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

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

According to our data, American 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 airlines fly to Chicago?

American Airlines, United Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from Costa Rica according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago 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. Monday has historically seen more delays on average compared to the rest of the week.

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

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

How often are flights from Costa Rica to Chicago delayed?

Historically, on average around 12% of flights between Costa Rica and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 167 minutes.

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

As of November 2025, 6 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Sat, with 33% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

Average flight duration from Costa Rica to Chicago depends on which airport you fly into and out of. Flying from Liberia to Chicago O'Hare Intl Airport is 5h 19m on average, while flying from San José to Chicago O'Hare Intl Airport is 5h 29m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

Prices for flights from Costa Rica to Chicago refresh daily.

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

The number of operators available for flights from Costa Rica to Chicago is 6 as of November 2025.

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

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 Costa Rica to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$115 Cheap Flights from Costa Rica to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Costa Rica to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Costa Rica to Chicago

Enter your travel dates to find the best prices.

10:36 am - 9:04 pmSJO-MDW

10h 28m1 stop

6:12 am - 1:42 pmMDW-SJO

7h 30m1 stop

$262Frontier

Find Deal

Sat, Dec 27 - Fri, Jan 2

1:30 pm - 10:36 pmSJO-ORD

9h 06m1 stop

9:23 am - 3:30 pmORD-SJO

30h 07m1 stop

$263Multiple Airlines

Find Deal

Thu, Jan 22 - Tue, Jan 27

1:30 pm - 8:18 amSJO-ORD

18h 48m1 stop

5:15 am - 12:22 pmORD-SJO

7h 07m1 stop

$264Spirit Airlines

Find Deal

Fri, Jan 23 - Mon, Jan 26

1:30 pm - 10:36 pmSJO-ORD

9h 06m1 stop

2:15 pm - 12:22 pmORD-SJO

22h 07m2 stops

$265Multiple Airlines

Find Deal

Thu, Jan 29 - Fri, Feb 20

1:31 pm - 12:30 amSJO-ORD

10h 59m1 stop

2:26 pm - 1:48 pmORD-SJO

23h 22m1 stop

$267Multiple Airlines

Find Deal

Tue, Dec 23 - Tue, Jan 6

12:33 pm - 2:17 pmSJO-ORD

25h 44m2 stops

3:22 pm - 11:37 amORD-SJO

20h 15m2 stops

$269Spirit Airlines

Find Deal

Fri, Jan 30 - Mon, Feb 9

1:30 pm - 10:03 pmSJO-ORD

8h 33m1 stop

5:32 pm - 12:22 pmORD-SJO

18h 50m1 stop

$270Spirit Airlines

Find Deal

Sat, Jan 31 - Wed, Feb 18

3:55 pm - 11:06 amLIR-ORD

19h 11m1 stop

8:45 pm - 2:45 pmORD-LIR

18h 00m1 stop

$308Air Canada

Find Deal

Tue, Jan 20 - Sun, Jan 25

3:55 pm - 8:10 pmLIR-ORD

28h 15m1 stop

8:45 pm - 2:45 pmORD-LIR

18h 00m1 stop

$317Air Canada

Find Deal

Tue, Jan 20 - Sun, Jan 25

7:00 am - 5:29 pmSJO-MDW

10h 29m1 stop

9:33 am - 10:15 pmMDW-SJO

12h 42m2 stops

$344Delta

Find Deal

Wed, Jan 21 - Wed, Jan 28

Spirit Airlines flights from Costa Rica to Chicago

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

Spirit Airlines

Jan 23

SJO1:30 pmSan José Juan Santamaria Intl

18h 48m

1 stop

ORD8:18 amChicago O'Hare Intl

Jan 26

ORD5:15 amChicago O'Hare Intl

7h 07m

1 stop

SJO12:22 pmSan José Juan Santamaria Intl

$264

Find similar

Spirit Airlines

Jan 30

SJO12:33 pmSan José Juan Santamaria Intl

25h 44m

2 stops

ORD2:17 pmChicago O'Hare Intl

Feb 9

ORD3:22 pmChicago O'Hare Intl

20h 15m

2 stops

SJO11:37 amSan José Juan Santamaria Intl

$269

Find similar

Spirit Airlines

Jan 31

SJO1:30 pmSan José Juan Santamaria Intl

8h 33m

1 stop

ORD10:03 pmChicago O'Hare Intl

Feb 18

ORD5:32 pmChicago O'Hare Intl

18h 50m

1 stop

SJO12:22 pmSan José Juan Santamaria Intl

$270

Find similar

Air Canada flights from Costa Rica to Chicago

Our best Air Canada deals on Costa Rica to Chicago flight tickets

Air Canada

Jan 20

LIR3:55 pmLiberia

19h 11m

1 stop

ORD11:06 amChicago O'Hare Intl

Jan 25

ORD8:45 pmChicago O'Hare Intl

18h 00m

1 stop

LIR2:45 pmLiberia

$308

Find similar

Air Canada

Jan 20

LIR3:55 pmLiberia

28h 15m

1 stop

ORD8:10 pmChicago O'Hare Intl

Jan 25

ORD8:45 pmChicago O'Hare Intl

18h 00m

1 stop

LIR2:45 pmLiberia

$317

Find similar

Air Canada

Jan 13

LIR3:45 pmLiberia

30h 20m

1 stop

ORD10:05 pmChicago O'Hare Intl

Jan 15

ORD10:00 amChicago O'Hare Intl

28h 45m

1 stop

LIR2:45 pmLiberia

$334

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/27

10:36 am-9:04 pm

