How many flights depart from Chicago to Costa Rica on average per week?

As of January 2026, there are 27 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Sun, with 22% of flights taking off on this day.

How often are flights from Chicago to Costa Rica delayed?

Historically, on average around 14% of flights between Chicago and Costa Rica have experienced a delay on any given week. The average delay length over the past 12 months has been 179 minutes.

What is the most punctual flight time for Chicago to Costa Rica flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

How many flights depart from Chicago to Costa Rica on average per day?

As of January 2026, 3 flights take off from Chicago and land in Costa Rica each day. The most common flight departure time for this route is 7:00AM, with 69% of daily flights taking off at noon.

Which airline has the best punctuality record on Chicago to Costa Rica flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

What is the cheapest airline that flies from Chicago to Costa Rica?

Spirit Airlines, Air Canada, and Southwest are the most popular carriers operating from Chicago to Costa Rica

What airlines fly to Costa Rica?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Costa Rica from Chicago according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Costa Rica. Keep in mind that there are 8 different airlines that fly to Costa Rica on a routine basis, so you have a few additional options to choose from.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Wednesday has historically seen more delays on average compared to the rest of the week.

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?

There are 8 operators available for flights from Chicago to Costa Rica as of January 2026.

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.

$129 Cheap Flights from Chicago to Costa Rica in 2026

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:22 pm - 9:06 am

ORD

SJO

18h 44m

1 stop

2:54 pm - 12:04 am

SJO

ORD

9h 10m

1 stop

$346Copa Airlines

Wed, Feb 25 - Sun, Mar 1

4:19 pm - 3:30 pm

ORD

SJO

23h 11m

2 stops

1:30 pm - 11:47 pm

SJO

ORD

10h 17m

1 stop

$347Multiple Airlines

Thu, Feb 5 - Sat, Feb 7

10:55 am - 11:40 pm

ORD

SJO

13h 45m

3 stops

7:45 am - 6:15 pm

SJO

ORD

9h 30m

1 stop

$348Multiple Airlines

Tue, Apr 14 - Thu, Apr 23

5:05 am - 11:19 am

ORD

SJO

7h 14m

1 stop

12:31 pm - 11:41 pm

SJO

ORD

10h 10m

1 stop

$350Spirit Airlines

Tue, Apr 14 - Wed, Apr 22

5:30 pm - 10:30 pm

ORD

SJO

5h 00mnonstop

7:09 am - 12:38 pm

SJO

ORD

5h 29mnonstop

$351American Airlines

Thu, Feb 5 - Mon, Feb 9

4:43 pm - 11:40 am

ORD

SJO

18h 57m

2 stops

11:35 am - 11:47 pm

SJO

ORD

11h 12m

2 stops

$352Spirit Airlines

Thu, Mar 5 - Wed, Mar 11

7:55 pm - 2:15 pm

MDW

LIR

18h 20m

2 stops

3:25 pm - 10:55 pm

LIR

MDW

7h 30m

1 stop

$450Southwest

Wed, Feb 18 - Wed, Feb 25

6:15 am - 2:30 pm

MDW

LIR

8h 15m

1 stop

3:25 pm - 10:55 pm

LIR

MDW

7h 30m

1 stop

$475Southwest

Wed, Feb 18 - Wed, Feb 25

6:00 am - 1:50 pm

MDW

LIR

7h 50m

1 stop

2:05 pm - 10:31 pm

LIR

MDW

8h 26m

1 stop

$490Delta

Mon, Feb 23 - Fri, Feb 27

6:00 am - 1:50 pm

MDW

LIR

7h 50m

1 stop

3:05 pm - 10:31 pm

LIR

MDW

7h 26m

1 stop

$494Delta

Mon, Feb 9 - Thu, Feb 19

Spirit Airlines flights from Chicago to Costa Rica

Our best Spirit Airlines deals on Chicago to Costa Rica flight tickets

