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San José

$88+ Cheap flights from Illinois to San José (SJO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap flight deals from Illinois to San José

Cheapest flights from Illinois to San José
Explore the most affordable flight options available from Illinois to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - SJO
2 stops25h 02mMultiple Airlines
Sat 1/101:30 pmSJO - ORD
1 stop10h 16mMultiple Airlines
Deal found 12/24$389
This Air Canada deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:30 pmORD - SJO
1 stop27h 35mAir Canada
Sat 1/108:35 amSJO - ORD
1 stop9h 13mAir Canada
Deal found 12/24$401
This Gurufare deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 amORD - SJO
1 stop7h 37mFrontier
Wed 1/73:10 pmSJO - ORD
1 stop20h 25mFrontier
Deal found 12/24$413
This Kiwi.com deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - SJO
2 stops25h 02mMultiple Airlines
Fri 1/97:45 amSJO - ORD
1 stop24h 33mMultiple Airlines
Deal found 12/24$414
This Air Canada deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:30 pmORD - SJO
1 stop26h 25mAir Canada
Sat 1/108:35 amSJO - ORD
1 stop9h 13mAir Canada
Deal found 12/24$434
This American Airlines deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:21 amORD - SJO
1 stop17h 24mAmerican Airlines
Sat 1/316:00 amSJO - ORD
1 stop12h 10mAmerican Airlines
Deal found 12/24$443
This Gurufare deal was found by Cheapflights users on 12/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 amORD - SJO
1 stop7h 37mFrontier
Fri 1/92:58 pmSJO - ORD
1 stop20h 37mFrontier
Deal found 12/25$471
This American Airlines deal was found by Cheapflights users on 12/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmORD - SJO
Nonstop5h 04mAmerican Airlines
Fri 1/92:54 pmSJO - ORD
1 stop17h 44mAmerican Airlines
Deal found 12/25$472
This United Airlines deal was found by Cheapflights users on 12/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:50 pmORD - SJO
1 stop9h 42mUnited Airlines
Wed 12/312:20 pmSJO - ORD
1 stop8h 17mUnited Airlines
Deal found 12/25$476
This Kiwi.com deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - SJO
2 stops25h 02mMultiple Airlines
Sun 1/111:30 pmSJO - ORD
1 stop10h 16mMultiple Airlines
Deal found 12/24$479
This Delta deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:29 amMDW - SJO
2 stops12h 26mDelta
Thu 1/82:31 pmSJO - MDW
1 stop7h 36mDelta
Deal found 12/24$596
This American Airlines deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 pmSTL - SJO
1 stop16h 32mAmerican Airlines
Sat 1/107:09 amSJO - STL
1 stop11h 04mAmerican Airlines
Deal found 12/24$619

Find flight deals from Illinois to San José

Keep the following information in mind while searching for Illinois to San José flight deals. Data was last updated December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$289
(Kiwi.com)

One-way from

$88
(Super.com)

Popular in

December

Cheapest in

September

Average price

$660

Good round-trip deal

$445 or less

Good one-way deal

$319 or less
Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.
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From Illinois to San José Juan Santamaria Intl
Search Deals
One-way flight from Illinois to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Illinois to San José Juan Santamaria Intl.
Search Deals
Price to beat on a one-way flight from Illinois to San José Juan Santamaria Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 26, 2025.
Use the filters below to find and compare flights from Illinois to San José that are best for you.

