Cheap Flights from San Jose, CA to Chicago, IL from $74

Return flight: Chicago – San Jose
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On Cheapflightsplus.com you will find 5 connecting flights from San Jose to Chicago. You can compare airfare deals from 1 airlines and multiple travel sites from $161, 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: $74 (one-way), $127 (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 $161. Take a look at the list of flights with layovers from San Jose to Chicago from $161. There’re no direct flights. The fastest connecting flight – 6h 11m.
Price Departure Arrival Flight Duration Airline Flight
from $161
Find flight
06:10
San Jose
San Jose Municipal
 14:21
Chicago
O'Hare International
 6h 11m
layover
0h 26m - Phoenix
 American Airlines
AA761
AA739
from $161
Find flight
16:08
San Jose
San Jose Municipal
 00:46+1 день
Chicago
O'Hare International
 6h 38m
layover
1h 13m - Phoenix
 American Airlines
AA470
AA630
from $161
Find flight
13:16
San Jose
San Jose Municipal
 22:58
Chicago
O'Hare International
 7h 42m
layover
1h 35m - Dallas
 American Airlines
AA352
AA1294
from $161
Find flight
19:24
San Jose
San Jose Municipal
 06:13+1 день
Chicago
O'Hare International
 8h 49m
layover
3h 27m - Phoenix
 American Airlines
AA536
AA447
from $162
Find flight
09:50
San Jose
San Jose Municipal
 19:55
Chicago
O'Hare International
 8h 5m
layover
2h 28m - Phoenix
 American Airlines
AA2105
AA883
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on June 07, 2023
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
06:10 — 14:21
06:10 — 08:10 AA761 American Airlines
San Jose — Phoenix
26m stop
08:36 — 14:21 AA739 American Airlines
Phoenix — Chicago
6h 11m
including layover
Find flight
from$161
09:50 — 19:55
09:50 — 11:45 AA2105 American Airlines
San Jose — Phoenix
2h 28m stop
14:13 — 19:55 AA883 American Airlines
Phoenix — Chicago
8h 5m
including layover
Find flight
from$162
13:16 — 22:58
13:16 — 18:55 AA352 American Airlines
San Jose — Dallas
1h 35m stop
20:30 — 22:58 AA1294 American Airlines
Dallas — Chicago
7h 42m
including layover
Find flight
from$161
16:08 — 00:46
+1 day
16:08 — 18:06 AA470 American Airlines
San Jose — Phoenix
1h 13m stop
19:19 — 00:46 AA630 American Airlines
Phoenix — Chicago
6h 38m
including layover
Find flight
from$161
19:24 — 06:13
+1 day
19:24 — 21:19 AA536 American Airlines
San Jose — Phoenix
3h 27m stop
00:46 — 06:13 AA447 American Airlines
Phoenix — Chicago
8h 49m
including layover
Find flight
from$161
*Departure and arrival times - local. Updated on June 7, 2023

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 06:10 to 19:24 from 2 San Jose airports and arrive 06:10 to 19:24 to 7 Chicago airports. Average flight time is 7h 42m.

  • The fastest flight 6h 11m
  • Average flight time 7h 42m
  • The earliest flight 06:10
  • The latest flight 19:24
  • Distance 1840 ml

What is the lowest airfare San Jose to Chicago?

The cheapest plane ticket found by our users is $161. This airfare is for economy class on one-way AA761 flight by American Airlines for July 25, 2020 which leaves San Jose Municipal in San Jose at 06:10 am and arrives at Chicago O'Hare International at 14:21.

Economy class
$161
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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 1 regular airline . Most of the flights on this route are operated by American Airlines - 5 departures per week at the price of from $ 161 . And the most expensive tickets are offered by American Airlines airline - from $ 162.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 5 flights with layovers on the route. The fastest connecting flight is AA761 by American Airlines takes 6h 11m and the cheapest is AA761 by American Airlines for $161.

  • AA - American Airlines
    from $161
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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 $161
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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 1 airlines that use 3 aircraft brands. They range from huge modern airplanes to small-sized.

  • Airbus A319
    from $161
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  • Boeing 737-800
    from $161
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  • Airbus A320
    from $161
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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.

All flights from San Jose | All flights to Chicago

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