$155 Cheap Flights from Chicago (MDW) to San José (SJO)

View $155 flight on Tue, Nov 11, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $155 for one-way flights and $342 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Nov 25 - Tue, Dec 2
MDW
Chicago
SJO
San José
$342 Roundtrip, found 1 hour ago
$342
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Nov 25 from Chicago to San José, returning Tue, Dec 2, priced at $342 found 1 hour ago
Southwest Airlines
Wed, Nov 26 - Wed, Dec 10
MDW
Chicago
SJO
San José
$343 Roundtrip, found 1 day ago
$343
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 26 from Chicago to San José, returning Wed, Dec 10, priced at $343 found 1 day ago
Southwest Airlines
Mon, Nov 10 - Fri, Nov 21
MDW
Chicago
SJO
San José
$344 Roundtrip, found 2 hours ago
$344
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Nov 10 from Chicago to San José, returning Fri, Nov 21, priced at $344 found 2 hours ago
Delta
Thu, Jan 22 - Tue, Jan 27
MDW
Chicago
SJO
San José
$346 Roundtrip, just found
$346
Roundtrip
just found
Select Delta flight, departing Thu, Jan 22 from Chicago to San José, returning Tue, Jan 27, priced at $346 just found
Delta
Mon, Dec 8 - Mon, Dec 15
MDW
Chicago
SJO
San José
$346 Roundtrip, found 2 days ago
$346
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Dec 8 from Chicago to San José, returning Mon, Dec 15, priced at $346 found 2 days ago
Southwest Airlines
Mon, Dec 8 - Thu, Dec 11
MDW
Chicago
SJO
San José
$347 Roundtrip, found 2 days ago
$347
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Dec 8 from Chicago to San José, returning Thu, Dec 11, priced at $347 found 2 days ago
Delta
Fri, Jan 23 - Mon, Feb 2
MDW
Chicago
SJO
San José
$350 Roundtrip, found 2 hours ago
$350
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Jan 23 from Chicago to San José, returning Mon, Feb 2, priced at $350 found 2 hours ago
Delta
Sat, Dec 6 - Thu, Dec 11
MDW
Chicago
SJO
San José
$353 Roundtrip, found 2 days ago
$353
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Dec 6 from Chicago to San José, returning Thu, Dec 11, priced at $353 found 2 days ago
Southwest Airlines
Sat, Dec 6 - Thu, Dec 11
MDW
Chicago
SJO
San José
$354 Roundtrip, found 2 days ago
$354
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Chicago to San José, returning Thu, Dec 11, priced at $354 found 2 days ago
Frontier Airlines
Mon, Jan 12 - Sat, Jan 17
MDW
Chicago
SJO
San José
$368 Roundtrip, found 5 hours ago
$368
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Mon, Jan 12 from Chicago to San José, returning Sat, Jan 17, priced at $368 found 5 hours ago

Find the cheapest month to fly from Chicago (MDW) to San José (SJO)

November is typically the cheapest month to fly

From $339 - $1,338 per traveler.

Alternative airports near San José

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

Select flight to Juan Santamaria Intl. SJO. Cheapest option available. Average driving time to city center is 20 minutes. Flights from $385
SJO
Juan Santamaria Intl.
Cheapest
Average driving time to city center20 min
Flights from $385

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO) cost?
Grab a cheap one-way flight from $155 or cheap return flight from $342 from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO) 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 Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO)?
November is the cheapest month to fly from MDW to SJO. Traveling during an off-peak travel window is often the key to finding better deals on flights.
Which airlines fly direct from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO)?
Although Chicago, IL (MDW-Midway Intl.) has no direct flights to Juan Santamaria Intl. Airport (SJO), other airports have nonstop routes. Flying from O'Hare Intl. Airport (ORD) will get you to San José without any layovers.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to SJO flight.
How many flights per day from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO)?
There are no daily direct flights departing from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from MDW to SJO?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO)?
To touch down at Juan Santamaria Intl. Airport (SJO) on time, pick a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO) last-minute?
Holding off until right before your break to book a flight from MDW to SJO often results in higher prices. While you may come across some last-minute offers, they're not always guaranteed. Allow some flexibility in your schedule to boost your chances of snagging a bargain.
Is it cheaper to book a MDW to SJO flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to SJO flight and hotel package with Expedia could lead to significant savings. What's more, managing everything in one place will take the stress out of planning your trip. Simply pick your flights and choose from our wide range of hotels, then tailor your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO)?
It's generally possible to cancel or reschedule your MDW to SJO flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Juan Santamaría Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$341
Distance
2206 mi

Book with confidence

Chicago to San José Flights

The cheapest times to fly from Chicago to San José

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 Chicago to San José are during the month of November. You can find some of the cheapest flights from Chicago to San José with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Chicago to San José: 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 Chicago to San José

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 Chicago to San José in 2025. You can also book with separate airlines for your outbound and return journeys, from $155 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 Chicago to San José 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 Chicago to San José 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.

 

Chicago to San José Flights

Explore a world of travel with Expedia

*Available to One Key members.