Nonstop flights from Chicago to San Jose

2 airlines fly from 2 Chicago airports (MDW and ORD) to San Jose (SJC), with up to 3 flights a day.

MDWSJC

Routes

2 airport pairs

Chicago time

10:10a8:50pFirst departure 10:10 AM, last 8:50 PM

Three in the morning, 10:10 AM to 10:20 AM, then four in the evening, 7:58 PM to 8:50 PM.

Earliest first

10:10 AM→12:35 PMMDW to SJCSouthwest AirlinesBoeing 737-700Sun
10:15 AM→12:45 PMMDW to SJCSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri, Sat
10:20 AM→12:45 PMMDW to SJCSouthwest AirlinesBoeing 737 MAX 8Tue, Wed
7:58 PM→10:43 PMORD to SJCUnited AirlinesUntil Nov 30, back Dec 17Boeing 737Daily
8:30 PM→11:00 PMMDW to SJCSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat
8:40 PM→11:10 PMMDW to SJCSouthwest AirlinesBoeing 737 MAX 8Sun
8:50 PM→11:20 PMMDW to SJCSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri

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

Southwest Airlines flies most often, twice a day on the Boeing 737 MAX 8 and Boeing 737-700. United Airlines flies daily on the Boeing 737.

There are 3 flights every day of the week. The first arrival in San Jose is at 12:35 PM and the last at 11:20 PM.

MDW to SJC is the busiest airport pair, with 14 flights a week, then ORD to SJC with 7.

On ORD to SJC, United Airlines flies it until Nov 30 and is back on Dec 17.

Flying back, San Jose to Chicago has 28 nonstop flights a week.

Schedules as of Oct 9, 2026.