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Cheap flights from Chicago to San José from $84

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 1/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
Spirit Airlines Logo
3:22 pm - 12:22 pm
ORD
-
SJO
21h 00m2 stops
Spirit Airlines Logo
1:30 pm - 2:17 pm
SJO
-
ORD
24h 47m2 stops
$336Spirit Airlines
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
3:40 pm - 11:40 am
ORD
-
SJO
20h 00m2 stops
Multiple Airlines Logo
4:15 pm - 11:26 pm
SJO
-
ORD
31h 11m2 stops
$337Multiple Airlines
Thu, Feb 19 - Sat, Feb 28
Multiple Airlines Logo
2:26 pm - 1:48 pm
ORD
-
SJO
23h 22m1 stop
Multiple Airlines Logo
7:45 am - 6:16 pm
SJO
-
ORD
10h 31m1 stop
$338Multiple Airlines
Tue, Jan 6 - Sun, Jan 18
Spirit Airlines Logo
5:32 pm - 11:37 am
ORD
-
SJO
18h 05m2 stops
Spirit Airlines Logo
1:30 pm - 11:46 pm
SJO
-
ORD
10h 16m1 stop
$339Spirit Airlines
Wed, Jan 21 - Sat, Jan 24
Spirit Airlines Logo
8:43 pm - 12:22 pm
ORD
-
SJO
15h 39m1 stop
Spirit Airlines Logo
1:30 pm - 11:46 pm
SJO
-
ORD
10h 16m1 stop
$340Spirit Airlines
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
8:43 pm - 12:22 pm
ORD
-
SJO
15h 39m1 stop
Multiple Airlines Logo
7:45 am - 6:16 pm
SJO
-
ORD
10h 31m1 stop
$341Multiple Airlines
Fri, Jan 9 - Sun, Jan 18
American Airlines Logo
5:30 pm - 10:30 pm
ORD
-
SJO
5h 00mnonstop
American Airlines Logo
7:09 am - 12:38 pm
SJO
-
ORD
5h 29mnonstop
$343American Airlines
Tue, Feb 3 - Thu, Feb 5
Delta Logo
12:46 pm - 10:02 pm
MDW
-
SJO
9h 16m1 stop
Delta Logo
7:00 am - 10:42 pm
SJO
-
MDW
15h 42m1 stop
$358Delta
Sun, Feb 22 - Wed, Feb 25
Southwest Logo
6:15 am - 7:30 pm
MDW
-
SJO
13h 15m1 stop
Southwest Logo
1:50 pm - 10:15 pm
SJO
-
MDW
8h 25m1 stop
$359Southwest
Mon, Feb 2 - Thu, Feb 12
Delta Logo
9:33 am - 10:15 pm
MDW
-
SJO
12h 42m2 stops
Delta Logo
7:00 am - 5:45 pm
SJO
-
MDW
10h 45m1 stop
$362Delta
Sun, Feb 8 - Wed, Feb 18

Spirit Airlines flights from Chicago to San José

Our best Spirit Airlines deals on Chicago to San José flight tickets
Spirit Airlines
Jan 31
ORD3:22 pmChicago O'Hare Intl
21h 00m
2 stops
SJO12:22 pmSan José Juan Santamaria Intl
Feb 7
SJO1:30 pmSan José Juan Santamaria Intl
24h 47m
2 stops
ORD2:17 pmChicago O'Hare Intl
$336
Find similar
Spirit Airlines
Jan 21
ORD5:32 pmChicago O'Hare Intl
18h 05m
2 stops
SJO11:37 amSan José Juan Santamaria Intl
Jan 24
SJO1:30 pmSan José Juan Santamaria Intl
10h 16m
1 stop
ORD11:46 pmChicago O'Hare Intl
$339
Find similar
Spirit Airlines
Feb 10
ORD12:44 pmChicago O'Hare Intl
22h 53m
1 stop
SJO11:37 amSan José Juan Santamaria Intl
Feb 17
SJO1:31 pmSan José Juan Santamaria Intl
21h 56m
1 stop
ORD11:27 amChicago O'Hare Intl
$342
Find similar

