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$159+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
nov. 19 — nov. 261
1 adult
mar. 11/19
mar. 11/26
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The best prices from San José Juan Santamaria Intl to Chicago are usually found in August or February, booked 83 days in advance, depart on a Tuesday or Friday and return on a Wednesday

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 noviembre 14, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

October

Cheapest in

August

Round-trip from

$269
(OneTravel)

One-way from

$159
(Kiwi.com)
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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High demand for flights, 24% potential price rise
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Best time to find cheap flights, 19% potential price drop
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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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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 noviembre 14, 2024.

This FlightHub deal was found by Cheapflights users on 11/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/231:49 amSJO - ORD
2 stops12h 47mSpirit Airlines
mar. 12/3112:09 pmORD - SJO
1 stop12h 45mSpirit Airlines
Deal found 11/14$316
This eDestinos deal was found by Cheapflights users on 11/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/243:32 pmSJO - ORD
1 stop9h 30mVolaris
lun. 12/302:42 amORD - SJO
1 stop20h 30mVolaris
Deal found 11/12$325
This Expedia deal was found by Cheapflights users on 11/14. 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.
mar. 12/243:32 pmSJO - ORD
1 stop9h 30mMultiple Airlines
mié. 1/15:00 amORD - SJO
1 stop7h 24mMultiple Airlines
Deal found 11/14$326
This Copa Airlines deal was found by Cheapflights users on 11/14. 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.
jue. 11/142:27 pmSJO - ORD
1 stop8h 54mCopa Airlines
vie. 11/151:54 pmORD - SJO
1 stop18h 14mCopa Airlines
Deal found 11/14$351
This Priceline deal was found by Cheapflights users on 11/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/162:15 amSJO - ORD
1 stop10h 00mAvianca
mar. 11/191:35 pmORD - SJO
1 stop19h 45mAvianca
Deal found 11/13$461
This Kiwi.com deal was found by Cheapflights users on 11/14. 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.
mar. 12/245:20 pmSJO - MDW
2 stops15h 01mMultiple Airlines
mar. 12/316:49 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Deal found 11/14$478
This Southwest deal was found by Cheapflights users on 11/13. 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.
sáb. 11/232:40 pmSJO - MDW
1 stop8h 30mSouthwest
sáb. 11/309:30 amMDW - SJO
1 stop11h 10mSouthwest
Deal found 11/13$574
This Delta deal was found by Cheapflights users on 11/13. 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.
sáb. 12/77:00 amSJO - MDW
2 stops10h 01mDelta
jue. 2/271:05 pmMDW - SJO
1 stop9h 21mDelta
Deal found 11/13$628

Find flights from San José to Chicago within your budget

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 2,752,363 searches. Data last updated noviembre 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

lun. 12/23

1:49 am-2:36 pm

2 stops12h 47m

Chicago O'Hare Intl

mar. 12/31

12:09 pm-12:54 am

1 stop12h 45m

$316

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

mar. 12/24

3:32 pm-1:02 am

1 stop9h 30m

Chicago O'Hare Intl

lun. 12/30

2:42 am-11:12 pm

1 stop20h 30m

$325

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

mar. 12/24

3:32 pm-1:02 am

1 stop9h 30m

Chicago O'Hare Intl

mié. 1/1

5:00 am-12:24 pm

1 stop7h 24m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

dom. 1/12

1:57 am-10:45 pm

2 stops20h 48m

Chicago Midway

lun. 1/20

7:45 am-12:26 pm

1 stop28h 41m

$454

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mar. 3/4

9:55 am-6:50 pm

2 stops8h 55m

Chicago Midway

mar. 3/11

12:30 pm-7:40 pm

1 stop8h 10m

$543

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

sáb. 12/7

2:13 pm-10:06 pm

1 stop7h 53m

Chicago Midway

jue. 2/27

1:05 pm-10:26 pm

1 stop9h 21m

$628

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

dom. 4/13

9:40 am-8:49 pm

1 stop10h 09m

Chicago Midway

sáb. 4/19

9:44 pm-8:25 am

1 stop11h 41m

$1,053

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

mar. 4/29

1:41 pm-10:21 pm

3 stops31h 40m

$183

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

mar. 11/19

3:31 pm-1:02 am

1 stop9h 31m

$194

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mar. 11/19

12:26 pm-10:52 pm

2 stops34h 26m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 22 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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice 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, San José Province-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, San José Province-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José, San José Province-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José, San José Province-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, San José Province-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.

Travel insights for flights from San José to Chicago

Get recent, data-driven insights about flights from San José to Chicago including ideal travel times, pricing trends, and more.

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 November 8, 2024.

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 83 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, September is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $232). Flying from San José, San José Province to Chicago in June is currently the most expensive (average of $308). 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 noviembre 14, 2024.

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 33% 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 noviembre 14, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines and Southwest 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.
Southwest
8.1
Very good
5,045 reviews

Food

7.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Food

7.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Food

7.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,439 reviews
Southwest
8.1
Very good
5,045 reviews

Food

7.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,809 reviews
Southwest
8.1
Very good
5,045 reviews

Food

7.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Aeromexico
7.5
Good
2,018 reviews
Southwest
8.1
Very good
5,045 reviews

Food

7.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • 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 $278. Other airlines that can offer you cheap pricing are Volaris, from $325, and Southwest, from $543. Spirit Airlines is 34% 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 $159. Frontier flights start at $172 while deals on Avianca start at $242 one-way.

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

    On average you can expect to pay $1,044 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $215 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $278.

  • 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, September is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $232). Flying from San José, San José Province to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,752,363 searches. Data last updated noviembre 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$366FlexibilityNo cancel feeOn-time65%
AviancaCheapest$262Average$418FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$393Average$562FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$484Average$633FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$680FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$567Average$666FlexibilityNo cancel feeOn-time69%
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