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Cheap flights from Chicago to San José, San José Province from $142

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 1/25. 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.
5:10 am - 12:26 pmORD-SJO
7h 16m1 stop
1:31 pm - 11:02 pmSJO-ORD
9h 31m1 stop
$272Spirit Airlines
Find Deal
Tue, Jan 14 - Tue, Feb 4
5:10 am - 12:26 pmORD-SJO
7h 16m1 stop
1:57 am - 11:02 pmSJO-ORD
21h 05m1 stop
$280Spirit Airlines
Find Deal
Wed, Jan 15 - Mon, Jan 27
3:22 pm - 12:59 amORD-SJO
9h 37m1 stop
2:53 pm - 4:37 amSJO-ORD
13h 44m1 stop
Tue, Feb 11 - Tue, Feb 25
12:48 am - 1:57 pmORD-SJO
13h 09m1 stop
2:53 pm - 4:37 amSJO-ORD
13h 44m1 stop
Mon, Feb 10 - Tue, Feb 25
2:35 pm - 11:20 pmORD-SJO
8h 45m2 stops
8:30 pm - 1:15 pmSJO-ORD
16h 45m2 stops
$401Avianca
Find Deal
Fri, Dec 6 - Thu, Dec 12
2:35 pm - 9:20 amORD-SJO
18h 45m1 stop
7:50 pm - 1:15 pmSJO-ORD
17h 25m2 stops
$422Avianca
Find Deal
Sun, Jan 12 - Tue, Jan 21
5:35 am - 12:55 pmMDW-SJO
7h 20m1 stop
8:45 am - 10:20 pmSJO-MDW
12h 35m2 stops
$518Southwest
Find Deal
Sun, Mar 2 - Wed, Mar 12
8:40 am - 8:40 pmMDW-SJO
12h 00m2 stops
1:40 pm - 8:40 amSJO-MDW
19h 00m2 stops
$522Southwest
Find Deal
Fri, Dec 6 - Thu, Dec 12
6:00 am - 12:48 pmMDW-SJO
6h 48m1 stop
7:00 am - 5:01 pmSJO-MDW
10h 01m2 stops
$625Delta
Find Deal
Sat, Dec 7 - Wed, Dec 11
3:19 pm - 9:53 pmMDW-SJO
6h 34m1 stop
7:00 am - 4:12 pmSJO-MDW
9h 12m1 stop
$636Delta
Find Deal
Mon, Dec 2 - Tue, Dec 10
4:27 pm - 12:26 pmORD-SJO
19h 59m2 stops
$142Spirit Airlines
Find Deal
Sat, Jan 25
12:48 am - 1:57 pmORD-SJO
13h 09m1 stop
Wed, Feb 19
7:25 am - 12:33 pmORD-SJO
29h 08m2 stops
Sat, Feb 22
2:35 pm - 10:55 pmORD-SJO
8h 20m1 stop
$200Avianca
Find Deal
Fri, Jan 17
1:35 pm - 9:20 amORD-SJO
19h 45m1 stop
$205Avianca
Find Deal
Tue, Nov 26
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$295United Airlines
Find Deal
Sat, Nov 30
10:38 am - 9:57 pmMDW-SJO
11h 19m1 stop
$297Delta
Find Deal
Tue, Dec 10
6:00 am - 12:48 pmMDW-SJO
6h 48m1 stop
$299Delta
Find Deal
Tue, Dec 10
3:04 pm - 8:07 amORD-SJO
18h 03m1 stop
$311Copa Airlines
Find Deal
Fri, Mar 14
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$340United Airlines
Find Deal
Sun, Dec 8
2:42 am - 11:11 pmORD-SJO
20h 29m1 stop
2:53 pm - 4:37 amSJO-ORD
13h 44m1 stop
Mon, Nov 25 - Wed, Dec 11
2:42 am - 11:11 pmORD-SJO
20h 29m1 stop
1:49 am - 10:32 amSJO-ORD
8h 43m1 stop
Mon, Nov 25 - Tue, Dec 10
1:35 pm - 9:20 amORD-SJO
19h 45m1 stop
4:55 pm - 12:15 pmSJO-ORD
19h 20m1 stop
$496Avianca
Find Deal
Tue, Nov 26 - Tue, Dec 3
1:35 pm - 12:15 amORD-SJO
10h 40m1 stop
2:15 am - 12:15 pmSJO-ORD
10h 00m1 stop
$502Avianca
Find Deal
Mon, Nov 25 - Tue, Nov 26
6:00 am - 11:31 amORD-SJO
29h 31m3 stops
1:24 pm - 12:18 pmSJO-ORD
22h 54m2 stops
$573Spirit Airlines
Find Deal
Tue, Nov 26 - Wed, Dec 11
7:00 am - 8:55 pmORD-SJO
13h 55m1 stop
6:30 am - 7:23 amSJO-ORD
24h 53m1 stop
$717American Airlines
Find Deal
Mon, Nov 25 - Fri, Nov 29
6:20 pm - 11:25 amORD-SJO
17h 05m1 stop
2:20 pm - 11:59 pmSJO-ORD
9h 39m1 stop
$726United Airlines
Find Deal
Sun, Nov 24 - Mon, Dec 2
9:32 pm - 8:39 pmORD-SJO
23h 07m1 stop
2:20 pm - 10:44 pmSJO-ORD
8h 24m1 stop
$740United Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
7:39 pm - 12:26 pmORD-SJO
16h 47m1 stop
1:56 am - 8:03 pmSJO-ORD
18h 07m1 stop
$746Spirit Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
7:00 am - 8:55 pmORD-SJO
13h 55m2 stops
7:00 am - 7:08 pmSJO-ORD
12h 08m2 stops
$767American Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$558Avianca
Find Deal
Wed, Dec 4 - Sun, Dec 8
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$570Avianca
Find Deal
Wed, Jan 15 - Fri, Jan 24
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$622United Airlines
Find Deal
Sun, Dec 1 - Sat, Dec 14
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$626Avianca
Find Deal
Fri, Dec 13 - Fri, Dec 20
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$666Avianca
Find Deal
Sun, Dec 15 - Sun, Dec 22
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$687United Airlines
Find Deal
Sun, Jan 12 - Sat, Jan 18
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$712United Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
$714Avianca
Find Deal
Sun, Dec 1 - Wed, Dec 4
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$742United Airlines
Find Deal
Sat, Dec 14 - Sun, Jan 12
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$812United Airlines
Find Deal
Sun, Jan 12 - Sat, Jan 18

