HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$197+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San José to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from San José Juan Santamaria Intl to Chicago are usually found in August or February, booked 83 days in advance, depart on a Tuesday or Friday 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 January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$325
(eDestinos)

One-way from

$197
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$461
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago (CHI) flights.
Search Deals
From San José Juan Santamaria Intl to Chicago (CHI)
Search Deals
One-way flight from San José Juan Santamaria Intl to Chicago (CHI)
Search Deals
High demand for flights, 9% potential price rise
Search Deals
Best time to find cheap flights, 2% potential price drop
Search Deals
Average for round-trip flights in January 2025
Search Deals

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 January 16, 2025.

This eDestinos deal was found by Cheapflights users on 1/14. 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 5/61:04 amSJO - ORD
3 stops44h 17mSpirit Airlines
Mon 5/128:42 pmORD - SJO
2 stops15h 51mSpirit Airlines
Deal found 1/14$324
This Booking.com deal was found by Cheapflights users on 1/15. 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.
Tue 2/42:43 pmSJO - ORD
1 stop13h 54mMultiple Airlines
Tue 3/1110:25 amORD - SJO
1 stop14h 25mMultiple Airlines
Deal found 1/15$328
This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Tue 2/2512:29 pmSJO - MDW
2 stops18h 38mMultiple Airlines
Sat 3/112:43 pmMDW - SJO
1 stop22h 41mMultiple Airlines
Deal found 1/16$357
This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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.
Wed 1/222:15 amSJO - ORD
1 stop10h 00mAvianca
Fri 5/162:35 pmORD - SJO
1 stop19h 45mAvianca
Deal found 1/14$433
This Southwest deal was found by Cheapflights users on 1/14. 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.
Tue 3/111:55 pmSJO - MDW
1 stop8h 45mSouthwest
Tue 4/85:55 amMDW - SJO
1 stop7h 15mSouthwest
Deal found 1/14$544
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/241:42 pmSJO - MDW
1 stop9h 13mFrontier
Fri 5/306:44 pmMDW - SJO
1 stop18h 38mFrontier
Deal found 1/15$551
This Delta deal was found by Cheapflights users on 1/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:13 pmSJO - MDW
1 stop7h 34mDelta
Tue 10/286:00 amMDW - SJO
1 stop6h 48mDelta
Deal found 1/15$651

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 January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 5/6

1:04 am-10:21 pm

3 stops44h 17m

Chicago O'Hare Intl

Mon 5/12

8:42 pm-11:33 am

2 stops15h 51m

$324

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 2/4

2:43 pm-4:37 am

1 stop13h 54m

Chicago O'Hare Intl

Tue 3/11

10:25 am-11:50 pm

1 stop14h 25m

$328

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 2/25

12:29 pm-7:07 am

2 stops18h 38m

Chicago Midway

Sat 3/1

12:43 pm-11:24 am

1 stop22h 41m

$357

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 1/29

2:15 am-12:15 pm

1 stop10h 00m

Chicago O'Hare Intl

Mon 2/3

1:35 pm-9:20 am

1 stop19h 45m

$433

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 3/11

1:55 pm-11:40 pm

1 stop8h 45m

Chicago Midway

Tue 4/8

5:55 am-12:10 pm

1 stop7h 15m

$544

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/24

1:42 pm-11:55 pm

1 stop9h 13m

Chicago Midway

Fri 5/30

6:44 pm-12:22 pm

1 stop18h 38m

$551

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 2/3

7:00 am-6:11 pm

2 stops11h 11m

Chicago Midway

Mon 2/17

10:57 am-10:12 pm

1 stop11h 15m

$651

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/30

12:25 pm-9:52 am

1 stop21h 27m

$197

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 2/26

12:29 pm-7:29 pm

1 stop31h 00m

$202

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 2/26

12:29 pm-11:58 pm

2 stops11h 29m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 24 results
1
2
3

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 January.
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*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 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 January 10, 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 $320). 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 January 16, 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 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 January 16, 2025.
Peruse reviews from past customers who have flown with Spirit Airlines, Delta and Southwest 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
4,659 reviews

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

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
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

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
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

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
1,658 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

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.

Aeromexico
7.5
Good
1,849 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

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 $325. Other airlines that can offer you cheap pricing are Avianca, from $433, and Southwest, from $544. Spirit Airlines is 27% 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 $203. Frontier flights start at $221 while deals on Avianca start at $240 one-way.

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

    On average you can expect to pay $1,044 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $305 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $275.

  • 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$382FlexibilityNo cancel feeOn-time65%
AviancaCheapest$269Average$462FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$404Average$561FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$484Average$621FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$649FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$557Average$664FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.