$174 Cheap Flights from San José (SJO) to Chicago (MDW)

View $174 flight on Tue, Nov 25, 2025Opens in a new window

Popular airlines from Juan Santamaria Intl. Airport (SJO) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at $174 for one-way flights and $300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Dec 5 - Tue, Dec 9
SJO
San José
MDW
Chicago
$300 Roundtrip, found 2 days ago
$300
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Dec 5 from San José to Chicago, returning Tue, Dec 9, priced at $300 found 2 days ago
Delta
Thu, Dec 4 - Thu, Dec 11
SJO
San José
MDW
Chicago
$310 Roundtrip, found 5 days ago
$310
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Dec 4 from San José to Chicago, returning Thu, Dec 11, priced at $310 found 5 days ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
SJO
San José
MDW
Chicago
$318 Roundtrip, found 3 days ago
$318
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from San José to Chicago, returning Sun, Nov 16, priced at $318 found 3 days ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
SJO
San José
MDW
Chicago
$326 Roundtrip, found 3 days ago
$326
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from San José to Chicago, returning Sun, Nov 16, priced at $326 found 3 days ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
SJO
San José
MDW
Chicago
$332 Roundtrip, found 3 days ago
$332
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from San José to Chicago, returning Sun, Nov 16, priced at $332 found 3 days ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
SJO
San José
MDW
Chicago
$332 Roundtrip, found 3 days ago
$332
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from San José to Chicago, returning Sun, Nov 16, priced at $332 found 3 days ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
SJO
San José
MDW
Chicago
$333 Roundtrip, found 3 days ago
$333
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from San José to Chicago, returning Sun, Nov 16, priced at $333 found 3 days ago
Southwest Airlines
Fri, Nov 7 - Tue, Nov 11
SJO
San José
MDW
Chicago
$335 Roundtrip, found 7 hours ago
$335
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Fri, Nov 7 from San José to Chicago, returning Tue, Nov 11, priced at $335 found 7 hours ago
Southwest Airlines
Sat, Oct 25 - Tue, Nov 4
SJO
San José
MDW
Chicago
$340 Roundtrip, found 2 hours ago
$340
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Oct 25 from San José to Chicago, returning Tue, Nov 4, priced at $340 found 2 hours ago
Frontier Airlines
Sat, Feb 14 - Sat, Feb 21
SJO
San José
MDW
Chicago
$398 Roundtrip, found 17 hours ago
$398
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from San José to Chicago, returning Sat, Feb 21, priced at $398 found 17 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $199
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $199
Flights from San José (SJO) to Chicago (MDW)
Origin airport
Juan Santamaría Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$299
Distance
2206 mi

San José to Chicago Flights

The cheapest times to fly from San José to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San José to Chicago are during the month of December. You can find some of the cheapest flights from San José to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San José to Chicago

Sunday is one of the best days to book for cheap flights from San José to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San José to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San José to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $174 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San José to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San José to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $174 or cheap return flight from $300 from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW)?
December is the most affordable month to fly from SJO to MDW. Timing your trip outside of the busy season is often the key to scoring lower fares.
What is the cheapest airline that flies from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest SJO to MDW flight.
How many flights per day from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW)?
Nonstop flights from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from SJO to MDW?
Generally you'll find the largest variety of flight choices on a Friday. Tuesdays are often the quietest.* But this can vary depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW) route, fly before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Juan Santamaria Intl. Airport (SJO)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Juan Santamaria Intl. Airport (SJO). Check out the options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from SJO to MDW right before your trip is typically more expensive. But if you're flexible with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a SJO to MDW flight and hotel package?
Booking a SJO to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Pick from our wide range of stays and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Juan Santamaria Intl. Airport (SJO) to Midway Intl. Airport (MDW)?
Usually, it's possible to cancel or reschedule your SJO to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.