Cheap Flight Tickets from San Jose (SJC) to Chicago (MDW), Starting at $218

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

$218

WN Southwest Airlines • 1 stop • 8h 45m

Oct 22 – Oct 24

The cheapest round trip flight from San Jose to Chicago (SJC-MDW-SJC) is currently $218

🔍 Search Flights

Cheapest Direct Flight

$457

WN Southwest Airlines • nonstop • 6h 45m

Oct 23

The cheapest nonstop flight from San Jose to Chicago (SJC-MDW) is currently $457

🔍 Search Flights

Fastest Flight

6h 40m

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

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 22 - Oct 24, Economy
WN
San Jose → Chicago
8h 45m
6:20 AM - 5:35 PM • 1 stop
WN
San Jose → Chicago
8h 55m
10:40 AM - 3:15 PM • 1 stop
$218
Southwest Airlines
Oct 22 - Oct 24, Economy
WN
San Jose → Chicago
8h 45m
8:50 AM - 5:35 PM • 1 stop
WN
San Jose → Chicago
8h 55m
10:40 AM - 3:15 PM • 1 stop
$218
Southwest Airlines
Oct 22 - Oct 24, Economy
WN
San Jose → Chicago
21h 40m
9:10 AM - 12:10 AM • 1 stop
WN
San Jose → Chicago
7h 10m
2:05 PM - 4:35 PM • nonstop
$409
Southwest Airlines
Oct 22 - Oct 24, Economy
WN
San Jose → Chicago
12h 25m
7:00 AM - 4:45 PM • 1 stop
WN
San Jose → Chicago
7h 10m
2:05 PM - 4:35 PM • nonstop
$409
Southwest Airlines
Oct 22 - Oct 24, Economy
WN
San Jose → Chicago
9h
9:05 AM - 4:45 PM • 1 stop
WN
San Jose → Chicago
10h
6:05 AM - 10:05 AM • 1 stop
$458
Southwest Airlines
Oct 22 - Oct 24, Economy
DL
San Jose → Chicago
35h 50m
- • 1 stop
DL
San Jose → Chicago
12h 36m
- • 1 stop
$576
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 6:20 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 409
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 10:2000 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

More Flight Options for San Jose (SJC) and Chicago (MDW)

Why Fareleaders for SJC to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on San Jose to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on SJC to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of San Jose to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the San Jose (SJC) to Chicago (MDW)
Terms and Conditions*