MDW - SJO

$140 Find Cheap Flights from Chicago Midway Airport to San José - 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 José departing on 8/18. 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 José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José, 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 José, 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
$473
Southwest
Sun 11/8Fri 11/13
MDW - SJO • 1 stop
Cheapest one-way
$140
Southwest
Tue 8/18
MDW - SJO • 1 stop
Top airlines
Southwest
Cheapest • from $476 (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 Midway and San José. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Houston (HOU)
Cheapest • Avg $503 (round-trip)
Houston (HOU)
Shortest trip • 7h 00m (one-way)
Insights
Insights
Insights
Insights
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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 José!
Flight Deals
Booking Insights
Flight Deals

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

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

Sun, Nov 8 - Fri, Nov 13
Southwest Logo
5:15 am - 12:20 pm
MDW
-
SJO
7h 05m
1 stop
Southwest Logo
9:00 am - 8:25 pm
SJO
-
MDW
11h 25m
2 stops
$473Southwest
Wed, Aug 19 - Thu, Sep 3
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
Southwest Logo
9:00 am - 7:30 pm
SJO
-
MDW
9h 30m
2 stops
$476Southwest
Mon, Nov 16 - Sat, Nov 21
Southwest Logo
5:15 am - 1:15 pm
MDW
-
SJO
8h 00m
1 stop
Southwest Logo
3:50 pm - 8:40 am
SJO
-
MDW
16h 50m
2 stops
$478Southwest
Mon, Aug 24 - Sun, Aug 30
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
Southwest Logo
12:35 pm - 12:10 am
SJO
-
MDW
10h 35m
1 stop
$487Southwest
Mon, Nov 16 - Sat, Nov 21
Southwest Logo
5:15 am - 1:15 pm
MDW
-
SJO
8h 00m
1 stop
Southwest Logo
3:50 pm - 12:20 am
SJO
-
MDW
8h 30m
1 stop
$502Southwest
Sat, Oct 3 - Mon, Oct 12
Southwest Logo
5:00 am - 12:00 pm
MDW
-
SJO
8h 00m
1 stop
Southwest Logo
1:30 pm - 12:10 am
SJO
-
MDW
9h 40m
1 stop
$504Southwest
Sat, Oct 3 - Mon, Oct 12
Southwest Logo
5:00 am - 12:00 pm
MDW
-
SJO
8h 00m
1 stop
Southwest Logo
9:00 am - 8:15 pm
SJO
-
MDW
10h 15m
2 stops
$507Southwest
Thu, Oct 22 - Mon, Oct 26
Southwest Logo
8:55 pm - 12:00 pm
MDW
-
SJO
16h 05m
2 stops
Southwest Logo
1:30 pm - 12:45 am
SJO
-
MDW
10h 15m
2 stops
$508Southwest
Thu, Oct 15 - Mon, Oct 19
Southwest Logo
5:05 am - 12:00 pm
MDW
-
SJO
7h 55m
1 stop
Southwest Logo
9:00 am - 8:15 pm
SJO
-
MDW
10h 15m
2 stops
$510Southwest
Sun, Sep 27 - Sat, Oct 3
Southwest Logo
7:10 am - 6:40 pm
MDW
-
SJO
12h 30m
2 stops
Southwest Logo
9:00 am - 7:25 am
SJO
-
MDW
21h 25m
2 stops
$511Southwest
Booking Insights

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

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

Which airlines provide the cheapest flights from Chicago Midway Airport to San José?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to San José were found on Southwest ($476) and Delta ($611).

Find deals

Good to know

Cheapest flight$140
Flight from Chicago Midway Airport to San José

When to book flights from Midway to San José

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

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

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to San José was $140 for a one-way ticket and $476 for a round-trip.

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

    A passport is required to fly from Chicago Midway Airport to San José.

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

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

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

    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 José.

  • 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 José?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José 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 José?

    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 José with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJO 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 José?

    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 José from Chicago Midway Airport 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 Midway to San José

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José. 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 José? 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 4242 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

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.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
San José (SJO)