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$182+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago are usually found in January or November, booked 30 days in advance, depart on a Thursday or Tuesday and return on a Tuesday

Cheap 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 August 1, 2026.

This Copa Airlines deal was found by Cheapflights users on 7/29. 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 9/106:17 pm
SJO
-
ORD
1 stop18h 42m
Copa Airlines
Sat 9/193:20 pm
ORD
-
SJO
1 stop16h 50m
Copa Airlines
Deal found 7/29$408
This Copa Airlines deal was found by Cheapflights users on 7/30. 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.
Sun 11/13:59 am
SJO
-
ORD
1 stop8h 47m
Copa Airlines
Thu 11/52:13 pm
ORD
-
SJO
1 stop18h 54m
Copa Airlines
Deal found 7/30$412
This Southwest deal was found by Cheapflights users on 7/27. 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 9/299:00 am
SJO
-
MDW
1 stop9h 15m
Southwest
Thu 10/111:50 am
MDW
-
SJO
1 stop8h 50m
Southwest
Deal found 7/27$414
This Volaris deal was found by Cheapflights users on 7/30. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:15 pm
SJO
-
ORD
1 stop18h 54m
Multiple Airlines
Sun 8/306:21 am
ORD
-
SJO
1 stop18h 38m
Multiple Airlines
Deal found 7/30$414
This Southwest deal was found by Cheapflights users on 7/30. 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 9/231:40 pm
SJO
-
MDW
1 stop8h 35m
Southwest
Mon 9/285:00 am
MDW
-
SJO
1 stop8h 45m
Southwest
Deal found 7/30$422
This Copa Airlines deal was found by Cheapflights users on 7/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:55 pm
SJO
-
ORD
1 stop18h 51m
Copa Airlines
Wed 11/252:13 pm
ORD
-
SJO
1 stop18h 54m
Copa Airlines
Deal found 7/28$423
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:40 pm
SJO
-
MDW
1 stop7h 40m
Southwest
Tue 9/2911:10 am
MDW
-
SJO
2 stops8h 35m
Southwest
Deal found 7/28$426
This Copa Airlines deal was found by Cheapflights users on 7/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/112:04 pm
SJO
-
ORD
1 stop12h 07m
Copa Airlines
Sun 11/82:13 pm
ORD
-
SJO
1 stop20h 46m
Copa Airlines
Deal found 7/28$427
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sat 9/51:15 pm
SJO
-
MDW
1 stop7h 50m
Southwest
Sun 9/1310:15 am
MDW
-
SJO
2 stops9h 25m
Southwest
Deal found 7/27$429
This Copa Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 9/1110:03 am
SJO
-
ORD
1 stop13h 59m
Copa Airlines
Sat 9/198:01 am
ORD
-
SJO
1 stop25h 18m
Copa Airlines
Deal found 7/30$441
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:05 pm
SJO
-
ORD
1 stop8h 39m
JetBlue
Thu 10/297:00 am
ORD
-
SJO
1 stop6h 59m
JetBlue
Deal found 7/30$444
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/211:40 pm
SJO
-
MDW
1 stop7h 40m
Southwest
Mon 9/285:00 am
MDW
-
SJO
1 stop8h 45m
Southwest
Deal found 7/31$453

Find 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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$408
(Copa Airlines)

One-way from

$182
(Viva)

Popular in

July

Cheapest in

January

Average price

$468

Good round-trip deal

$492 or less

Good one-way deal

$264 or less
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
Highest demand for flights based on searches. 11% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from San José Juan Santamaria Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from San José Juan Santamaria Intl to Chicago (CHI).
Search Deals

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 August 1, 2026.
Use the filters below to find and compare flights from San José to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 8/25

4:15 pm-12:09 pm

1 stop18h 54m

Chicago O'Hare Intl

Sun 8/30

6:21 am-11:59 pm

1 stop18h 38m

$414

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/23

1:40 pm-11:15 pm

1 stop8h 35m

Chicago Midway

Mon 9/28

9:20 am-6:45 pm

2 stops10h 25m

$438

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 10/14

5:45 am-12:57 am

1 stop18h 12m

Chicago O'Hare Intl

Sun 10/18

3:20 pm-9:04 am

1 stop18h 44m

$457

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/25

9:00 am-9:35 pm

1 stop11h 35m

Chicago Midway

Mon 9/28

5:00 am-12:45 pm

1 stop8h 45m

$468

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 10/6

9:00 am-6:35 pm

1 stop8h 35m

Chicago Midway

Sat 10/10

11:25 am-7:40 pm

2 stops9h 15m

$490

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 8/29

5:45 am-1:02 am

1 stop18h 17m

Chicago O'Hare Intl

Sat 9/5

3:20 pm-10:58 am

1 stop20h 38m

$506

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 8/24

8:45 am-1:02 am

1 stop15h 17m

Chicago O'Hare Intl

Sat 8/29

8:02 am-7:10 am

1 stop24h 08m

$506

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 8/25

10:03 am-1:59 pm

1 stop26h 56m

Chicago O'Hare Intl

Sat 8/29

8:02 am-8:19 am

1 stop25h 17m

$506

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 8/28

10:03 am-1:02 am

1 stop13h 59m

Chicago O'Hare Intl

Sun 8/30

8:02 am-9:04 am

1 stop26h 02m

$506

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 8/25

6:17 pm-1:59 pm

1 stop18h 42m

Chicago O'Hare Intl

Mon 8/31

8:02 am-8:19 am

1 stop25h 17m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 39 resultsSorted by cheapest first
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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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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-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-Chicago flight deals on Cheapflights vs. FlightHub >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 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-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

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

Currently, January is the cheapest month in which you can book a flight from San José to Chicago (average of $385). Flying from San José to Chicago in July is currently the most expensive (average of $638). 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 August 1, 2026.

When flying from San José to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from San José to Chicago?

Airfare is typical for this route at the moment.
San José to Chicago flights typically cost between $372 and $571 in September.
The cheapest round-trip price found within the last 5 days was $408 on Copa Airlines (Sep 10-Sep 19).

How often are flights from San José to Chicago delayed?

About 7% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 245 minutes.

What is the most punctual flight time for San José to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on San José to Chicago flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 5% of flights being delayed.

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

To ensure you get the cheapest price possible for a flight from San José to Chicago, you should look to book at least 29 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.

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 August 1, 2026.
Read through reviews of airlines operating flights from San José to Chicago, such as Southwest,Copa Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Copa Airlines
7.6
Good
1,562 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,062 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,845 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Avianca
6.5
Okay
2,522 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 5 different airlines.

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

    Southwest and Copa Airlines can get you from San José to Chicago in just under 8h 35m. Your travel time can differ by up to 9h 37m. San José and Chicago are separated by a distance of 2206 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Copa Airlines, at $189, was found to be the cheapest airline from San José to Chicago.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Users have found that Copa Airlines is 60% 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 American Airlines, which is currently one of the cheapest options available, starting at $163. Copa Airlines flights start at $198 while deals on United Airlines start at $246 one-way.

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

    On average you can expect to pay $388 for a flight from San José to Chicago. The cheapest flight overall is $201 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $341.

  • 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, January is the cheapest month in which you can book a flight from San José to Chicago (average of $385). Flying from San José to Chicago in July is currently the most expensive (average of $638). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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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

Top 5 airlines flying from San José to Chicago

Discover the top 5 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$189Average$493FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$332Average$515FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$484FlexibilityNo cancel feeOn-time69%
AviancaCheapest$375Average$636FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$390Average$589FlexibilityNo cancel feeOn-time63%

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