Cheap Flight Tickets from Chicago (MDW) to San Jose (SJC), Starting at $755

Good to Know: Cheapest and Fastest MDW - SJC Flights

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

Cheapest Round Trip Flight

$755

WN Southwest Airlines • 1 stop • 17h

Oct 16 – Dec 03

The cheapest round trip flight from Chicago to San Jose (MDW-SJC-MDW) is currently $755

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Cheapest Direct Flight

$863

WN Southwest Airlines • nonstop • 7h 20m

Oct 16

The cheapest nonstop flight from Chicago to San Jose (MDW-SJC) is currently $863

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Fastest Flight

7h 15m

The fastest nonstop flight from Chicago to San Jose (MDW-SJC) takes 7h 15m

Top Airlines Flying from Chicago to San Jose

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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

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

Oct 16 - Dec 03, Economy
WN
Chicago → San Jose
17h
11:55 AM - 8:15 PM • 1 stop
WN
Chicago → San Jose
27h 20m
5:30 PM - 12:10 PM • 1 stop
$755
Southwest Airlines
Oct 16 - Dec 03, Economy
WN
Chicago → San Jose
37h 35m
11:55 AM - 8:50 AM • 1 stop
WN
Chicago → San Jose
27h 20m
5:30 PM - 12:10 PM • 1 stop
$755
Southwest Airlines
Oct 16 - Dec 03, Economy
WN
Chicago → San Jose
15h 50m
9:45 AM - 5:35 PM • 1 stop
WN
Chicago → San Jose
11h 45m
8:35 PM - 5:40 AM • 1 stop
$781
Southwest Airlines
Oct 16 - Dec 03, Economy
DL
Chicago → San Jose
19h 15m
10:59 AM - 8:54 PM • 2 stops
DL
Chicago → San Jose
13h 50m
6:20 AM - 4:50 PM • 1 stop
$948
Delta Airlines
Oct 16 - Dec 03, Economy
DL
Chicago → San Jose
13h 37m
10:03 AM - 4:20 PM • 2 stops
DL
Chicago → San Jose
14h 10m
6:00 AM - 4:50 PM • 2 stops
$953
Delta Airlines
Oct 16 - Dec 03, Economy
DL
Chicago → San Jose
17h 12m
1:27 PM - 9:59 PM • 2 stops
DL
Chicago → San Jose
14h 10m
6:00 AM - 4:50 PM • 2 stops
$953
Delta Airlines

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

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

FAQs on Chicago to San Jose Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to SJC?
The most popular airline flying from Chicago to San Jose are
Can I fly from MDW to SJC non-stop?
Yes, you can fly MDW to SJC non-stop on
Which airlines fly nonstop between Chicago and San Jose?
The non-stop flights between Chicago and San Jose are .
What’s the earliest departure time from MDW to SJC Airport?
The earliest flight leaves MDW at 9:45 am and lands in SJC - Norman Y. Mineta San Jose International
What are the airports in San Jose?
SJC
Can I make changes to my Chicago to San Jose 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 MDW to SJC?
Read the fare rules of the Chicago to San Jose 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 Chicago and San Jose?
operate flights between Chicago and San Jose
How long does a flight from Chicago to San Jose take?
It takes approximately 4 hour to fly non-stop from MDW to SJC, which is 1837.59 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to San Jose (SJC) ?
In the past couple of days, the cheapest tickets to SJC from MDW were found on DL : USD 948
Do I need a passport to fly between MDW and SJC?
No
What’s the latest departure time from MDW to SJC ?
The last flight leaves MDW at 9:15 pm

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

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

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