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Cheap flights from Chicago O'Hare Intl Airport to San José from $96

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 O'Hare Intl Airport to San José departing on 1/21. 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 O'Hare Intl Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
$257Spirit Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
$258Spirit Airlines
Find Deal
Sun, Nov 9 - Fri, Nov 14
Spirit Airlines Logo
5:00 am - 12:15 pmORD-SJO
7h 15m1 stop
Spirit Airlines Logo
1:20 pm - 11:13 pmSJO-ORD
9h 53m1 stop
$259Spirit Airlines
Find Deal
Tue, Nov 25 - Thu, Nov 27
Multiple Airlines Logo
10:52 am - 12:25 pmORD-SJO
25h 33m1 stop
Multiple Airlines Logo
1:30 pm - 4:25 pmSJO-ORD
26h 55m1 stop
$260Multiple Airlines
Find Deal
Thu, Nov 13 - Wed, Nov 19
Spirit Airlines Logo
8:28 am - 11:39 amORD-SJO
27h 11m2 stops
Spirit Airlines Logo
1:30 pm - 9:47 amSJO-ORD
20h 17m1 stop
$261Spirit Airlines
Find Deal
Tue, Nov 11 - Mon, Nov 17
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
Spirit Airlines Logo
1:20 pm - 11:13 pmSJO-ORD
9h 53m1 stop
$262Spirit Airlines
Find Deal
Wed, Nov 12 - Thu, Nov 20
Multiple Airlines Logo
8:41 am - 12:21 amORD-SJO
15h 40m1 stop
Multiple Airlines Logo
5:45 am - 1:15 pmSJO-ORD
7h 30m1 stop
$263Multiple Airlines
Find Deal
Wed, Jan 21 - Fri, Jan 30
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
$264Spirit Airlines
Find Deal
Mon, Nov 10 - Fri, Nov 14
Multiple Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
Multiple Airlines Logo
2:20 am - 3:10 pmSJO-ORD
12h 50m1 stop
$265Multiple Airlines
Find Deal
Tue, Nov 18 - Fri, Nov 21
Avianca Logo
2:35 pm - 9:50 pmORD-SJO
7h 15mnonstop
Avianca Logo
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$301Avianca
Find Deal
Wed, Jan 21 - Wed, Jan 28

Spirit Airlines flights from Chicago O'Hare Intl Airport to San José

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to San José flight tickets
Spirit Airlines
Nov 12
ORD5:10 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
Nov 18
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
$257
Find similar
Spirit Airlines
Nov 9
ORD5:10 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
Nov 14
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
$258
Find similar
Spirit Airlines
Nov 25
ORD5:00 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:15 pmSan José Juan Santamaria Intl
Nov 27
SJO1:20 pmSan José Juan Santamaria Intl
9h 53m
1 stop
ORD11:13 pmChicago O'Hare Intl
$259
Find similar

American Airlines flights from Chicago O'Hare Intl Airport to San José

Our best American Airlines deals on Chicago O'Hare Intl Airport to San José flight tickets
American Airlines
Nov 6
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
Nov 15
SJO6:00 amSan José Juan Santamaria Intl
5h 29m
ORD11:29 amChicago O'Hare Intl
$329
Find similar
American Airlines
Nov 6
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
Nov 9
SJO6:00 amSan José Juan Santamaria Intl
5h 29m
ORD11:29 amChicago O'Hare Intl
$334
Find similar
American Airlines
Nov 3
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
Nov 10
SJO6:00 amSan José Juan Santamaria Intl
5h 29m
ORD11:29 amChicago O'Hare Intl
$337
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 October 23, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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

