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$83+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San José Juan Santamaria Intl are usually found in July or October, booked 20 days in advance, depart on a Monday or Tuesday 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 July 3, 2025.

Round-trip from

$286
(Priceline)

One-way from

$83
(Priceline)

Popular in

December

Cheapest in

July

Average price

$449

Good round-trip deal

$511 or less

Good one-way deal

$207 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. 9% potential increase in price ($61 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 July 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 July 3, 2025.

This SmartFares deal was found by Cheapflights users on 7/2. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:47 pmORD - SJO
2 stops15h 25mSpirit Airlines
Sat 8/2312:18 pmSJO - ORD
2 stops30h 24mSpirit Airlines
Deal found 7/2$302
This Priceline deal was found by Cheapflights users on 7/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/25:01 amORD - SJO
1 stop8h 30mFrontier
Sat 8/91:47 pmSJO - ORD
1 stop8h 42mFrontier
Deal found 7/3$308
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/245:45 amMDW - SJO
1 stop6h 50mSouthwest
Wed 8/271:40 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 6/30$322
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/96:00 amORD - SJO
1 stop17h 05mAmerican Airlines
Fri 7/1111:59 pmSJO - ORD
1 stop10h 00mAmerican Airlines
Deal found 6/30$322
This CheapOair deal was found by Cheapflights users on 7/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/255:05 amORD - SJO
1 stop7h 07mMultiple Airlines
Fri 8/294:13 pmSJO - ORD
1 stop17h 52mMultiple Airlines
Deal found 7/1$328
This Copa Airlines deal was found by Cheapflights users on 7/2. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:56 amORD - SJO
1 stop12h 05mCopa Airlines
Sun 11/94:08 amSJO - ORD
1 stop8h 38mCopa Airlines
Deal found 7/2$337
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/169:12 pmMDW - SJO
1 stop14h 20mMultiple Airlines
Sat 8/2312:18 pmSJO - MDW
2 stops24h 38mMultiple Airlines
Deal found 7/2$366

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 July 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

Thu 8/21

8:47 pm-11:12 am

2 stops15h 25m

San José Juan Santamaria Intl

Sat 8/23

12:18 pm-7:42 pm

2 stops30h 24m

$302

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 8/2

5:01 am-12:31 pm

1 stop8h 30m

San José Juan Santamaria Intl

Sat 8/9

1:47 pm-11:29 pm

1 stop8h 42m

$308

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 8/24

5:45 am-11:35 am

1 stop6h 50m

San José Juan Santamaria Intl

Wed 8/27

1:40 pm-11:20 pm

1 stop8h 40m

$322

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 7/9

6:00 am-10:05 pm

1 stop17h 05m

San José Juan Santamaria Intl

Fri 7/11

11:59 pm-10:59 am

1 stop10h 00m

$322

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 8/25

5:05 am-11:12 am

1 stop7h 07m

San José Juan Santamaria Intl

Fri 8/29

4:13 pm-11:05 am

1 stop17h 52m

$328

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 8/16

9:12 pm-10:32 am

1 stop14h 20m

San José Juan Santamaria Intl

Sat 8/23

12:18 pm-1:56 pm

2 stops24h 38m

$366

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 8/16

5:01 am-12:31 pm

1 stop8h 30m

$83

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 8/16

8:47 pm-11:12 am

2 stops15h 25m

$133

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 9/14

6:00 am-11:14 am

2 stops30h 14m

$151

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 7/14

8:09 am-3:17 pm

1 stop8h 08m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 17 results
1
2

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 June 27, 2025.

The best time to book flights from Chicago to San José, San José Province is 20 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 July 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. Sunday 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?

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 July 3, 2025.
Read through reviews of airlines operating flights from Chicago to San José, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Copa Airlines
7.5
Good
1,467 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 8 different airlines.

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

    Currently priced at $302, 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 Frontier and Southwest - these airlines can fly you to your destination from $308 and $322, respectively. Spirit Airlines is currently priced 49% 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 Frontier, with whom users have recently found tickets for as low as $83. However, be on the lookout for offers from Spirit Airlines and American Airlines, 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 $202. On average you can expect to pay $767. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $302.

  • 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 Orlando. Fort Lauderdale follows Orlando in terms of the most common layover location on Chicago to San José, San José Province flights.

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

    Most Orlando visitors opt to spend their time experiencing Walt Disney World Resort, Universal Orlando Resort, and International Drive. Walt Disney World Resort, Universal Orlando Resort and International Drive are located about 16.2 mi, 10.2 mi, and 9.9 mi, respectively from Orlando if you are interested in checking them out. Those looking to explore during their layover in Orlando can rent a car from Orlando for about $24 per day.

  • What are some popular points of interest to see during a layover in Fort Lauderdale?

    The majority of Fort Lauderdale visitors spend their time at Las Olas Beach, Port Everglades, and Fort Lauderdale Beach Park. Those on a layover in Fort Lauderdale interested in visiting Las Olas Beach, Port Everglades, or Fort Lauderdale Beach Park can do so by traveling 4.1 mi, 2.1 mi, and 4.2 mi, respectively from Fort Lauderdale. Those looking to explore during their layover in Fort Lauderdale can rent a car from Fort Lauderdale for about $23 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

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Top 8 airlines flying from Chicago to San José

Discover the top 8 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$274Average$449FlexibilityNo cancel feeOn-time65%
AviancaCheapest$317Average$459FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$635FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$367Average$608FlexibilityNo cancel feeOn-time70%
DeltaCheapest$438Average$716FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$444Average$670FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$477Average$626FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$480Average$751FlexibilityNo cancel feeOn-time69%

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