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Cheap flights from Chicago to San José, San José Province from $117

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 2/26. 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.

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 to San José

The cheapest plane tickets to San José found on KAYAK recently.
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
1:25 pm - 10:03 pmSJO-ORD
8h 38m1 stop
$272Spirit Airlines
Find Deal
Sat, Feb 22 - Wed, Feb 26
3:56 pm - 12:26 pmORD-SJO
20h 30m1 stop
1:57 am - 8:13 pmSJO-ORD
18h 16m1 stop
$280Spirit Airlines
Find Deal
Wed, Feb 5 - Fri, Feb 7
3:56 pm - 12:59 amORD-SJO
9h 03m1 stop
1:31 pm - 11:32 pmSJO-ORD
10h 01m1 stop
$282Spirit Airlines
Find Deal
Thu, Feb 6 - Tue, Feb 11
7:25 am - 12:20 pmORD-SJO
28h 55m2 stops
1:25 pm - 11:58 pmSJO-ORD
10h 33m1 stop
Sat, Feb 22 - Wed, Feb 26
2:42 am - 2:22 pmORD-SJO
11h 40m1 stop
1:31 pm - 11:32 pmSJO-ORD
10h 01m1 stop
Fri, Jan 31 - Thu, Feb 6
2:35 pm - 8:40 amORD-SJO
18h 05m2 stops
8:30 pm - 1:15 pmSJO-ORD
16h 45m2 stops
$410Avianca
Find Deal
Sun, Jan 26 - Thu, Jan 30
8:25 am - 8:40 pmMDW-SJO
12h 15m1 stop
9:55 am - 6:50 pmSJO-MDW
8h 55m2 stops
$538Southwest
Find Deal
Wed, Feb 26 - Tue, Mar 4
8:30 am - 8:40 pmMDW-SJO
12h 10m2 stops
9:55 am - 10:05 pmSJO-MDW
12h 10m2 stops
$543Southwest
Find Deal
Wed, Feb 26 - Tue, Mar 4
10:57 am - 10:12 pmMDW-SJO
11h 15m1 stop
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
$636Delta
Find Deal
Mon, Feb 24 - Tue, Mar 4
9:33 am - 10:12 pmMDW-SJO
12h 39m2 stops
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
$641Delta
Find Deal
Mon, Feb 24 - Tue, Mar 4
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
$117Spirit Airlines
Find Deal
Wed, Feb 26
5:11 am - 12:26 pmORD-SJO
7h 15m1 stop
$119Spirit Airlines
Find Deal
Mon, Feb 10
6:55 am - 12:59 amORD-SJO
18h 04m1 stop
$126Spirit Airlines
Find Deal
Thu, Feb 6
2:35 pm - 11:20 pmORD-SJO
8h 45m2 stops
$161Avianca
Find Deal
Fri, Jan 24
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$295United Airlines
Find Deal
Sat, Jan 11
9:45 am - 6:39 pmORD-SJO
9h 54m2 stops
$299American Airlines
Find Deal
Tue, Mar 25
12:51 pm - 9:24 pmMDW-SJO
9h 33m1 stop
$299Delta
Find Deal
Tue, Mar 25
2:35 pm - 7:00 pmORD-SJO
29h 25m2 stops
$312Avianca
Find Deal
Fri, Mar 14
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$370United Airlines
Find Deal
Sat, Apr 5
9:34 am - 10:12 pmMDW-SJO
12h 38m2 stops
$374Delta
Find Deal
Thu, Jan 9
8:14 pm - 11:41 amORD-SJO
15h 27m1 stop
1:57 am - 4:10 pmSJO-ORD
14h 13m2 stops
$668Spirit Airlines
Find Deal
Fri, Dec 27 - Tue, Jan 14
8:14 pm - 11:41 amORD-SJO
15h 27m1 stop
1:57 am - 8:13 pmSJO-ORD
18h 16m1 stop
$671Spirit Airlines
Find Deal
Fri, Dec 27 - Tue, Jan 14
8:00 pm - 1:17 pmORD-SJO
17h 17m1 stop
6:30 am - 7:49 pmSJO-ORD
13h 19m1 stop
$726United Airlines
Find Deal
Sat, Dec 28 - Tue, Dec 31
9:29 pm - 11:58 pmORD-SJO
26h 29m1 stop
8:45 am - 10:56 pmSJO-ORD
14h 11m1 stop
$771United Airlines
Find Deal
Sat, Dec 28 - Tue, Dec 31
7:09 am - 9:00 pmORD-SJO
13h 51m1 stop
6:15 am - 6:25 pmSJO-ORD
12h 10m1 stop
$786American Airlines
Find Deal
Thu, Dec 26 - Tue, Dec 31
9:45 am - 8:04 pmORD-SJO
10h 19m2 stops
11:52 am - 12:26 amSJO-ORD
12h 34m1 stop
$791American Airlines
Find Deal
Sat, Dec 28 - Tue, Dec 31
5:45 am - 12:50 pmORD-SJO
7h 05m1 stop
2:15 pm - 11:56 pmSJO-ORD
9h 41m1 stop
$811Delta
Find Deal
Wed, Dec 25 - Tue, Dec 31
6:00 am - 12:50 pmMDW-SJO
6h 50m1 stop
7:05 am - 2:34 pmSJO-MDW
7h 29m1 stop
$856Delta
Find Deal
Wed, Dec 25 - Wed, Jan 1
2:35 pm - 9:45 pmORD-SJO
7h 10m1 stop
2:15 am - 12:15 pmSJO-ORD
10h 00m1 stop
$1,104Avianca
Find Deal
Sun, Dec 29 - Wed, Jan 1
1:35 pm - 12:15 amORD-SJO
10h 40m1 stop
5:45 am - 1:15 pmSJO-ORD
7h 30m1 stop
$1,143Avianca
Find Deal
Wed, Dec 25 - Wed, Jan 1
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$612Avianca
Find Deal
Sun, Jan 12 - Sun, Jan 26
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$622United Airlines
Find Deal
Sat, May 3 - Sat, May 17
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$685United Airlines
Find Deal
Sun, Jan 12 - Sun, Jan 19
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$712United Airlines
Find Deal
Sat, May 31 - Sun, Jun 8
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$772United 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
$792United Airlines
Find Deal
Sat, Apr 5 - Sat, Apr 19
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
1:00 pm - 7:28 pmSJO-ORD
5h 28mnonstop
$802United Airlines
Find Deal
Sat, May 24 - Sat, May 31
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$809United Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 1
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$812United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 18
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$816United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 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
Feb 22
ORD5:00 amChicago O'Hare Intl
7h 20m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
Feb 26
SJO1:25 pmSan José Juan Santamaria Intl
8h 38m
1 stop
ORD10:03 pmChicago O'Hare Intl
Spirit Airlines
Feb 5
ORD3:56 pmChicago O'Hare Intl
20h 30m
1 stop
SJO12:26 pmSan José Juan Santamaria Intl
Feb 7
SJO1:57 amSan José Juan Santamaria Intl
18h 16m
1 stop
ORD8:13 pmChicago O'Hare Intl
Spirit Airlines
Feb 6
ORD3:56 pmChicago O'Hare Intl
9h 03m
1 stop
SJO12:59 amSan José Juan Santamaria Intl
Feb 11
SJO1:31 pmSan José Juan Santamaria Intl
10h 01m
1 stop
ORD11:32 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
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
Feb 14
MDW6:48 pmChicago Midway
16h 43m
1 stop
SJO11:31 amSan José Juan Santamaria Intl
Feb 22
SJO12:55 pmSan José Juan Santamaria Intl
9h 09m
1 stop
MDW10:04 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 February is your next best option. Flight prices from Chicago to San José, San José Province during February average around $527.

