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$106+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago are usually found in November or January, booked 30 days in advance, depart on a Friday or Thursday 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$215
(eDestinos)

One-way from

$106
(Cheapflightsfares)

Popular in

June

Cheapest in

November

Average price

$410

Good round-trip deal

$325 or less

Good one-way deal

$175 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. 4% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

This eDestinos deal was found by Cheapflights users on 11/1. 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.
Fri 11/71:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Sun 11/165:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Deal found 11/1$215
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sat 11/221:20 pmSJO - ORD
1 stop10h 09mSpirit Airlines
Tue 12/25:00 amORD - SJO
1 stop7h 15mSpirit Airlines
Deal found 11/2$232
This Mytrip deal was found by Cheapflights users on 11/1. 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.
Tue 11/181:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Thu 12/111:52 pmORD - SJO
2 stops22h 33mSpirit Airlines
Deal found 11/1$234
This OneTravel deal was found by Cheapflights users on 11/2. 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 11/221:20 pmSJO - ORD
1 stop19h 57mSpirit Airlines
Thu 12/115:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/2$239
This eDestinos deal was found by Cheapflights users on 11/2. 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.
Wed 11/1212:34 pmSJO - ORD
1 stop10h 32mSpirit Airlines
Sat 11/155:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Deal found 11/2$244
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 12/51:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Mon 12/85:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/1$247
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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.
Sat 11/81:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Wed 11/125:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Deal found 11/1$249
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 12/51:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Wed 12/105:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/1$252
This OneTravel deal was found by Cheapflights users on 11/1. 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.
Thu 12/41:31 pmSJO - ORD
1 stop21h 37mSpirit Airlines
Thu 12/115:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/1$253
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Wed 12/31:20 pmSJO - ORD
1 stop24h 37mMultiple Airlines
Sat 12/63:26 pmORD - SJO
1 stop20h 59mMultiple Airlines
Deal found 11/2$256
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/1212:39 pmSJO - MDW
1 stop10h 00mMultiple Airlines
Sun 1/112:01 pmMDW - SJO
2 stops21h 26mMultiple Airlines
Deal found 11/1$288
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/47:45 amSJO - MDW
1 stop14h 08mMultiple Airlines
Thu 12/112:16 pmMDW - SJO
1 stop25h 14mMultiple Airlines
Deal found 11/1$311

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 November 3, 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 - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 12/24

2:21 pm-8:49 am

2 stops18h 28m

Chicago Midway

Mon 12/29

6:00 am-9:55 pm

1 stop15h 55m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 12/25

2:21 pm-10:22 pm

1 stop8h 01m

Chicago Midway

Wed 12/31

9:50 am-9:55 pm

1 stop12h 05m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 11/23

7:00 am-4:38 pm

1 stop9h 38m

Chicago Midway

Thu 11/27

10:47 am-10:07 pm

1 stop11h 20m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 12/23

7:00 am-4:20 pm

1 stop9h 20m

Chicago Midway

Mon 12/29

6:00 am-9:55 pm

1 stop15h 55m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 12/24

2:21 pm-8:49 am

2 stops18h 28m

Chicago Midway

Wed 12/31

9:50 am-9:55 pm

1 stop12h 05m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 11/26

7:00 am-11:40 pm

1 stop16h 40m

Chicago Midway

Mon 12/1

6:00 am-10:07 pm

1 stop16h 07m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 11/25

2:31 pm-11:40 pm

1 stop9h 09m

Chicago Midway

Tue 12/2

12:50 pm-10:20 pm

1 stop9h 30m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 11/26

7:00 am-12:02 am

1 stop17h 02m

Chicago O'Hare Intl

Sun 11/30

6:45 am-10:07 pm

1 stop15h 22m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 12/28

7:00 am-9:14 pm

1 stop14h 14m

Chicago O'Hare Intl

Tue 12/30

8:07 pm-12:56 pm

1 stop16h 49m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 12/23

7:00 am-9:01 am

2 stops26h 01m

Chicago O'Hare Intl

Tue 12/30

8:07 pm-12:56 pm

1 stop16h 49m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 42 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust 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-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San José-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from San José-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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-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 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 October 31, 2025.

To ensure you get the cheapest price possible for a flight from San José to Chicago, you should look to book at least 30 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, October is the cheapest month in which you can book a flight from San José to Chicago (average of $198). Flying from San José to Chicago in March is currently the most expensive (average of $351). 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 November 3, 2025.

One of the essential ways to save on airfare from San José to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 33% on airfare.

Weekly flight availability from San José to Chicago

Explore weekly flight availability from San José to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 3, 2025.

The most flights from SJO to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

What’s the top layover airport for flights from San José to Chicago?

Share of 1-stop round-trip flights from San José to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Guatemala City (GUA) – chosen by Cheapflights users on 50% of 1-stop itineraries from San José to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from San José to Chicago?

Average round-trip fare for 1-stop flights from San José to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Guatemala City (GUA) is the most affordable 1-stop option, with an average round-trip price of $391.

What’s the fastest layover option from San José to Chicago?

Shortest average travel time for 1-stop one-way flights from San José to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Guatemala City (GUA) have the shortest average one-way travel time for 1-stop routes: 7h 40m.

Which airport typically offers the quickest layover for flights from San José to Chicago?

Average layover duration for 1-stop one-way flights from San José to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Bogotá (BOG) offer the fastest connection on this route, with an average layover time of 1h 55m.

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 November 3, 2025.
Read through reviews of airlines operating flights from San José to Chicago, such as Southwest, Copa Airlines, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Copa Airlines
7.6
Good
1,561 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 is 1 daily outbound flight to Chicago from 6 different airlines.

  • How long is the flight from San José to Chicago?

    Delta can get you from San José to Chicago in just under 18h 28m. Your travel time can differ by up to . San José and Chicago are separated by a distance of 2206 mi.

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

    Spirit Airlines, at $230, was found to be the cheapest airline from San José to Chicago.Alternate airlines to your destination round-trip include Avianca and Copa Airlines. Users have found that Spirit Airlines is 49% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from San José 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 $151. Avianca flights start at $167 while deals on Delta start at $194 one-way.

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

    On average you can expect to pay $351 for a flight from San José to Chicago. The cheapest flight overall is $145 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $232.

  • 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 to Chicago?

    Currently, October is the cheapest month in which you can book a flight from San José to Chicago (average of $198). Flying from San José to Chicago in March is currently the most expensive (average of $351). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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Hammond
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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$230Average$398FlexibilityNo cancel feeOn-time65%
AviancaCheapest$249Average$485FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$458FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$324Average$463FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$425Average$525FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$434Average$573FlexibilityNo cancel feeOn-time69%

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