Cheap Flight Tickets from Chicago (MDW) to San Jose (SJC), Starting at $187

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

$187

WN Southwest Airlines • 1 stop • 5h 25m

Aug 09 – Aug 14

The cheapest round trip flight from Chicago to San Jose (MDW-SJC-MDW) is currently $187

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Cheapest Direct Flight

$207

WN Southwest Airlines • nonstop • 3h 50m

Aug 09

The cheapest nonstop flight from Chicago to San Jose (MDW-SJC) is currently $207

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Fastest Flight

3h 45m

The fastest nonstop flight from Chicago to San Jose (MDW-SJC) takes 3h 45m

Top Airlines Flying from Chicago to San Jose

Southwest Airlines-WN

Southwest 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.

Aug 09 - Aug 14, Economy
WN
Chicago → San Jose
5h 25m
6:00 AM - 2:25 PM • 1 stop
WN
Chicago → San Jose
11h 50m
6:15 AM - 5:20 PM • 1 stop
$187
Southwest Airlines
Aug 09 - Aug 14, Economy
WN
Chicago → San Jose
5h 25m
5:25 AM - 12:35 PM • 1 stop
WN
Chicago → San Jose
11h 50m
6:15 AM - 5:20 PM • 1 stop
$190
Southwest Airlines
Aug 09 - Aug 14, Economy
WN
Chicago → San Jose
17h 5m
6:00 AM - 2:25 PM • 1 stop
WN
Chicago → San Jose
6h 40m
11:00 PM - 5:00 AM • nonstop
$954
Southwest Airlines
Aug 09 - Aug 14, Economy
WN
Chicago → San Jose
18h 35m
9:55 PM - 7:10 AM • 1 stop
WN
Chicago → San Jose
6h 40m
11:00 PM - 5:00 AM • nonstop
$973
Southwest Airlines
Aug 09 - Aug 14, Economy
WN
Chicago → San Jose
7h 10m
8:40 PM - 11:10 PM • nonstop
WN
Chicago → San Jose
13h 25m
11:55 AM - 10:00 PM • 2 stops
$1048
Southwest Airlines
Aug 09 - Aug 14, Economy
WN
Chicago → San Jose
10h 15m
6:30 AM - 10:45 AM • 1 stop
WN
Chicago → San Jose
9h 10m
8:40 PM - 4:30 AM • 1 stop
$1052
Southwest 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 5:25 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 WN : USD 187
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 9:55 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to sjc?
You can find budget-friendly flights from Chicago Midway International Airport (mdw) to Norman Y. Mineta San Jose International Airport (sjc) on Southwest Airlines (WN). Low fares are available, especially if you book in advance. Consider booking your flight 18 days prior to departure for the best savings.
What's the popular airline to fly from mdw to sjc?
You can fly from Chicago Midway International Airport (mdw) to Norman Y. Mineta San Jose International Airport (sjc) on Southwest Airlines, which offers business class service with priority check-in, lounge access, and flatbed seats for a comfortable flight.
What's the cheapest day of the week to fly from mdw to sjc?
The cheapest day to fly from Chicago Midway International Airport (mdw) to Norman Y. Mineta San Jose International Airport (sjc) is Monday, as it tends to have lower fares compared to other days of the week.
What's the cheapest month to fly from mdw to sjc?
The cheapest month to fly from Chicago Midway International Airport (mdw) to Norman Y. Mineta San Jose International Airport (sjc) is August, which typically offers low fares on flights.
Which airline/airlines fly from mdw to sjc?
Volaris Airline offers flights from Chicago Midway International Airport (mdw) to Norman Y. Mineta San Jose International Airport (sjc). You can also consider flying with United Airlines, Frontier Airlines, Allegiant, Aeromexico, Delta Airlines, WestJet Airlines, American Airlines, and Southwest Airlines for your one-way trip.
What are the available flights from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport?
You can find available flights on Southwest Airlines (WN) from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport, with a cost of an airfare starting at $200 for one-way tickets.
How can I book a Business class ticket on this airline for my trip?
To book a Business class ticket on Southwest Airlines (WN), visit fareleaders.com website and compare airfares, then click on the 'Book' button to reserve your seat.
What is the cost of an airfare from Milwaukee to San Jose?
The cost of an airfare from Milwaukee to San Jose varies depending on the airline and time of booking. You can check fares on fareleaders.com website for the latest deals.
Can I find deals on flights with awesome airlines like airport?
Yes, you can find deals on flights with airlines like Southwest Airlines (WN) on fareleaders.com website, where you can compare airfares and find the best option for your trip.
Is it possible to compare airfares and fares on fareleaders.com website in July?
Yes, you can compare airfares and fares on fareleaders.com website in July, as well as other months, to find the cheapest flights for your next trip.
How do I look for busco airlines and their flight schedules?
You can search for busco airlines and their flight schedules on fareleaders.com website, where you can also compare airfares and fares.
What are some popular travel destinations to visit in December?
Some popular travel destinations to visit in December include San Jose, Chicago, and other cities with great weather and festive atmosphere.

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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