$124 Cheap Flights from Chicago (MDW) to San Jose (SJC)

View $124 flight on Sun, Oct 26, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $124 for one-way flights and $190 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Oct 23 - Sun, Oct 26
MDW
Chicago
SJC
San Jose
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Chicago to San Jose, returning Sun, Oct 26, priced at $190 found 1 day ago
Frontier Airlines
Thu, Oct 23 - Sun, Oct 26
MDW
Chicago
SJC
San Jose
$236 Roundtrip, found 2 days ago
$236
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Chicago to San Jose, returning Sun, Oct 26, priced at $236 found 2 days ago
Delta
Fri, Dec 5 - Wed, Dec 10
MDW
Chicago
SJC
San Jose
$316 Roundtrip, found 11 hours ago
$316
Roundtrip
found 11 hours ago
Select Delta flight, departing Fri, Dec 5 from Chicago to San Jose, returning Wed, Dec 10, priced at $316 found 11 hours ago
Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
MDW
Chicago
SJC
San Jose
$327 Roundtrip, found 4 hours ago
$327
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Chicago to San Jose, returning Tue, Nov 18, priced at $327 found 4 hours ago
Delta
Fri, Jan 9 - Mon, Jan 12
MDW
Chicago
SJC
San Jose
$332 Roundtrip, found 3 days ago
$332
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 9 from Chicago to San Jose, returning Mon, Jan 12, priced at $332 found 3 days ago
Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
MDW
Chicago
SJC
San Jose
$336 Roundtrip, found 4 hours ago
$336
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Chicago to San Jose, returning Tue, Nov 18, priced at $336 found 4 hours ago
Southwest Airlines
Fri, Dec 5 - Wed, Dec 10
MDW
Chicago
SJC
San Jose
$341 Roundtrip, found 11 hours ago
$341
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Fri, Dec 5 from Chicago to San Jose, returning Wed, Dec 10, priced at $341 found 11 hours ago
Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
MDW
Chicago
SJC
San Jose
$341 Roundtrip, found 4 hours ago
$341
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Chicago to San Jose, returning Tue, Nov 18, priced at $341 found 4 hours ago
Southwest Airlines
Sat, Nov 1 - Sat, Nov 15
MDW
Chicago
SJC
San Jose
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to San Jose, returning Sat, Nov 15, priced at $346 found 1 day ago
Southwest Airlines
Tue, Nov 11 - Wed, Nov 12
MDW
Chicago
SJC
San Jose
$347 Roundtrip, found 17 hours ago
$347
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Chicago to San Jose, returning Wed, Nov 12, priced at $347 found 17 hours ago

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

January is typically the cheapest month to fly

From $138 - $760 per traveler.

Alternative airports near San Jose

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to San Francisco Intl. SFO. Average driving time to city center is 40 minutes. Flights from $410
SFO
San Francisco Intl.
Average driving time to city center40 min
Flights from $410
Select flight to Oakland Intl. OAK. Average driving time to city center is 41 minutes. Flights from $527
OAK
Oakland Intl.
Average driving time to city center41 min
Flights from $527

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC) cost?
Grab a cheap one-way flight from $124 or cheap return flight from $190 from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
October is the least expensive month to fly from MDW to SJC. Planning your trip for the off-season is often the key to finding better deals on flights.
Which airlines fly direct from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
You can fly straight from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC) on a Southwest Airlines flight.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
To find the cheapest airline flying from MDW to SJC, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
On average, there's only 1 direct flight taking off from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC) every day. If this doesn't suit your schedule, consider flights with a layover. Just customize your search on Expedia to include one stop or more to discover a better alternative.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
More travelers fly between MDW and SJC at 8 AM than at any other time of day. Looking for a quieter experience? Travel outside of rush hours and you're likely to save on your fare as well.
What day of the week has the most flights from MDW to SJC?
If you travel on a Friday, you'll get the biggest range of options for flights from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC).
What is the earliest flight from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
The first flight of the day jetting off from Midway Intl. Airport (MDW) is at around 8:35AM UTC-6. Hop on this flight and you'll land at Norman Y. Mineta San Jose Intl. Airport (SJC) at approximately 11:25AM UTC-8. The entire trip takes 4h 50m.
How long does it take to fly from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
Flights from MDW to SJC have an average travel time of 4 hours and 49 minutes. The distance between the two airports is 1,850 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
To land at Norman Y. Mineta San Jose Intl. Airport (SJC) on time, pick a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for San Jose from Midway Intl. Airport (MDW)?
Midway Intl. Airport (MDW) has direct flights to San Jose. Here are some of the airports you can fly to without stops:

  • San Francisco Intl. Airport (SFO)
  • Norman Y. Mineta San Jose Intl. Airport (SJC)
  • Oakland Intl. Airport (OAK)

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC) last-minute?
Booking your plane ticket from MDW to SJC right before your journey is typically more expensive. However, if there's some wiggle room with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to SJC flight and hotel package?
You'll generally save money by securing a MDW to SJC flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After selecting your preferred accommodations and flights, you can add extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC)?
In most instances, you can cancel or reschedule your MDW to SJC flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you need more information, head to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$190
Distance
1833 mi
Average flight time
3 hours 28 mins

Book with confidence

Chicago to San Jose Flights

The cheapest times to fly from Chicago to San Jose

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San Jose are during the month of October. You can find some of the cheapest flights from Chicago to San Jose with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to San Jose

Sunday is one of the best days to book for cheap flights from Chicago to San Jose: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to San Jose

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San Jose in 2025. You can also book with separate airlines for your outbound and return journeys, from $124 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San Jose flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San Jose airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to San Jose Flights

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*Available to One Key members.