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Cheap flights from Chicago to Costa Rica from $90

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 Costa Rica departing on 10/17. 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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Cheap round-trip flights

Spirit Airlines Logo
11:57 am - 10:27 amORD-SJO
23h 30m2 stops
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
$252Spirit Airlines
Find Deal
ven., oct. 3 - mar., oct. 14
Spirit Airlines Logo
5:05 am - 11:14 amORD-SJO
7h 09m1 stop
Spirit Airlines Logo
11:37 am - 10:50 amSJO-ORD
22h 13m2 stops
$253Spirit Airlines
Find Deal
mar., sept. 30 - sam., oct. 4
Delta Logo
10:30 am - 12:00 pmORD-LIR
26h 30m2 stops
Delta Logo
1:05 pm - 12:40 pmLIR-ORD
22h 35m2 stops
$300Delta
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dim., oct. 26 - jeu., oct. 30
Delta Logo
5:30 am - 12:00 pmORD-LIR
7h 30m1 stop
Delta Logo
1:25 pm - 11:54 pmLIR-ORD
9h 29m1 stop
$309Delta
Find Deal
mar., sept. 30 - ven., oct. 3
American Airlines Logo
8:26 am - 1:37 pmORD-LIR
5h 11mnonstop
American Airlines Logo
2:37 pm - 8:15 pmLIR-ORD
5h 38mnonstop
$334American Airlines
Find Deal
sam., nov. 8 - sam., nov. 15
American Airlines Logo
5:18 am - 2:07 pmORD-LIR
8h 49m1 stop
American Airlines Logo
2:37 pm - 8:15 pmLIR-ORD
5h 38mnonstop
$339American Airlines
Find Deal
sam., nov. 8 - sam., nov. 15
United Airlines Logo
7:49 am - 12:55 pmORD-LIR
5h 06mnonstop
United Airlines Logo
8:35 am - 10:56 pmLIR-ORD
14h 21m1 stop
$344United Airlines
Find Deal
sam., déc. 6 - lun., déc. 15
Southwest Logo
9:00 am - 6:55 pmMDW-SJO
10h 55m2 stops
Southwest Logo
12:55 pm - 11:55 pmSJO-MDW
10h 00m2 stops
$345Southwest
Find Deal
mar., sept. 30 - ven., oct. 3
United Airlines Logo
8:49 am - 6:37 pmORD-LIR
9h 48m1 stop
United Airlines Logo
8:35 am - 7:46 pmLIR-ORD
11h 11m1 stop
$349United Airlines
Find Deal
sam., déc. 6 - lun., déc. 15
Southwest Logo
5:50 am - 1:15 pmMDW-SJO
7h 25m1 stop
Southwest Logo
9:00 am - 10:35 pmSJO-MDW
13h 35m2 stops
$349Southwest
Find Deal
jeu., nov. 6 - mar., nov. 11

Southwest flights from Chicago to Costa Rica

Our best Southwest deals on Chicago to Costa Rica flight tickets
Southwest
Sep 30
MDW6:25 amChicago Midway
13h 30m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Oct 4
SJO12:20 pmSan José Juan Santamaria Intl
7h 40m
1 stop
MDW9:00 pmChicago Midway
$340
Find similar
Southwest
Sep 30
MDW9:00 amChicago Midway
10h 55m
2 stops
SJO6:55 pmSan José Juan Santamaria Intl
Oct 3
SJO12:55 pmSan José Juan Santamaria Intl
10h 00m
2 stops
MDW11:55 pmChicago Midway
$345
Find similar
Southwest
Nov 6
MDW5:50 amChicago Midway
7h 25m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
Nov 11
SJO9:00 amSan José Juan Santamaria Intl
13h 35m
2 stops
MDW10:35 pmChicago Midway
$349
Find similar

Spirit Airlines flights from Chicago to Costa Rica

Our best Spirit Airlines deals on Chicago to Costa Rica flight tickets
Spirit Airlines
Oct 3
ORD11:57 amChicago O'Hare Intl
23h 30m
2 stops
SJO10:27 amSan José Juan Santamaria Intl
Oct 14
SJO12:35 pmSan José Juan Santamaria Intl
10h 10m
1 stop
ORD11:45 pmChicago O'Hare Intl
$252
Find similar
Spirit Airlines
Sep 30
ORD5:05 amChicago O'Hare Intl
7h 09m
1 stop
SJO11:14 amSan José Juan Santamaria Intl
Oct 4
SJO11:37 amSan José Juan Santamaria Intl
22h 13m
2 stops
ORD10:50 amChicago O'Hare Intl
$253
Find similar
Spirit Airlines
Dec 4
ORD8:41 amChicago O'Hare Intl
15h 40m
1 stop
SJO12:21 amSan José Juan Santamaria Intl
Dec 10
SJO1:19 pmSan José Juan Santamaria Intl
7h 41m
1 stop
ORD9:00 pmChicago O'Hare Intl
$254
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Costa Rica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated septembre 17, 2025.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

