SJO - MDW

$241 Find Cheap Flights from San José 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 José to Midway departing on 10/1. 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
$453
Typical prices: $366-$529
Southwest
Mon 9/21Mon 9/28
SJO - MDW • 1 stop
Cheapest one-way
$292
Southwest
Thu 10/1
SJO - MDW • 1 stop
Top airlines
Southwest
Cheapest • from $453 (round-trip)
Southwest
Best reviews • 8.0 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
November
Cheapest • 36% price drop
October
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
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

Mon, Sep 21 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:20 pm-
7h 40m
Southwest Logo
5:00 am - 12:45 pm-
8h 45m
$453Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:20 pm-
7h 40m
Southwest Logo
7:55 am - 6:45 pm-
11h 50m
$458Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
9:00 am - 9:35 pm-
11h 35m
Southwest Logo
5:00 am - 12:45 pm-
8h 45m
$468Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
9:00 am - 9:00 pm-
11h 00m
Southwest Logo
7:55 am - 6:45 pm-
11h 50m
$473Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
9:00 am - 10:25 pm-
12h 25m
Southwest Logo
5:00 am - 12:45 pm-
8h 45m
$473Southwest
Wed, Sep 9 - Sun, Sep 20
JetBlue Logo
9:00 am - 7:15 pm-
9h 15m
JetBlue Logo
8:05 am - 6:40 pm-
11h 35m
$488JetBlue
Fri, Oct 23 - Mon, Nov 2
Southwest Logo
9:00 am - 8:10 pm-
10h 10m
Southwest Logo
5:10 am - 1:15 pm-
8h 05m
$515Southwest
Fri, Nov 6 - Sun, Nov 15
Southwest Logo
2:10 pm - 1:05 am-
10h 55m
Southwest Logo
5:15 am - 12:20 pm-
7h 05m
$515Southwest
Fri, Oct 30 - Mon, Nov 9
Southwest Logo
1:30 pm - 10:20 pm-
7h 50m
Southwest Logo
5:15 am - 12:20 pm-
7h 05m
$515Southwest
Sat, Oct 24 - Sat, Nov 14
Delta Logo
1:25 pm - 6:00 pm-
27h 35m
Delta Logo
6:44 pm - 1:05 pm-
18h 21m
$529Delta
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.

How much is a round-trip flight from San José 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 José to Chicago Midway Airport departing in September.

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from San José usually cost between $515 and $767 in September.
The lowest price found in the past 5 days was $453 on Southwest (Sep 21-Sep 28).

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 November, where tickets cost $358 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $881 and $848 respectively.

Find deals

Good to know

Low season

March

Cheapest flight

$241
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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 $292 for a one-way ticket and $453 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.
8.0
SouthwestOverall score based on 4222 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
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
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

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

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)