What is the most punctual flight time for $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

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

Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

According to our data, Qatar Airways have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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

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

How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?

Historically, on average around 11% of flights between $[0, place:'genitive'] and $[1, place:'genitive'] have experienced a delay on any given week. The average delay length over the past 12 months has been 196 minutes.

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

As of November 2025, there are 6 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.

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 38% of people opting to fly with this airline when traveling to Costa Rica. Keep in mind that there are 9 different airlines that fly to Costa Rica on a routine basis, so you have a few additional options to choose from.

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 9 operators available for flights from Chicago to Costa Rica as of November 2025.

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 2025/26

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Find the cheapest flights from Chicago to Costa Rica

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:22 pm - 12:22 pmORD-SJO

16h 00m1 stop

1:30 pm - 11:46 pmSJO-ORD

10h 16m1 stop

$285Spirit Airlines

Find Deal

Thu, Jan 22 - Mon, Jan 26

7:29 am - 12:22 pmORD-SJO

28h 53m1 stop

12:33 pm - 11:46 pmSJO-ORD

11h 13m2 stops

$286Spirit Airlines

Find Deal

Tue, Feb 3 - Tue, Feb 10

5:00 am - 12:25 pmORD-SJO

7h 25m1 stop

8:07 am - 10:11 pmSJO-ORD

14h 04m2 stops

$287Multiple Airlines

Find Deal

Sat, Dec 6 - Sat, Dec 13

8:51 pm - 11:37 amORD-SJO

14h 46m1 stop

1:30 pm - 11:46 pmSJO-ORD

10h 16m1 stop

$293Multiple Airlines

Find Deal

Sun, Jan 18 - Mon, Jan 26

6:10 am - 1:43 pmMDW-SJO

7h 33m1 stop

1:35 pm - 10:17 pmSJO-MDW

8h 42m1 stop

$311Frontier

Find Deal

Fri, Jan 9 - Sat, Jan 10

6:00 am - 1:52 pmMDW-SJO

7h 52m1 stop

3:07 pm - 6:12 pmSJO-MDW

27h 05m1 stop

$334Frontier

Find Deal

Sat, Dec 6 - Sat, Dec 13

9:14 pm - 1:45 pmORD-LIR

17h 31m1 stop

2:45 pm - 1:01 pmLIR-ORD

21h 16m1 stop

$393Air Canada

Find Deal

Sun, Mar 22 - Fri, Mar 27

9:14 pm - 1:45 pmORD-LIR

17h 31m1 stop

2:45 pm - 5:48 pmLIR-ORD

26h 03m1 stop

$394Air Canada

Find Deal

Sun, Mar 22 - Fri, Mar 27

6:15 am - 2:30 pmMDW-LIR

8h 15m1 stop

2:05 pm - 11:55 pmLIR-MDW

8h 50m1 stop

$398Southwest

Find Deal

Tue, Mar 3 - Tue, Mar 10

8:50 pm - 2:15 pmMDW-LIR

17h 25m2 stops

3:25 pm - 10:55 pmLIR-MDW

7h 30m1 stop

$403Southwest

Find Deal

Sun, Feb 1 - Wed, Feb 11

Frontier flights from Chicago to Costa Rica

Our best Frontier deals on Chicago to Costa Rica flight tickets

Frontier

Jan 9

MDW6:10 amChicago Midway

7h 33m

1 stop

SJO1:43 pmSan José Juan Santamaria Intl

Jan 10

SJO1:35 pmSan José Juan Santamaria Intl

8h 42m

1 stop

MDW10:17 pmChicago Midway

$311

Find similar

Frontier

Dec 6

MDW6:00 amChicago Midway

7h 52m

1 stop

SJO1:52 pmSan José Juan Santamaria Intl

Dec 13

SJO3:07 pmSan José Juan Santamaria Intl

27h 05m

1 stop

MDW6:12 pmChicago Midway

$334

Find similar

Frontier

Dec 31

MDW6:12 amChicago Midway

7h 30m

1 stop

SJO1:42 pmSan José Juan Santamaria Intl

Jan 7

SJO3:10 pmSan José Juan Santamaria Intl

20h 21m

1 stop

MDW11:31 amChicago Midway

$383

Find similar

Delta flights from Chicago to Costa Rica

Our best Delta deals on Chicago to Costa Rica flight tickets

Delta

Jan 19

MDW10:46 amChicago Midway

11h 29m

1 stop

SJO10:15 pmSan José Juan Santamaria Intl

Jan 30

SJO7:00 amSan José Juan Santamaria Intl

10h 29m

1 stop

MDW5:29 pmChicago Midway

$410

Find similar

Delta

Jan 19

MDW9:32 amChicago Midway

12h 43m

2 stops

SJO10:15 pmSan José Juan Santamaria Intl

Jan 30

SJO7:00 amSan José Juan Santamaria Intl

10h 29m

1 stop

MDW5:29 pmChicago Midway

$414

Find similar

Delta

Feb 9

MDW10:46 amChicago Midway

11h 29m

1 stop

SJO10:15 pmSan José Juan Santamaria Intl

Feb 23

SJO7:00 amSan José Juan Santamaria Intl

10h 45m

1 stop

MDW5:45 pmChicago Midway

$440

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 1/22

8:22 pm-12:22 pm

1 stop16h 00m

San José Juan Santamaria Intl

Mon 1/26

1:30 pm-11:46 pm

1 stop10h 16m

$285

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/3

7:29 am-12:22 pm

1 stop28h 53m

San José Juan Santamaria Intl

Tue 2/10

12:33 pm-11:46 pm

2 stops11h 13m

$286

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 12/6

5:00 am-12:25 pm

1 stop7h 25m

San José Juan Santamaria Intl

Sat 12/13

8:07 am-10:11 pm

