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$203+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from San José Juan Santamaria Intl to Chicago are usually found in February or August, booked 83 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$328
(eDestinos)

One-way from

$203
(Mytrip)

Popular in

October

Cheapest in

February

Average price

$518
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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High demand for flights, 9% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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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 December 18, 2024.

This Booking.com deal was found by Cheapflights users on 12/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/243:32 pmSJO - ORD
1 stop9h 30mMultiple Airlines
Thu 1/96:06 pmORD - SJO
1 stop17h 12mMultiple Airlines
Deal found 12/16$348
This eDestinos deal was found by Cheapflights users on 12/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/311:49 amSJO - ORD
1 stop9h 15mSpirit Airlines
Sun 1/126:06 pmORD - SJO
1 stop17h 12mSpirit Airlines
Deal found 12/17$372
This Priceline deal was found by Cheapflights users on 12/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/233:45 pmSJO - ORD
1 stop20h 30mAvianca
Wed 1/292:35 pmORD - SJO
1 stop18h 45mAvianca
Deal found 12/17$427
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Thu 12/2611:38 amSJO - ORD
1 stop9h 12mFrontier
Sat 1/45:18 pmORD - SJO
1 stop16h 57mFrontier
Deal found 12/16$545
This Air Canada deal was found by Cheapflights users on 12/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:55 amSJO - ORD
1 stop10h 37mAir Canada
Tue 12/319:50 amORD - SJO
1 stop11h 35mAir Canada
Deal found 12/18$547
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/211:08 pmSJO - MDW
2 stops19h 37mMultiple Airlines
Sat 1/42:20 pmMDW - SJO
1 stop19h 55mMultiple Airlines
Deal found 12/18$591
This Booking.com deal was found by Cheapflights users on 12/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2611:38 amSJO - MDW
1 stop25h 46mFrontier
Sat 1/42:20 pmMDW - SJO
1 stop19h 55mFrontier
Deal found 12/16$615
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/282:05 pmSJO - ORD
Nonstop5h 25mUnited Airlines
Mon 1/64:15 pmORD - SJO
1 stop7h 43mUnited Airlines
Deal found 12/17$633
This Delta deal was found by Cheapflights users on 12/16. 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.
Sat 12/217:05 amSJO - MDW
1 stop9h 12mDelta
Sat 1/49:30 amMDW - SJO
2 stops12h 25mDelta
Deal found 12/16$660
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/259:55 amSJO - MDW
2 stops11h 30mSouthwest
Tue 1/77:15 amMDW - SJO
2 stops13h 25mSouthwest
Deal found 12/17$758

Find flights from San José to Chicago within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 1/26

1:57 am-10:07 am

1 stop8h 10m

Chicago O'Hare Intl

Mon 1/27

6:06 pm-11:18 am

1 stop17h 12m

$328

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/23

8:30 pm-1:15 pm

2 stops16h 45m

Chicago O'Hare Intl

Sun 1/26

2:35 pm-8:40 am

2 stops18h 05m

$338

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 2/4

1:31 pm-11:32 pm

1 stop10h 01m

Chicago O'Hare Intl

Mon 2/10

3:56 pm-12:59 am

3 stops33h 03m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 1/26

1:57 am-3:02 pm

2 stops13h 05m

Chicago Midway

Mon 2/3

11:33 am-11:18 am

1 stop23h 45m

$405

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/1

8:45 am-6:35 pm

1 stop8h 50m

Chicago Midway

Mon 5/5

5:50 am-12:10 pm

1 stop7h 20m

$569

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/28

2:15 pm-10:06 pm

1 stop7h 51m

Chicago Midway

Wed 1/8

10:57 am-10:12 pm

1 stop11h 15m

$729

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 12/29

11:38 am-1:24 pm

1 stop25h 46m

Chicago Midway

Wed 1/1

2:20 pm-10:15 am

1 stop19h 55m

$973

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 2/24

2:43 pm-4:37 am

1 stop13h 54m

$203

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 2/24

12:24 pm-3:12 pm

1 stop26h 48m

$205

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 1/26

1:57 am-5:20 pm

2 stops15h 23m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 25 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy3 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José, San José Province-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from San José to Chicago

Get recent, data-driven insights about flights from San José to Chicago including ideal travel times, pricing trends, and more.

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 December 13, 2024.

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, September is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $232). Flying from San José, San José Province to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

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 in the afternoon could potentially save you up to 42% 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 December 18, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Frontier 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.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,552 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,723 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,879 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $328. Other airlines that can offer you cheap pricing are Avianca, from $338, and Southwest, from $569. Spirit Airlines is 24% 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 $206. Avianca flights start at $215 while deals on Frontier start at $294 one-way.

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

    On average you can expect to pay $1,088 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $330 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $259.

  • 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, September is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $232). Flying from San José, San José Province to Chicago in June is currently the most expensive (average of $308). 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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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$383FlexibilityNo cancel feeOn-time65%
AviancaCheapest$264Average$455FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$404Average$561FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$484Average$628FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$680FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$561Average$663FlexibilityNo cancel feeOn-time69%
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