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San José

$74+ Cheap flights from Chicago (CHI) 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Sep 8 — Sep 151
Mon 9/8
Mon 9/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San José Juan Santamaria Intl are usually found in September or July, booked 26 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap flight deals from Chicago to San José

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 3, 2025.

Round-trip from

$263
(Mytrip)

One-way from

$74
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$445

Good round-trip deal

$546 or less

Good one-way deal

$217 or less
From Chicago (CHI) to San José Juan Santamaria Intl
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One-way flight from Chicago (CHI) to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 10% potential increase in price ($71 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 September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to San José Juan Santamaria Intl.
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Price to beat on a one-way flight from Chicago (CHI) to San José Juan Santamaria Intl.
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Find flight deals from Chicago to San José

Cheapest flights from Chicago to San José
Explore the most affordable flight options available from Chicago to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 3, 2025.

This Mytrip deal was found by Cheapflights users on 9/2. 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.
Sat 10/46:44 pmORD - SJO
1 stop17h 46mSpirit Airlines
Fri 10/1011:37 amSJO - ORD
2 stops22h 10mSpirit Airlines
Deal found 9/2$263
This Mytrip deal was found by Cheapflights users on 9/3. 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.
Sat 10/46:44 pmORD - SJO
1 stop17h 46mSpirit Airlines
Sat 10/1111:37 amSJO - ORD
2 stops11h 08mSpirit Airlines
Deal found 9/3$264
This Priceline deal was found by Cheapflights users on 9/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:40 pmORD - SJO
2 stops17h 50mSpirit Airlines
Fri 10/1712:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/2$265
This Mytrip deal was found by Cheapflights users on 9/3. 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.
Mon 9/156:05 pmORD - SJO
2 stops18h 09mSpirit Airlines
Wed 9/2412:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Deal found 9/3$266
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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.
Thu 12/48:41 amORD - SJO
1 stop15h 40mSpirit Airlines
Mon 12/81:19 pmSJO - ORD
1 stop7h 41mSpirit Airlines
Deal found 9/2$267
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Sat 10/117:41 pmORD - SJO
1 stop16h 49mSpirit Airlines
Thu 10/1612:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/2$268
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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.
Thu 10/25:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Fri 10/1012:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/2$269
This Mytrip deal was found by Cheapflights users on 9/2. 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.
Tue 9/166:44 pmORD - SJO
1 stop17h 30mSpirit Airlines
Fri 9/1911:37 amSJO - ORD
2 stops22h 15mSpirit Airlines
Deal found 9/2$270
This Mytrip deal was found by Cheapflights users on 9/3. 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.
Tue 9/166:44 pmORD - SJO
1 stop17h 30mSpirit Airlines
Thu 9/2512:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Deal found 9/3$271
This KAYAK deal was found by Cheapflights users on 9/2. 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.
Sat 11/17:41 pmORD - SJO
1 stop17h 49mSpirit Airlines
Tue 11/111:19 pmSJO - ORD
1 stop10h 23mSpirit Airlines
Deal found 9/2$272
This KAYAK deal was found by Cheapflights users on 9/2. 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.
Mon 11/35:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Wed 11/121:19 pmSJO - ORD
1 stop10h 23mSpirit Airlines
Deal found 9/2$273
This KAYAK deal was found by Cheapflights users on 9/3. 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.
Thu 9/256:44 pmORD - SJO
1 stop17h 30mSpirit Airlines
Thu 10/212:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Deal found 9/3$274

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 September 3, 2025.
Use the filters below to find and compare flights from Chicago to San José that are best for you.

Fly from

Chicago

Fly to

San José

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/11

5:05 am-12:14 pm

1 stop7h 09m

San José Juan Santamaria Intl

Fri 11/21

2:20 am-3:10 pm

1 stop12h 50m

$264

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 10/11

6:40 pm-11:30 am

2 stops17h 50m

San José Juan Santamaria Intl

Fri 10/17

12:35 pm-11:45 pm

1 stop10h 10m

$265

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 10/19

5:05 am-11:30 am

1 stop7h 25m

San José Juan Santamaria Intl

Sat 10/25

12:35 pm-11:45 pm

1 stop10h 10m

$267

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 10/23

7:41 pm-11:30 am

1 stop16h 49m

San José Juan Santamaria Intl

Tue 10/28

12:35 pm-1:03 am

1 stop11h 28m

$270

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/1

7:41 pm-12:30 pm

1 stop17h 49m

San José Juan Santamaria Intl

Wed 11/12

1:19 pm-11:42 pm

1 stop10h 23m

$272

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/1

7:41 pm-12:30 pm

1 stop17h 49m

San José Juan Santamaria Intl

Tue 11/11

1:19 pm-11:42 pm

1 stop10h 23m

$272

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 10/17

7:41 pm-11:30 am

1 stop16h 49m

San José Juan Santamaria Intl

Fri 10/24

12:35 pm-11:45 pm

1 stop10h 10m

$272

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 11/2

5:05 am-12:30 pm

1 stop7h 25m

San José Juan Santamaria Intl

Wed 11/12

1:19 pm-9:00 pm

1 stop7h 41m

$273

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 11/2

7:41 pm-12:30 pm

1 stop16h 49m

San José Juan Santamaria Intl

Tue 11/11

1:19 pm-9:00 pm

1 stop7h 41m

$273

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 10/16

7:41 pm-11:30 am

1 stop16h 49m

San José Juan Santamaria Intl

Thu 10/23

12:35 pm-11:45 pm

1 stop10h 10m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/1

Showing 1-10 of 40 results
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Best time to book a flight from Chicago to San José