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
Dec 6
ORD2:35 pmChicago O'Hare Intl
8h 45m
2 stops
SJO11:20 pmSan José Juan Santamaria Intl
Dec 12
SJO8:30 pmSan José Juan Santamaria Intl
16h 45m
2 stops
ORD1:15 pmChicago O'Hare Intl
Avianca
Jan 12
ORD2:35 pmChicago O'Hare Intl
18h 45m
1 stop
SJO9:20 amSan José Juan Santamaria Intl
Jan 21
SJO7:50 pmSan José Juan Santamaria Intl
17h 25m
2 stops
ORD1:15 pmChicago O'Hare Intl
Avianca
Jan 17
ORD2:35 pmChicago O'Hare Intl
8h 20m
1 stop
SJO10:55 pmSan José Juan Santamaria Intl
Jan 27
SJO4:55 pmSan José Juan Santamaria Intl
19h 20m
1 stop
ORD12:15 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
Mar 2
MDW5:35 amChicago Midway
7h 20m
1 stop
SJO12:55 pmSan José Juan Santamaria Intl
Mar 12
SJO8:45 amSan José Juan Santamaria Intl
12h 35m
2 stops
MDW10:20 pmChicago Midway
Southwest
Dec 6
MDW8:40 amChicago Midway
12h 00m
2 stops
SJO8:40 pmSan José Juan Santamaria Intl
Dec 12
SJO1:40 pmSan José Juan Santamaria Intl
19h 00m
2 stops
MDW8:40 amChicago Midway
Southwest
Feb 26
MDW5:45 amChicago Midway
7h 10m
1 stop
SJO12:55 pmSan José Juan Santamaria Intl
Mar 4
SJO9:55 amSan José Juan Santamaria Intl
8h 55m
2 stops
MDW6:50 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 $476. 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 $497.

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 $452. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $686.

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 $468. 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 37 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 $574. 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 $307.

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 49% 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 November 2024, prices for Chicago to San José, San José Province flights are approximately 9% 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

$142

Fastest flight time

5h 21m

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 $142. 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 21m
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 34m 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 $237Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
AviancaPriceFrom $238Free CancellationRating
7.0
2,794 reviews
Search Avianca flights
JetBluePriceFrom $345Free CancellationRating
7.4
3,389 reviews
Search JetBlue flights
Copa AirlinesPriceFrom $406Free CancellationRating
7.7
1,779 reviews
Search Copa Airlines flights
SouthwestPriceFrom $479Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $550Free CancellationRating
8.0
8,755 reviews
Search Delta flights
American AirlinesPriceFrom $565Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $581Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
AeromexicoPriceFrom $676Free CancellationRating
7.5
2,004 reviews
Search Aeromexico flights

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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