SJO - MDW

$183 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 4/17. 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
$350
Frontier
Thu 4/2Fri 4/10
SJO - MDW • 1 stop
Cheapest one-way
$204
Multiple Airlines
Fri 4/17
SJO - MDW • 2 stops
Top airlines
Frontier
Cheapest • from $350 (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
Orlando (MCO)
Cheapest • Avg $581 (round-trip)
Orlando (MCO)
Shortest trip • 8h 13m (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 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

Thu, Apr 2 - Fri, Apr 10
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
Frontier Logo
5:30 am - 9:01 am
MDW
-
SJO
28h 31m
1 stop
$350Frontier
Sat, Apr 4 - Thu, Apr 9
Frontier Logo
12:59 pm - 10:29 pm
SJO
-
MDW
8h 30m
1 stop
Frontier Logo
6:00 am - 12:12 pm
MDW
-
SJO
7h 12m
1 stop
$365Frontier
Thu, Apr 2 - Fri, Apr 10
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
Frontier Logo
5:30 am - 9:01 am
MDW
-
SJO
28h 31m
1 stop
$425Frontier
Tue, Apr 7 - Sat, Apr 11
Multiple Airlines Logo
12:19 pm - 10:19 pm
SJO
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
$430Multiple Airlines
Tue, Apr 7 - Mon, Apr 13
Multiple Airlines Logo
12:19 pm - 10:19 pm
SJO
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
$434Multiple Airlines
Sat, Apr 4 - Fri, Apr 10
Frontier Logo
12:59 pm - 10:29 pm
SJO
-
MDW
8h 30m
1 stop
Frontier Logo
2:56 pm - 9:01 am
MDW
-
SJO
19h 05m
2 stops
$464Frontier
Wed, Apr 15 - Mon, Apr 20
Multiple Airlines Logo
7:00 am - 8:04 am
SJO
-
MDW
24h 04m
1 stop
Multiple Airlines Logo
4:14 pm - 11:59 pm
MDW
-
SJO
32h 45m
2 stops
$472Multiple Airlines
Tue, Sep 15 - Mon, Sep 21
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
2 stops
$474Southwest
Thu, Aug 27 - Sun, Aug 30
Delta Logo
1:21 pm - 12:30 pm
SJO
-
MDW
22h 09m
2 stops
Delta Logo
6:00 am - 11:56 am
MDW
-
SJO
6h 56m
1 stop
$476Delta
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
9:00 am - 7:15 pm
SJO
-
MDW
9h 15m
1 stop
Southwest Logo
10:30 am - 6:40 pm
MDW
-
SJO
9h 10m
1 stop
$477Southwest
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.

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

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 San José to Chicago Midway Airport were found on Frontier ($350) and Southwest ($474).

Find deals

Good to know

Cheapest flight$204
Most popular time to fly with an average 51% 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 3 days, the lowest price for a flight from San José to Chicago Midway Airport was $183 for a one-way ticket and $350 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 4324 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
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 San José to Midway

Information on your arrival and departure airports

San José (SJO)
Midway (MDW)