Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to San José, San José Province from $114

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 2/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to San José.

Cheap last minute flights

Planning a quick getaway from Chicago to San José? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San José, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to San José

Find recent round-trip train or bus tickets from Chicago to San José.

All round-trip flight deals from Chicago to San José

The cheapest plane tickets from Chicago to San José found on KAYAK recently.
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
2:43 pm - 4:37 amSJO-ORD
13h 54m1 stop
Wed, Feb 26 - Wed, Mar 5
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
1:26 pm - 12:07 amSJO-ORD
10h 41m1 stop
$288Spirit Airlines
Find Deal
Mon, Feb 24 - Wed, Mar 5
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
2:43 pm - 4:37 amSJO-ORD
13h 54m1 stop
Mon, Feb 24 - Mon, Mar 3
3:09 pm - 8:07 amORD-SJO
16h 58m1 stop
4:09 am - 1:42 pmSJO-ORD
8h 33m1 stop
$426Copa Airlines
Find Deal
Sat, Mar 8 - Sat, Mar 15
1:35 pm - 12:15 amORD-SJO
10h 40m1 stop
4:55 pm - 12:15 pmSJO-ORD
19h 20m1 stop
$429Avianca
Find Deal
Sun, Feb 23 - Sat, Mar 1
2:05 pm - 9:20 amORD-SJO
19h 15m1 stop
2:15 am - 12:15 pmSJO-ORD
10h 00m1 stop
$432Avianca
Find Deal
Sat, Feb 8 - Wed, Feb 12
7:50 am - 7:40 pmMDW-SJO
12h 50m2 stops
1:10 pm - 10:50 pmSJO-MDW
8h 40m1 stop
$510Southwest
Find Deal
Thu, May 1 - Wed, May 7
11:10 am - 7:40 pmMDW-SJO
9h 30m1 stop
1:10 pm - 10:50 pmSJO-MDW
8h 40m1 stop
$525Southwest
Find Deal
Thu, May 1 - Wed, May 7
10:57 am - 10:12 pmMDW-SJO
11h 15m1 stop
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
$678Delta
Find Deal
Mon, Feb 24 - Wed, Mar 5
9:33 am - 10:12 pmMDW-SJO
12h 39m2 stops
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
$682Delta
Find Deal
Mon, Feb 24 - Wed, Mar 5
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
$114Spirit Airlines
Find Deal
Fri, Feb 21
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
$123Spirit Airlines
Find Deal
Tue, Feb 25
1:35 pm - 12:15 amORD-SJO
10h 40m1 stop
$188Avianca
Find Deal
Fri, Feb 7
1:35 pm - 12:15 amORD-SJO
10h 40m1 stop
$189Avianca
Find Deal
Wed, Jan 29
9:25 am - 9:24 pmMDW-SJO
12h 59m2 stops
$305Delta
Find Deal
Tue, Mar 25
7:15 pm - 12:15 pmORD-SJO
18h 00m2 stops
$311Southwest
Find Deal
Sat, Jul 12
7:35 am - 7:40 pmMDW-SJO
13h 05m2 stops
$320Southwest
Find Deal
Thu, Jun 19
10:57 am - 10:12 pmMDW-SJO
11h 15m1 stop
$335Delta
Find Deal
Wed, Feb 5
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$346United Airlines
Find Deal
Sun, Feb 9
7:35 am - 6:16 pmORD-SJO
10h 41m1 stop
$350United Airlines
Find Deal
Sat, Feb 1
1:35 pm - 12:15 amORD-SJO
10h 40m1 stop
2:43 pm - 4:37 amSJO-ORD
13h 54m1 stop
Fri, Jan 24 - Wed, Feb 12
2:05 pm - 9:20 amORD-SJO
19h 15m1 stop
2:43 pm - 4:37 amSJO-ORD
13h 54m1 stop
Tue, Jan 28 - Tue, Feb 4
6:56 am - 3:56 pmORD-SJO
9h 00m1 stop
5:23 pm - 12:11 pmSJO-ORD
18h 48m1 stop
$426Copa Airlines
Find Deal
Fri, Jan 24 - Tue, Jan 28
1:35 pm - 9:20 amORD-SJO
19h 45m1 stop
1:31 pm - 11:32 pmSJO-ORD
10h 01m1 stop
Mon, Jan 27 - Sat, Feb 8
6:06 pm - 12:59 amORD-SJO
30h 53m3 stops
12:25 pm - 2:23 pmSJO-ORD
25h 58m3 stops
$513Spirit Airlines
Find Deal
Sun, Jan 26 - Thu, Jan 30
6:06 pm - 12:59 amORD-SJO
30h 53m3 stops
1:31 pm - 10:55 pmSJO-ORD
33h 24m3 stops
$525Spirit Airlines
Find Deal
Sun, Jan 26 - Tue, Jan 28
1:57 pm - 9:58 pmORD-SJO
8h 01m1 stop
3:06 pm - 11:27 pmSJO-ORD
8h 21m1 stop
$531Copa Airlines
Find Deal
Fri, Jan 24 - Thu, Jan 30
9:45 am - 7:50 pmORD-SJO
10h 05m2 stops
6:00 am - 12:27 amSJO-ORD
18h 27m1 stop
$652American Airlines
Find Deal
Sun, Jan 26 - Sun, Feb 2
10:35 am - 10:00 pmORD-SJO
11h 25m1 stop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$728United Airlines
Find Deal
Fri, Jan 24 - Sat, Feb 1
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
6:40 am - 8:25 pmSJO-ORD
13h 45m1 stop
$733United Airlines
Find Deal
Sun, Jan 26 - Sun, Feb 2
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$711United Airlines
Find Deal
Sat, Jun 7 - Sat, Jun 14
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
1:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$723United Airlines
Find Deal
Sun, Feb 23 - Sun, Mar 9
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$753United Airlines
Find Deal
Sat, Apr 19 - Sat, Apr 26
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$804United Airlines
Find Deal
Sat, Jun 7 - Sat, Jun 14
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$823United Airlines
Find Deal
Sun, Feb 9 - Sat, Feb 15
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$828United Airlines
Find Deal
Sun, May 25 - Sun, Jun 1
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$855United Airlines
Find Deal
Sat, Apr 26 - Sat, May 3
7:35 am - 11:56 amORD-SJO
5h 21mnonstop
1:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$858United Airlines
Find Deal
Sun, Mar 9 - Sun, Mar 16
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$870United Airlines
Find Deal
Sat, Apr 19 - Sat, May 10
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:28 pmSJO-ORD
5h 28mnonstop
$933United Airlines
Find Deal
Sat, Jul 19 - Sat, Jul 26

