Cheap Flights from Chicago (MDW) to San Jose (SJC) from HK$2,596~

View HK$2,596 flight on Mon, 12 Jan 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at HK$2,596 for one-way flights and HK$4,523 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$4,523 Return, found 6 days ago
HK$4,523
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$4,523 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$4,772 Return, found 6 days ago
HK$4,772
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$4,772 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$4,814 Return, found 6 days ago
HK$4,814
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$4,814 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$4,986 Return, found 6 days ago
HK$4,986
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$4,986 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$5,050 Return, found 6 days ago
HK$5,050
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$5,050 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$5,459 Return, found 6 days ago
HK$5,459
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$5,459 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$5,470 Return, found 6 days ago
HK$5,470
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$5,470 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$5,512 Return, found 6 days ago
HK$5,512
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$5,512 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$5,749 Return, found 6 days ago
HK$5,749
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$5,749 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$5,921 Return, found 6 days ago
HK$5,921
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$5,921 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$6,320 Return, found 6 days ago
HK$6,320
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$6,320 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$6,362 Return, found 6 days ago
HK$6,362
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$6,362 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$6,684 Return, found 6 days ago
HK$6,684
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$6,684 found 6 days ago
Delta
Mon, 12 Jan - Sat, 17 Jan
MDW
Chicago
SJC
San Jose
HK$7,168 Return, found 6 days ago
HK$7,168
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Jan from Chicago to San Jose, returning Sat, 17 Jan, priced at HK$7,168 found 6 days ago

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

January is typically the cheapest month to fly

From HK$1,074 - HK$6,389 per traveller.

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 HK$4,523. 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 canceled 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 kilometers 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 traveling 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.

Travel information

Origin airport
Midway Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Return price
HK$4,523
Distance
2933 km
Average flight time
4 hours 16 mins

Book with confidence

Flights from Chicago to San Jose

Book cheap flights from Chicago (MDW) to San Jose (SJC) on Expedia.com.hk. Find the best flight deals to destinations around the world for your next leisure or business travel on Expedia.com.hk.

Search for flights from Chicago (MDW) to San Jose (SJC) to find great flight deals suitable to your travel date and time. Expedia.com.hk flight booking search engine is simple to use and looking for cheap flights is as easy as a click of a mouse or on your mobile devices.

Be assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago (MDW) to San Jose (SJC) trip. Call us at 3077-4857 (direct number - 24 hours day for English).

Save more when combine your San Jose flight with a hotel for a package deal! Discover additional savings by booking in advance. Now you can find activities in San Jose and things to do in San Jose for your perfect vacation with Expedia Thing to Do.

If you would like to book flights to San Jose more flexibly, many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to San Jose is HK$2,596 now!

 

Flights from Chicago to San Jose

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