Jose — Los Angeles 6h 5m stop 19:23 — 20:37 NK636 Spirit Airlines Los Angeles — Las Vegas 9h 50m stop 06:27 — 12:04 NK187 Spirit Airlines Las Vegas — Chicago	22h 14m including layover	Find flight from$140
17:39 — 05:18 +1 day	17:39 — 19:05 NK249 Spirit Airlines San Jose — Las Vegas 1h 4m stop 20:09 — 21:27 NK912 Spirit Airlines Las Vegas — Los Angeles 1h 48m stop 23:15 — 05:18 NK1679 Spirit Airlines Los Angeles — Chicago	9h 39m including layover	Find flight from$181
18:58 — 17:40 +1 day	19:08 — 20:35 NK2901 Spirit Airlines San Jose — Las Vegas 9h 6m stop 05:25 — 10:07 NK2708 Spirit Airlines Las Vegas — Dallas 4h 57m stop 16:27 — 18:49 NK241 Spirit Airlines Dallas — Chicago	20h 42m including layover	Find flight from$127
18:58 — 12:05 +1 day	18:58 — 20:26 NK2901 Spirit Airlines San Jose — Las Vegas 3h 1m stop 23:27 — 00:47 NK211 Spirit Airlines Las Vegas — Los Angeles 5h 13m stop 06:00 — 12:05 NK466 Spirit Airlines Los Angeles — Chicago	15h 7m including layover	Find flight from$170
20:44 — 12:05 +1 day	20:44 — 22:14 NK436 Spirit Airlines San Jose — Las Vegas 1h 13m stop 23:27 — 00:47 NK211 Spirit Airlines Las Vegas — Los Angeles 5h 13m stop 06:00 — 12:05 NK466 Spirit Airlines Los Angeles — Chicago	13h 21m including layover	Find flight from$170
20:44 — 17:40 +1 day	20:44 — 22:14 NK436 Spirit Airlines San Jose — Las Vegas 7h 18m stop 05:32 — 10:13 NK2708 Spirit Airlines Las Vegas — Dallas 4h 57m stop 15:10 — 17:40 NK241 Spirit Airlines Dallas — Chicago	18h 56m including layover	Find flight from$187

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on April 1, 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 05:50 to 22:55 from 2 San Jose airports and arrive 05:50 to 22:55 to 7 Chicago airports. Average flight time is 4h 20m.

The fastest flight 4h 15m
Average flight time 4h 20m
The earliest flight 05:50
The latest flight 22:55
Distance 1840 ml

The cheapest months to travel to Chicago are november (from 77 $), january (from 77 $), february (from 90 $).

The most expensive months are december (from 92 $), february (from 90 $), january (from 77 $).

What is the lowest airfare San Jose to Chicago?

The cheapest plane ticket found by our users is $77. This airfare is for economy class on one-way NK2901 flight by Spirit Airlines for November 11, 2024 which leaves San Jose Municipal in San Jose at 19:08 am and arrives at Chicago O'Hare International at 04:45.

Economy class

$77

Find

Business class

Find

First class

Find

Popular Airlines on the Route

The flight San Jose — Chicago is served by 5 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 191 departures per week at the price of from $ 127 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 880.

Direct flights

There are 5 nonstop flights on the route. The fastest direct flight is UA467 by United Airlines takes 4h 15m and the cheapest is NK2901 by Spirit Airlines for $304.

UA - United Airlines

from $304

Find

See more direct flights

Connecting Flights

There are 408 flights with layovers on the route. The fastest connecting flight is UA772 by United Airlines takes 5h 47m and the cheapest is NK2901 by Spirit Airlines for $77.

AS - Alaska Airlines

from $127

Find
F9 - Frontier Airlines

from $77

Find
Y4 - Volaris

from $356

Find
UA - United Airlines

from $266

Find
NK - Spirit Airlines

from $77

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 $77
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

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

Find
San Jose — Dallas

from $75

Find
San Jose — Portland

from $78

Find
San Jose — Chicago

from $74

Find
San Jose — Burbank

from $76

Find
San Jose — Boston

from $74

Find
San Jose — Honolulu

from $73

Find
San Jose — Nashville

from $77

Find
San Jose — Boise

from $65

Find
San Jose — Detroit

from $71

Find

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

Find
San Jose — Cancun

from $57

Find
San Jose — London

from $64

Find
San Jose — Puerto Vallarta

from $65

Find
San Jose — Paris

from $55

Find
San Jose — Manila

from $62

Find

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.
To find a plane ticket, please select dates.