MDW - SJC

$104 Find Cheap Flights from Chicago Midway Airport to San Jose

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Jose departing on 3/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Jose

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Jose, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Jose, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

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Everything you should know

Cheapest round-trip
$349
Overall average: $597
Southwest
Mon 2/23Mon 3/2
MDW - SJC • Non-stop
Cheapest one-way
$104
Typical prices: $132-$407
Frontier
Wed 3/11
MDW - SJC • 2 stops
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal eases navigation.
For a cost-efficient transfer, use Caltrain from Santa Clara.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $349 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 24% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Jose!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Jose that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Jose

Mon, Feb 23 - Mon, Mar 2
Southwest Logo
8:05 am - 10:55 am
MDW
-
SJC
4h 50mnonstop
Southwest Logo
6:30 am - 12:40 pm
SJC
-
MDW
4h 10mnonstop
$349Southwest
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
5:00 pm - 9:15 pm
MDW
-
SJC
6h 15m
1 stop
Southwest Logo
6:30 am - 12:40 pm
SJC
-
MDW
4h 10mnonstop
$355Southwest
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
8:05 am - 10:55 am
MDW
-
SJC
4h 50mnonstop
Southwest Logo
3:30 pm - 12:25 am
SJC
-
MDW
6h 55m
1 stop
$359Southwest
Sat, May 16 - Wed, May 20
Southwest Logo
10:10 am - 3:45 pm
MDW
-
SJC
7h 35m
2 stops
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$360Southwest
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
5:00 pm - 9:15 pm
MDW
-
SJC
6h 15m
1 stop
Southwest Logo
7:50 pm - 5:15 am
SJC
-
MDW
7h 25m
1 stop
$364Southwest
Thu, Mar 12 - Sun, Mar 22
Southwest Logo
8:00 pm - 10:40 pm
MDW
-
SJC
4h 40mnonstop
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$368Southwest
Tue, Feb 17 - Wed, Feb 18
Delta Logo
1:49 pm - 8:53 pm
MDW
-
SJC
9h 04m
1 stop
Delta Logo
10:35 pm - 9:54 am
SJC
-
MDW
9h 19m
1 stop
$369Delta
Thu, Apr 9 - Wed, Apr 15
Southwest Logo
10:05 am - 2:15 pm
MDW
-
SJC
6h 10m
1 stop
Southwest Logo
9:45 am - 7:30 pm
SJC
-
MDW
7h 45m
2 stops
$370Southwest
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
3:25 pm - 9:10 pm
MDW
-
SJC
7h 45m
2 stops
Southwest Logo
10:00 am - 8:10 pm
SJC
-
MDW
8h 10m
1 stop
$374Southwest
Sat, May 16 - Wed, May 20
Southwest Logo
10:10 am - 3:45 pm
MDW
-
SJC
7h 35m
2 stops
Southwest Logo
1:45 pm - 11:20 pm
SJC
-
MDW
7h 35m
2 stops
$375Southwest
Booking Insights

KAYAK's insights & trends for Midway to San Jose flights

Get data-powered insights and trends into flights from Midway to San Jose to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to San Jose?

The average price of all round-trip flights from Chicago Midway Airport to San Jose clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to San Jose, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from San Jose, Tuesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Chicago Midway Airport to San Jose?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to San Jose, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to San Jose is September, where tickets cost $365 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $676 and $597 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to San Jose?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $423, prices are generally cheapest when you fly direct.

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Expert advice

Expert advice for your flight from Midway to San Jose

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Bill Fink

Bill Fink

Expert on SJC

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more

Good to know

Low seasonOctober
Cheapest flight$104
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Chicago Midway Airport to San Jose

When to book flights from Midway to San Jose

Are your dates flexible? Find out the best times to travel from Midway to San Jose based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San Jose flights

  • What is the cheapest flight from Chicago Midway Airport to San Jose?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Jose was $104 for a one-way ticket and $349 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San Jose?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San Jose?

    American Airlines, Hawaiian Airlines, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Chicago Midway Airport to San Jose flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Jose?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Jose flight route.

  • On which days can I fly direct from Chicago Midway Airport to San Jose?

    You can catch a nonstop flight from Chicago Midway Airport to San Jose on Monday, Tuesday, Thursday, Friday, Saturday, and Sunday.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San Jose?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to San Jose.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Jose?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Jose from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to San Jose?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Jose with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJC can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Jose?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Jose from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to San Jose

  • Looking for a cheap flight? 25% of our users found flights on this route for $193 or less one-way and $380 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to San Jose?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San Jose.
Find which airlines fly direct from Chicago Midway Airport to San Jose Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San Jose

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

San Jose to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to San Jose

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Jose. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to San Jose? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4268 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

3 hour delay. Had to change plans and was still delayed.

2.0 MediocreAnonymous, Jan 2026
SFO - SAN
Read more Southwest reviews

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Everything you need to know for your flight from Midway to San Jose

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
San Jose (SJC)