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

Our best Copa Airlines deals on Chicago to San José, San José Province flight tickets
Copa Airlines
Mar 8
ORD3:09 pmChicago O'Hare Intl
16h 58m
1 stop
SJO8:07 amSan José Juan Santamaria Intl
Mar 15
SJO4:09 amSan José Juan Santamaria Intl
8h 33m
1 stop
ORD1:42 pmChicago O'Hare Intl
Copa Airlines
Jan 24
ORD1:57 pmChicago O'Hare Intl
8h 01m
1 stop
SJO9:58 pmSan José Juan Santamaria Intl
Jan 30
SJO3:06 pmSan José Juan Santamaria Intl
8h 21m
1 stop
ORD11:27 pmChicago O'Hare Intl

Frontier flights from Chicago to San José, San José Province

Our best Frontier deals on Chicago to San José, San José Province flight tickets
Frontier
Feb 21
MDW6:48 pmChicago Midway
16h 43m
1 stop
SJO11:31 amSan José Juan Santamaria Intl
Mar 1
SJO12:55 pmSan José Juan Santamaria Intl
9h 09m
1 stop
MDW10:04 pmChicago Midway
Frontier
May 23
MDW6:44 pmChicago Midway
18h 38m
1 stop
SJO12:22 pmSan José Juan Santamaria Intl
May 31
SJO1:42 pmSan José Juan Santamaria Intl
9h 13m
1 stop
MDW11:55 pmChicago Midway
Frontier
May 23
MDW6:44 pmChicago Midway
18h 38m
1 stop
SJO12:22 pmSan José Juan Santamaria Intl
May 31
SJO1:42 pmSan José Juan Santamaria Intl
9h 13m
1 stop
MDW11:55 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 $484. If you’re not able to fly to San José, San José Province in May, then August is your next best option. Flight prices from Chicago to San José, San José Province during August average around $557.

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 $481. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $845.

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 $452. 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 $838 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 2 weeks ahead of your departure date. In general, you can expect to find flights to San José, San José Province for around $580 when searching 2 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 $450 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 January 2025, prices for Chicago to San José, San José Province flights are approximately 38% 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

$114

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 $114. The best round-trip flight deal from Chicago to San José, San José Province found on momondo in the last 72 hours is $284.
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 25m 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 $239Free CancellationRating
6.3
8,108 reviews
Search Spirit Airlines flights
AviancaPriceFrom $293Free CancellationRating
6.9
2,565 reviews
Search Avianca flights
JetBluePriceFrom $387Free CancellationRating
7.4
3,186 reviews
Search JetBlue flights
Copa AirlinesPriceFrom $430Free CancellationRating
7.6
1,653 reviews
Search Copa Airlines flights
SouthwestPriceFrom $479Free CancellationRating
8.1
4,647 reviews
Search Southwest flights
DeltaPriceFrom $550Free CancellationRating
8.0
8,508 reviews
Search Delta flights
American AirlinesPriceFrom $569Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $581Free CancellationRating
7.4
8,971 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 $468, but momondo users have found Avianca deals from Chicago to San José, San José Province from as low as $293 round-trip. Avianca has been scored 6.9/10 in 2,565 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
Monteverde
Alajuela
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.


An easier way to manage your San José, San José Province trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 1/28
Tue 2/4
Email me momondo's favorite deals

Find better results for your trip to Costa Rica