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Find low faresSouthwest® flights from San Jose, CA to Chicago (Midway) from $175
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Low fares from San Jose, CA to Chicago (Midway)
$
San Jose, CA (SJC)to
Chicago (Midway) (MDW)
Depart: 04/29/2026
One-way
Basic
From
$175
Seen: 21 hrs ago
San Jose, CA (SJC)to
Chicago (Midway) (MDW)
Depart: 04/07/2026
One-way
Basic
From
$175
Seen: 12 hrs ago
San Jose, CA (SJC)to
Chicago (Midway) (MDW)
Depart: 05/05/2026
One-way
Basic
From
$175
Seen: 14 hrs ago
San Jose, CA (SJC)to
Chicago (Midway) (MDW)
Depart: 04/15/2026
One-way
Basic
From
$175
Seen: 12 hrs ago
San Jose, CA (SJC)to
Chicago (Midway) (MDW)
Depart: 04/20/2026
One-way
Basic
From
$175
Seen: 4 hrs ago
San Jose, CA (SJC)to
Chicago (Midway) (MDW)
Depart: 04/11/2026
One-way
Basic
From
$175
Seen: 3 hrs ago
Explore flights from San Jose, CA to Chicago (Midway)
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Flight Details
Departing from:
Norman Y. Mineta San José International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
4 hours 8 minutes
Distance:
1838 miles
Route Information
156† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 1‡ Nonstop flight on Saturday
- 1‡ Nonstop flight on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Questions we hear the most
The average flight time from San Jose, CA to Chicago (Midway) is 4 hours 8 minutes.
There are 156 weekly flights from San Jose, CA to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from San Jose, CA to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from San Jose, CA to Chicago (Midway) once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly San Jose, CA to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from San Jose, CA to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.