
Popular airlines from Chicago Midway Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)
- Delta
Delta
- Plan, book, fly with confidence
trending down icon Be in the knowGet alerts if flight prices drop or rise*bex rewards loyalty icon Book smarterSave up to 40% on select hotels after you book a flight*payments icon
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$329 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, 23 Aug - Sat, 30 Aug
MDW
Chicago
SJC
San Jose
S$329 Return, found 6 days ago
S$329
Return
found 6 days ago

Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
SJC
San Jose
S$394 Return, found 14 hours ago
S$394
Return
found 14 hours ago

Wed, 20 Aug - Wed, 27 Aug
MDW
Chicago
SJC
San Jose
S$395 Return, found 5 days ago
S$395
Return
found 5 days ago

Wed, 20 Aug - Wed, 27 Aug
MDW
Chicago
SJC
San Jose
S$420 Return, found 5 days ago
S$420
Return
found 5 days ago

Wed, 20 Aug - Wed, 27 Aug
MDW
Chicago
SJC
San Jose
S$421 Return, found 4 days ago
S$421
Return
found 4 days ago

Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
SJC
San Jose
S$510 Return, found 14 hours ago
S$510
Return
found 14 hours ago

Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$597 Return, found 1 day ago
S$597
Return
found 1 day ago

Fri, 29 Aug - Fri, 5 Sep
MDW
Chicago
SJC
San Jose
S$638 Return, found 14 hours ago
S$638
Return
found 14 hours ago

Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$657 Return, found 1 day ago
S$657
Return
found 1 day ago

Tue, 5 Aug - Wed, 6 Aug
MDW
Chicago
SJC
San Jose
S$659 Return, found 1 day ago
S$659
Return
found 1 day 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$757 per traveller.
Graph displaying average flight prices per month
Origin airport | Midway Intl. |
Destination airport | Norman Y. Mineta San Jose Intl. |
Airlines serving | Delta |
Return price | S$329 |
Distance | 2933 km |
Average flight time | 3 hours 36 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$329*.
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
Explore a world of travel with Expedia
- Trending Routes
- Trending Flights
- Top Flights Destinations
- More Carriers
- Nearby Airports
- Cheap Flights from Other Airports
- Expedia's Latest Trends
Popular flights from Chicago
Popular flights to San Jose
- Newark Liberty Intl. Airport to San Jose (EWR - SJC)
- San Diego to San Jose (SAN - SJC)
- Los Angeles to San Jose (LAX - SJC)
- Raleigh to San Jose (RDU - SJC)
- London to San Jose (LCY - SJC)
- Miami to San Jose (MIA - SJC)
- New York to San Jose (LGA - SJC)
- Orange County to San Jose (SNA - SJC)
- Washington to San Jose (IAD - SJC)
- New York to San Jose (JFK - SJC)
- Busan to San Jose (PUS - SJC)
- Baltimore to San Jose (BWI - SJC)
Popular flights to San Jose
Top Flight Destinations Near Here
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Myrtle Beach
- Flights to Chicago
- Flights to San Diego
- Flights to Panama City Beach
- Flights to Destin
- Flights to Los Angeles
- Flights to Ocean City
- Flights to Miami
- Flights to Gulf Shores
- Flights to Boston
- Flights to Nashville
- Flights to Pigeon Forge
- Flights to San Francisco
- Flights to Atlanta
- Flights to Houston
- Flights to Virginia Beach
- Flights to Atlantic City
More Carriers
San Jose Airports
San Francisco
Oakland
Chicago Airports
Chicago
S$278.40
Nearby Airports
- O'Hare Intl. Airport (ORD)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- Waukesha County Airport (UES)
- Purdue University Airport (LAF)
- Central Illinois Regional Airport (BMI)
- Kalamazoo-Battle Creek Intl. Airport (AZO)
- Dane County Regional Airport (MSN)
- University Of Illinois Urbana-Champaign Williard Airport (CMI)
Expedia's Latest Trends
Flights
- San Francisco to Grand Canyon (SFO - GCN)
- Los Angeles to Baltimore (LAX - BWI)
- New York to San Francisco (JFK - SFO)
- San Francisco to Los Angeles (SFO - LAX)
- Kuala Lumpur to Los Angeles (KUL - LAX)
- San Francisco to Vancouver (SFO - YVR)
- Toronto to San Francisco (YYZ - SFO)
- Buffalo to Los Angeles (BUF - LAX)
- San Francisco to New York (SFO - JFK)
- Vancouver to San Francisco (YVR - SFO)
- Los Angeles to Aspen (LAX - ASE)
- Los Angeles to San Francisco (LAX - SFO)
- Singapore to Los Angeles (SIN - LAX)
- San Francisco to Las Vegas (SFO - LAS)
- Las Vegas to Los Angeles (LAS - LAX)
- Los Angeles to Tampa (LAX - TPA)
- Singapore to Ontario (SIN - ONT)
- Los Angeles to Boston (LAX - BOS)
- San Francisco to Seattle (SFO - SEA)
- Los Angeles to Singapore (LAX - SIN)
- San Francisco to Singapore (SFO - SIN)
- Los Angeles to Las Vegas (LAX - LAS)
- Los Angeles to Vancouver (LAX - YVR)
- Singapore to San Francisco (SIN - SFO)
- Phoenix to Los Angeles (PHX - LAX)
- Los Angeles to New York (LAX - NYC)
- Las Vegas to San Francisco (LAS - SFO)
- Singapore to San Diego (SIN - SAN)
- Los Angeles to Orlando (LAX - MCO)
- New York to Los Angeles (NYC - LAX)
*Available to Expedia members.