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

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

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

Monday 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 10% of their flights experiencing any sort of delay.

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

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

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

As of January 2026, there are 23 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Fri, with 26% of flights taking off on this day.

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 9:00AM, with 73% of daily flights taking off at noon.

What airlines fly to Costa Rica?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Costa Rica from Chicago according to our data. United 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.

How often are flights from Chicago to Costa Rica delayed?

Historically, on average around 10% 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 173 minutes.

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.

$90 Cheap Flights from Chicago to Costa Rica in 2026

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:39 am - 12:52 pm

ORD

SJO

26h 13m1 stop

2:07 pm - 12:01 am

SJO

ORD

8h 54m1 stop

$344Frontier

Thu, Apr 9 - Mon, Apr 13

5:15 am - 12:22 pm

ORD

SJO

7h 07m1 stop

1:30 pm - 11:47 pm

SJO

ORD

10h 17m1 stop

$345Spirit Airlines

Mon, Jan 19 - Thu, Feb 5

12:42 pm - 12:22 pm

ORD

SJO

23h 40m2 stops

5:45 am - 1:15 pm

SJO

ORD

7h 30m1 stop

$346Multiple Airlines

Wed, Jan 21 - Wed, Jan 28

7:34 am - 4:48 pm

ORD

SJO

9h 14m1 stop

10:08 am - 12:04 am

SJO

ORD

13h 56m1 stop

$347Copa Airlines

Wed, Feb 4 - Sat, Feb 14

6:00 am - 10:15 pm

MDW

SJO

16h 15m1 stop

2:25 pm - 10:31 pm

SJO

MDW

8h 06m1 stop

$359Delta

Sun, Feb 1 - Thu, Feb 12

8:55 am - 7:30 pm

MDW

SJO

10h 35m1 stop

9:40 am - 10:55 pm

SJO

MDW

13h 15m1 stop

$360Southwest

Tue, Feb 3 - Tue, Feb 10

6:00 am - 10:15 pm

MDW

SJO

16h 15m1 stop

2:31 pm - 12:46 pm

SJO

MDW

22h 15m2 stops

$364Delta

Sun, Feb 1 - Wed, Feb 11

8:45 pm - 2:45 pm

ORD

LIR

18h 00m1 stop

3:45 pm - 8:10 pm

LIR

ORD

28h 25m2 stops

$435Avianca

Thu, Jan 15 - Sun, Jan 18

8:45 pm - 2:45 pm

ORD

LIR

18h 00m1 stop

3:55 pm - 11:06 am

LIR

ORD

19h 11m1 stop

$458Avianca

Tue, Jan 6 - Thu, Jan 15

6:15 am - 2:15 pm

MDW

LIR

8h 00m1 stop

3:10 pm - 12:20 am

LIR

MDW

9h 10m2 stops

$480Southwest

Tue, Feb 3 - Thu, Feb 12

Frontier flights from Chicago to Costa Rica

Our best Frontier deals on Chicago to Costa Rica flight tickets

Frontier

Apr 9

ORD11:39 amChicago O'Hare Intl

26h 13m

1 stop

SJO12:52 pmSan José Juan Santamaria Intl

Apr 13

SJO2:07 pmSan José Juan Santamaria Intl

8h 54m

1 stop

ORD12:01 amChicago O'Hare Intl

$344

Find similar

Frontier

Jan 9

ORD4:49 pmChicago O'Hare Intl

19h 25m

1 stop

SJO12:14 pmSan José Juan Santamaria Intl

Jan 12

SJO2:58 pmSan José Juan Santamaria Intl

25h 54m

1 stop

ORD4:52 pmChicago O'Hare Intl

$378

Find similar

Frontier

Jan 5

MDW6:12 amChicago Midway

7h 30m

1 stop

SJO1:42 pmSan José Juan Santamaria Intl

Jan 10

SJO1:35 pmSan José Juan Santamaria Intl

8h 52m

1 stop

MDW10:27 pmChicago Midway

$379

Find similar

Avianca flights from Chicago to Costa Rica

Our best Avianca deals on Chicago to Costa Rica flight tickets

Avianca

Jan 20

ORD4:10 pmChicago O'Hare Intl

7h 30m

1 stop

SJO11:40 pmSan José Juan Santamaria Intl

Jan 31

SJO5:00 amSan José Juan Santamaria Intl

9h 50m

1 stop

ORD2:50 pmChicago O'Hare Intl

$348

Find similar

Avianca

Jan 17

ORD4:10 pmChicago O'Hare Intl

16h 30m

1 stop

SJO8:40 amSan José Juan Santamaria Intl

Jan 20

SJO5:00 amSan José Juan Santamaria Intl

9h 50m

1 stop

ORD2:50 pmChicago O'Hare Intl

$358

Find similar

Avianca

Jan 15

ORD8:45 pmChicago O'Hare Intl

18h 00m

1 stop

LIR2:45 pmLiberia

Jan 18

LIR3:45 pmLiberia

28h 25m

2 stops

ORD8:10 pmChicago O'Hare Intl

$435

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 4/9

11:39 am-12:52 pm

1 stop26h 13m

San José Juan Santamaria Intl

Mon 4/13

2:07 pm-12:01 am

1 stop8h 54m

$344

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 1/19