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 $478. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $691.

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 $646 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?

We recommend purchasing flights from Chicago to San José, San José Province 12 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to San José, San José Province for $566. Keep in mind that you might also find cheap flights to San José, San José Province outside of this time window. In fact, momondo users recently found flights from Chicago to San José, San José Province for $310.

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.

Can stopping save me money on Chicago to San José, San José Province flights?

You could potentially save up to 60% on your flight if you consider stops on a Chicago to San José, San José Province flight.

How have Chicago to San José, San José Province flight prices changed over time?

As of December 2024, prices for Chicago to San José, San José Province flights are approximately 100% 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

$117

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 $117. The best round-trip flight deal from Chicago to San José, San José Province found on momondo in the last 72 hours is $272.
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 54m 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 $240Free CancellationRating
6.3
8,107 reviews
Search Spirit Airlines flights
AviancaPriceFrom $250Free CancellationRating
7.0
2,639 reviews
Search Avianca flights
JetBluePriceFrom $345Free CancellationRating
7.4
3,260 reviews
Search JetBlue flights
Copa AirlinesPriceFrom $413Free CancellationRating
7.7
1,712 reviews
Search Copa Airlines flights
SouthwestPriceFrom $479Free CancellationRating
8.1
4,765 reviews
Search Southwest flights
DeltaPriceFrom $554Free CancellationRating
8.0
8,580 reviews
Search Delta flights
American AirlinesPriceFrom $565Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $579Free CancellationRating
7.4
9,009 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to San José, San José Province

    United Airlines 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 $815, but momondo users have found United Airlines deals from Chicago to San José, San José Province from as low as $579 round-trip. United Airlines has been scored 7.4/10 in 9,009 reviews.

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

    The best Avianca deal for Chicago to San José, San José Province flight tickets found on momondo in the last 72 hours was $250, round-trip. It should be noted that an average Avianca flight deal for this route in this time was higher, at $433 round-trip. Avianca operates 3 flights out of Chicago into San José, San José Province in an average week, so prices vary by time and availability. 2,639 Avianca reviews by users on momondo have scored the airline at 7.0/10.


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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