$166 Cheap Flights from Chicago (MDW) to San José (SJO)

View $166 flight on Sat, Aug 16, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $166 for one-way flights and $364 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Oct 11 - Sat, Oct 18
MDW
Chicago
SJO
San José
$364 Roundtrip, found 1 hour ago
$364
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 11 from Chicago to San José, returning Sat, Oct 18, priced at $364 found 1 hour ago
Southwest Airlines
Wed, Sep 17 - Wed, Sep 24
MDW
Chicago
SJO
San José
$366 Roundtrip, found 4 days ago
$366
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Sep 17 from Chicago to San José, returning Wed, Sep 24, priced at $366 found 4 days ago
Frontier Airlines
Sat, Oct 11 - Sat, Oct 18
MDW
Chicago
SJO
San José
$371 Roundtrip, found 1 hour ago
$371
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 11 from Chicago to San José, returning Sat, Oct 18, priced at $371 found 1 hour ago
Frontier Airlines
Fri, Oct 10 - Sat, Oct 18
MDW
Chicago
SJO
San José
$374 Roundtrip, found 12 hours ago
$374
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Oct 10 from Chicago to San José, returning Sat, Oct 18, priced at $374 found 12 hours ago
Southwest Airlines
Mon, Oct 27 - Wed, Nov 5
MDW
Chicago
SJO
San José
$387 Roundtrip, found 1 day ago
$387
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to San José, returning Wed, Nov 5, priced at $387 found 1 day ago
Southwest Airlines
Wed, Oct 1 - Wed, Oct 15
MDW
Chicago
SJO
San José
$396 Roundtrip, found 3 days ago
$396
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Chicago to San José, returning Wed, Oct 15, priced at $396 found 3 days ago
Southwest Airlines
Wed, Oct 1 - Wed, Oct 15
MDW
Chicago
SJO
San José
$401 Roundtrip, found 3 days ago
$401
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Chicago to San José, returning Wed, Oct 15, priced at $401 found 3 days ago
Frontier Airlines
Sat, Aug 16 - Thu, Aug 21
MDW
Chicago
SJO
San José
$402 Roundtrip, just found
$402
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Aug 16 from Chicago to San José, returning Thu, Aug 21, priced at $402 just found
Southwest Airlines
Wed, Sep 17 - Wed, Sep 24
MDW
Chicago
SJO
San José
$407 Roundtrip, found 1 day ago
$407
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 17 from Chicago to San José, returning Wed, Sep 24, priced at $407 found 1 day ago
Delta
Tue, Feb 3 - Thu, Feb 12
MDW
Chicago
SJO
San José
$676 Roundtrip, found 2 hours ago
$676
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Feb 3 from Chicago to San José, returning Thu, Feb 12, priced at $676 found 2 hours ago

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

February is typically the cheapest month to fly

From $319 - $2,663 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to San José (SJO)
Origin airport
Midway Intl.
Destination airport
Juan Santamaría Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$363
Distance
2206 mi

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 October. 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 $166 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Juan Santamaria Intl. Airport (SJO) cost?
Discover the latest flight deals from MDW to SJO by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to SJO?
The cheapest flights from MDW to SJO are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to SJO?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to SJO. Sort your results by "Price (lowest to highest)" to snap up a great deal.
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.

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*Available to One Key members.