5:15 am-12:22 pm

1 stop7h 07m

San José Juan Santamaria Intl

Thu 2/5

1:30 pm-11:47 pm

1 stop10h 17m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 1/21

12:42 pm-12:22 pm

2 stops23h 40m

San José Juan Santamaria Intl

Wed 1/28

5:45 am-1:15 pm

1 stop7h 30m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/4

7:34 am-4:48 pm

1 stop9h 14m

San José Juan Santamaria Intl

Sat 2/14

10:08 am-12:04 am

1 stop13h 56m

$347

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/1

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Thu 2/12

2:25 pm-10:31 pm

1 stop8h 06m

$359

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 2/3

8:55 am-7:30 pm

1 stop10h 35m

San José Juan Santamaria Intl

Tue 2/10

9:40 am-10:55 pm

1 stop13h 15m

$360

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/1

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Wed 2/11

2:31 pm-12:46 pm

2 stops22h 15m

$364

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Thu 1/15

8:45 pm-2:45 pm

1 stop18h 00m

Liberia

Sun 1/18

3:45 pm-8:10 pm

2 stops28h 25m

$435

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Tue 1/6

8:45 pm-2:45 pm

1 stop18h 00m

Liberia

Thu 1/15

3:55 pm-11:06 am

1 stop19h 11m

$458

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 2/3

6:15 am-2:15 pm

1 stop8h 00m

Liberia

Thu 2/12

3:10 pm-12:20 am

2 stops9h 10m

$480

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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 $379.

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 $544. 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 $727. 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 $506. 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 $533 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 $438 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	$224
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 $224. The best round-trip flight deal from Chicago to Costa Rica found on momondo in the last 72 hours is $442.

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 46.32% of the total bookings. Other popular models include Boeing 737 MAX 9 with 27.46%, Boeing 737-900 with 17.10%, and Boeing 737-800 with 5.28%.

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 $221	Free Cancellation	Rating 7.9 8,023 reviews	Search Delta flights
Spirit Airlines	PriceFrom $257	Free Cancellation	Rating 6.3 8,265 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $307	Free Cancellation	Rating 6.6 2,497 reviews	Search Avianca flights
Copa Airlines	PriceFrom $309	Free Cancellation	Rating 7.6 1,565 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $344	Free Cancellation	Rating 7.2 11,081 reviews	Search American Airlines flights
Frontier	PriceFrom $345	Free Cancellation	Rating 5.7 3,063 reviews	Search Frontier flights
Southwest	PriceFrom $394	Free Cancellation	Rating 8.0 4,257 reviews	Search Southwest flights
United Airlines	PriceFrom $406	Free Cancellation	Rating 7.4 9,137 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 $145

Flights to Liberiafrom $222

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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 2/25. 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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Frontier flights from Chicago to Costa Rica

Our best Frontier deals on Chicago to Costa Rica flight tickets

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See travel insights to Costa Rica from

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?

Frontier, Spirit Airlines, and Air Canada 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 10% 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 173 minutes.

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

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

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

Monday 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 10% 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 9:00AM, with 73% 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 23 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Fri, with 26% 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