2 stops14h 04m

$287

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 1/18

8:51 pm-11:37 am

1 stop14h 46m

San José Juan Santamaria Intl

Mon 1/26

1:30 pm-11:46 pm

1 stop10h 16m

$293

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 1/9

6:10 am-1:43 pm

1 stop7h 33m

San José Juan Santamaria Intl

Sat 1/10

1:35 pm-10:17 pm

1 stop8h 42m

$311

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 12/6

6:00 am-1:52 pm

1 stop7h 52m

San José Juan Santamaria Intl

Sat 12/13

3:07 pm-6:12 pm

1 stop27h 05m

$334

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 3/22

9:14 pm-1:45 pm

1 stop17h 31m

Liberia

Fri 3/27

2:45 pm-1:01 pm

1 stop21h 16m

$393

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 3/22

9:14 pm-1:45 pm

1 stop17h 31m

Liberia

Fri 3/27

2:45 pm-5:48 pm

1 stop26h 03m

$394

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 3/3

6:15 am-2:30 pm

1 stop8h 15m

Liberia

Tue 3/10

2:05 pm-11:55 pm

1 stop8h 50m

$398

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sun 2/1

8:50 pm-2:15 pm

2 stops17h 25m

Liberia

Wed 2/11

3:25 pm-10:55 pm

1 stop7h 30m

$403

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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 $314, 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 $542. 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 $770. 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 $736. 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 $544 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 $434 on momondo.

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

There are 2 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 8% 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 $396.

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?
There are 9 operators available for flights from Chicago to Costa Rica as of November 2025.
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 48.07% of the total bookings. Other popular models include Boeing 737-900 with 22.60%, Boeing 737 MAX 9 with 21.60%, and Boeing 737-800 with 3.58%.

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 8,002 reviews	Search Delta flights
Spirit Airlines	PriceFrom $259	Free Cancellation	Rating 6.3 8,160 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $307	Free Cancellation	Rating 6.6 2,477 reviews	Search Avianca flights
Copa Airlines	PriceFrom $314	Free Cancellation	Rating 7.6 1,566 reviews	Search Copa Airlines flights
Frontier	PriceFrom $345	Free Cancellation	Rating 5.8 3,104 reviews	Search Frontier flights
American Airlines	PriceFrom $347	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $394	Free Cancellation	Rating 8.0 4,251 reviews	Search Southwest flights
United Airlines	PriceFrom $431	Free Cancellation	Rating 7.4 9,028 reviews	Search United Airlines flights
JetBlue	PriceFrom $432	Free Cancellation	Rating 7.2 2,902 reviews	Search JetBlue 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 $143

Flights to Liberiafrom $210

Flights to Limon

Flights to Tamarindo

Flights to Golfito

Flights to Buenos Aires, Puntarenas

Flights to Palmar Sur

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 1/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Price Alerts

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Find the cheapest flights from Chicago to Costa Rica

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Frontier flights from Chicago to Costa Rica

Our best Frontier deals on Chicago to Costa Rica flight tickets

Delta flights from Chicago to Costa Rica

Our best Delta 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

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?

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 2 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 8% 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, Frontier, and Air Canada are the most popular carriers operating from Chicago to Costa Rica

What airlines fly to Costa Rica?

How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?

Historically, on average around 11% of flights between $[0, place:'genitive'] and $[1, place:'genitive'] have experienced a delay on any given week. The average delay length over the past 12 months has been 196 minutes.

What is the most punctual flight time for $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

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

Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

According to our data, Qatar Airways have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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

As of November 2025, there are 6 flights per week flying from Chicago to Costa Rica. The most common day of the week flights depart is Mon, with 17% 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