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Cheap flights from Chicago to San José from $79

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 10/18. 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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Find the cheapest flights from Chicago to San José

Cheap round-trip flights

Spirit Airlines Logo
5:05 am - 11:14 amORD-SJO
7h 09m1 stop
Spirit Airlines Logo
11:37 am - 10:50 amSJO-ORD
22h 13m2 stops
$253Spirit Airlines
Find Deal
mar., sep. 30 - sáb., oct. 4
Spirit Airlines Logo
6:58 pm - 11:30 amORD-SJO
17h 32m2 stops
Spirit Airlines Logo
11:37 am - 10:50 amSJO-ORD
22h 13m2 stops
$254Spirit Airlines
Find Deal
sáb., oct. 11 - sáb., oct. 18
Spirit Airlines Logo
7:43 pm - 11:30 amORD-SJO
16h 47m1 stop
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
$255Spirit Airlines
Find Deal
vie., oct. 10 - mar., oct. 14
Logo
5:05 am - 12:14 pmORD-SJO
7h 09m1 stop
Logo
2:20 am - 3:10 pmSJO-ORD
12h 50m1 stop
$273
Find Deal
sáb., nov. 8 - vie., nov. 14
Logo
5:05 am - 12:14 pmORD-SJO
7h 09m1 stop
Logo
2:20 am - 3:10 pmSJO-ORD
12h 50m1 stop
$282
Find Deal
vie., nov. 7 - vie., nov. 7
Avianca Logo
9:03 am - 6:55 pmORD-SJO
10h 52m2 stops
Avianca Logo
5:00 am - 5:08 pmSJO-ORD
11h 08m2 stops
$286Avianca
Find Deal
sáb., mar. 14 - sáb., mar. 21
Southwest Logo
6:25 am - 6:55 pmMDW-SJO
13h 30m1 stop
Southwest Logo
12:20 pm - 9:00 pmSJO-MDW
7h 40m1 stop
$340Southwest
Find Deal
mar., sep. 30 - sáb., oct. 4
Delta Logo
6:00 am - 10:07 pmMDW-SJO
16h 07m1 stop
Delta Logo
7:00 am - 11:32 pmSJO-MDW
16h 32m1 stop
$344Delta
Find Deal
mié., nov. 19 - lun., nov. 24
Southwest Logo
8:45 pm - 11:20 amMDW-SJO
15h 35m2 stops
Southwest Logo
1:40 pm - 11:10 pmSJO-MDW
8h 30m1 stop
$345Southwest
Find Deal
vie., oct. 3 - dom., oct. 5
Delta Logo
6:00 am - 10:07 pmMDW-SJO
16h 07m1 stop
Delta Logo
7:00 am - 6:08 pmSJO-MDW
11h 08m2 stops
$348Delta
Find Deal
lun., nov. 17 - lun., nov. 24

Spirit Airlines flights from Chicago to San José, San José Province

Our best Spirit Airlines deals on Chicago to San José, San José Province flight tickets
Spirit Airlines
Sep 30
ORD5:05 amChicago O'Hare Intl
7h 09m
1 stop
SJO11:14 amSan José Juan Santamaria Intl
Oct 4
SJO11:37 amSan José Juan Santamaria Intl
22h 13m
2 stops
ORD10:50 amChicago O'Hare Intl
$253
Find similar
Spirit Airlines
Oct 11
ORD6:58 pmChicago O'Hare Intl
17h 32m
2 stops
SJO11:30 amSan José Juan Santamaria Intl
Oct 18
SJO11:37 amSan José Juan Santamaria Intl
22h 13m
2 stops
ORD10:50 amChicago O'Hare Intl
$254
Find similar
Spirit Airlines
Oct 10
ORD7:43 pmChicago O'Hare Intl
16h 47m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
Oct 14
SJO12:35 pmSan José Juan Santamaria Intl
10h 10m
1 stop
ORD11:45 pmChicago O'Hare Intl
$255
Find similar

Southwest flights from Chicago to San José, San José Province

Our best Southwest deals on Chicago to San José, San José Province flight tickets
Southwest
Sep 30
MDW6:25 amChicago Midway
13h 30m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Oct 4
SJO12:20 pmSan José Juan Santamaria Intl
7h 40m
1 stop
MDW9:00 pmChicago Midway
$340
Find similar
Southwest
Oct 3
MDW8:45 pmChicago Midway
15h 35m
2 stops
SJO11:20 amSan José Juan Santamaria Intl
Oct 5
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
$345
Find similar
Southwest
Nov 6
MDW5:50 amChicago Midway
7h 25m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
Nov 11
SJO9:00 amSan José Juan Santamaria Intl
13h 35m
2 stops
MDW10:35 pmChicago Midway
$349
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to San José, San José Province 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 septiembre 15, 2025.
Use the filters below to find and compare flights from Chicago to San José, San José Province that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mar. 9/30

