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Cheap flights from Chicago to San José from $83

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 8/16. 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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Cheap round-trip flights

Spirit Airlines Logo
8:47 pm - 11:12 amORD-SJO
15h 25m2 stops
Spirit Airlines Logo
12:18 pm - 7:42 pmSJO-ORD
30h 24m2 stops
$302Spirit Airlines
Find Deal
Thu, Aug 21 - Sat, Aug 23
Frontier Logo
5:01 am - 12:31 pmORD-SJO
8h 30m1 stop
Frontier Logo
1:47 pm - 11:29 pmSJO-ORD
8h 42m1 stop
$308Frontier
Find Deal
Sat, Aug 2 - Sat, Aug 9
Spirit Airlines Logo
8:53 pm - 11:18 amORD-SJO
15h 25m2 stops
Spirit Airlines Logo
1:41 pm - 12:08 pmSJO-ORD
21h 27m2 stops
$310Spirit Airlines
Find Deal
Sat, Oct 18 - Fri, Oct 24
Southwest Logo
5:45 am - 11:35 amMDW-SJO
6h 50m1 stop
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
$322Southwest
Find Deal
Sun, Aug 24 - Wed, Aug 27
American Airlines Logo
8:34 pm - 1:20 pmORD-SJO
17h 46m1 stop
American Airlines Logo
6:44 am - 7:45 pmSJO-ORD
12h 01m2 stops
$326American Airlines
Find Deal
Fri, Oct 17 - Tue, Oct 28
 Logo
5:05 am - 11:12 amORD-SJO
7h 07m1 stop
 Logo
4:13 pm - 11:05 amSJO-ORD
17h 52m1 stop
Mon, Aug 25 - Fri, Aug 29
 Logo
6:56 am - 3:13 pmORD-SJO
9h 17m1 stop
 Logo
7:30 am - 10:22 pmSJO-ORD
13h 52m1 stop
Thu, Aug 21 - Tue, Aug 26
Copa Airlines Logo
6:56 am - 7:01 pmORD-SJO
12h 05m1 stop
Copa Airlines Logo
4:08 am - 12:46 pmSJO-ORD
8h 38m1 stop
$337Copa Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Copa Airlines Logo
6:56 am - 7:01 pmORD-SJO
12h 05m1 stop
Copa Airlines Logo
8:47 am - 12:05 amSJO-ORD
15h 18m1 stop
$352Copa Airlines
Find Deal
Tue, Nov 11 - Fri, Nov 14
Southwest Logo
8:30 am - 7:05 pmMDW-SJO
11h 35m1 stop
Southwest Logo
8:50 am - 9:55 pmSJO-MDW
12h 05m2 stops
$379Southwest
Find Deal
Sun, Aug 24 - Wed, Aug 27

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
Aug 24
MDW5:45 amChicago Midway
6h 50m
1 stop
SJO11:35 amSan José Juan Santamaria Intl
Aug 27
SJO1:40 pmSan José Juan Santamaria Intl
8h 40m
1 stop
MDW11:20 pmChicago Midway
Southwest
Aug 24
MDW8:30 amChicago Midway
11h 35m
1 stop
SJO7:05 pmSan José Juan Santamaria Intl
Aug 27
SJO8:50 amSan José Juan Santamaria Intl
12h 05m
2 stops
MDW9:55 pmChicago Midway
Southwest
Sep 14
MDW5:45 amChicago Midway
6h 50m
1 stop
SJO11:35 amSan José Juan Santamaria Intl
Sep 17
SJO1:40 pmSan José Juan Santamaria Intl
8h 40m
1 stop
MDW11:20 pmChicago Midway

American Airlines flights from Chicago to San José, San José Province

Our best American Airlines deals on Chicago to San José, San José Province flight tickets
American Airlines
Jul 9
ORD6:00 amChicago O'Hare Intl
17h 05m
1 stop
SJO10:05 pmSan José Juan Santamaria Intl
Jul 11
SJO11:59 pmSan José Juan Santamaria Intl
10h 00m
1 stop
ORD10:59 amChicago O'Hare Intl
American Airlines
Oct 17
ORD8:34 pmChicago O'Hare Intl
17h 46m
1 stop
SJO1:20 pmSan José Juan Santamaria Intl
Oct 28
SJO6:44 amSan José Juan Santamaria Intl
12h 01m
2 stops
ORD7:45 pmChicago O'Hare Intl
American Airlines
Jul 5
ORD11:53 amChicago O'Hare Intl
11h 12m
1 stop
SJO10:05 pmSan José Juan Santamaria Intl
Jul 11
SJO11:59 pmSan José Juan Santamaria Intl
18h 25m
1 stop
ORD7:24 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 July is, on average, the cheapest month to fly to San José, San José Province from Chicago, with most prices found around $449. If you’re not able to fly to San José, San José Province in July, then October is your next best option. Flight prices from Chicago to San José, San José Province during October average around $552.

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 $581. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $823.

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 $771 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 $599 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 $468 on momondo.

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

There are 1 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 July 2025, prices for Chicago to San José, San José Province flights are approximately 10% 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

$83

Fastest flight time

5h 12m

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 $83. The best round-trip flight deal from Chicago to San José, San José Province found on momondo in the last 72 hours is $302.
The fastest flight from Chicago to San José, San José Province takes 5h 12m
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)

  • 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 $274Free CancellationRating
6.3
8,086 reviews
Search Spirit Airlines flights
AviancaPriceFrom $317Free CancellationRating
6.7
2,363 reviews
Search Avianca flights
JetBluePriceFrom $345Free CancellationRating
7.3
2,916 reviews
Search JetBlue flights
Copa AirlinesPriceFrom $367Free CancellationRating
7.5
1,467 reviews
Search Copa Airlines flights
DeltaPriceFrom $438Free CancellationRating
8.0
7,982 reviews
Search Delta flights
American AirlinesPriceFrom $444Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $477Free CancellationRating
8.0
4,266 reviews
Search Southwest flights
United AirlinesPriceFrom $480Free CancellationRating
7.4
8,861 reviews
Search United Airlines flights
  • Avianca Flights From Chicago to San José, San José Province

    Avianca operates around 2 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 $459, but momondo users have found Avianca deals from Chicago to San José, San José Province from as low as $317 round-trip. Avianca has been scored 6.7/10 in 2,363 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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1 adult
Tue 7/8
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