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$128+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 November, booked 56 days in advance, depart on a Wednesday or Tuesday and return on a Monday

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 June 12, 2025.

Round-trip from

$289
(Mytrip)

One-way from

$128
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$524

Good round-trip deal

$432 or less

Good one-way deal

$242 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. 3% potential increase in price ($15 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 June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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 8/265:05 amSJO - ORD
1 stop10h 00mAvianca
Sat 8/305:25 pmORD - SJO
1 stop7h 10mAvianca
Deal found 6/10$289
This Copa Airlines deal was found by Cheapflights users on 6/12. 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.
Wed 10/2910:05 amSJO - ORD
1 stop13h 16mCopa Airlines
Wed 11/56:56 amORD - SJO
1 stop12h 00mCopa Airlines
Deal found 6/12$294
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 7/112:28 pmSJO - ORD
1 stop10h 17mSpirit Airlines
Mon 7/77:39 pmORD - SJO
1 stop16h 40mSpirit Airlines
Deal found 6/11$295
This CheapOair deal was found by Cheapflights users on 6/11. 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 9/252:48 pmSJO - ORD
1 stop13h 54mMultiple Airlines
Tue 9/305:05 amORD - SJO
1 stop7h 13mMultiple Airlines
Deal found 6/11$303
This Frontier deal was found by Cheapflights users on 6/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/161:47 pmSJO - ORD
1 stop8h 42mFrontier
Sat 8/236:00 amORD - SJO
1 stop7h 24mFrontier
Deal found 6/11$326
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 10/81:53 pmSJO - ORD
1 stop10h 06mAmerican Airlines
Wed 10/156:00 amORD - SJO
1 stop8h 00mAmerican Airlines
Deal found 6/10$365
This Southwest deal was found by Cheapflights users on 6/10. 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 9/241:40 pmSJO - MDW
1 stop8h 40mSouthwest
Tue 9/306:25 amMDW - SJO
1 stop13h 30mSouthwest
Deal found 6/10$379
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 6/211:00 pmSJO - ORD
Nonstop5h 34mUnited Airlines
Mon 6/309:00 pmORD - SJO
1 stop14h 11mUnited Airlines
Deal found 6/11$443
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Sun 7/207:30 amSJO - MDW
2 stops29h 34mMultiple Airlines
Mon 7/282:54 pmMDW - SJO
2 stops13h 41mMultiple Airlines
Deal found 6/11$485
This Delta deal was found by Cheapflights users on 6/12. 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.
Wed 10/81:13 pmSJO - MDW
1 stop7h 31mDelta
Wed 10/156:00 amMDW - SJO
1 stop6h 48mDelta
Deal found 6/12$680
This eDestinos deal was found by Cheapflights users on 6/10. 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.
Thu 10/91:07 pmSJO - MDW
3 stops26h 16mAeromexico
Wed 10/156:00 amMDW - SJO
2 stops18h 36mAeromexico
Deal found 6/10$1,048
This LATAM Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 9/235:00 pmSJO - MDW
2 stops15h 51mLATAM Airlines
Tue 9/3010:35 amMDW - SJO
2 stops30h 00mLATAM Airlines
Deal found 6/11$2,085

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 June 12, 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

Tue 8/26

5:05 am-4:05 pm

1 stop10h 00m

Chicago O'Hare Intl

Sat 8/30

5:25 pm-11:35 pm

1 stop7h 10m

$289

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/10

8:46 am-12:22 am

1 stop14h 36m

Chicago O'Hare Intl

Wed 9/24

3:07 pm-8:20 am

1 stop18h 13m

$294

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 7/1

12:28 pm-11:45 pm

1 stop10h 17m

Chicago O'Hare Intl

Mon 7/7

7:39 pm-11:19 am

1 stop16h 40m

$295

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 8/29

4:13 pm-11:05 am

1 stop17h 52m

Chicago O'Hare Intl

Tue 9/2

6:34 pm-11:18 am

1 stop17h 44m

$310

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 8/16

1:47 pm-11:29 pm

1 stop8h 42m

Chicago O'Hare Intl

Sat 8/23

6:00 am-12:24 pm

1 stop7h 24m

$326

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 8/14

2:15 pm-11:48 pm

1 stop8h 33m

Chicago O'Hare Intl

Mon 8/18

6:03 am-12:55 pm

1 stop7h 52m

$366

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 8/26

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

Sat 8/30

10:10 am-6:55 pm

1 stop9h 45m

$379

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 6/21

1:00 pm-7:34 pm

Nonstop5h 34m

Chicago O'Hare Intl

Mon 6/30

9:00 pm-10:11 am

1 stop14h 11m

$443

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 7/20

7:30 am-2:04 pm

2 stops29h 34m

Chicago Midway

Mon 7/28

2:54 pm-3:35 am

2 stops13h 41m

$485

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 7/29

1:21 pm-11:58 am

1 stop21h 37m

Chicago Midway

Sat 8/2

6:00 am-1:05 pm

1 stop8h 05m

$1,234

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 22 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 June 9, 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 June 12, 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 45% 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 June 12, 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
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
1,451 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,706 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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 7 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 $289. Other airlines that can offer you cheap pricing are Copa Airlines, from $294, and Spirit Airlines, from $295. Avianca is 38% 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 $162. Avianca flights start at $163 while deals on Frontier start at $201 one-way.

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

    On average you can expect to pay $375 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $231 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $281.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 7 airlines flying from San José to Chicago

Discover the top 7 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$264Average$412FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$314Average$485FlexibilityNo cancel feeOn-time70%
AviancaCheapest$318Average$488FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$425Average$527FlexibilityNo cancel feeOn-time63%
DeltaCheapest$434Average$563FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$437Average$617FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$446Average$570FlexibilityNo cancel feeOn-time71%

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