MDW - SJC

$181 Find Cheap Flights from Chicago Midway Airport to San Jose - Compare and Save

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 8/11. 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
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Everything you should know

Cheapest round-trip
$361
Typical prices: $477-$387
Southwest
Wed 7/15Wed 7/22
MDW - SJC • Non-stop
Cheapest one-way
$181
Typical prices: $128-$200
Southwest
Tue 8/11
MDW - SJC • Non-stop
Top airlines
Cheapest • from $361 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 28m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 100% price drop
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

Wed, Jul 15 - Wed, Jul 22
Southwest Logo
8:55 pm - 11:30 pm
MDW
-
SJC
4h 35mnonstop
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$361Southwest
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
10:05 am - 12:30 pm
MDW
-
SJC
4h 25mnonstop
Southwest Logo
1:30 pm - 11:10 pm
SJC
-
MDW
7h 40m
1 stop
$371Southwest
Wed, Aug 12 - Wed, Aug 26
Southwest Logo
2:05 pm - 8:20 pm
MDW
-
SJC
8h 15m
2 stops
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
$372Southwest
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
5:25 am - 11:25 am
MDW
-
SJC
8h 00m
2 stops
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$376Southwest
Tue, Oct 20 - Mon, Oct 26
Southwest Logo
10:30 am - 1:00 pm
MDW
-
SJC
4h 30mnonstop
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
$380Southwest
Wed, Aug 26 - Tue, Sep 1
Delta Logo
1:51 pm - 8:24 pm
MDW
-
SJC
8h 33m
1 stop
Delta Logo
12:40 pm - 10:36 pm
SJC
-
MDW
7h 56m
1 stop
$381Delta
Wed, Aug 12 - Wed, Aug 26
Southwest Logo
2:05 pm - 8:20 pm
MDW
-
SJC
8h 15m
2 stops
Southwest Logo
1:25 pm - 10:50 pm
SJC
-
MDW
7h 25m
1 stop
$382Southwest
Wed, Jul 15 - Fri, Jul 17
Southwest Logo
8:55 pm - 11:30 pm
MDW
-
SJC
4h 35mnonstop
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$384Southwest
Wed, Jul 15 - Wed, Jul 22
Southwest Logo
5:25 am - 11:25 am
MDW
-
SJC
8h 00m
2 stops
Southwest Logo
7:50 pm - 5:25 am
SJC
-
MDW
7h 35m
1 stop
$386Southwest
Tue, Oct 20 - Mon, Oct 26
Southwest Logo
6:20 am - 11:00 am
MDW
-
SJC
6h 40m
1 stop
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
$390Southwest
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.

How much is a round-trip flight from Chicago Midway Airport to San Jose, California?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to San Jose, California departing in July.

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 Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from San Jose, Saturday 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 February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $1,108 and $972 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 $522, prices are generally cheapest when you fly direct.

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.

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.

Good to know

Low seasonApril
Cheapest flight$181
Best time to beat the crowds with an average 55% drop in price.
Most popular time to fly with an average 54% increase in price.
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 5 days, the lowest price for a flight from Chicago Midway Airport to San Jose was $181 for a one-way ticket and $361 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, JetBlue, Alaska Airlines, and Hawaiian 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?

    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 $128 or less one-way and $443 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.
7.9
SouthwestOverall score based on 4235 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

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

Information on your arrival and departure airports