$122+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
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.Cheap flight deals from San José to Chicago
Cheapest flights from San José to ChicagoExplore 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 January 29, 2026.
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 January 29, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 1/27. 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.
This OneTravel deal was found by Cheapflights users on 1/26. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This OneTravel deal was found by Cheapflights users on 1/27. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Avianca Connect deal was found by Cheapflights users on 1/28. 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 Avianca Connect is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Avianca Connect deal was found by Cheapflights users on 1/26. 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 Avianca Connect is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This OneTravel deal was found by Cheapflights users on 1/28. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 January 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (Cheapflightsfares) |
One-way from | $122 (FlightHub) |
Popular in | April |
Cheapest in | January |
Average price | $378 |
Good round-trip deal | $298 or less |
Good one-way deal | $160 or less |
Cheapflights Fare Finder
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
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 4/16
7:45 am-6:15 pm
1 stop9h 30m
Chicago O'Hare Intl
Mon 4/20
6:34 pm-3:05 pm
1 stop21h 31m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 4/13
7:45 am-8:25 am
1 stop23h 40m
Chicago O'Hare Intl
Sun 4/19
6:34 pm-3:05 pm
1 stop21h 31m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 2/14
1:31 pm-7:54 am
2 stops18h 23m
Chicago O'Hare Intl
Sat 2/21
8:59 am-11:40 am
2 stops26h 41m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 4/28
7:45 am-6:15 pm
1 stop9h 30m
Chicago O'Hare Intl
Mon 5/4
6:34 pm-3:05 pm
1 stop21h 31m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 2/26
2:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Thu 3/5
7:39 am-12:56 pm
Nonstop5h 17m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 3/1
6:08 pm-12:31 pm
1 stop18h 23m
Chicago O'Hare Intl
Thu 3/5
7:34 am-6:55 pm
1 stop11h 21m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 3/1
6:08 pm-12:31 pm
1 stop18h 23m
Chicago O'Hare Intl
Sun 3/8
3:22 pm-7:05 am
1 stop16h 43m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 3/1
5:51 pm-12:31 pm
1 stop18h 40m
Chicago O'Hare Intl
Wed 3/4
7:34 am-4:38 pm
1 stop9h 04m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 4/23
7:45 am-6:15 pm
1 stop9h 30m
Chicago O'Hare Intl
Sun 4/26
6:34 pm-3:05 pm
1 stop21h 31m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 2/13
7:00 am-10:31 pm
1 stop15h 31m
Chicago Midway
Mon 3/2
12:45 pm-10:02 pm
1 stop9h 17m
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 January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
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?
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 January 23, 2026.
To ensure you get the cheapest price possible for a flight from San José to Chicago, you should look to book at least 30 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, October is the cheapest month in which you can book a flight from San José to Chicago (average of $195). Flying from San José to Chicago in March is currently the most expensive (average of $337). 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 January 29, 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.
Weekly flight availability from San José to Chicago
Explore weekly flight availability from San José to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 29, 2026.
The most flights from SJO to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
What’s the top layover airport for flights from San José to Chicago?
Share of 1-stop round-trip flights from San José 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 to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from San José to Chicago?
Average round-trip fare for 1-stop flights from San José 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 to Chicago?
Shortest average travel time for 1-stop one-way flights from San José 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 to Chicago?
Average layover duration for 1-stop one-way flights from San José 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.
How often are flights from San José to Chicago delayed?
About 13% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 189 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?
Monday 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.
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 January 29, 2026.
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.
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBrowse 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.
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 January 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$348 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$249 | Average$484 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$311 | Average$448 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$465 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$400 | Average$504 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |