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Direct (non-stop) flights from San Jose (SJC) to Chicago (MDW)

Find comprehensive flight information, schedules, and booking details for direct flights from San Jose (SJC) to Chicago (MDW). This popular route is operated by 1 airline, offering multiple daily departures.• Flight Duration: 4h 00m - 4h 10m (average flight time)• Distance: 1843 miles (2965 km) (air miles between airports)• Daily Flights: 1-2 flights (scheduled departures per day)

SJC
San Jose (SJC)
MDW
Chicago (MDW)

FLIGHT TIME

4h 00m - 4h 10m

FLIGHT DISTANCE

1843 miles (2965 km)
Flight time
4h 5m - 4h 5m
Earliest flight
08:00
Last flight
08:00
Distance
1843 miles (2965 km)
Cheapest month
March
Airlines
1 (Show)
Flights per week
7

Flight Schedule

December 2025
Sun
Mon
Tue
Wed
Thu
Fri
Sat

Airlines with direct flights from San Jose (SJC) to Chicago (MDW)

Southwest Airlines (WN)

Route Insights

Pricing patterns: March typically offers lower prices due to reduced demand outside peak travel seasons.

Best departure times: Peak departure times are 8:00, offering more flight options and potentially better connections.

San Jose (SJC) - Chicago (MDW) flight price statistics

$565

Approximate

The numbers are average prices found based on user searches for direct flights between the airports. It's calculated from the cheapest prices found per month for a round-trip with 1 adult and can vary depending on the amount of data we have for this particular route.

$396
Jan
$558
Feb
$386
Mar
$767
Apr
$517
May
$465
Jun
$856
Jul
$757
Aug
$454
Sep
$577
Oct
$546
Nov
$503
Dec
Approximate prices for one round-trip flight from San Jose (SJC) to Chicago (MDW). Graph is not to scale.

Related Information

Airports: SJC • MDW Airport

Airlines operating this route: Southwest Airlines (WN)

Frequently Asked Questions

How many flights operate from SJC to MDW?

There is 1 direct flight operating from SJC to MDW. Approximately 1-2 flights daily.

Which airlines operate flights from SJC to MDW?

1 airline operates on this route: Southwest Airlines.

How long is the flight from SJC to MDW?

The flight duration from SJC to MDW is approximately 4h 00m - 4h 10m.

What is the distance from SJC to MDW?

The distance from SJC to MDW is 1843 miles (2965 km).

What is the flight time range for this route?

Flight times on this route range from 4h 5m - 4h 5m.

What are the earliest and latest flight departure times?

The earliest flight departs at 08:00 and the latest flight departs at 08:00.

What is the cheapest month to fly from SJC to MDW?

March is typically the cheapest month to fly on this route.

How many flights operate per week on this route?

Approximately 7 flights operate per week from SJC to MDW.

What types of aircraft operate on this route?

This route is served by Boeing 737-800 (winglets) Passenger/BBJ2.

What is the average flight price from SJC to MDW?

The average flight price for a round-trip ticket from SJC to MDW is approximately $565 USD. Prices can vary based on booking time, season, and airline.

When is the best time to book flights from SJC to MDW for the lowest prices?

March is typically the cheapest month to fly from SJC to MDW. Booking in advance and avoiding peak travel seasons can help you find better deals.

How far is MDW from SJC?

The distance from SJC to MDW is 1843 miles (2965 km). This is a long-haul flight route.

How long does it take to fly from SJC to MDW?

The flight time from SJC to MDW is approximately 4h 00m - 4h 10m. Actual flight duration may vary based on weather conditions, aircraft type, and routing.