MDW - SJC

$83 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 10/29. 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

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

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

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

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Expert advice
Booking Insights
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

Sat, Oct 25 - Sun, Nov 2
Southwest Logo
4:10 pm - 6:40 pmMDW-SJC
4h 30mnonstop
Southwest Logo
5:30 am - 11:40 amSJC-MDW
4h 10mnonstop
$181Southwest
Find Deal
Thu, Oct 23 - Sun, Oct 26
Southwest Logo
7:50 am - 10:20 amMDW-SJC
4h 30mnonstop
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$197Southwest
Find Deal
Fri, Oct 31 - Wed, Nov 5
Southwest Logo
8:45 am - 11:20 amMDW-SJC
4h 35mnonstop
Southwest Logo
6:30 am - 12:40 pmSJC-MDW
4h 10mnonstop
$203Southwest
Find Deal
Fri, Oct 31 - Wed, Nov 5
Southwest Logo
8:45 am - 11:20 amMDW-SJC
4h 35mnonstop
Southwest Logo
7:40 pm - 5:00 amSJC-MDW
7h 20m1 stop
$213Southwest
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
6:24 pm - 11:32 amMDW-SJC
19h 08m1 stop
Frontier Logo
12:27 pm - 12:36 amSJC-MDW
10h 09m1 stop
$215Frontier
Find Deal
Fri, Oct 31 - Wed, Nov 5
Southwest Logo
8:45 am - 11:20 amMDW-SJC
4h 35mnonstop
Southwest Logo
7:00 am - 4:50 pmSJC-MDW
7h 50m2 stops
$218Southwest
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
9:26 pm - 11:32 amMDW-SJC
16h 06m2 stops
Frontier Logo
12:27 pm - 12:36 amSJC-MDW
10h 09m1 stop
$238Frontier
Find Deal
Fri, Oct 31 - Wed, Nov 5
Delta Logo
3:00 pm - 8:26 pmMDW-SJC
7h 26m1 stop
Delta Logo
7:35 pm - 8:55 amSJC-MDW
11h 20m2 stops
$254Delta
Find Deal
Fri, Oct 3 - Tue, Oct 7
Delta Logo
12:43 pm - 7:49 pmMDW-SJC
9h 06m1 stop
Delta Logo
12:40 pm - 10:14 pmSJC-MDW
7h 34m1 stop
$257Delta
Find Deal
Wed, Dec 3 - Wed, Dec 10
Delta Logo
9:59 am - 6:18 pmMDW-SJC
10h 19m2 stops
Delta Logo
7:45 pm - 9:19 amSJC-MDW
11h 34m2 stops
$259Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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 $181 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
January
Cheapest • 14% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$181
Overall average: $451
Southwest
Sat 10/25Sun 11/2
MDW - SJC • Non-stop
Cheapest one-way
$83
Typical prices: $267-478
Southwest
Wed 10/29
MDW - SJC • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Jose!
Expert advice

Expert advice for your flight from Midway to San Jose

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway offers a compact terminal with three concourses, making navigation easy. Enjoy local dining options like Billy Goat Tavern before your flight.

Read more about MDWby Stefanie Waldek
SJC

For a cost-efficient transfer to San Francisco, take a rideshare to Santa Clara Caltrain station, offering timely service to downtown SF.

Read more about SJCby Bill Fink
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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 Fink

Bill Fink

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
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 Wednesdays 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 January, where tickets cost $378 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $487 and $467 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $477 on average.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$83
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 3% 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 $83 for a one-way ticket and $181 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?

    Alaska Airlines, American Airlines, Hawaiian Airlines, and Delta 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?

    There are nonstop flights from Chicago Midway Airport to San Jose on a daily basis.

  • 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 $161 or less one-way and $333 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 4248 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It was a perfect flight in all aspects! Both legs!

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

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)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.