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Cheap flights from Chicago to San José from $74

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 11/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:05 am - 11:30 amORD-SJO
7h 25m1 stop
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
$251Spirit Airlines
Find Deal
sáb., nov. 1 - vie., nov. 7
Spirit Airlines Logo
4:03 pm - 11:30 amORD-SJO
20h 27m2 stops
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
$253Spirit Airlines
Find Deal
jue., oct. 30 - dom., nov. 2
Multiple Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
Multiple Airlines Logo
4:08 am - 12:46 pmSJO-ORD
8h 38m1 stop
$254Multiple Airlines
Find Deal
mar., nov. 11 - lun., nov. 17
Avianca Logo
2:35 pm - 9:50 pmORD-SJO
7h 15mnonstop
Avianca Logo
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$267Avianca
Find Deal
mié., ene. 21 - mié., ene. 28
Avianca Logo
2:35 pm - 11:15 pmORD-SJO
8h 40m1 stop
Avianca Logo
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$268Avianca
Find Deal
mié., ene. 21 - mié., ene. 28
American Airlines Logo
5:18 pm - 10:28 pmORD-SJO
5h 10mnonstop
American Airlines Logo
6:00 am - 11:31 amSJO-ORD
5h 31mnonstop
$291American Airlines
Find Deal
sáb., dic. 6 - mar., dic. 9
Copa Airlines Logo
2:07 pm - 7:33 amORD-SJO
17h 26m1 stop
Copa Airlines Logo
4:08 am - 12:46 pmSJO-ORD
8h 38m1 stop
$294Copa Airlines
Find Deal
jue., nov. 20 - dom., nov. 23
American Airlines Logo
5:25 pm - 10:25 pmORD-SJO
5h 00mnonstop
American Airlines Logo
7:09 am - 12:38 pmSJO-ORD
5h 29mnonstop
$296American Airlines
Find Deal
lun., feb. 2 - dom., feb. 8
Southwest Logo
5:05 am - 1:15 pmMDW-SJO
8h 10m1 stop
Southwest Logo
9:00 am - 9:00 pmSJO-MDW
12h 00m2 stops
$330Southwest
Find Deal
mar., nov. 11 - mar., nov. 18
Southwest Logo
5:00 am - 12:00 pmMDW-SJO
8h 00m1 stop
Southwest Logo
2:15 pm - 10:10 pmSJO-MDW
7h 55m1 stop
$359Southwest
Find Deal
jue., oct. 30 - lun., nov. 3

Spirit Airlines flights from Chicago to San José

Our best Spirit Airlines deals on Chicago to San José flight tickets
Spirit Airlines
Nov 1
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
Nov 7
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
$251
Find similar
Spirit Airlines
Oct 30
ORD4:03 pmChicago O'Hare Intl
20h 27m
2 stops
SJO11:30 amSan José Juan Santamaria Intl
Nov 2
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
$253
Find similar
Spirit Airlines
Oct 21
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
Oct 31
SJO12:35 pmSan José Juan Santamaria Intl
11h 28m
1 stop
ORD1:03 amChicago O'Hare Intl
$256
Find similar

Delta flights from Chicago to San José

Our best Delta deals on Chicago to San José flight tickets
Delta
Dec 10
MDW12:50 pmChicago Midway
9h 22m
1 stop
SJO10:12 pmSan José Juan Santamaria Intl
Dec 17
SJO7:00 amSan José Juan Santamaria Intl
16h 49m
1 stop
MDW11:49 pmChicago Midway
$306
Find similar
Delta
Dec 10
MDW6:00 amChicago Midway
16h 12m
1 stop
SJO10:12 pmSan José Juan Santamaria Intl
Dec 17
SJO7:00 amSan José Juan Santamaria Intl
25h 54m
2 stops
MDW8:54 amChicago Midway
$310
Find similar
Delta
Oct 31
MDW6:00 amChicago Midway
6h 58m
1 stop
SJO11:58 amSan José Juan Santamaria Intl
Nov 16
SJO7:00 amSan José Juan Santamaria Intl
16h 40m
1 stop
MDW11:40 pmChicago Midway
$344
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 octubre 14, 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

sáb. 11/1

5:05 am-11:30 am

1 stop7h 25m

San José Juan Santamaria Intl

vie. 11/7

1:30 pm-12:27 am

1 stop10h 57m

$251

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 10/30

4:03 pm-11:30 am

2 stops20h 27m

San José Juan Santamaria Intl

dom. 11/2

1:30 pm-12:27 am

1 stop10h 57m

$253

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mar. 11/11

5:10 am-12:25 pm

1 stop7h 15m

San José Juan Santamaria Intl

lun. 11/17

4:08 am-12:46 pm

1 stop8h 38m

$254

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mié. 1/21

2:35 pm-9:50 pm

Nonstop7h 15m

San José Juan Santamaria Intl

mié. 1/28

5:45 am-1:15 pm

Nonstop7h 30m

$267

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mié. 1/21

2:35 pm-11:15 pm

1 stop8h 40m

San José Juan Santamaria Intl

mié. 1/28

5:45 am-1:15 pm

Nonstop7h 30m

$268

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 12/6

5:18 pm-10:28 pm

Nonstop5h 10m

San José Juan Santamaria Intl

mar. 12/9

6:00 am-11:31 am

Nonstop5h 31m

$291

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 11/20

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

dom. 11/23

4:08 am-12:46 pm

1 stop8h 38m

$294

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

lun. 2/2

5:25 pm-10:25 pm

Nonstop5h 00m

San José Juan Santamaria Intl

dom. 2/8

7:09 am-12:38 pm

Nonstop5h 29m

$296

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 11/11

5:05 am-1:15 pm

1 stop8h 10m

San José Juan Santamaria Intl

mar. 11/18

9:00 am-9:00 pm

2 stops12h 00m

$330

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

jue. 10/30

5:00 am-12:00 pm

1 stop8h 00m

San José Juan Santamaria Intl

lun. 11/3

2:15 pm-10:10 pm

1 stop7h 55m

$359

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 $377.

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 $546. 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 $787. 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 $748.

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 $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 for as low as $438 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.

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

You could potentially save up to 22% 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 October 2025, prices for Chicago to San José flights are approximately 50% 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

$188

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 $188. The best round-trip flight deal from Chicago to San José found on momondo in the last 72 hours is $461.
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 near San José: 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
Spirit AirlinesPriceFrom $263Free CancellationRating
6.3
8,097 reviews
Search Spirit Airlines flights
DeltaPriceFrom $290Free CancellationRating
7.9
7,972 reviews
Search Delta flights
AviancaPriceFrom $307Free CancellationRating
6.6
2,451 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,548 reviews
Search Copa Airlines flights
FrontierPriceFrom $345Free CancellationRating
5.8
3,136 reviews
Search Frontier flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,238 reviews
Search Southwest flights
American AirlinesPriceFrom $420Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
JetBluePriceFrom $432Free CancellationRating
7.2
2,906 reviews
Search JetBlue flights
United AirlinesPriceFrom $443Free CancellationRating
7.4
8,975 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.

An easier way to manage your San José trip

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