ven. 10/3

11:57 am-10:27 am

2 stops23h 30m

San José Juan Santamaria Intl

mar. 10/14

12:35 pm-11:45 pm

1 stop10h 10m

$252

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mar. 9/30

5:05 am-11:14 am

1 stop7h 09m

San José Juan Santamaria Intl

sam. 10/4

11:37 am-10:50 am

2 stops22h 13m

$253

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

dim. 10/26

10:30 am-12:00 pm

2 stops26h 30m

Liberia

jeu. 10/30

1:05 pm-12:40 pm

2 stops22h 35m

$300

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

mar. 9/30

5:30 am-12:00 pm

1 stop7h 30m

Liberia

ven. 10/3

1:25 pm-11:54 pm

1 stop9h 29m

$309

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

sam. 11/8

8:26 am-1:37 pm

Nonstop5h 11m

Liberia

sam. 11/15

2:37 pm-8:15 pm

Nonstop5h 38m

$334

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

sam. 11/8

5:18 am-2:07 pm

1 stop8h 49m

Liberia

sam. 11/15

2:37 pm-8:15 pm

Nonstop5h 38m

$339

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

sam. 12/6

7:49 am-12:55 pm

Nonstop5h 06m

Liberia

lun. 12/15

8:35 am-10:56 pm

1 stop14h 21m

$344

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 9/30

9:00 am-6:55 pm

2 stops10h 55m

San José Juan Santamaria Intl

ven. 10/3

12:55 pm-11:55 pm

2 stops10h 00m

$345

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

sam. 12/6

8:49 am-6:37 pm

1 stop9h 48m

Liberia

lun. 12/15

8:35 am-7:46 pm

1 stop11h 11m

$349

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

jeu. 11/6

5:50 am-1:15 pm

1 stop7h 25m

San José Juan Santamaria Intl

mar. 11/11

9:00 am-10:35 pm

2 stops13h 35m

$349

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Costa Rica from

How to get the cheapest flight ticket from Chicago to Costa Rica

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 cheapest month to fly to Costa Rica?

The cheapest month to fly to Costa Rica from Chicago is in September. Flight prices, which tend to average around $340, are often lower during this time because this is during the off-season. If you’re not able to fly to Costa Rica in September, then July is your next best option. Flight prices from Chicago to Costa Rica during July average around $455.

What is the cheapest day to depart on your flight to Costa Rica?

According to our data, Tuesday is the cheapest day to fly to Costa Rica from Chicago. The lowest ticket price found for a Tuesday departure recently was $541. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $815. These prices are subject to change though, so be sure to set up a Price Alert for flights to Costa Rica.

What is the cheapest time of day to depart on your flight to Costa Rica?

In the evening is the cheapest time of day to fly from Chicago to Costa Rica when you can find flight prices for as low as $436. Flying to Costa Rica in the evening is an ideal time because this is during off-peak travel hours. Flights to Costa Rica are more costly in the morning, with an average ticket price of $763. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Costa Rica flight route?

Fly from Chicago O'Hare Intl to San José Juan Santamaria Intl for the best Chicago - Costa Rica flight prices

How far in advance should I book a flight to Costa Rica?

You are more likely to see cheaper flights to Costa Rica from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Costa Rica for around $571 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Costa Rica from Chicago for as low as $445 on momondo.

What cabin class options are available on Chicago to Costa Rica flights?

There are 3 cabin classes available to choose from on Chicago to Costa Rica 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 Costa Rica flights?

You could potentially save up to 62% on your flight if you consider stops on a Chicago to Costa Rica flight.

Cheap Chicago to Costa Rica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Costa Rica

Best Price Found

$217

Fastest flight time

5h 00m

Direct flights

Every day

Airports in Costa Rica

2 airports
The best one-way flight to Costa Rica from Chicago in the past 72 hours is $217. The best round-trip flight deal from Chicago to Costa Rica found on momondo in the last 72 hours is $560.
The fastest flight from Chicago to Costa Rica takes 5h 00m
Direct flights go from Chicago to Costa Rica every day.
There are 2 airports near Costa Rica: Liberia (LIR), San José Juan Santamaria Intl (SJO)
Search flight deals

  • When did momondo last update prices for flights from Chicago to Costa Rica?

    Prices for flights from Chicago to Costa Rica are updated daily.

  • How many operators does momondo search for flights from Chicago to Costa Rica?

  • How old do you have to be to fly from Chicago to Costa Rica?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Costa Rica.

  • What documentation or ID do you need to fly to Costa Rica?

    The necessary travel and health documents for your Costa Rica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Costa Rica?

Best airlines flying from Chicago to Costa Rica

Compare and see reviews for airlines that fly from Chicago to Costa Rica with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $263Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
AviancaPriceFrom $307Free CancellationRating
6.7
2,436 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,533 reviews
Search Copa Airlines flights
FrontierPriceFrom $345Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
JetBluePriceFrom $432Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $442Free CancellationRating
7.9
7,961 reviews
Search Delta flights
American AirlinesPriceFrom $442Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $467Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Costa Rica?

Finding the right flight to Costa Rica from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Costa Rica quick and easy, saving you time and money.

Can I find flights from Chicago to Costa Rica with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Costa Rica flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Costa Rica?

Once all potential Chicago to Costa Rica flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Costa Rica right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Costa Rica, momondo offers a useful price alert feature which will track prices for flights to Costa Rica from Chicago and alert you when they change.

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