Spirit Airlines

Apr 14

ORD5:05 amChicago O'Hare Intl

7h 14m

1 stop

SJO11:19 amSan José Juan Santamaria Intl

Apr 22

SJO12:31 pmSan José Juan Santamaria Intl

10h 10m

1 stop

ORD11:41 pmChicago O'Hare Intl

$350

Spirit Airlines

Mar 5

ORD4:43 pmChicago O'Hare Intl

18h 57m

2 stops

SJO11:40 amSan José Juan Santamaria Intl

Mar 11

SJO11:35 amSan José Juan Santamaria Intl

11h 12m

2 stops

ORD11:47 pmChicago O'Hare Intl

$352

Spirit Airlines

Mar 10

ORD8:16 pmChicago O'Hare Intl

15h 24m

2 stops

SJO10:40 amSan José Juan Santamaria Intl

Mar 18

SJO12:24 pmSan José Juan Santamaria Intl

9h 53m

1 stop

ORD11:17 pmChicago O'Hare Intl

$356

Copa Airlines flights from Chicago to Costa Rica

Our best Copa Airlines deals on Chicago to Costa Rica flight tickets

Copa Airlines

Feb 25

ORD2:22 pmChicago O'Hare Intl

19h 38m

1 stop

SJO10:00 amSan José Juan Santamaria Intl

Mar 1

SJO2:54 pmSan José Juan Santamaria Intl

9h 10m

1 stop

ORD12:04 amChicago O'Hare Intl

$346

Copa Airlines

Feb 4

ORD7:34 amChicago O'Hare Intl

11h 28m

1 stop

SJO7:02 pmSan José Juan Santamaria Intl

Feb 9

SJO5:50 amSan José Juan Santamaria Intl

18h 14m

1 stop

ORD12:04 amChicago O'Hare Intl

$359

Copa Airlines

Feb 4

ORD2:22 pmChicago O'Hare Intl

16h 44m

1 stop

SJO7:06 amSan José Juan Santamaria Intl

Feb 8

SJO4:09 amSan José Juan Santamaria Intl

8h 22m

1 stop

ORD12:31 pmChicago O'Hare Intl

$382

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/25

2:22 pm-9:06 am

1 stop18h 44m

San José Juan Santamaria Intl

Sun 3/1

2:54 pm-12:04 am

1 stop9h 10m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/5

4:19 pm-3:30 pm

2 stops23h 11m

San José Juan Santamaria Intl

Sat 2/7

1:30 pm-11:47 pm

1 stop10h 17m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 4/14

10:55 am-11:40 pm

3 stops13h 45m

San José Juan Santamaria Intl

Thu 4/23

7:45 am-6:15 pm

1 stop9h 30m

$348

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 4/14

5:05 am-11:19 am

1 stop7h 14m

San José Juan Santamaria Intl

Wed 4/22

12:31 pm-11:41 pm

1 stop10h 10m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/5

5:30 pm-10:30 pm

Nonstop5h 00m

San José Juan Santamaria Intl

Mon 2/9

7:09 am-12:38 pm

Nonstop5h 29m

$351

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 3/5

4:43 pm-11:40 am

2 stops18h 57m

San José Juan Santamaria Intl

Wed 3/11

11:35 am-11:47 pm

2 stops11h 12m

$352

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Wed 2/18

7:55 pm-2:15 pm

2 stops18h 20m

Liberia

Wed 2/25

3:25 pm-10:55 pm

1 stop7h 30m

$450

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Wed 2/18

6:15 am-2:30 pm

1 stop8h 15m

Liberia

Wed 2/25

3:25 pm-10:55 pm

1 stop7h 30m

$475

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Mon 2/23

6:00 am-1:50 pm

1 stop7h 50m

Liberia

Fri 2/27

2:05 pm-10:31 pm

1 stop8h 26m

$490

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Mon 2/9

6:00 am-1:50 pm

1 stop7h 50m

Liberia

Thu 2/19

3:05 pm-10:31 pm

1 stop7h 26m

$494

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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

Prices

Airlines

Delays

Other information

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 $315, 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 October is your next best option. Flight prices from Chicago to Costa Rica during October average around $381.

