Nonstop flights from San Jose to Chicago

2 airlines fly from San Jose (SJC) to 2 Chicago airports (MDW and ORD), with up to 4 flights a day.

SJCMDW

Routes

2 airport pairs

When they leave

San Jose time

6:10a11:00pFirst departure 6:10 AM, last 11:00 PM

Four in the morning, 6:10 AM to 11:20 AM, then one afternoon flight at 2:08 PM, then one evening flight at 11:00 PM.

Every flight

Earliest first

6:10 AM→12:20 PMSJC to MDWSouthwest AirlinesBoeing 737 MAX 8Sun
6:30 AM→12:52 PMSJC to ORDUnited AirlinesUntil Nov 29, back Dec 17Boeing 737Daily
9:55 AM→4:00 PMSJC to MDWSouthwest AirlinesBoeing 737Tue, Wed, Sat
11:20 AM→5:30 PMSJC to MDWSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
2:08 PM→8:35 PMSJC to ORDUnited AirlinesUntil Nov 29, back Dec 17Airbus A320Daily
11:00 PM→5:00 AM⁺¹SJC to MDWSouthwest AirlinesBoeing 737 MAX 8Daily

Schedules last checked Sep 19, 2026. Times are local.

Flying from San Jose to Chicago

Southwest Airlines flies twice a day on the Boeing 737 MAX 8, Boeing 737 and Boeing 737-700. United Airlines flies twice a day on the Airbus A320 and Boeing 737.

There are 4 flights every day of the week. The first arrival in Chicago is at 12:20 PM and the last at 5:00 AM the next day.

SJC to MDW is the busiest airport pair, with 14 flights a week, then SJC to ORD with 14.

On SJC to ORD, United Airlines flies it until Nov 29 and is back on Dec 17.

Flying back, Chicago to San Jose has 21 nonstop flights a week.

Return flights

Chicago to San JoseView

Find the cheapest day to fly from San Jose to Chicago.

Schedules as of Oct 9, 2026.