5:05 am-11:14 am

1 stop7h 09m

San José Juan Santamaria Intl

sáb. 10/4

11:37 am-10:50 am

2 stops22h 13m

$253

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 10/11

6:58 pm-11:30 am

2 stops17h 32m

San José Juan Santamaria Intl

sáb. 10/18

11:37 am-10:50 am

2 stops22h 13m

$254

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

vie. 10/10

7:43 pm-11:30 am

1 stop16h 47m

San José Juan Santamaria Intl

mar. 10/14

12:35 pm-11:45 pm

1 stop10h 10m

$255

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 11/8

5:05 am-12:14 pm

1 stop7h 09m

San José Juan Santamaria Intl

vie. 11/14

2:20 am-3:10 pm

1 stop12h 50m

$273

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

vie. 11/7

5:05 am-12:14 pm

1 stop7h 09m

San José Juan Santamaria Intl

vie. 11/7

2:20 am-3:10 pm

1 stop12h 50m

$282

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 3/14

9:03 am-6:55 pm

2 stops10h 52m

San José Juan Santamaria Intl

sáb. 3/21

5:00 am-5:08 pm

2 stops11h 08m

$286

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 9/30

6:25 am-6:55 pm

1 stop13h 30m

San José Juan Santamaria Intl

sáb. 10/4

12:20 pm-9:00 pm

1 stop7h 40m

$340

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mié. 11/19

6:00 am-10:07 pm

1 stop16h 07m

San José Juan Santamaria Intl

lun. 11/24

7:00 am-11:32 pm

1 stop16h 32m

$344

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

vie. 10/3

8:45 pm-11:20 am

2 stops15h 35m

San José Juan Santamaria Intl

dom. 10/5

1:40 pm-11:10 pm

1 stop8h 30m

$345

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

lun. 11/17

6:00 am-10:07 pm

1 stop16h 07m

San José Juan Santamaria Intl

lun. 11/24

7:00 am-6:08 pm

2 stops11h 08m

$348

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, San José Province

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 typical price of a round-trip flight between Chicago and San José, San José Province?

What is the cheapest month to fly to San José, San José Province?

The month of September is, on average, the cheapest month to fly to San José, San José Province from Chicago, with most prices found around $340. If you’re not able to fly to San José, San José Province in September, then July is your next best option. Flight prices from Chicago to San José, San José Province during July average around $455.

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

The cheapest day to depart from Chicago to San José, San José Province is on a Tuesday when prices can be found for as low as $541. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $815.

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

In the evening is the cheapest time of day to fly from Chicago to San José, San José Province when you can find flight prices for as low as $453. Flying to San José, San José Province in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to San José, San José Province, so prices are often more expensive at around $763 per ticket.

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, San José Province?

You are more likely to see cheaper flights to San José, San José Province from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San José, San José Province for around $571 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José, San José Province from Chicago for as low as $445 on momondo.

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

There are 2 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.

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

As of September 2025, prices for Chicago to San José, San José Province flights are approximately 3% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to San José, San José Province

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

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

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

Best Price Found

$217

Fastest flight time

5h 00m

Direct flights

Every day

Airports in San José, San José Province

1 airport
The best one-way flight to San José, San José Province from Chicago in the past 72 hours is $217. The best round-trip flight deal from Chicago to San José, San José Province found on momondo in the last 72 hours is $562.
The fastest flight from Chicago to San José, San José Province takes 5h 00m
Direct flights go from Chicago to San José, San José Province every day.
There is 1 airport near San José, San José Province: 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 6h 55m 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, San José Province?

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

Best airlines flying from Chicago to San José, San José Province

Compare and see reviews for airlines that fly from Chicago to San José, San José Province with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $263Free CancellationRating
6.3
8,015 reviews
Search Spirit Airlines flights
AviancaPriceFrom $307Free CancellationRating
6.7
2,435 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,531 reviews
Search Copa Airlines flights
FrontierPriceFrom $345Free CancellationRating
5.8
3,172 reviews
Search Frontier flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
JetBluePriceFrom $432Free CancellationRating
7.2
2,912 reviews
Search JetBlue flights
DeltaPriceFrom $442Free CancellationRating
7.9
7,954 reviews
Search Delta flights
American AirlinesPriceFrom $442Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $467Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Alajuela
Monteverde
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.

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