Flight Routes from San Jose to Chicago

Compare cheap outbound and return flights from San Jose (SJC) to Chicago (CHI) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€341
Fastest outbound flight
Fastest inbound flight
non-stop flights
61x / week
Flight distance
2,963 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from San Jose (SJC) to Chicago (CHI)

Select a travel date in the flight schedule for the route from San Jose (SJC) to Chicago (CHI) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsSJC–CHI · 13 of 13
fromto
dep.arr.
durationstopovers
  1. October 18 – 24, 2026
  2. October 25 – 31, 2026
  3. November 1 – 7, 2026
    No flights could be found for the active filters.
    1. SJCMDW
      nonstop
      1. Southwest Airlines
    2. SJCMDW
      nonstop
      1. Southwest Airlines
    3. SJCORD
      nonstop
      1. United Airlines
    4. SJCMDW
      nonstop
      1. Southwest Airlines
    5. SJCMDW
      nonstop
      1. Southwest Airlines
    6. SJCMDW
      nonstop
      1. Southwest Airlines
    7. SJCMDW
      nonstop
      1. Southwest Airlines
    8. SJCMDW
      nonstop
      1. Southwest Airlines
    9. SJCMDW
      nonstop
      1. Southwest Airlines
    10. SJCORD
      nonstop
      1. United Airlines
    11. SJCMDW
      nonstop
      1. Southwest Airlines
    12. SJCMDW
      nonstop
      1. Southwest Airlines
    13. SJCMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around San Jose and Chicago

      Departure airport Airport San Jose International Airport, CA (SJC)
      Arrival airport Airport Chicago-IL, all airports (CHI)
      Destination country Flights to United States
      Departure airport - Destination country San Jose International Airport, CA - United States
      Alternative routes to United States
      Alternative flights to Chicago
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