Fly from

Illinois

Fly to

San José

Route

Depart

Return

Price

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Mon 2/9

9:59 am-10:15 pm

1 stop12h 16m

San José Juan Santamaria Intl

Wed 2/18

2:25 pm-11:36 pm

1 stop9h 11m

$318

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Mon 2/9

8:31 am-10:30 pm

1 stop13h 59m

San José Juan Santamaria Intl

Wed 2/18

3:04 pm-8:32 am

2 stops17h 28m

$327

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/12

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Mon 2/16

6:08 pm-12:31 pm

1 stop18h 23m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 2/6

2:22 pm-9:52 pm

1 stop7h 30m

San José Juan Santamaria Intl

Wed 2/11

5:50 am-12:04 am

1 stop18h 14m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/3

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Tue 2/10

6:08 pm-12:31 pm

1 stop18h 23m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/4

2:22 pm-9:52 pm

1 stop7h 30m

San José Juan Santamaria Intl

Sun 2/8

6:08 pm-12:31 pm

1 stop18h 23m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 1/18

2:13 pm-8:21 am

1 stop18h 08m

San José Juan Santamaria Intl

Sun 1/25

2:20 pm-12:24 am

1 stop10h 04m

$346

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Mon 2/2

1:35 pm-10:30 pm

1 stop8h 55m

San José Juan Santamaria Intl

Mon 2/9

4:02 pm-9:08 am

1 stop17h 06m

$352

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Fri 1/30

9:33 am-9:02 pm

2 stops11h 29m

San José Juan Santamaria Intl

Fri 2/6

4:02 pm-11:59 pm

1 stop7h 57m

$353

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 1/21

9:55 am-10:15 pm

1 stop12h 20m

San José Juan Santamaria Intl

Tue 1/27

7:00 am-4:55 pm

1 stop9h 55m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 57 results
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Best time to book a flight from Illinois to San José

Have a flexible travel schedule? Discover the best time to fly to San José from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to San José

What is the cheapest month to book a flight from Illinois to San José?

Currently, October is the cheapest month in which you can book a flight from Illinois to San José (average of $248). Flying from Illinois to San José in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to SJO?

Find hourly flight availability from Illinois to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 26, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 56% on flights from Illinois to San José by exploring options for tickets in the evening.

What is the cheapest day to fly from Illinois to San José?

Use this chart to determine the cheapest time to fly round-trip from Illinois to San José. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to San José flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Illinois to San José

Explore weekly flight availability from Illinois to San José. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 26, 2025.

The most flights from USIL to SJO are scheduled on a Wednesday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Illinois to San José?

Related info for your journey

Find useful and relevant information for your journey from Illinois to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San José from Illinois?

    For a flight from Illinois to San José, you will be flying into Juan Santamaria Intl. San José Juan Santamaria Intl (SJO) is just 8.8 mi from the center of the city.

  • How long is the flight from Illinois to San José?

    For as low as $318, Delta can have you in San José from Illinois in 12h 16m. The distance between Illinois and San José is about 2022 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Illinois to San José one-way?

    $96 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $136 and $150, respectively.

  • What are the most popular routes from Illinois to San José?

    Most travelers choose Chicago O'Hare Intl - San José Juan Santamaria Intl, Chicago Midway - San José Juan Santamaria Intl or Lambert-St Louis - San José Juan Santamaria Intl when deciding on the best route from Illinois to San José.

  • What are the cheapest flights from Illinois to San José?

    Looking at all options, your cheapest flight can be booked for $224. While the most popular route (Chicago O'Hare Intl - San José Juan Santamaria Intl) can be booked for $222 on average, our data indicates $860 when flying from Illinois to San José.

  • Can I find deals for flights from Illinois to San José that include hotel bookings?

    Yes. In addition to deals on Illinois to San José flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to San José?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to San José.

  • Can I find deals for business class flights from Illinois to San José?

    Yes. Cheapflights offers flight deals from Illinois to San José by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to San José?

    Currently, October is the cheapest month in which you can book a flight from Illinois to San José (average of $248). Flying from Illinois to San José in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Alajuela
Monteverde
Jacó
Heredia
Dominical

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Alternative routes for Illinois to San José

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Illinois to San José

Discover the top 8 airlines that operate flights from Illinois to San José. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$221Average$645FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$258Average$383FlexibilityNo cancel feeOn-time65%
AviancaCheapest$307Average$452FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$309Average$504FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$349Average$674FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$394Average$596FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$426Average$647FlexibilityNo cancel feeOn-time69%

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