Copa Airlines flights from Chicago to San José

Our best Copa Airlines deals on Chicago to San José flight tickets
Copa Airlines
Feb 3
ORD2:22 pmChicago O'Hare Intl
16h 44m
1 stop
SJO7:06 amSan José Juan Santamaria Intl
Feb 11
SJO11:01 amSan José Juan Santamaria Intl
13h 03m
1 stop
ORD12:04 amChicago O'Hare Intl
$346
Find similar
Copa Airlines
Dec 23
ORD2:07 pmChicago O'Hare Intl
17h 03m
1 stop
SJO7:10 amSan José Juan Santamaria Intl
Dec 29
SJO11:00 amSan José Juan Santamaria Intl
13h 05m
1 stop
ORD12:05 amChicago O'Hare Intl
$405
Find similar
Copa Airlines
Dec 25
ORD2:07 pmChicago O'Hare Intl
26h 42m
3 stops
SJO4:49 pmSan José Juan Santamaria Intl
Dec 28
SJO5:53 pmSan José Juan Santamaria Intl
18h 59m
1 stop
ORD12:52 pmChicago O'Hare Intl
$536
Find similar

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 December 15, 2025.
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

Sat 1/31

3:22 pm-12:22 pm

2 stops21h 00m

San José Juan Santamaria Intl

Sat 2/7

1:30 pm-2:17 pm

2 stops24h 47m

$336

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/19

3:40 pm-11:40 am

2 stops20h 00m

San José Juan Santamaria Intl

Sat 2/28

4:15 pm-11:26 pm

2 stops31h 11m

$337

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/6

2:26 pm-1:48 pm

1 stop23h 22m

San José Juan Santamaria Intl

Sun 1/18

7:45 am-6:16 pm

1 stop10h 31m

$338

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 1/21

5:32 pm-11:37 am

2 stops18h 05m

San José Juan Santamaria Intl

Sat 1/24

1:30 pm-11:46 pm

1 stop10h 16m

$339

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/16

8:43 pm-12:22 pm

1 stop15h 39m

San José Juan Santamaria Intl

Fri 1/23

1:30 pm-11:46 pm

1 stop10h 16m

$340

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/9

8:43 pm-12:22 pm

1 stop15h 39m

San José Juan Santamaria Intl

Sun 1/18

7:45 am-6:16 pm

1 stop10h 31m

$341

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/3

5:30 pm-10:30 pm

Nonstop5h 00m

San José Juan Santamaria Intl

Thu 2/5

7:09 am-12:38 pm

Nonstop5h 29m

$343

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/22

12:46 pm-10:02 pm

1 stop9h 16m

San José Juan Santamaria Intl

Wed 2/25

7:00 am-10:42 pm

1 stop15h 42m

$358

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/2

6:15 am-7:30 pm

1 stop13h 15m

San José Juan Santamaria Intl

Thu 2/12

1:50 pm-10:15 pm

1 stop8h 25m

$359

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/8

9:33 am-10:15 pm

2 stops12h 42m

San José Juan Santamaria Intl

Wed 2/18

7:00 am-5:45 pm

1 stop10h 45m

$362

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 $315. 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 $379.

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 $542. 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 $733. 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 evening. Our users have found flights to San José in the evening for as low as $453. Flights in the morning are often more expensive with an average ticket price of $674.

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 $534 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 $429 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?

No. A direct flight is the cheapest option for a flight between Chicago to San José.

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

As of December 2025, prices for Chicago to San José flights are approximately 95% more expensive 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

$294

Fastest flight time

5h 00m

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 $294. The best round-trip flight deal from Chicago to San José found on momondo in the last 72 hours is $466.
The fastest flight from Chicago to San José takes 5h 00m
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 00m 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 $221Free CancellationRating
7.9
8,010 reviews
Search Delta flights
Spirit AirlinesPriceFrom $258Free CancellationRating
6.3
8,186 reviews
Search Spirit Airlines flights
AviancaPriceFrom $307Free CancellationRating
6.6
2,485 reviews
Search Avianca flights
Copa AirlinesPriceFrom $309Free CancellationRating
7.6
1,556 reviews
Search Copa Airlines flights
FrontierPriceFrom $345Free CancellationRating
5.8
3,082 reviews
Search Frontier flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
SouthwestPriceFrom $394Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
United AirlinesPriceFrom $427Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights

  • American Airlines Flights From Chicago to San José

    American Airlines operates around 6 flights from Chicago to San José every week. The average price of these flights found in the last 72 hours has been $599, but momondo users have found American Airlines deals from Chicago to San José from as low as $348 round-trip. American Airlines has been scored 7.2/10 in 11,048 reviews.

  • Avianca Flights From Chicago to San José

    The best Avianca deal for Chicago to San José flight tickets found on momondo in the last 72 hours was $307, round-trip. It should be noted that an average Avianca flight deal for this route in this time was higher, at $456 round-trip. Avianca operates 2 flights out of Chicago into San José in an average week, so prices vary by time and availability. 2,484 Avianca reviews by users on momondo have scored the airline at 6.6/10.

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
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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