S$165 Cheap Flights from Chicago to San Jose

View S$165 flight on Tue, 19 Aug, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at S$165 for one-way flights and S$394 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
SJC
San Jose
S$394 Return, found 3 days ago
S$394
Return
found 3 days ago
Select Delta flight, departing Fri, 29 Aug from Chicago to San Jose, returning Fri, 5 Sep, priced at S$394 found 3 days ago
Delta
Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
SJC
San Jose
S$510 Return, found 3 days ago
S$510
Return
found 3 days ago
Select Delta flight, departing Fri, 29 Aug from Chicago to San Jose, returning Fri, 5 Sep, priced at S$510 found 3 days ago
Delta
Thu, 7 Aug - Mon, 18 Aug
MDW
Chicago
SJC
San Jose
S$549 Return, found 22 hours ago
S$549
Return
found 22 hours ago
Select Delta flight, departing Thu, 7 Aug from Chicago to San Jose, returning Mon, 18 Aug, priced at S$549 found 22 hours ago
Delta
Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$597 Return, found 4 days ago
S$597
Return
found 4 days ago
Select Delta flight, departing Tue, 5 Aug from Chicago to San Jose, returning Wed, 6 Aug, priced at S$597 found 4 days ago
Delta
Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
SJC
San Jose
S$638 Return, found 3 days ago
S$638
Return
found 3 days ago
Select Delta flight, departing Fri, 29 Aug from Chicago to San Jose, returning Fri, 5 Sep, priced at S$638 found 3 days ago
Delta
Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$657 Return, found 4 days ago
S$657
Return
found 4 days ago
Select Delta flight, departing Tue, 5 Aug from Chicago to San Jose, returning Wed, 6 Aug, priced at S$657 found 4 days ago
Delta
Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$659 Return, found 4 days ago
S$659
Return
found 4 days ago
Select Delta flight, departing Tue, 5 Aug from Chicago to San Jose, returning Wed, 6 Aug, priced at S$659 found 4 days ago
Delta
Thu, 7 Aug - Mon, 18 Aug
MDW
Chicago
SJC
San Jose
S$706 Return, found 22 hours ago
S$706
Return
found 22 hours ago
Select Delta flight, departing Thu, 7 Aug from Chicago to San Jose, returning Mon, 18 Aug, priced at S$706 found 22 hours ago
Delta
Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$723 Return, found 4 days ago
S$723
Return
found 4 days ago
Select Delta flight, departing Tue, 5 Aug from Chicago to San Jose, returning Wed, 6 Aug, priced at S$723 found 4 days ago
Delta
Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$783 Return, found 4 days ago
S$783
Return
found 4 days ago
Select Delta flight, departing Tue, 5 Aug from Chicago to San Jose, returning Wed, 6 Aug, priced at S$783 found 4 days ago

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

October is typically the cheapest month to fly

From S$177 - S$761 per traveller.

Graph displaying average flight prices per month

Chicago to San Jose route information
Origin airport
Midway Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Airlines serving
Delta
Return price
S$393
Distance
2933 km
Average flight time
3 hours 35 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 20 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 from S$165 and roundtrip prices from S$394*.
 

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 San Jose. 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$394. 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

Oakland

Chicago Airports

Chicago

O'Hare Intl. to San Jose
S$352.50
*Available to Expedia members.