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San José

$129+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap 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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$260
(KAYAK)

One-way from

$129
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$528

Good round-trip deal

$396 or less

Good one-way deal

$217 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
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One-way flight from Illinois to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 11% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Illinois to San José Juan Santamaria Intl.
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Price to beat on a one-way flight from Illinois to San José Juan Santamaria Intl.
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Find 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 November 6, 2025.

This KAYAK deal was found by Cheapflights users on 11/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Thu 12/111:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/5$260
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:48 amORD - SJO
1 stop8h 32mMultiple Airlines
Wed 11/191:30 pmSJO - ORD
1 stop10h 57mMultiple Airlines
Deal found 11/5$261
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:20 amORD - SJO
1 stop8h 00mMultiple Airlines
Thu 12/111:31 pmSJO - ORD
1 stop10h 38mMultiple Airlines
Deal found 11/5$263
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 11/145:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Fri 12/51:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/5$264
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/55:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/6$265
This Flightnetwork deal was found by Cheapflights users on 11/6. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/285:00 amORD - SJO
1 stop7h 15mSpirit Airlines
Thu 12/41:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/6$267
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Fri 12/121:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/5$268
This Super.com deal was found by Cheapflights users on 11/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:00 amORD - SJO
1 stop7h 15mSpirit Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/5$269
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/104:01 pmORD - SJO
2 stops20h 24mMultiple Airlines
Sat 12/133:07 pmSJO - ORD
1 stop17h 09mMultiple Airlines
Deal found 11/5$270
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:48 amORD - SJO
1 stop8h 32mMultiple Airlines
Mon 11/241:20 pmSJO - ORD
1 stop9h 53mMultiple Airlines
Deal found 11/5$271
This KAYAK deal was found by Cheapflights users on 11/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/103:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Sat 12/1312:39 pmSJO - ORD
2 stops11h 30mSpirit Airlines
Deal found 11/6$272
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Tue 12/161:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/6$273

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 November 6, 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

Fri 12/5

10:42 am-1:52 pm

1 stop27h 10m

San José Juan Santamaria Intl

Sun 12/7

12:39 pm-10:33 pm

1 stop9h 54m

$341

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/20

7:05 am-10:15 pm

1 stop15h 10m

San José Juan Santamaria Intl

Sat 1/31

7:00 am-7:21 pm

1 stop12h 21m

$346

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 1/9

2:01 pm-11:37 am

2 stops21h 36m

San José Juan Santamaria Intl

Fri 1/16

12:33 pm-8:45 pm

1 stop8h 12m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

10:35 am-10:15 pm

2 stops11h 40m

San José Juan Santamaria Intl

Wed 2/4

2:31 pm-8:42 am

1 stop18h 11m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 1/26

7:05 am-10:15 pm

1 stop15h 10m

San José Juan Santamaria Intl

Sat 1/31

7:00 am-9:04 pm

2 stops14h 04m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

10:35 am-10:15 pm

2 stops11h 40m

San José Juan Santamaria Intl

Sun 2/1

7:00 am-11:57 pm

1 stop16h 57m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/27

6:00 pm-10:15 pm

2 stops28h 15m

San José Juan Santamaria Intl

Sun 2/1

7:00 am-6:49 pm

1 stop11h 49m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

9:52 am-10:15 pm

1 stop12h 23m

San José Juan Santamaria Intl

Mon 2/2

7:00 am-9:04 pm

2 stops14h 04m

$350

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Fri 11/21

3:53 pm-10:19 am

2 stops18h 26m

San José Juan Santamaria Intl

Sun 11/23

11:24 am-11:57 pm

1 stop12h 33m

$352

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Fri 1/9

7:43 pm-1:43 pm

2 stops18h 00m

San José Juan Santamaria Intl

Mon 1/12

12:33 pm-10:33 pm

1 stop10h 00m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 60 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 $247). Flying from Illinois to San José in December is currently the most expensive (average of $395). 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 November 6, 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 Wednesday at noon 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 November 6, 2025.

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

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 $449, Delta can have you in San José from Illinois in 7h 50m. The distance between Illinois and San José is about 2206 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?

    $151 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Delta, with prices starting from $152 and $155, 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 $151. While the most popular route (Chicago O'Hare Intl - San José Juan Santamaria Intl) can be booked for $236 on average, our data indicates $442 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 $247). Flying from Illinois to San José in December is currently the most expensive (average of $395). 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
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó
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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Minneapolis to San José flights
Seattle to Liberia flights
San Francisco to Liberia flights
Atlanta to Liberia flights
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Philadelphia to San José flights
Dallas/Fort Worth to Liberia flights
Hobby to Liberia flights
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Top 9 airlines flying from Illinois to San José

Discover the top 9 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$221Average$669FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$259Average$404FlexibilityNo cancel feeOn-time65%
AviancaCheapest$307Average$462FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$518FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$347Average$668FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$394Average$602FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$432Average$649FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$443Average$707FlexibilityNo cancel feeOn-time69%

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