Cheap Flights from San Jose, CA to Chicago, IL from $124

Return flight: Chicago – San Jose
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On Cheapflightsplus.com you will find 2 direct and 479 connecting flights from San Jose to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $124, 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: $124 (one-way), $213 (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 $124. The fastest direct flight takes 4h 22m and the fastest connecting – 5h 58m.
Price Departure Arrival Flight Duration Airline Flight
from $229
Find flight
06:30
San Jose
San Jose Municipal
 12:55
Chicago
O'Hare International
 4h 25m United Airlines
UA356
from $93
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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 $110
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 $108
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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 $126
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
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 09, 2025
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
06:00 — 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$105
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$105
06:20 — 12:42
06:20 — 12:42 UA374 United Airlines
San Jose — Chicago
4h 22m
Find flight
from$241
06:30 — 12:55
06:30 — 12:55 UA356 United Airlines
San Jose — Chicago
4h 25m
Find flight
from$229
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$105
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$105
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$110
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$108
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$108
15:23 — 10:55
+1 day
15:23 — 16:45 NK2506 Spirit Airlines
San Jose — San Diego
4h 3m stop
20:48 — 22:07 NK2021 Spirit Airlines
San Diego — Las Vegas
7h 8m stop
05:15 — 10:55 NK2619 Spirit Airlines
Las Vegas — Chicago
17h 32m
including layover
Find flight
from$108
15:26 — 10:50
+1 day
15:23 — 16:45 NK2506 Spirit Airlines
San Jose — San Diego
55m stop
17:43 — 19:01 NK2507 Spirit Airlines
San Diego — Las Vegas
10h 4m stop
05:15 — 10:55 NK2619 Spirit Airlines
Las Vegas — Chicago
17h 24m
including layover
Find flight
from$108
15:26 — 10:50
+1 day
15:23 — 16:45 NK2506 Spirit Airlines
San Jose — San Diego
2h 36m stop
18:58 — 20:17 NK2296 Spirit Airlines
San Diego — Las Vegas
8h 26m stop
05:15 — 10:55 NK2619 Spirit Airlines
Las Vegas — Chicago
17h 24m
including layover
Find flight
from$108
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$101
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$93
16:33 — 10:55
+1 day
16:33 — 17:58 NK2183 Spirit Airlines
San Jose — Las Vegas
11h 17m stop
05:15 — 10:55 NK2619 Spirit Airlines
Las Vegas — Chicago
16h 22m
including layover
Find flight
from$105
*Departure and arrival times - local. Updated on September 9, 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

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 - 156 departures per week at the price of from $ 163 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 7302.

Direct flights

There are 2 nonstop flights on the route. The fastest direct flight is UA374 by United Airlines takes 4h 22m.

  • UA - United Airlines
    from $229
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See more direct flights

Connecting Flights

There are 479 flights with layovers on the route. The fastest connecting flight is UA1325 by United Airlines takes 5h 58m.

  • AS - Alaska Airlines
    from $163
    Find
  • F9 - Frontier Airlines
    from $110
    Find
  • HA - Hawaiian Airlines
    from $155
    Find
  • UA - United Airlines
    from $240
    Find
  • NK - Spirit Airlines
    from $93
    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 $93
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  • Reid-Hillview-RHV
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Chicago airports

  • O'Hare International-ORD
    Find
  • Midway-MDW
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  • Dupage County-DPA
    Find
  • 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
    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.

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.

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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