Cheap Flights from Chicago to San Jose

Popular airlines from Chicago Midway Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)

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Cheap Flights from Chicago to San Jose (MDW-SJC)

Prices were available within the past 7 days and start at for one-way flights and S$736 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$736 Return, found 4 hours ago
S$736
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$736 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$970 Return, found 4 hours ago
S$970
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$970 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$977 Return, found 4 hours ago
S$977
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$977 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,218 Return, found 4 hours ago
S$1,218
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,218 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,375 Return, found 4 hours ago
S$1,375
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,375 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,771 Return, found 4 hours ago
S$1,771
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,771 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,778 Return, found 4 hours ago
S$1,778
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,778 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,824 Return, found 4 hours ago
S$1,824
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,824 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,831 Return, found 4 hours ago
S$1,831
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,831 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,928 Return, found 4 hours ago
S$1,928
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,928 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,980 Return, found 4 hours ago
S$1,980
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,980 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$1,994 Return, found 4 hours ago
S$1,994
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$1,994 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$2,001 Return, found 4 hours ago
S$2,001
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$2,001 found 4 hours ago
Delta
Sat, 13 Dec - Sun, 4 Jan
MDW
Chicago
SJC
San Jose
S$2,150 Return, found 4 hours ago
S$2,150
Return
found 4 hours ago
Select Delta flight, departing Sat, 13 Dec from Chicago to San Jose, returning Sun, 4 Jan, priced at S$2,150 found 4 hours ago

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Find the cheapest month to fly from Chicago (MDW) to San Jose (SJC)

January is typically the cheapest month to fly

From S$180 - S$1,004 per traveller.
Chicago to San Jose route information
Origin airport
Midway Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Airlines serving
Delta
Return price
S$736
Distance
2933 km
Average flight time
5 hours 8 mins

Perfect flights from Chicago to San Jose

Your Journey from Chicago to San Jose

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to San Jose caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Midway Intl. to Norman Y. Mineta San Jose Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 14 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to San Jose Flights

Experience the joy of finding cheap flights from Midway Intl. to Norman Y. Mineta San Jose Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares and roundtrip prices from S$736*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to San Jose with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant San Jose

Picture yourself stepping off the plane in San Jose and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to San Jose Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to San Jose.
 

Beyond the Flight – Exploring San Jose

With Expedia, your adventure extends beyond the flight. Explore San Jose at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to San Jose with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to San Jose with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from MDW to San Jose Intl. Airport?
Round-trip journeys from Midway Airport to Norman Y. Mineta San Jose Intl. Airport (SJC) start from S$736. This price is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Midway Airport to San Jose Intl. Airport?
Most flights can be cancelled online, but every air carrier has different terms and conditions. If you do have to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Airport to Norman Y. Mineta San Jose Intl. Airport (SJC) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for MDW to SJC flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from Midway Airport to San Jose Intl. Airport?
It takes approximately 6 hours and 18 minutes to fly from MDW (MDW) to San Jose Intl. Airport (SJC). But with some movies and a few interesting magazines, the time will go by quicker.
How far is the flight from Chicago Airport to San Jose Intl. Airport?
It's around 3,000 kilometres between Chicago and San Jose, so you'll be in your seat for a while. Keep yourself occupied by packing things like playing cards (if you're travelling with friends) or a thrilling novel.
Which airlines fly direct from MDW to San Jose Intl. Airport?
Check out the airfares with Southwest Airlines (WN) if you want to fly directly from MDW to San Jose Intl. Airport. This top airline offers 30 flights monthly, so you're sure to find one that fits your schedule.
Are Midway Airport to San Jose Intl. Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to nab a fantastic last-minute deal from Chicago Airport to SJC, but it's also possible to miss out entirely! As many airlines release seats up to a year in advance, it's worth keeping an eye on fares early and being ready to book when you see a bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can be certain you're always getting the latest offers.

Explore a world of travel with Expedia

San Jose Airports

San Francisco

Chicago Airports

Chicago

O'Hare Intl. to San Jose
S$368.60
*Available to Expedia members.