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$116+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 September, 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 June 12, 2025.

Round-trip from

$298
(FlightHub)

One-way from

$116
(Priceline)

Popular in

December

Cheapest in

July

Average price

$559

Good round-trip deal

$493 or less

Good one-way deal

$202 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 ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/810:46 amORD - SJO
2 stops25h 25mSpirit Airlines
Tue 7/2212:16 pmSJO - ORD
1 stop9h 57mSpirit Airlines
Deal found 6/12$298
This Booking.com deal was found by Cheapflights users on 6/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/810:46 amORD - SJO
2 stops25h 25mMultiple Airlines
Tue 7/155:05 amSJO - ORD
1 stop10h 00mMultiple Airlines
Deal found 6/12$302
This Copa Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 9/167:54 amORD - SJO
1 stop14h 59mCopa Airlines
Fri 9/2610:05 amSJO - ORD
1 stop13h 17mCopa Airlines
Deal found 6/11$310
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:00 amORD - SJO
1 stop7h 29mFrontier
Sat 11/152:49 pmSJO - ORD
1 stop19h 37mFrontier
Deal found 6/11$348
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/65:00 amORD - SJO
1 stop7h 55mAmerican Airlines
Wed 8/131:55 pmSJO - ORD
1 stop8h 04mAmerican Airlines
Deal found 6/11$362
This Priceline deal was found by Cheapflights users on 6/9. 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.
Thu 7/105:25 pmORD - SJO
2 stops15h 15mAvianca
Mon 7/147:45 pmSJO - ORD
1 stop19h 20mAvianca
Deal found 6/9$385
This Southwest deal was found by Cheapflights users on 6/11. 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.
Mon 9/228:05 amMDW - SJO
2 stops11h 50mSouthwest
Sun 9/2812:35 pmSJO - MDW
1 stop7h 40mSouthwest
Deal found 6/11$407
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Thu 7/319:12 pmMDW - SJO
1 stop14h 17mMultiple Airlines
Fri 8/88:50 amSJO - MDW
2 stops13h 27mMultiple Airlines
Deal found 6/11$454
This Delta deal was found by Cheapflights users on 6/9. 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.
Sun 11/96:00 amMDW - SJO
1 stop6h 52mDelta
Sun 11/162:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 6/9$691

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 June 12, 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 7/8

10:46 am-11:11 am

2 stops25h 25m

San José Juan Santamaria Intl

Tue 7/22

12:16 pm-11:13 pm

1 stop9h 57m

$298

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 7/8

10:46 am-11:11 am

2 stops25h 25m

San José Juan Santamaria Intl

Tue 7/15

5:05 am-4:05 pm

1 stop10h 00m

$302

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 9/16

7:54 am-9:53 pm

1 stop14h 59m

San José Juan Santamaria Intl

Fri 9/26

10:05 am-12:22 am

1 stop13h 17m

$310

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/8

6:00 am-1:29 pm

1 stop7h 29m

San José Juan Santamaria Intl

Sat 11/15

2:49 pm-10:26 am

1 stop19h 37m

$348

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 8/6

5:00 am-11:55 am

1 stop7h 55m

San José Juan Santamaria Intl

Wed 8/13

1:55 pm-10:59 pm

1 stop8h 04m

$362

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 7/10

5:25 pm-7:40 am

2 stops15h 15m

San José Juan Santamaria Intl

Mon 7/14

7:45 pm-4:05 pm

1 stop19h 20m

$385

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/22

8:05 am-6:55 pm

2 stops11h 50m

San José Juan Santamaria Intl

Sun 9/28

12:35 pm-9:15 pm

1 stop7h 40m

$407

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 7/31

9:12 pm-10:29 am

1 stop14h 17m

San José Juan Santamaria Intl

Fri 8/8

8:50 am-11:17 pm

2 stops13h 27m

$454

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 11/9

6:00 am-12:52 pm

1 stop6h 52m

San José Juan Santamaria Intl

Sun 11/16

2:17 pm-9:44 pm

1 stop7h 27m

$691

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 7/8

10:46 am-11:11 am

2 stops25h 25m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 21 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 June 9, 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 June 12, 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.

Rainfall in San José by month

Plan your trip to San José by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 in.

Temperature in San José by month

Plan your trip to San José by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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 June 12, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to San José have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
1,451 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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.
Aeromexico
7.5
Good
1,706 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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 $298, 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 Copa Airlines and Frontier - these airlines can fly you to your destination from $310 and $348, respectively. Spirit Airlines is currently priced 50% 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 $116. However, be on the lookout for offers from Frontier 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 $200. On average you can expect to pay $795. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $310.

  • 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. Orlando follows Fort Lauderdale 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 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 $24 per day.

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

    The majority of Orlando visitors spend their time at Walt Disney World Resort, Universal Orlando Resort, and International Drive. Those on a layover in Orlando interested in visiting Walt Disney World Resort, Universal Orlando Resort, or International Drive can do so by traveling 16.2 mi, 10.2 mi, and 9.9 mi, respectively from Orlando. Those looking to explore during their layover in Orlando can rent a car from Orlando for about $24 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$274Average$438FlexibilityNo cancel feeOn-time65%
AviancaCheapest$323Average$462FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$635FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$376Average$607FlexibilityNo cancel feeOn-time70%
DeltaCheapest$438Average$716FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$446Average$679FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$479Average$636FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$493Average$755FlexibilityNo cancel feeOn-time69%

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