HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$174+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
May 30 — Jun 61
Sat 5/30
Sat 6/6
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.
Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago are usually found in January or October, booked 30 days in advance, depart on a Tuesday or Thursday 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 April 30, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/26. 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 7/171:21 pm
SJO
-
ORD
1 stop22h 04m
Multiple Airlines
Fri 7/315:10 am
ORD
-
SJO
1 stop8h 05m
Multiple Airlines
Deal found 4/26$357
This CheapOair deal was found by Cheapflights users on 4/25. 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.
Thu 8/279:35 am
SJO
-
ORD
1 stop12h 39m
Multiple Airlines
Sun 8/305:10 am
ORD
-
SJO
1 stop8h 05m
Multiple Airlines
Deal found 4/25$360
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 7/311:21 pm
SJO
-
ORD
1 stop9h 38m
Multiple Airlines
Wed 8/197:55 am
ORD
-
SJO
1 stop29h 20m
Multiple Airlines
Deal found 4/26$363
This United Airlines deal was found by Cheapflights users on 4/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/232:05 pm
SJO
-
ORD
Nonstop5h 30m
United Airlines
Sun 1/39:25 am
ORD
-
SJO
1 stop13h 07m
United Airlines
Deal found 4/27$365
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 8/159:35 am
SJO
-
ORD
1 stop12h 30m
Frontier
Wed 8/195:30 pm
ORD
-
SJO
1 stop15h 50m
Frontier
Deal found 4/29$366
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:00 pm
SJO
-
ORD
1 stop9h 15m
Spirit Airlines
Thu 5/285:05 am
ORD
-
SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/30$367
This Copa Airlines 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1910:03 am
SJO
-
ORD
1 stop13h 54m
Copa Airlines
Wed 10/283:13 pm
ORD
-
SJO
1 stop18h 08m
Copa Airlines
Deal found 4/28$368
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/232:05 pm
SJO
-
ORD
Nonstop5h 30m
United Airlines
Wed 1/69:25 am
ORD
-
SJO
1 stop11h 14m
United Airlines
Deal found 4/28$369
This Travelocity deal was found by Cheapflights users on 4/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:35 am
SJO
-
ORD
1 stop22h 36m
Frontier
Wed 7/225:13 pm
ORD
-
SJO
1 stop16h 07m
Frontier
Deal found 4/25$370
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.
Fri 9/1112:44 pm
SJO
-
ORD
1 stop21h 19m
United Airlines
Tue 9/157:45 pm
ORD
-
SJO
1 stop16h 53m
United Airlines
Deal found 4/29$371
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:35 am
SJO
-
ORD
1 stop12h 39m
Multiple Airlines
Sat 8/295:10 am
ORD
-
SJO
1 stop8h 05m
Multiple Airlines
Deal found 4/27$372
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:35 am
SJO
-
ORD
1 stop12h 38m
Multiple Airlines
Wed 5/271:50 pm
ORD
-
SJO
2 stops22h 55m
Multiple Airlines
Deal found 4/30$376

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 April 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(Kiwi.com)

One-way from

$174
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$474

Good round-trip deal

$406 or less

Good one-way deal

$230 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. 7% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 30, 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

Fri 6/19

4:10 am-5:26 pm

1 stop12h 16m

Chicago O'Hare Intl

Sun 6/21

1:00 am-11:06 am

1 stop11h 06m

$368

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 5/21

10:05 am-1:15 am

1 stop14h 10m

Chicago O'Hare Intl

Mon 5/25

3:21 pm-9:06 am

1 stop18h 45m

$368

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 9/18

1:25 pm-9:09 am

1 stop18h 44m

Chicago O'Hare Intl

Tue 9/22

8:51 am-7:37 pm

1 stop11h 46m

$371

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 7/14

12:30 am-10:20 am

1 stop8h 50m

Chicago O'Hare Intl

Wed 8/5

9:40 pm-10:11 am

1 stop13h 31m

$380

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 6/11

12:30 am-12:45 am

1 stop23h 15m

Chicago O'Hare Intl

Tue 6/16

9:21 pm-10:11 am

1 stop13h 50m

$397

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 5/24

12:30 am-12:45 am

1 stop23h 15m

Chicago O'Hare Intl

Mon 6/1

9:21 pm-10:11 am

1 stop13h 50m

$402

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 7/15

4:08 am-1:57 pm

1 stop8h 49m

Chicago O'Hare Intl

Tue 7/21

3:21 pm-7:12 am

1 stop16h 51m

$420

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 9/25

11:00 am-1:02 am

1 stop13h 02m

Chicago O'Hare Intl

Sat 10/3

3:20 pm-7:10 am

1 stop16h 50m

$420

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 9/13

10:03 am-1:02 am

1 stop13h 59m

Chicago O'Hare Intl

Sat 9/19

8:01 am-6:59 pm

1 stop11h 58m

$420

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 9/12

12:44 pm-11:16 pm

1 stop9h 32m

Chicago O'Hare Intl

Thu 9/17

7:30 am-7:37 pm

1 stop13h 07m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4

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*3 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 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

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.

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

Currently, November is the cheapest month in which you can book a flight from San José to Chicago (average of $111). Flying from San José to Chicago in December is currently the most expensive (average of $194). 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, 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?

How often are flights from San José to Chicago delayed?

About 8% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 238 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 6% of flights being delayed.

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, 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
4,314 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Copa Airlines
7.5
Good
1,578 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,677 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,681 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,635 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

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

    Copa Airlines, United Airlines, and Delta can get you from San José to Chicago in just under 7h 22m. Your travel time can differ by up to 11h 22m. 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?

    Spirit Airlines, at $179, was found to be the cheapest airline from San José to Chicago.Alternate airlines to your destination round-trip include Copa Airlines and Avianca. Users have found that Spirit 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 $183. Copa Airlines flights start at $198 while deals on Spirit Airlines start at $230 one-way.

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

    On average you can expect to pay $500 for a flight from San José to Chicago. The cheapest flight overall is $177 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $342.

  • 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, November is the cheapest month in which you can book a flight from San José to Chicago (average of $111). Flying from San José to Chicago in December is currently the most expensive (average of $194). 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
Hammond
Porter

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

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, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$179Average$289FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$189Average$454FlexibilityNo cancel feeOn-time70%
AviancaCheapest$249Average$410FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$332Average$496FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$387Average$474FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$463Average$505FlexibilityNo cancel feeOn-time63%

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.