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Cheap flights from Chicago to San José from $127

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 6/17. 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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0 bags

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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.
Spirit Airlines Logo
5:05 am - 11:33 amORD-SJO
7h 28m1 stop
Spirit Airlines Logo
11:32 am - 11:29 pmSJO-ORD
10h 57m1 stop
$236Spirit Airlines
Find Deal
Mon, Jun 2 - Thu, Jun 5
Spirit Airlines Logo
7:35 pm - 11:33 amORD-SJO
16h 58m1 stop
Spirit Airlines Logo
11:32 am - 11:29 pmSJO-ORD
10h 57m1 stop
$251Spirit Airlines
Find Deal
Mon, Jun 2 - Thu, Jun 5
Spirit Airlines Logo
7:35 pm - 11:33 amORD-SJO
16h 58m1 stop
Spirit Airlines Logo
11:32 am - 11:29 pmSJO-ORD
10h 57m1 stop
$252Spirit Airlines
Find Deal
Mon, Jun 2 - Thu, Jun 5
Copa Airlines Logo
3:07 pm - 8:20 amORD-SJO
18h 13m1 stop
Copa Airlines Logo
4:10 am - 1:42 pmSJO-ORD
8h 32m1 stop
$289Copa Airlines
Find Deal
Thu, Oct 9 - Tue, Oct 14
Avianca Logo
5:25 pm - 7:40 amORD-SJO
15h 15m2 stops
Avianca Logo
3:05 pm - 2:25 pmSJO-ORD
22h 20m2 stops
$340Avianca
Find Deal
Sat, Jun 7 - Thu, Jun 12
Avianca Logo
3:45 pm - 11:15 pmORD-SJO
8h 30m1 stop
Avianca Logo
8:00 pm - 2:25 pmSJO-ORD
17h 25m2 stops
$348Avianca
Find Deal
Wed, Jun 18 - Thu, Jun 26
Delta Logo
6:00 am - 11:48 amMDW-SJO
6h 48m1 stop
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
$446Delta
Find Deal
Wed, Sep 3 - Mon, Sep 8
Southwest Logo
7:10 am - 6:55 pmMDW-SJO
12h 45m2 stops
Southwest Logo
8:50 am - 6:25 pmSJO-MDW
8h 35m1 stop
$451Southwest
Find Deal
Fri, Sep 19 - Wed, Sep 24
Southwest Logo
8:30 am - 7:05 pmMDW-SJO
11h 35m1 stop
Southwest Logo
12:55 pm - 11:15 pmSJO-MDW
9h 20m1 stop
$462Southwest
Find Deal
Sun, Sep 21 - Mon, Oct 6
Delta Logo
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
$484Delta
Find Deal
Fri, Sep 19 - Wed, Sep 24

Avianca flights from Chicago to San José, San José Province

Our best Avianca deals on Chicago to San José, San José Province flight tickets
Avianca
Jun 7
ORD5:25 pmChicago O'Hare Intl
15h 15m
2 stops
SJO7:40 amSan José Juan Santamaria Intl
Jun 12
SJO3:05 pmSan José Juan Santamaria Intl
22h 20m
2 stops
ORD2:25 pmChicago O'Hare Intl
Avianca
Jun 18
ORD3:45 pmChicago O'Hare Intl
8h 30m
1 stop
SJO11:15 pmSan José Juan Santamaria Intl
Jun 26
SJO8:00 pmSan José Juan Santamaria Intl
17h 25m
2 stops
ORD2:25 pmChicago O'Hare Intl
Avianca
Jun 7
ORD5:25 pmChicago O'Hare Intl
15h 15m
2 stops
SJO7:40 amSan José Juan Santamaria Intl
Jun 14
SJO3:05 pmSan José Juan Santamaria Intl
22h 20m
2 stops
ORD2:25 pmChicago O'Hare Intl

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
Jun 2
ORD5:05 amChicago O'Hare Intl
7h 28m
1 stop
SJO11:33 amSan José Juan Santamaria Intl
Jun 5
SJO11:32 amSan José Juan Santamaria Intl
10h 57m
1 stop
ORD11:29 pmChicago O'Hare Intl
Spirit Airlines
Jun 2
ORD7:35 pmChicago O'Hare Intl
16h 58m
1 stop
SJO11:33 amSan José Juan Santamaria Intl
Jun 5
SJO11:32 amSan José Juan Santamaria Intl
10h 57m
1 stop
ORD11:29 pmChicago O'Hare Intl
Spirit Airlines
Jun 2
ORD7:35 pmChicago O'Hare Intl
16h 58m
1 stop
SJO11:33 amSan José Juan Santamaria Intl
Jun 5
SJO11:32 amSan José Juan Santamaria Intl
10h 57m
1 stop
ORD11:29 pmChicago O'Hare Intl

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 $504. If you’re not able to fly to San José, San José Province in May, then July is your next best option. Flight prices from Chicago to San José, San José Province during July average around $509.

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 $839.

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. 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 5 weeks ahead of your departure date. In general, you can expect to find flights to San José, San José Province for around $595 when searching 5 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 $481 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 April 2025, prices for Chicago to San José, San José Province flights are approximately 15% 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

$127

Fastest flight time

5h 14m

Direct flights

Mon, Thu, 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 $127. The best round-trip flight deal from Chicago to San José, San José Province found on momondo in the last 72 hours is $236.
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, Thursday, 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 $249Free CancellationRating
6.3
7,961 reviews
Search Spirit Airlines flights
AviancaPriceFrom $337Free CancellationRating
6.7
2,317 reviews
Search Avianca flights
JetBluePriceFrom $345Free CancellationRating
7.3
2,922 reviews
Search JetBlue flights
Copa AirlinesPriceFrom $416Free CancellationRating
7.5
1,411 reviews
Search Copa Airlines flights
DeltaPriceFrom $442Free CancellationRating
8.0
7,936 reviews
Search Delta flights
American AirlinesPriceFrom $451Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $479Free CancellationRating
8.0
4,295 reviews
Search Southwest flights
United AirlinesPriceFrom $544Free CancellationRating
7.4
8,696 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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