Cheap Flight Tickets from San Jose (SJC) to Chicago (MDW), Starting at $257

Good to Know: Cheapest and Fastest SJC - MDW Flights

Useful information for finding best airline tickets from Norman Y. Mineta San Jose International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$257

WN Southwest Airlines • 1 stop • 12h 5m

Aug 28 – Sep 01

The cheapest round trip flight from San Jose to Chicago (SJC-MDW-SJC) is currently $257

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Cheapest Direct Flight

$257

WN Southwest Airlines • nonstop • 6h 50m

Aug 28

The cheapest nonstop flight from San Jose to Chicago (SJC-MDW) is currently $257

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Fastest Flight

6h 40m

The fastest nonstop flight from San Jose to Chicago (SJC-MDW) takes 6h 40m

Top Airlines Flying from San Jose to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from San Jose (SJC) to Chicago (MDW)

Compare and book low fare round-trip air tickets from San Jose to Chicago. Ideal for travelers with confirmed return itineraries.

Aug 28 - Sep 01, Economy
WN
San Jose → Chicago
12h 5m
7:55 AM - 5:20 PM • 1 stop
WN
San Jose → Chicago
7h 10m
8:30 PM - 11:00 PM • nonstop
$257
Southwest Airlines
Aug 28 - Sep 01, Economy
WN
San Jose → Chicago
6h 50m
11:20 AM - 5:30 PM • nonstop
WN
San Jose → Chicago
7h 10m
8:30 PM - 11:00 PM • nonstop
$257
Southwest Airlines
Aug 28 - Sep 01, Economy
WN
San Jose → Chicago
11h 50m
8:30 PM - 5:40 AM • 1 stop
WN
San Jose → Chicago
7h 5m
10:20 AM - 12:45 PM • nonstop
$257
Southwest Airlines
Aug 28 - Sep 01, Economy
WN
San Jose → Chicago
10h 30m
3:15 PM - 11:45 PM • 1 stop
WN
San Jose → Chicago
7h 5m
10:20 AM - 12:45 PM • nonstop
$257
Southwest Airlines
Aug 28 - Sep 01, Economy
WN
San Jose → Chicago
6h 50m
11:20 AM - 5:30 PM • nonstop
WN
San Jose → Chicago
13h 35m
2:05 PM - 8:20 PM • 2 stops
$257
Southwest Airlines
Aug 28 - Sep 01, Economy
WN
San Jose → Chicago
6h 50m
11:20 AM - 5:30 PM • nonstop
WN
San Jose → Chicago
12h
3:30 PM - 8:50 PM • 1 stop
$257
Southwest Airlines

Fly from San Jose to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from San Jose to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on San Jose to Chicago Flights

What are the airports in San Jose?
SJC
What’s the most popular airline flying from SJC to MDW?
The most popular airline flying from San Jose to Chicago are
Can I fly from SJC to MDW non-stop?
Yes, you can fly SJC to MDW non-stop on
Which airlines fly nonstop between San Jose and Chicago?
The non-stop flights between San Jose and Chicago are .
What’s the earliest departure time from SJC to MDW Airport?
The earliest flight leaves SJC at 7:55 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my San Jose to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from SJC to MDW?
Read the fare rules of the San Jose to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from San Jose and Chicago?
operate flights between San Jose and Chicago
How long does a flight from San Jose to Chicago take?
It takes approximately 4 hour to fly non-stop from SJC to MDW, which is 1837.59 miles by air.
Which airlines provide the cheapest flights from San Jose (SJC) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from SJC were found on WN : USD 257
Do I need a passport to fly between SJC and MDW?
No
What’s the latest departure time from SJC to MDW ?
The last flight leaves SJC at 11:00 pm

San Jose (SJC) to Chicago (MDW): Airport Information

Origin Airport Norman Y. Mineta San Jose International , San Jose, US
Destination Airport Chicago Midway International , Chicago, US
Distance 1838 miles

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