Chicago to San Jose Flights

CHI-SJC Flight Tickets Booking by Date


Book cheap flights to San Jose from Chicago today with using OutTrippin’s ticket finder. We help you compare flights, carriers and seating classes all year round. Be sure to find the right flight to match your budget, plans and travel preferences.

Direct Flights from Chicago to San Jose

Departure atFlightAirlineFind tickets
12.03.2021Southwest Airlines (WN 1473)294

Round-trip Tickets from Chicago to San Jose

Departure atReturn atFlightStopsFind tickets
12.03.202118.03.2021Southwest Airlines (WN 1473)Direct 294
12.03.202119.03.2021Frontier Airlines (F9 411)1 Stop 175
13.03.202119.03.2021United Airlines (UA 1027)1 Stop 237

CHI-SJC Compare Airline Prices

Departure atReturn atStopsPriceFlight numberAirlineFind tickets
12.03.202119.03.20211 Stop175 411175
13.03.202119.03.20212 Stops237 1027237
06.08.202108.08.2021Direct341 2832341
16.08.202120.08.20212 Stops384 2052384
17.08.202120.08.2021Direct338 1704338

* Total price includes taxes + fees for 1 adult. Additional bag fees and other fees may apply.

Chicago-San Jose Flight is Served by Airlines

  • American Airlines Flights
  • Alaska Airlines Flights
  • Southwest Airlines Flights

Departure Chicago Midway International Airport (Chicago)

Weather: [simple-weather location=”Chicago, United States” days=”2″]
  • Airport Name: Chicago Midway International Airport
  • Country Code: US
  • City Code: CHI
  • Airport Code: MDW
  • Flightable: Active
  • Time Zone: America/Chicago
  • Latitude: 41.788136
  • Longitude: -87.74087

Destination Norman Y. Mineta San Jose International Airport (San Jose)

Weather: [simple-weather location=”San Jose, United States” days=”2″]

*Flight prices are indicative, based on passenger numbers and may vary dependent on your individual flight dates. Complete a new search to view live pricing.

* Checked baggage is not included but may be added for a fee. Carry-on baggage limits, including size restrictions, will be strictly applied. Passengers with more than the applicable carry-on baggage allowance will need to check in baggage, and charges will apply.