SJO - MDW

$279 Find Cheap Flights from San José to Chicago Midway Airport

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 José to Midway departing on 10/7. 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 Chicago Midway Airport

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

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Everything you should know

Cheapest round-trip
$404
Southwest
Tue 9/15Fri 9/25
SJO - MDW • 1 stop
Cheapest one-way
$279
Multiple Airlines
Wed 10/7
SJO - MDW • 2 stops
Top airlines
Southwest
Cheapest • from $404 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between San José and Midway. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Houston (IAH)
Cheapest • Avg $362 (round-trip)
Orlando (MCO)
Shortest trip • 8h 03m (one-way)
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 100% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from San José to Midway (SJO-MDW)

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

Tue, Sep 15 - Fri, Sep 25
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
$404Southwest
Mon, Sep 28 - Thu, Oct 1
Southwest Logo
9:00 am - 10:20 pm
SJO
-
MDW
12h 20m
2 stops
Southwest Logo
5:05 am - 12:00 pm
MDW
-
SJO
7h 55m
1 stop
$408Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$414Southwest
Tue, Sep 15 - Sun, Sep 20
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
7:10 am - 6:40 pm
MDW
-
SJO
12h 30m
2 stops
$415Southwest
Fri, Sep 18 - Thu, Sep 24
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
$420Southwest
Wed, Oct 7 - Tue, Oct 13
Southwest Logo
1:00 pm - 11:00 pm
SJO
-
MDW
9h 00m
1 stop
Southwest Logo
8:35 pm - 6:00 am
MDW
-
SJO
10h 25m
1 stop
$430Southwest
Tue, Sep 15 - Fri, Sep 18
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
7:55 am - 6:40 pm
MDW
-
SJO
11h 45m
2 stops
$435Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
9:00 am - 8:10 pm
SJO
-
MDW
10h 10m
2 stops
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$438Southwest
Tue, Sep 15 - Mon, Sep 21
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$439Southwest
Sun, Sep 27 - Thu, Oct 1
Southwest Logo
9:00 am - 9:20 pm
SJO
-
MDW
11h 20m
1 stop
Southwest Logo
6:45 am - 12:35 pm
MDW
-
SJO
6h 50m
1 stop
$441Southwest
Booking Insights

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

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

What is the cheapest month to fly from San José 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 José 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 José to Chicago Midway Airport is June, where tickets cost $0 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $846 and $711 respectively.

Find deals

Good to know

Cheapest flight$279
Most popular time to fly with an average 53% increase in price.
Flight from San José to Chicago Midway Airport

When to book flights from San José to Midway

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

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

    In the last 5 days, the lowest price for a flight from San José to Chicago Midway Airport was $279 for a one-way ticket and $404 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in San José and on arrival in Chicago Midway Airport.

  • Which airports will I be using when flying from San José to Chicago Midway Airport?

    San José and Chicago Midway Airport are both served by 1 main airport. You will leave San José from San José Juan Santamaria Intl and will be arriving at Chicago Midway.

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

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from San José 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 José 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 José 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 José 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 José 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 José with another airline. Booking your flights between San José 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 José 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 José up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from San José to Midway

 
See real verified KAYAK customer reviews for airlines flying from San José 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 José 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.
7.9
SouthwestOverall score based on 4235 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
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.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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

Information on your arrival and departure airports

San José (SJO)
Midway (MDW)