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Cheap flights from Chicago to San José, San José Province from $88

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, San José Province departing on 3/26. 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

These are some of the best round-trip flight deals from Chicago to San José that have been recently found on momondo from popular airlines, departing in the coming months.
9:09 am - 11:54 pmORD-SJO
15h 45m2 stops
2:48 pm - 5:42 amSJO-ORD
13h 54m1 stop
Wed, Apr 30 - Tue, May 6
5:55 pm - 11:50 pmORD-SJO
6h 55m1 stop
2:48 pm - 5:42 amSJO-ORD
13h 54m1 stop
Wed, Mar 26 - Thu, Apr 24
9:09 am - 11:18 amORD-SJO
27h 09m2 stops
3:31 pm - 11:05 amSJO-ORD
18h 34m1 stop
Sat, Apr 26 - Sat, May 3
8:53 pm - 11:18 amORD-SJO
15h 25m2 stops
12:23 pm - 12:08 pmSJO-ORD
22h 45m2 stops
$240Spirit Airlines
Find Deal
Sat, May 10 - Tue, May 13
9:09 am - 11:18 amORD-SJO
27h 09m2 stops
3:31 pm - 11:05 amSJO-ORD
18h 34m1 stop
Sat, Apr 26 - Sat, May 3
5:10 am - 11:21 amORD-SJO
7h 11m1 stop
12:26 pm - 1:38 amSJO-ORD
12h 12m2 stops
$273Spirit Airlines
Find Deal
Tue, Mar 25 - Wed, Apr 2
7:50 am - 7:40 pmMDW-SJO
12h 50m2 stops
1:10 pm - 10:50 pmSJO-MDW
8h 40m1 stop
$519Southwest
Find Deal
Mon, Apr 28 - Tue, May 13
12:44 pm - 10:12 pmMDW-SJO
9h 28m1 stop
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
$520Delta
Find Deal
Thu, Mar 6 - Sat, Mar 8
11:10 am - 7:40 pmMDW-SJO
9h 30m1 stop
1:10 pm - 11:35 pmSJO-MDW
9h 25m1 stop
$524Southwest
Find Deal
Fri, May 9 - Fri, May 16
6:04 am - 11:55 amMDW-SJO
6h 51m1 stop
1:20 pm - 10:26 pmSJO-MDW
8h 06m1 stop
$528Delta
Find Deal
Sat, Apr 26 - Sat, May 3

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
May 10
ORD8:53 pmChicago O'Hare Intl
15h 25m
2 stops
SJO11:18 amSan José Juan Santamaria Intl
May 13
SJO12:23 pmSan José Juan Santamaria Intl
22h 45m
2 stops
ORD12:08 pmChicago O'Hare Intl
Spirit Airlines
Mar 4
ORD7:13 pmChicago O'Hare Intl
16h 06m
1 stop
SJO11:19 amSan José Juan Santamaria Intl
Mar 10
SJO12:50 amSan José Juan Santamaria Intl
23h 09m
2 stops
ORD12:59 amChicago O'Hare Intl
Spirit Airlines
Mar 30
ORD9:08 pmChicago O'Hare Intl
15h 13m
2 stops
SJO11:21 amSan José Juan Santamaria Intl
Apr 7
SJO12:50 amSan José Juan Santamaria Intl
11h 58m
2 stops
ORD1:48 pmChicago O'Hare Intl

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
Apr 28
MDW7:50 amChicago Midway
12h 50m
2 stops
SJO7:40 pmSan José Juan Santamaria Intl
May 13
SJO1:10 pmSan José Juan Santamaria Intl
8h 40m
1 stop
MDW10:50 pmChicago Midway
Southwest
May 9
MDW11:10 amChicago Midway
9h 30m
1 stop
SJO7:40 pmSan José Juan Santamaria Intl
May 16
SJO1:10 pmSan José Juan Santamaria Intl
9h 25m
1 stop
MDW11:35 pmChicago Midway
Southwest
May 11
MDW9:35 amChicago Midway
11h 05m
2 stops
SJO7:40 pmSan José Juan Santamaria Intl
May 17
SJO1:35 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:30 pmChicago Midway

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 May is, on average, the cheapest month to fly to San José, San José Province from Chicago, with most prices found around $481. If you’re not able to fly to San José, San José Province in May, then June is your next best option. Flight prices from Chicago to San José, San José Province during June average around $535.

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 Wednesday when prices can be found for as low as $498. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $844.

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

In the afternoon 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 afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to San José, San José Province, so prices are often more expensive at around $852 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 6 weeks ahead of your departure date. In general, you can expect to find flights to San José, San José Province for around $578 when searching 6 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 $470 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 February 2025, prices for Chicago to San José, San José Province flights are approximately 22% 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

$88

Fastest flight time

5h 14m

Direct flights

Mon, Sat and Sun

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 $88. The best round-trip flight deal from Chicago to San José, San José Province found on momondo in the last 72 hours is $226.
The fastest flight from Chicago to San José, San José Province takes 5h 14m
Direct flights go from Chicago to San José, San José Province on Monday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Avianca.
There is 1 airport near San José, San José Province: San José Juan Santamaria Intl (SJO)

  • 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 35m 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 $238Free CancellationRating
6.3
8,013 reviews
Search Spirit Airlines flights
AviancaPriceFrom $337Free CancellationRating
6.8
2,435 reviews
Search Avianca flights
JetBluePriceFrom $345Free CancellationRating
7.4
3,070 reviews
Search JetBlue flights
Copa AirlinesPriceFrom $459Free CancellationRating
7.6
1,510 reviews
Search Copa Airlines flights
DeltaPriceFrom $517Free CancellationRating
8.0
8,220 reviews
Search Delta flights
SouthwestPriceFrom $540Free CancellationRating
8.1
4,411 reviews
Search Southwest flights
American AirlinesPriceFrom $565Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $582Free CancellationRating
7.4
8,766 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
San Lorenzo

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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