$83 Cheap Flights from Chicago (MDW) to San Jose (SJC)

View $83 flight on Tue, Aug 19, 2025Opens in a new window

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 $83 for one-way flights and $157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Oct 7 - Wed, Oct 8
MDW
Chicago
SJC
San Jose
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 7 from Chicago to San Jose, returning Wed, Oct 8, priced at $157 found 2 days ago
Southwest Airlines
Tue, Aug 12 - Tue, Sep 9
MDW
Chicago
SJC
San Jose
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to San Jose, returning Tue, Sep 9, priced at $171 found 1 day ago
Southwest Airlines
Sat, Oct 18 - Tue, Oct 21
MDW
Chicago
SJC
San Jose
$175 Roundtrip, found 17 hours ago
$175
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Oct 18 from Chicago to San Jose, returning Tue, Oct 21, priced at $175 found 17 hours ago
Southwest Airlines
Tue, Aug 12 - Tue, Sep 9
MDW
Chicago
SJC
San Jose
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to San Jose, returning Tue, Sep 9, priced at $176 found 1 day ago
Southwest Airlines
Tue, Sep 30 - Tue, Oct 7
MDW
Chicago
SJC
San Jose
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Sep 30 from Chicago to San Jose, returning Tue, Oct 7, priced at $183 found 2 days ago
Southwest Airlines
Sat, Oct 18 - Tue, Oct 21
MDW
Chicago
SJC
San Jose
$185 Roundtrip, found 17 hours ago
$185
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Oct 18 from Chicago to San Jose, returning Tue, Oct 21, priced at $185 found 17 hours ago
Southwest Airlines
Sat, Oct 18 - Tue, Oct 21
MDW
Chicago
SJC
San Jose
$188 Roundtrip, found 17 hours ago
$188
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Oct 18 from Chicago to San Jose, returning Tue, Oct 21, priced at $188 found 17 hours ago
Southwest Airlines
Sat, Oct 18 - Tue, Oct 21
MDW
Chicago
SJC
San Jose
$190 Roundtrip, found 17 hours ago
$190
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Oct 18 from Chicago to San Jose, returning Tue, Oct 21, priced at $190 found 17 hours ago
Delta
Sat, Aug 16 - Tue, Aug 19
MDW
Chicago
SJC
San Jose
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Delta flight, departing Sat, Aug 16 from Chicago to San Jose, returning Tue, Aug 19, priced at $257 just found
Frontier Airlines
Thu, Aug 14 - Sun, Aug 17
MDW
Chicago
SJC
San Jose
$306 Roundtrip, found 21 hours ago
$306
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Chicago to San Jose, returning Sun, Aug 17, priced at $306 found 21 hours ago

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

October is typically the cheapest month to fly

From $138 - $592 per traveler.

Graph displaying average flight prices per month

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 $461
SFO
San Francisco Intl.
Average driving time to city center40 min
Flights from $461
Select flight to Oakland Intl. OAK. Cheapest option available. Average driving time to city center is 41 minutes. Flights from $337
OAK
Oakland Intl.
Cheapest
Average driving time to city center41 min
Flights from $337
Flights from Chicago (MDW) to San Jose (SJC)
Origin airport
Midway Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$156
Distance
1833 mi
Average flight time
3 hours 36 mins

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 $83 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC) cost?
Cheap round-trip flights from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC) start from $209. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and United flight leaving MDW on August 6 2025 and touching down at SJC. The price was last updated on July 10 2025 and has not changed since.
What is the cheapest month to fly from MDW to SJC?
The cheapest flights from MDW to SJC are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to SJC?
Travel from MDW to SJC with Southwest Airlines. This carrier currently offers the cheapest one-way fare for this route, starting at $105. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 10 2025. Prices were last updated on July 10 2025 and have not changed since.
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.

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