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$152+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$299
(Cheapflightsfares)

One-way from

$152
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$519

Good round-trip deal

$478 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 ($18 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 30, 2025.

This CheapOair deal was found by Cheapflights users on 4/29. 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.
Sat 6/73:31 pmSJO - ORD
1 stop18h 34mMultiple Airlines
Fri 6/137:39 pmORD - SJO
1 stop16h 38mMultiple Airlines
Deal found 4/29$298
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/511:32 amSJO - ORD
1 stop10h 57mSpirit Airlines
Mon 6/94:35 pmORD - SJO
2 stops19h 58mSpirit Airlines
Deal found 4/29$301
This Copa Airlines deal was found by Cheapflights users on 4/29. 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 8/1410:05 amSJO - ORD
1 stop13h 17mCopa Airlines
Mon 8/187:54 amORD - SJO
1 stop14h 59mCopa Airlines
Deal found 4/29$311
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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.
Thu 8/213:05 pmSJO - ORD
2 stops22h 20mAvianca
Thu 8/285:25 pmORD - SJO
2 stops15h 15mAvianca
Deal found 4/28$316
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 6/65:52 amSJO - MDW
2 stops13h 25mMultiple Airlines
Fri 6/139:12 pmMDW - SJO
1 stop14h 25mMultiple Airlines
Deal found 4/28$372
This Southwest deal was found by Cheapflights users on 4/29. 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 9/111:40 pmSJO - MDW
1 stop9h 25mSouthwest
Mon 9/155:05 amMDW - SJO
1 stop8h 40mSouthwest
Deal found 4/29$426
This Delta deal was found by Cheapflights users on 4/29. 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 5/31:20 pmSJO - MDW
1 stop8h 02mDelta
Sat 5/106:00 amMDW - SJO
1 stop8h 05mDelta
Deal found 4/29$435
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 4/301:30 pmSJO - ORD
1 stop8h 43mUnited Airlines
Sun 5/45:15 amORD - SJO
1 stop15h 22mUnited Airlines
Deal found 4/29$435
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 5/51:50 pmSJO - ORD
1 stop16h 35mAmerican Airlines
Sat 5/109:45 amORD - SJO
2 stops9h 50mAmerican Airlines
Deal found 4/29$448
This LATAM Airlines deal was found by Cheapflights users on 4/29. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:00 pmSJO - MDW
2 stops15h 51mLATAM Airlines
Mon 9/16:15 pmMDW - SJO
2 stops22h 20mLATAM Airlines
Deal found 4/29$2,416

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 30, 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

Sat 6/7

3:31 pm-11:05 am

1 stop18h 34m

Chicago O'Hare Intl

Fri 6/13

7:39 pm-11:17 am

1 stop16h 38m

$298

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 6/5

11:32 am-11:29 pm

1 stop10h 57m

Chicago O'Hare Intl

Mon 6/9

4:35 pm-11:33 am

2 stops19h 58m

$301

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 8/14

10:05 am-12:22 am

1 stop13h 17m

Chicago O'Hare Intl

Mon 8/18

7:54 am-9:53 pm

1 stop14h 59m

$311

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 8/21

3:05 pm-2:25 pm

2 stops22h 20m

Chicago O'Hare Intl

Thu 8/28

5:25 pm-7:40 am

2 stops15h 15m

$316

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 6/6

5:52 am-8:17 pm

2 stops13h 25m

Chicago Midway

Fri 6/13

9:12 pm-10:37 am

1 stop14h 25m

$372

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/11

1:40 pm-12:05 am

1 stop9h 25m

Chicago Midway

Mon 9/15

5:05 am-12:45 pm

1 stop8h 40m

$426

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 8/29

7:55 am-9:40 pm

1 stop12h 45m

Chicago O'Hare Intl

Tue 9/2

6:00 am-12:26 pm

1 stop7h 26m

$438

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 5/15

6:03 am-6:11 pm

1 stop11h 08m

Chicago O'Hare Intl

Wed 5/21

8:22 am-6:35 pm

2 stops11h 13m

$448

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/15

1:18 pm-9:44 pm

1 stop7h 26m

Chicago Midway

Sat 9/20

6:00 am-11:53 am

1 stop6h 53m

$478

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/30

5:00 pm-9:51 am

2 stops15h 51m

Chicago Midway

Mon 9/1

6:15 pm-3:35 pm

2 stops22h 20m

$2,416

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 23 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 25, 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 30, 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 30, 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
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
LATAM Airlines
7.5
Good
1,767 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Copa Airlines
7.5
Good
1,411 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $299. Other airlines that can offer you cheap pricing are Avianca, from $316, and Copa Airlines, from $367. Spirit Airlines is 37% 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 $152. Avianca flights start at $178 while deals on United Airlines 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 $402 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 $248.

  • 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

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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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$242Average$406FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$311Average$506FlexibilityNo cancel feeOn-time70%
AviancaCheapest$321Average$491FlexibilityNo cancel feeOn-time71%
DeltaCheapest$434Average$563FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$446Average$569FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$446Average$660FlexibilityNo cancel feeOn-time69%

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