Wed 11/12

5:10 am-12:25 pm

1 stop7h 15m

San José Juan Santamaria Intl

Tue 11/18

1:30 pm-12:27 am

1 stop10h 57m

$257

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 11/9

5:10 am-12:25 pm

1 stop7h 15m

San José Juan Santamaria Intl

Fri 11/14

1:30 pm-12:27 am

1 stop10h 57m

$258

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/25

5:00 am-12:15 pm

1 stop7h 15m

San José Juan Santamaria Intl

Thu 11/27

1:20 pm-11:13 pm

1 stop9h 53m

$259

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 11/13

10:52 am-12:25 pm

1 stop25h 33m

San José Juan Santamaria Intl

Wed 11/19

1:30 pm-4:25 pm

1 stop26h 55m

$260

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/11

8:28 am-11:39 am

2 stops27h 11m

San José Juan Santamaria Intl

Mon 11/17

1:30 pm-9:47 am

1 stop20h 17m

$261

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 11/12

5:10 am-12:25 pm

1 stop7h 15m

San José Juan Santamaria Intl

Thu 11/20

1:20 pm-11:13 pm

1 stop9h 53m

$262

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 1/21

8:41 am-12:21 am

1 stop15h 40m

San José Juan Santamaria Intl

Fri 1/30

5:45 am-1:15 pm

1 stop7h 30m

$263

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 11/10

5:10 am-12:25 pm

1 stop7h 15m

San José Juan Santamaria Intl

Fri 11/14

1:30 pm-12:27 am

1 stop10h 57m

$264

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/18

5:10 am-12:25 pm

1 stop7h 15m

San José Juan Santamaria Intl

Fri 11/21

2:20 am-3:10 pm

1 stop12h 50m

$265

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 1/21

2:35 pm-9:50 pm

Nonstop7h 15m

San José Juan Santamaria Intl

Wed 1/28

5:45 am-1:15 pm

Nonstop7h 30m

$301

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 O'Hare Intl Airport 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, October is the cheapest month to fly from Chicago O'Hare Intl Airport to San José. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $364. If you don’t want to visit San José in October, then you should wait until September to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $445.

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 O'Hare Intl Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $546. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago O'Hare Intl Airport to San José on a Saturday will generally be more expensive and average around $784. 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 O'Hare Intl Airport 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 $749.

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

Fly from Chicago O'Hare Intl to San José Juan Santamaria Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San José for around $555 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 O'Hare Intl Airport for as low as $438 on momondo.

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

There are 2 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to San José flight prices changed over time?

As of October 2025, prices for Chicago O'Hare Intl Airport to San José flights are approximately 4% more expensive when compared to flights at the same time last year.

When to book flights from Chicago O'Hare Intl Airport to San José

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

Cheap Chicago O'Hare Intl Airport to San José (ORD to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to San José

Best Price Found

$214

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 O'Hare Intl Airport in the past 72 hours is $214. The best round-trip flight deal from Chicago O'Hare Intl Airport to San José found on momondo in the last 72 hours is $455.
The fastest flight from Chicago O'Hare Intl Airport to San José takes 5h 00m
Direct flights go from Chicago O'Hare Intl Airport to San José every day.
There is 1 airport near San José: San José Juan Santamaria Intl (SJO)
Search flight deals

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

    There are 2224.7 mi between Chicago O'Hare Intl and San José Juan Santamaria Intl. Flights usually cover this in 7h 09m, depending on flying conditions and air traffic around both airports.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to San José?

  • What is the most popular airline from Chicago O'Hare Intl Airport to San José?

Best airlines flying from Chicago O'Hare Intl Airport to San José

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $261Free CancellationRating
6.3
8,103 reviews
Search Spirit Airlines flights
DeltaPriceFrom $290Free CancellationRating
7.9
7,982 reviews
Search Delta flights
AviancaPriceFrom $307Free CancellationRating
6.6
2,460 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,560 reviews
Search Copa Airlines flights
FrontierPriceFrom $345Free CancellationRating
5.8
3,128 reviews
Search Frontier flights
American AirlinesPriceFrom $385Free CancellationRating
7.2
11,033 reviews
Search American Airlines flights
JetBluePriceFrom $432Free CancellationRating
7.2
2,908 reviews
Search JetBlue flights
SouthwestPriceFrom $441Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
United AirlinesPriceFrom $443Free CancellationRating
7.4
8,995 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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to San José for you.

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

Flights from Chicago to San José with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San José.

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

Yes. momondo can track prices for Chicago to San José flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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