SJC - MDW

$163 Find Cheap Flights from San Jose to Chicago Midway Airport - 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 San Jose to Midway departing on 9/9. 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

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Everything you should know

Cheapest round-trip
$331
Typical prices: $459-$596
Southwest
Tue 8/4Fri 8/7
SJC - MDW • 1 stop
Cheapest non-stop
$332
Typical prices: $459-$571
Southwest
Sat 8/8Tue 8/11
SJC - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $332 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 4h 05m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
San Diego (SAN)
Cheapest • Avg $383 (round-trip)
Denver (DEN)
Shortest trip • 5h 47m (one-way)
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 26% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Midway!
Flight Deals
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Expert advice
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Midway 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 San Jose to Midway

Tue, Aug 4 - Fri, Aug 7
Southwest Logo
7:40 pm - 5:40 am
SJC
-
MDW
8h 00m
1 stop
Southwest Logo
7:10 am - 12:50 pm
MDW
-
SJC
7h 40m
2 stops
$331Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
8:30 pm - 11:00 pm
MDW
-
SJC
4h 30mnonstop
$332Southwest
Wed, Aug 26 - Sun, Aug 30
Southwest Logo
9:55 am - 4:00 pm
SJC
-
MDW
4h 05mnonstop
Southwest Logo
7:10 am - 1:15 pm
MDW
-
SJC
8h 05m
1 stop
$337Southwest
Wed, Aug 12 - Mon, Aug 17
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
8:50 pm - 11:20 pm
MDW
-
SJC
4h 30mnonstop
$338Southwest
Mon, Aug 24 - Tue, Aug 25
Delta Logo
4:30 pm - 8:39 am
SJC
-
MDW
14h 09m
2 stops
Delta Logo
1:51 pm - 8:24 pm
MDW
-
SJC
8h 33m
1 stop
$341Delta
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
8:30 pm - 11:00 pm
MDW
-
SJC
4h 30mnonstop
$342Southwest
Wed, Aug 19 - Sun, Aug 23
Southwest Logo
6:45 am - 4:00 pm
SJC
-
MDW
7h 15m
2 stops
Southwest Logo
7:10 am - 1:15 pm
MDW
-
SJC
8h 05m
1 stop
$343Southwest
Sun, Sep 6 - Wed, Sep 9
Southwest Logo
8:10 am - 5:00 pm
SJC
-
MDW
6h 50m
1 stop
Southwest Logo
2:05 pm - 8:20 pm
MDW
-
SJC
8h 15m
2 stops
$344Southwest
Wed, Aug 26 - Sun, Aug 30
Southwest Logo
7:40 pm - 5:40 am
SJC
-
MDW
8h 00m
1 stop
Southwest Logo
7:10 am - 1:15 pm
MDW
-
SJC
8h 05m
1 stop
$347Southwest
Wed, Aug 5 - Mon, Aug 10
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
7:00 am - 12:20 pm
MDW
-
SJC
7h 20m
1 stop
$348Southwest
Booking Insights

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

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

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

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

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

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

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from San Jose to Chicago Midway Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Chicago Midway Airport, 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 San Jose to Chicago Midway Airport is October, where tickets cost $464 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $919 and $840 respectively.

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

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 $959, prices are generally cheapest when you fly direct.

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Expert advice

Expert advice for your flight from San Jose to Midway

 
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 seasonJanuary
Cheapest flight$163
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 46% increase in price.
Flight from San Jose to Chicago Midway Airport

When to book flights from San Jose to Midway

Are your dates flexible? Find out the best times to travel from San Jose to Midway 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 San Jose to Chicago Midway Airport flights

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

    In the last 5 days, the lowest price for a flight from San Jose to Chicago Midway Airport was $163 for a one-way ticket and $332 for a round-trip.

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

    A passport is not required to fly from San Jose to Chicago Midway Airport.

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

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

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

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

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

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

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

    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 San Jose to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Jose 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 San Jose to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to San Jose with another airline. Booking your flights between San Jose and MDW 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 San Jose to Chicago Midway Airport?

    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 Chicago Midway Airport from San Jose 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 San Jose to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $219 or less one-way and $466 or less round-trip.

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

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from San Jose to Midway

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Chicago. 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 San Jose to Midway? 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 4249 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Wifi didn’t work, no service, seats are hard as rocks

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

Information on your arrival and departure airports

San Jose (SJC)
Midway (MDW)