MDW - SJO

$151 Find Cheap Flights from Chicago Midway Airport to San José

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 4/11. 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 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$395
Frontier
Wed 4/8Fri 5/29
MDW - SJO • 1 stop
Cheapest one-way
$151
Multiple Airlines
Sat 4/11
MDW - SJO • 1 stop
Top airlines
Frontier
Cheapest • from $395 (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 Midway and San José. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Houston (HOU)
Cheapest • Avg $513 (round-trip)
Atlanta (ATL)
Shortest trip • 7h 39m (one-way)
Insights
Insights
Insights
Insights
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 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

Wed, Apr 8 - Fri, May 29
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
35h 27m
2 stops
$395Frontier
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
10:06 am - 11:05 pm
SJO
-
MDW
11h 59m
1 stop
$426Frontier
Sat, Apr 4 - Thu, Apr 9
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
$445Frontier
Mon, Apr 13 - Thu, Apr 16
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
Multiple Airlines Logo
7:45 am - 10:19 pm
SJO
-
MDW
13h 34m
2 stops
$452Multiple Airlines
Thu, Apr 2 - Sat, Apr 11
Frontier Logo
6:00 am - 12:12 pm
MDW
-
SJO
7h 12m
1 stop
Frontier Logo
10:06 am - 11:05 pm
SJO
-
MDW
11h 59m
1 stop
$453Frontier
Tue, Apr 14 - Fri, Apr 17
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
SJO
28h 08m
2 stops
Multiple Airlines Logo
4:35 pm - 1:00 pm
SJO
-
MDW
19h 25m
2 stops
$458Multiple Airlines
Mon, Apr 20 - Wed, Apr 29
Southwest Logo
5:35 am - 12:10 pm
MDW
-
SJO
7h 35m
1 stop
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
$474Southwest
Mon, Apr 27 - Tue, May 5
Southwest Logo
7:30 am - 7:00 pm
MDW
-
SJO
12h 30m
2 stops
Southwest Logo
9:00 am - 7:45 pm
SJO
-
MDW
9h 45m
2 stops
$478Southwest
Thu, Apr 9 - Thu, Apr 16
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
$479Southwest
Sat, Apr 4 - Thu, Apr 9
Frontier Logo
2:56 pm - 12:12 pm
MDW
-
SJO
22h 16m
1 stop
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
$480Frontier
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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to San José were found on Frontier ($395) and Southwest ($474).

Find deals

Good to know

Cheapest flight$151
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 3 days, the lowest price for a flight from Chicago Midway Airport to San José was $151 for a one-way ticket and $395 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.
8.0
SouthwestOverall score based on 4324 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

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

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

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.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

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)