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 $525. 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 $721. 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 afternoon is the cheapest time of day to fly from Chicago to Costa Rica when you can find flight prices for as low as $505. Flying to Costa Rica in the afternoon is an ideal time because this is during off-peak travel hours. Flights to Costa Rica are more costly at noon, with an average ticket price of $664. Departure times at noon 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 $524 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 $465 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 36% 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	$280
Fastest flight time	5h 00m
Direct flights	Every day
Airports in Costa Rica	40 airports

The best one-way flight to Costa Rica from Chicago in the past 72 hours is $280. The best round-trip flight deal from Chicago to Costa Rica found on momondo in the last 72 hours is $419.

The fastest flight from Chicago to Costa Rica takes 5h 00m

Direct flights go from Chicago to Costa Rica every day.

There are 40 airports in Costa Rica. From Chicago there are direct flights to 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?
There are 8 operators available for flights from Chicago to Costa Rica as of January 2026.
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?
Based on momondo bookings for flights between Chicago and Costa Rica, the leading plane model is Boeing 737 MAX 8, making up 47.36% of the total bookings. Other popular models include Boeing 737 MAX 9 with 22.48%, Boeing 737-900 with 13.23%, and Boeing 737-800 with 11.93%.

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
Delta	PriceFrom $206	Free Cancellation	Rating 7.9 8,112 reviews	Search Delta flights
Avianca	PriceFrom $250	Free Cancellation	Rating 6.6 2,493 reviews	Search Avianca flights
Spirit Airlines	PriceFrom $255	Free Cancellation	Rating 6.3 8,370 reviews	Search Spirit Airlines flights
Copa Airlines	PriceFrom $256	Free Cancellation	Rating 7.6 1,558 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $340	Free Cancellation	Rating 7.2 11,193 reviews	Search American Airlines flights
Frontier	PriceFrom $345	Free Cancellation	Rating 5.7 3,058 reviews	Search Frontier flights
Southwest	PriceFrom $394	Free Cancellation	Rating 8.0 4,268 reviews	Search Southwest flights
United Airlines	PriceFrom $397	Free Cancellation	Rating 7.4 9,193 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.

An easier way to manage your Costa Rica 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.

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Popular cities in Costa Rica

Flights to San Joséfrom $146

Flights to Liberiafrom $224

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Cheap flights from Chicago to Costa Rica from $129

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 3/9. 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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Spirit Airlines flights from Chicago to Costa Rica

Our best Spirit Airlines deals on Chicago to Costa Rica flight tickets

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

What is the cheapest month to fly to Costa Rica?

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

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

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?

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 36% on your flight if you consider stops on a Chicago to Costa Rica flight.

What is the cheapest airline that flies from Chicago to Costa Rica?

Spirit Airlines, Air Canada, and Southwest are the most popular carriers operating from Chicago to Costa Rica

What airlines fly to Costa Rica?

How often are flights from Chicago to Costa Rica delayed?

Historically, on average around 14% of flights between Chicago and Costa Rica have experienced a delay on any given week. The average delay length over the past 12 months has been 179 minutes.

What is the most punctual flight time for Chicago to Costa Rica flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Wednesday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Costa Rica flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

How many flights depart from Chicago to Costa Rica on average per day?

As of January 2026, 3 flights take off from Chicago and land in Costa Rica each day. The most common flight departure time for this route is 7:00AM, with 69% of daily flights taking off at noon.

How many flights depart from Chicago to Costa Rica on average per week?

As of January 2026, there are 27 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Sun, with 22% of flights taking off on this day.

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

Fastest flight time

Direct flights

Airports in Costa Rica

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

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?

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

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

Why use momondo?

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

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

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

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

An easier way to manage your Costa Rica 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.

Find better results for your trip to Costa Rica

Popular cities in Costa Rica

Popular flights according to clicks in the last 7 days on momondo