Have a flexible travel schedule? Discover the best time to fly to San José from Chicago 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 Chicago to San José

How far ahead should I book a flight from Chicago to San José, San José Province?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San José. Price data was last updated on August 29, 2025.

The best time to book flights from Chicago to San José, San José Province is 26 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to San José, San José Province?

Currently, September is the cheapest month in which you can book a flight from Chicago to San José, San José Province (average of $398). Flying from Chicago to San José, San José Province in March is currently the most expensive (average of $555). 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 CHI to SJO?

Find hourly flight availability from Chicago 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 September 3, 2025.

One of the essential ways to save on airfare from Chicago to San José, San José Province is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 42% on airfare.

What is the cheapest day to fly from Chicago to San José, San José Province?

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

Travelers seeking maximum savings on their Chicago to San José, San José Province 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.

How much does it cost to fly round-trip from Chicago to San José, San José Province?

What’s the top layover airport for flights from Chicago to San José, San José Province?

Share of 1-stop round-trip flights from Chicago to San José, San José Province chosen by Cheapflights users in the past 12 months, using the same layover each way.

Fort Lauderdale (FLL) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to San José, San José Province on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San José, San José Province?

Average round-trip fare for 1-stop flights from Chicago to San José, San José Province, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Orlando (MCO) is the most affordable 1-stop option, with an average round-trip price of $392.

What’s the fastest layover option from Chicago to San José, San José Province?

Shortest average travel time for 1-stop one-way flights from Chicago to San José, San José Province, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 10h 58m.

Which airport typically offers the quickest layover for flights from Chicago to San José, San José Province?

Average layover duration for 1-stop one-way flights from Chicago to San José, San José Province, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Orlando (MCO) offer the fastest connection on this route, with an average layover time of 4h 58m.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José. Reviews last updated September 3, 2025.
Read through reviews of airlines operating flights from Chicago to San José, such as Southwest, Copa Airlines, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Copa Airlines
7.6
Good
1,525 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,012 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

    Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to San José from Chicago. Booking flights from Chicago to Juan Santamaria Intl (SJO) should be relatively easy as there are 0 daily inbound flights from Chicago from 9 different airlines.

  • How long is the flight from Chicago to San José, San José Province?

    For as low as $340, Spirit Airlines can have you in San José, San José Province from Chicago in 6h 40m. The distance between Chicago and San José, San José Province is about 2206 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to San José, San José Province round-trip?

    Currently priced at $273, Spirit Airlines will fly you from Chicago to San José, San José Province and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Avianca and Copa Airlines - these airlines can fly you to your destination from $307 and $314, respectively. Spirit Airlines is currently priced 53% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to San José, San José Province one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $74. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago to San José, San José Province for a low price.

  • What are the cheapest flights from Chicago to San José, San José Province?

    The cheapest flight price from Chicago to San José, San José Province is $176. On average you can expect to pay $818. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $198.

  • Where are the most common layover locations when flying from Chicago to San José, San José Province?

    Most of the time, Chicago to San José, San José Province flights that have layovers will stop in Fort Lauderdale.

  • What are some popular things to do or see while on a layover in Fort Lauderdale?

    Most Fort Lauderdale visitors opt to spend their time experiencing Las Olas Beach, Port Everglades, and Fort Lauderdale Beach Park. Las Olas Beach, Port Everglades and Fort Lauderdale Beach Park are located about 4.1 mi, 2.1 mi, and 4.2 mi, respectively from Fort Lauderdale if you are interested in checking them out. Those looking to explore during their layover in Fort Lauderdale can rent a car from Fort Lauderdale for about $26 per day.

  • Where are the least popular layover locations for Chicago to San José, San José Province flights?

    Chicago to San José, San José Province flights have a layover in Panama City the least frequently.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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 Chicago to San José, San José Province?

    Currently, September is the cheapest month in which you can book a flight from Chicago to San José, San José Province (average of $398). Flying from Chicago to San José, San José Province in March is currently the most expensive (average of $555). 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

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Top 9 airlines flying from Chicago to San José

Discover the top 9 airlines that operate flights from Chicago 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 September 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$273Average$453FlexibilityNo cancel feeOn-time65%
AviancaCheapest$307Average$459FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$595FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$431Average$618FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$432Average$649FlexibilityNo cancel feeOn-time62%
DeltaCheapest$438Average$677FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$443Average$663FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$467Average$745FlexibilityNo cancel feeOn-time69%

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