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Cheap flights from Chicago to San José from $82

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 9/17. 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 (CHI-SJO)

Cheap round-trip flights

Spirit Airlines Logo
9:24 pm - 12:30 pmORD-SJO
16h 06m2 stops
Spirit Airlines Logo
1:35 pm - 1:03 amSJO-ORD
11h 28m1 stop
$285Spirit Airlines
Find Deal
Sat, Nov 1 - Tue, Nov 4
Spirit Airlines Logo
11:37 am - 11:14 amORD-SJO
24h 37m2 stops
Spirit Airlines Logo
12:19 pm - 10:42 amSJO-ORD
21h 23m2 stops
$286Spirit Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Spirit Airlines Logo
9:24 pm - 12:30 pmORD-SJO
16h 06m2 stops
Spirit Airlines Logo
1:35 pm - 7:16 pmSJO-ORD
29h 41m2 stops
$287Spirit Airlines
Find Deal
Sat, Nov 1 - Tue, Nov 4
Logo
11:57 am - 10:27 amORD-SJO
23h 30m2 stops
Logo
7:30 am - 10:18 amSJO-ORD
25h 48m3 stops
$306
Find Deal
Sat, Sep 13 - Wed, Sep 17
Logo
7:29 pm - 3:13 pmORD-SJO
20h 44m2 stops
Logo
1:19 pm - 11:42 pmSJO-ORD
10h 23m1 stop
$331
Find Deal
Sun, Oct 12 - Wed, Nov 5
Delta Logo
6:00 am - 12:50 pmMDW-SJO
6h 50m1 stop
Delta Logo
2:17 pm - 9:44 pmSJO-MDW
7h 27m1 stop
$394Delta
Find Deal
Thu, Nov 6 - Tue, Nov 11
Delta Logo
9:30 am - 10:15 pmMDW-SJO
12h 45m2 stops
Delta Logo
7:00 am - 9:44 pmSJO-MDW
14h 44m1 stop
$398Delta
Find Deal
Sat, Nov 15 - Fri, Nov 21
Frontier Logo
6:10 am - 12:24 pmMDW-SJO
7h 14m1 stop
Frontier Logo
1:53 pm - 10:08 amSJO-MDW
19h 15m1 stop
$408Frontier
Find Deal
Sat, Aug 23 - Sat, Aug 30
Southwest Logo
6:25 am - 6:55 pmMDW-SJO
13h 30m1 stop
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
$427Southwest
Find Deal
Tue, Sep 9 - Fri, Sep 12
Southwest Logo
7:00 am - 8:30 pmMDW-SJO
13h 30m1 stop
Southwest Logo
9:00 am - 7:35 pmSJO-MDW
10h 35m2 stops
$431Southwest
Find Deal
Tue, Nov 11 - Tue, Nov 18

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
Nov 1
ORD9:24 pmChicago O'Hare Intl
16h 06m
2 stops
SJO12:30 pmSan José Juan Santamaria Intl
Nov 4
SJO1:35 pmSan José Juan Santamaria Intl
11h 28m
1 stop
ORD1:03 amChicago O'Hare Intl
$285
Find similar
Spirit Airlines
Sep 13
ORD11:37 amChicago O'Hare Intl
24h 37m
2 stops
SJO11:14 amSan José Juan Santamaria Intl
Sep 20
SJO12:19 pmSan José Juan Santamaria Intl
21h 23m
2 stops
ORD10:42 amChicago O'Hare Intl
$286
Find similar
Spirit Airlines
Nov 1
ORD9:24 pmChicago O'Hare Intl
16h 06m
2 stops
SJO12:30 pmSan José Juan Santamaria Intl
Nov 4
SJO1:35 pmSan José Juan Santamaria Intl
29h 41m
2 stops
ORD7:16 pmChicago O'Hare Intl
$287
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 9
MDW6:25 amChicago Midway
13h 30m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Sep 12
SJO1:40 pmSan José Juan Santamaria Intl
9h 25m
1 stop
MDW12:05 amChicago Midway
$427
Find similar
Southwest
Nov 11
MDW7:00 amChicago Midway
13h 30m
1 stop
SJO8:30 pmSan José Juan Santamaria Intl
Nov 18
SJO9:00 amSan José Juan Santamaria Intl
10h 35m
2 stops
MDW7:35 pmChicago Midway
$431
Find similar
Southwest
Sep 13
MDW10:10 amChicago Midway
9h 45m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Sep 16
SJO8:50 amSan José Juan Santamaria Intl
8h 35m
1 stop
MDW6:25 pmChicago Midway
$452
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 August 18, 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

Sat 11/1

9:24 pm-12:30 pm

2 stops16h 06m

San José Juan Santamaria Intl

Tue 11/4

1:35 pm-1:03 am

1 stop11h 28m

$285

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 9/13

11:37 am-11:14 am

2 stops24h 37m

San José Juan Santamaria Intl

Sat 9/20

12:19 pm-10:42 am

2 stops21h 23m

$286

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/1

9:24 pm-12:30 pm

2 stops16h 06m

San José Juan Santamaria Intl

Tue 11/4

1:35 pm-7:16 pm

2 stops29h 41m

$287

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 9/13

11:57 am-10:27 am

2 stops23h 30m

San José Juan Santamaria Intl

Wed 9/17

7:30 am-10:18 am

3 stops25h 48m

$306

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 10/12

7:29 pm-3:13 pm

2 stops20h 44m

San José Juan Santamaria Intl

Wed 11/5

1:19 pm-11:42 pm

1 stop10h 23m

$331

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 11/6

6:00 am-12:50 pm

1 stop6h 50m

San José Juan Santamaria Intl

Tue 11/11

2:17 pm-9:44 pm

1 stop7h 27m

$394

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 11/15

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

Fri 11/21

7:00 am-9:44 pm

1 stop14h 44m

$398

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 8/23

6:10 am-12:24 pm

1 stop7h 14m

San José Juan Santamaria Intl

Sat 8/30

1:53 pm-10:08 am

1 stop19h 15m

$408

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/9

6:25 am-6:55 pm

1 stop13h 30m

San José Juan Santamaria Intl

Fri 9/12

1:40 pm-12:05 am

1 stop9h 25m

$427

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 11/11

7:00 am-8:30 pm

1 stop13h 30m

San José Juan Santamaria Intl

Tue 11/18

9:00 am-7:35 pm

2 stops10h 35m

$431

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 $445. 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 $822.

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 $768 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 $601 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 $457 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 August 2025, prices for Chicago to San José, San José Province flights are approximately 12% more expensive 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

$82

Fastest flight time

6h 50m

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 $82. The best round-trip flight deal from Chicago to San José, San José Province found on momondo in the last 72 hours is $285.
The fastest flight from Chicago to San José, San José Province takes 6h 50m
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 50m 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 $275Free CancellationRating
6.3
8,038 reviews
Search Spirit Airlines flights
AviancaPriceFrom $319Free CancellationRating
6.7
2,407 reviews
Search Avianca flights
Copa AirlinesPriceFrom $343Free CancellationRating
7.5
1,510 reviews
Search Copa Airlines flights
SouthwestPriceFrom $431Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
JetBluePriceFrom $432Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
DeltaPriceFrom $438Free CancellationRating
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $444Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $470Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights

  • Avianca Flights From Chicago to San José, San José Province

    Avianca operates around 3 flights from Chicago to San José, San José Province every week. The average price of these flights found in the last 72 hours has been $462, but momondo users have found Avianca deals from Chicago to San José, San José Province from as low as $319 round-trip. Avianca has been scored 6.7/10 in 2,407 reviews.

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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