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Cheap flights from Chicago to San José from $123

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San José departing on 2/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:16 pm - 12:22 pm
ORD
-
SJO
16h 06m
1 stop
Multiple Airlines Logo
12:31 pm - 10:56 am
SJO
-
ORD
21h 25m
2 stops
$342Multiple Airlines
sáb., feb. 28 - dom., mar. 8
Spirit Airlines Logo
8:41 pm - 10:42 am
ORD
-
SJO
15h 01m
2 stops
Spirit Airlines Logo
12:31 pm - 11:41 pm
SJO
-
ORD
10h 10m
1 stop
$343Spirit Airlines
mar., abr. 7 - jue., abr. 16
Spirit Airlines Logo
8:16 pm - 11:40 am
ORD
-
SJO
15h 24m
2 stops
Spirit Airlines Logo
1:31 pm - 7:54 am
SJO
-
ORD
18h 23m
2 stops
$344Spirit Airlines
vie., feb. 27 - jue., mar. 5
Multiple Airlines Logo
2:56 pm - 10:40 am
MDW
-
SJO
19h 44m
1 stop
Multiple Airlines Logo
11:38 am - 9:45 pm
SJO
-
MDW
9h 07m
1 stop
$344Multiple Airlines
sáb., mar. 7 - sáb., mar. 14
Spirit Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m
1 stop
Spirit Airlines Logo
1:31 pm - 9:13 pm
SJO
-
ORD
7h 42m
1 stop
$345Spirit Airlines
dom., feb. 22 - sáb., feb. 28
Spirit Airlines Logo
8:41 pm - 11:19 am
ORD
-
SJO
15h 38m
1 stop
Spirit Airlines Logo
12:24 pm - 11:17 pm
SJO
-
ORD
9h 53m
1 stop
$346Spirit Airlines
mar., mar. 24 - jue., abr. 2
Spirit Airlines Logo
8:41 pm - 11:19 am
ORD
-
SJO
15h 38m
1 stop
Spirit Airlines Logo
12:24 pm - 11:17 pm
SJO
-
ORD
9h 53m
1 stop
$347Spirit Airlines
lun., mar. 30 - lun., abr. 13
Multiple Airlines Logo
8:05 am - 11:40 am
ORD
-
SJO
27h 35m
2 stops
Multiple Airlines Logo
1:31 pm - 11:03 pm
SJO
-
ORD
9h 32m
1 stop
$348Multiple Airlines
sáb., feb. 14 - vie., feb. 20
Multiple Airlines Logo
8:41 pm - 10:42 am
ORD
-
SJO
15h 01m
2 stops
Multiple Airlines Logo
12:24 pm - 10:50 pm
SJO
-
ORD
9h 26m
1 stop
$349Multiple Airlines
lun., mar. 30 - jue., abr. 9
Southwest Logo
5:00 am - 12:50 pm
MDW
-
SJO
7h 50m
1 stop
Southwest Logo
9:45 am - 8:15 pm
SJO
-
MDW
10h 30m
1 stop
$355Southwest
mié., feb. 25 - vie., mar. 6

Southwest flights from Chicago to San José

Our best Southwest deals on Chicago to San José flight tickets
Southwest
Feb 25
MDW5:00 amChicago Midway
7h 50m
1 stop
SJO12:50 pmSan José Juan Santamaria Intl
Mar 6
SJO9:45 amSan José Juan Santamaria Intl
10h 30m
1 stop
MDW8:15 pmChicago Midway
$355
Southwest
Mar 4
MDW5:00 amChicago Midway
7h 50m
1 stop
SJO12:50 pmSan José Juan Santamaria Intl
Mar 10
SJO1:55 pmSan José Juan Santamaria Intl
9h 00m
1 stop
MDW11:55 pmChicago Midway
$378
Southwest
Apr 8
MDW12:15 pmChicago Midway
7h 45m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
Apr 15
SJO9:00 amSan José Juan Santamaria Intl
9h 45m
1 stop
MDW7:45 pmChicago Midway
$383

Delta flights from Chicago to San José

Our best Delta deals on Chicago to San José flight tickets
Delta
Feb 2
ORD5:30 amChicago O'Hare Intl
16h 45m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Feb 7
SJO3:54 pmSan José Juan Santamaria Intl
8h 02m
1 stop
ORD11:56 pmChicago O'Hare Intl
$371
Delta
Feb 2
ORD5:30 amChicago O'Hare Intl
16h 45m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Feb 10
SJO7:00 amSan José Juan Santamaria Intl
14h 05m
2 stops
ORD9:05 pmChicago O'Hare Intl
$376
Delta
Feb 2
ORD11:15 amChicago O'Hare Intl
11h 00m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Feb 9
SJO7:00 amSan José Juan Santamaria Intl
14h 00m
1 stop
ORD9:00 pmChicago O'Hare Intl
$385

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to San José 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, momondo users made 832,500 searches. Data last updated enero 28, 2026.
Use the filters below to find and compare flights from Chicago to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 2/28

