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$140+ Cheap flights from San José (SJO) to Chicago (CHI)

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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago are usually found in August or July, booked 83 days in advance, depart on a Tuesday or Monday and return on a Tuesday

Cheap flight deals from San José to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Chicago (CHI). 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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$294
(Cheapflightsfares)

One-way from

$140
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$541

Good round-trip deal

$540 or less

Good one-way deal

$255 or less
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago (CHI) flights.
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From San José Juan Santamaria Intl to Chicago (CHI)
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One-way flight from San José Juan Santamaria Intl to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from San José Juan Santamaria Intl to Chicago (CHI).
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Price to beat on a one-way flight from San José Juan Santamaria Intl to Chicago (CHI).
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Find flight deals from San José to Chicago

Cheapest flights from San José to Chicago
Explore the most affordable flight options available from San José to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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.
Fri 5/2311:32 amSJO - ORD
1 stop10h 57mSpirit Airlines
Mon 5/267:35 pmORD - SJO
1 stop16h 58mSpirit Airlines
Deal found 4/16$294
This OneTravel deal was found by Cheapflights users on 4/16. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/234:48 pmSJO - ORD
1 stop11h 54mMultiple Airlines
Sat 8/301:40 amORD - SJO
1 stop13h 17mMultiple Airlines
Deal found 4/16$313
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/235:52 amSJO - MDW
2 stops13h 25mMultiple Airlines
Sun 5/259:12 pmMDW - SJO
1 stop14h 15mMultiple Airlines
Deal found 4/16$394
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Sat 5/241:00 pmSJO - ORD
Nonstop5h 34mUnited Airlines
Sun 6/17:41 amORD - SJO
Nonstop5h 14mUnited Airlines
Deal found 4/17$431
This Copa Airlines deal was found by Cheapflights users on 4/17. 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 5/16:07 pmSJO - ORD
1 stop18h 40mCopa Airlines
Mon 5/53:07 pmORD - SJO
1 stop17h 28mCopa Airlines
Deal found 4/17$432
This Southwest deal was found by Cheapflights users on 4/16. 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.
Thu 8/141:40 pmSJO - MDW
1 stop9h 25mSouthwest
Tue 8/199:10 amMDW - SJO
1 stop10h 45mSouthwest
Deal found 4/16$436
This Avianca deal was found by Cheapflights users on 4/17. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/161:40 amSJO - ORD
1 stop34h 35mAvianca
Sun 8/243:45 pmORD - SJO
2 stops8h 50mAvianca
Deal found 4/17$443
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Sat 9/137:35 amSJO - ORD
1 stop11h 01mAmerican Airlines
Tue 9/236:00 amORD - SJO
1 stop7h 55mAmerican Airlines
Deal found 4/17$449
This Booking.com deal was found by Cheapflights users on 4/15. 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.
Sat 6/281:47 pmSJO - MDW
1 stop23h 02mFrontier
Sat 7/56:20 amMDW - SJO
1 stop7h 11mFrontier
Deal found 4/15$476
This Delta deal was found by Cheapflights users on 4/16. 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.
Mon 9/151:18 pmSJO - MDW
1 stop7h 26mDelta
Fri 9/196:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 4/16$478

Cheapflights Fare Finder

Customize your flight search to find flights from San José to Chicago 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 April 17, 2025.
Use the filters below to find and compare flights from San José to Chicago that are best for you.

Fly from

San José

Fly to

Chicago

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 5/23

11:32 am-11:29 pm

1 stop10h 57m

Chicago O'Hare Intl

Mon 5/26

7:35 pm-11:33 am

1 stop16h 58m

$294

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 8/23

4:48 pm-5:42 am

1 stop11h 54m

Chicago O'Hare Intl

Sat 8/30

1:40 am-1:57 pm

1 stop13h 17m

$313

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/23

5:52 am-8:17 pm

2 stops13h 25m

Chicago Midway

Sun 5/25

9:12 pm-10:27 am

1 stop14h 15m

$394

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 5/24

1:00 pm-7:34 pm

Nonstop5h 34m

Chicago O'Hare Intl

Sun 6/1

7:41 am-11:55 am

Nonstop5h 14m

$431

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 5/1

6:07 pm-1:47 pm

1 stop18h 40m

Chicago O'Hare Intl

Mon 5/5

3:07 pm-7:35 am

1 stop17h 28m

$432

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 8/16

1:40 am-1:15 pm

1 stop34h 35m

Chicago O'Hare Intl

Sun 8/24

3:45 pm-11:35 pm

2 stops8h 50m

$443

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 9/13

7:35 am-7:36 pm

1 stop11h 01m

Chicago O'Hare Intl

Tue 9/23

6:00 am-12:55 pm

1 stop7h 55m

$449

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 6/28

1:47 pm-1:49 pm

1 stop23h 02m

Chicago Midway

Sat 7/5

6:20 am-12:31 pm

1 stop7h 11m

$476

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/23

1:10 pm-11:35 pm

1 stop9h 25m

Chicago Midway

Sun 5/25

9:55 am-7:40 pm

1 stop10h 45m

$484

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/3

1:20 pm-10:22 pm

1 stop8h 02m

Chicago Midway

Sat 5/10

6:00 am-11:59 am

1 stop6h 59m

$556

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 22 results
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Compare providers for flights from San José to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San José to Chicago in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San José, San José Province-Chicago flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on San José, San José Province-Chicago flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from San José, San José Province-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José, San José Province-Chicago flights, Cheapflights users trust AranGrant the most. AranGrant has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San José, San José Province-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San José to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from San José to Chicago. Price data was last updated on April 11, 2025.

The price you pay for your flight from San José, San José Province to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 83 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $245). Flying from San José, San José Province to Chicago in March is currently the most expensive (average of $321). 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 SJO to CHI?

Find hourly flight availability from San José to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

One of the essential ways to save on airfare from San José, San José Province to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 46% on airfare.

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 17, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from San José to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Copa Airlines
7.6
Good
1,409 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
LATAM Airlines
7.5
Good
1,761 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from San José to Chicago. 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 from for flights from San José to 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 Chicago from San José. Booking flights from Juan Santamaria Intl (SJO) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 6 different airlines.

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

    Cheapflights users have booked flights from San José, San José Province to Chicago round-trip from $294. Other airlines that can offer you cheap pricing are United Airlines, from $437, and American Airlines, from $448. Spirit Airlines is 38% cheaper than the average price of flights available within the next 90 days to this destination.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $140. Copa Airlines flights start at $237 while deals on Avianca start at $241 one-way.

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

    On average you can expect to pay $409 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $235 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $263.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $245). Flying from San José, San José Province to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for San José to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
San José to O'Hare Intl flights
San José to Midway flights
San José to St. Louis flights
Liberia to O'Hare Intl flights

Top 6 airlines flying from San José to Chicago

Discover the top 6 airlines that operate flights from San José to Chicago. 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$198Average$389FlexibilityNo cancel feeOn-time65%
AviancaCheapest$321Average$491FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$326Average$512FlexibilityNo cancel feeOn-time70%
DeltaCheapest$434Average$649FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$446Average$571FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$473Average$664FlexibilityNo cancel feeOn-time69%

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