Cheap Flight Tickets from San Jose (SJC) to Chicago (MDW), Starting at $292

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

$302

WN Southwest Airlines • 1 stop • 11h 55m

Oct 17 – Oct 25

The cheapest round trip flight from San Jose to Chicago (SJC-MDW-SJC) is currently $302

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Cheapest Direct Flight

$292

WN Southwest Airlines • nonstop • 6h 40m

Oct 17

The cheapest nonstop flight from San Jose to Chicago (SJC-MDW) is currently $292

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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.

Oct 17 - Oct 25, Economy
WN
San Jose → Chicago
11h 55m
11:30 AM - 8:45 PM • 1 stop
WN
San Jose → Chicago
7h 15m
10:00 AM - 12:35 PM • nonstop
$302
Southwest Airlines
Oct 16 - Oct 25, Economy
WN
San Jose → Chicago
9h 5m
6:05 AM - 1:50 PM • 1 stop
WN
San Jose → Chicago
7h 15m
9:20 PM - 11:55 PM • nonstop
$352
Southwest Airlines
Oct 16 - Oct 25, Economy
WN
San Jose → Chicago
13h 35m
10:20 AM - 8:35 PM • 2 stops
WN
San Jose → Chicago
13h 35m
5:10 AM - 11:25 AM • 1 stop
$358
Southwest Airlines
Oct 17 - Oct 25, Economy
DL
San Jose → Chicago
12h 16m
12:57 PM - 10:33 PM • 1 stop
DL
San Jose → Chicago
10h 35m
7:15 PM - 11:50 PM • 1 stop
$426
Delta Airlines
Oct 17 - Oct 25, Economy
DL
San Jose → Chicago
13h 47m
6:20 AM - 4:47 PM • 1 stop
DL
San Jose → Chicago
10h 26m
2:03 PM - 6:29 PM • 1 stop
$426
Delta Airlines
Oct 16 - Oct 25, Economy
DL
San Jose → Chicago
12h 16m
12:57 PM - 10:33 PM • 1 stop
DL
San Jose → Chicago
10h 26m
2:03 PM - 6:29 PM • 1 stop
$476
Delta 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 6:00 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 302
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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