8:16 pm-12:22 pm

1 stop16h 06m

San José Juan Santamaria Intl

dom. 3/8

12:31 pm-10:56 am

2 stops21h 25m

$342

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mar. 4/7

8:41 pm-10:42 am

2 stops15h 01m

San José Juan Santamaria Intl

jue. 4/16

12:31 pm-11:41 pm

1 stop10h 10m

$343

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

vie. 2/27

8:16 pm-11:40 am

2 stops15h 24m

San José Juan Santamaria Intl

jue. 3/5

1:31 pm-7:54 am

2 stops18h 23m

$344

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

sáb. 3/7

2:56 pm-10:40 am

1 stop19h 44m

San José Juan Santamaria Intl

sáb. 3/14

11:38 am-9:45 pm

1 stop9h 07m

$344

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

dom. 2/22

5:15 am-12:22 pm

1 stop7h 07m

San José Juan Santamaria Intl

sáb. 2/28

1:31 pm-9:13 pm

1 stop7h 42m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mar. 3/24

8:41 pm-11:19 am

1 stop15h 38m

San José Juan Santamaria Intl

jue. 4/2

12:24 pm-11:17 pm

1 stop9h 53m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

lun. 3/30

8:41 pm-11:19 am

1 stop15h 38m

San José Juan Santamaria Intl

lun. 4/13

12:24 pm-11:17 pm

1 stop9h 53m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 2/14

8:05 am-11:40 am

2 stops27h 35m

San José Juan Santamaria Intl

vie. 2/20

1:31 pm-11:03 pm

1 stop9h 32m

$348

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

lun. 3/30

8:41 pm-10:42 am

2 stops15h 01m

San José Juan Santamaria Intl

jue. 4/9

12:24 pm-10:50 pm

1 stop9h 26m

$349

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mié. 2/25

5:00 am-12:50 pm

1 stop7h 50m

San José Juan Santamaria Intl

vie. 3/6

9:45 am-8:15 pm

1 stop10h 30m

$355

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José from

How to get the cheapest flight ticket from Chicago to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San José?

In general, September is the cheapest month to fly from Chicago to San José. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $314. If you don’t want to visit San José in September, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of $381.

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $519. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to San José on a Saturday will generally be more expensive and average around $712. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $503. Flights at noon are often more expensive with an average ticket price of $664.

What is the cheapest Chicago to San José Juan Santamaria Intl flight route?

Fly from Chicago O'Hare Intl to San José Juan Santamaria Intl for the best Chicago - San José Juan Santamaria Intl flight prices

How far in advance should I book a flight to San José?

You are more likely to see cheaper flights to San José from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San José for around $523 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José from Chicago for as low as $462 on momondo.

What cabin class options are available on Chicago to San José Juan Santamaria Intl flights?

There are 3 cabin classes available to choose from on Chicago to San José Juan Santamaria Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to San José flights?

You could potentially save up to 17% on your flight if you consider stops on a Chicago to San José flight.

How have Chicago to San José flight prices changed over time?

As of January 2026, prices for Chicago to San José flights are approximately 20% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to San José (CHI to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San José

Best Price Found

$280

Fastest flight time

5h 02m

Direct flights

Every day

Airports in San José

1 airport
The best one-way flight to San José from Chicago in the past 72 hours is $280. The best round-trip flight deal from Chicago to San José found on momondo in the last 72 hours is $419.
The fastest flight from Chicago to San José takes 5h 02m
Direct flights go from Chicago to San José every day.
There is 1 airport in San José. From Chicago there are direct flights to San José Juan Santamaria Intl (SJO).
Search flight deals

  • How far is Chicago to San José Juan Santamaria Intl by plane?

    San José Juan Santamaria Intl is 2215.9 mi away from Chicago. Typically, this will take 5h 02m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago to San José Juan Santamaria Intl Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago to San José Juan Santamaria Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents required for your trip to San José Juan Santamaria Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San José Juan Santamaria Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to San José?

  • What is the most popular airline from Chicago to San José?

Best airlines flying from Chicago to San José

Compare and see reviews for airlines that fly from Chicago to San José with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $206Free CancellationRating
7.9
8,120 reviews
Search Delta flights
AviancaPriceFrom $250Free CancellationRating
6.6
2,487 reviews
Search Avianca flights
Spirit AirlinesPriceFrom $255Free CancellationRating
6.3
8,385 reviews
Search Spirit Airlines flights
Copa AirlinesPriceFrom $256Free CancellationRating
7.5
1,560 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $340Free CancellationRating
7.2
11,199 reviews
Search American Airlines flights
FrontierPriceFrom $345Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,268 reviews
Search Southwest flights
United AirlinesPriceFrom $397Free CancellationRating
7.4
9,206 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to San José

    United Airlines operates around 5 flights from Chicago to San José every week. The average price of these flights found in the last 72 hours has been $610, but momondo users have found United Airlines deals from Chicago to San José from as low as $397 round-trip. United Airlines has been scored 7.4/10 in 9,206 reviews.

  • American Airlines Flights From Chicago to San José

    The best American Airlines deal for Chicago to San José flight tickets found on momondo in the last 72 hours was $340, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $565 round-trip. American Airlines operates 7 flights out of Chicago into San José in an average week, so prices vary by time and availability. 11,199 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Dominical
San Gerardo de Dota
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San José. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to San José from Chicago with this policy.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Price alerts on flights to San José from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your San José trip

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vie. 2/27
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