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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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Sep 7 — Sep 141
Sun 9/7
Sun 9/14
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 May, booked 56 days in advance, depart on a Wednesday or Friday 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 September 2, 2025.

Round-trip from

$180
(CheapOair)

One-way from

$106
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$447

Good round-trip deal

$347 or less

Good one-way deal

$197 or less
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. 2% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 2, 2025.

This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Wed 10/86:40 pmORD - SJO
2 stops17h 50mSpirit Airlines
Deal found 9/2$180
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Tue 10/75:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 9/2$213
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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.
Tue 9/2312:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Sun 9/285:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Deal found 9/2$219
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1812:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Mon 9/225:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Deal found 9/2$222
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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 11/81:19 pmSJO - ORD
1 stop10h 23mSpirit Airlines
Wed 11/125:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Deal found 9/2$229
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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.
Tue 9/3012:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Fri 10/107:41 pmORD - SJO
1 stop16h 49mSpirit Airlines
Deal found 9/2$230
This SmartFares deal was found by Cheapflights users on 9/2. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Sun 10/125:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 9/2$231
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Tue 10/77:41 pmORD - SJO
2 stops16h 00mSpirit Airlines
Deal found 9/2$237
This Southwest deal was found by Cheapflights users on 9/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/201:15 pmSJO - MDW
1 stop8h 30mSouthwest
Fri 9/2611:15 amMDW - SJO
1 stop8h 40mSouthwest
Deal found 9/2$335
This Southwest deal was found by Cheapflights users on 9/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/211:00 pmSJO - MDW
1 stop9h 35mSouthwest
Wed 11/127:00 amMDW - SJO
1 stop13h 30mSouthwest
Deal found 9/2$337
This Southwest deal was found by Cheapflights users on 9/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:00 amSJO - MDW
1 stop9h 55mSouthwest
Mon 11/108:00 amMDW - SJO
1 stop12h 30mSouthwest
Deal found 9/2$339
This Southwest deal was found by Cheapflights users on 9/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/151:40 pmSJO - MDW
1 stop9h 25mSouthwest
Sat 9/276:15 amMDW - SJO
1 stop7h 00mSouthwest
Deal found 9/1$356

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 September 2, 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

Wed 10/1

12:19 pm-10:48 pm

1 stop9h 29m

Chicago O'Hare Intl

Wed 10/8

6:40 pm-11:30 am

2 stops17h 50m

$192

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 9/29

12:19 pm-10:52 am

1 stop21h 33m

Chicago O'Hare Intl

Sat 10/11

7:41 pm-11:30 am

1 stop16h 49m

$252

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 10/3

12:19 pm-10:42 am

2 stops21h 23m

Chicago O'Hare Intl

Tue 10/7

3:22 pm-10:41 am

2 stops20h 19m

$254

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 10/3

11:37 am-10:52 am

2 stops22h 15m

Chicago O'Hare Intl

Thu 10/9

7:41 pm-11:30 am

1 stop16h 49m

$263

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 9/16

12:19 pm-10:48 pm

1 stop9h 29m

Chicago O'Hare Intl

Mon 9/22

6:44 pm-11:14 am

1 stop17h 30m

$265

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 11/1

12:35 pm-1:03 am

1 stop11h 28m

Chicago O'Hare Intl

Sat 11/8

7:35 am-11:27 am

2 stops27h 52m

$266

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 10/4

11:37 am-10:47 am

2 stops22h 10m

Chicago O'Hare Intl

Tue 10/7

3:22 pm-10:41 am

2 stops20h 19m

$267

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 9/16

12:19 pm-10:48 pm

1 stop9h 29m

Chicago O'Hare Intl

Tue 9/30

2:04 pm-10:27 am

2 stops21h 23m

$268

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 10/7

11:37 am-11:45 pm

2 stops11h 08m

Chicago O'Hare Intl

Fri 10/10

7:41 pm-11:30 am

1 stop16h 49m

$275

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 10/17

11:37 am-10:47 am

2 stops22h 10m

Chicago O'Hare Intl

Mon 10/20

7:41 pm-11:30 am

1 stop16h 49m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/31

Showing 1-10 of 41 results
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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 August 29, 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 56 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 September 2, 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 at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 42% on airfare.

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

Share of 1-stop round-trip flights from San José, San José Province 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, San José Province to Chicago on Cheapflights.

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

Average round-trip fare for 1-stop flights from San José, San José Province 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, San José Province to Chicago?

Shortest average travel time for 1-stop one-way flights from San José, San José Province 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, San José Province to Chicago?

Average layover duration for 1-stop one-way flights from San José, San José Province 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 September 2, 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

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
1,521 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
8,010 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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 are 0 daily outbound flights to Chicago from 6 different airlines.

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

    A quick flight from San José, San José Province to Chicago can take about 7h 51m. Spirit Airlines provides one of the quickest options available for as low as $337. The distance between San José, San José Province and Chicago is about 2206 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $249. Other airlines that can offer you cheap pricing are Spirit Airlines, from $266, and Copa Airlines, from $314. Avianca is 47% cheaper than the average price of flights available within the next 90 days to this destination.

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

    On average you can expect to pay $365 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $132 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $166.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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 September 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$249Average$485FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$266Average$414FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$314Average$478FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$377Average$564FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$425Average$527FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$437Average$619FlexibilityNo cancel feeOn-time69%

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