1 stop10h 28m

Chicago Midway

Fri 1/2

6:12 am-1:42 pm

1 stop7h 30m

$262

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/22

1:30 pm-10:36 pm

1 stop9h 06m

Chicago O'Hare Intl

Tue 1/27

9:23 am-3:30 pm

1 stop30h 07m

$263

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 1/23

1:30 pm-8:18 am

1 stop18h 48m

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:22 pm

1 stop7h 07m

$264

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/29

1:30 pm-10:36 pm

1 stop9h 06m

Chicago O'Hare Intl

Fri 2/20

2:15 pm-12:22 pm

2 stops22h 07m

$265

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 12/23

1:31 pm-12:30 am

1 stop10h 59m

Chicago O'Hare Intl

Tue 1/6

2:26 pm-1:48 pm

1 stop23h 22m

$267

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 1/30

12:33 pm-2:17 pm

2 stops25h 44m

Chicago O'Hare Intl

Mon 2/9

3:22 pm-11:37 am

2 stops20h 15m

$269

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 1/31

1:30 pm-10:03 pm

1 stop8h 33m

Chicago O'Hare Intl

Wed 2/18

5:32 pm-12:22 pm

1 stop18h 50m

$270

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 1/20

3:55 pm-11:06 am

1 stop19h 11m

Chicago O'Hare Intl

Sun 1/25

8:45 pm-2:45 pm

1 stop18h 00m

$308

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 1/20

3:55 pm-8:10 pm

1 stop28h 15m

Chicago O'Hare Intl

Sun 1/25

8:45 pm-2:45 pm

1 stop18h 00m

$317

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 1/21

7:00 am-5:29 pm

1 stop10h 29m

Chicago Midway

Wed 1/28

9:33 am-10:15 pm

2 stops12h 42m

$344

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

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 Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Costa Rica, with most prices found around $418. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Costa Rica to Chicago during October average around $424.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $448. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Costa Rica to Chicago for around $579.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Costa Rica to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $506.

What is the cheapest Costa Rica to Chicago flight route?

Fly from Liberia to Chicago O'Hare Intl for the best Costa Rica - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Costa Rica when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $462 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Costa Rica for as low as $370 on momondo.

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

There are 2 cabin classes available to choose from on Costa Rica to Chicago 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 Costa Rica to Chicago flights?

No. A direct flight is the cheapest option for a flight between Costa Rica to Chicago.

Cheap Costa Rica to Chicago flight deals and tips

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

Best Price Found	$198
Fastest flight time	5h 19m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Costa Rica in the past 72 hours is $198. The best round-trip flight deal from Costa Rica to Chicago found on momondo in the last 72 hours is $429.

The fastest flight from Costa Rica to Chicago takes 5h 19m

Direct flights go from Costa Rica to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

When did momondo last update prices for flights from Costa Rica to Chicago?
Prices for flights from Costa Rica to Chicago refresh daily.
How many operators does momondo search for flights from Costa Rica to Chicago?
The number of operators available for flights from Costa Rica to Chicago is 6 as of November 2025.
How old do you have to be to fly from Costa Rica to Chicago?
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 Costa Rica to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Costa Rica to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Costa Rica to Chicago is Boeing 737 MAX 9, representing 41.96% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 37.50%, Airbus A320-100/200 at 3.79%, and Airbus A320neo at 3.35%.

Best airlines flying from Costa Rica to Chicago

Compare and see reviews for airlines that fly from Costa Rica to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $228	Free Cancellation	Rating 6.3 8,159 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $249	Free Cancellation	Rating 6.6 2,474 reviews	Search Avianca flights
Copa Airlines	PriceFrom $314	Free Cancellation	Rating 7.6 1,561 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $324	Free Cancellation	Rating 7.2 11,043 reviews	Search American Airlines flights
Southwest	PriceFrom $425	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights
United Airlines	PriceFrom $434	Free Cancellation	Rating 7.4 9,056 reviews	Search United Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Costa Rica.

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

Yes. All flights to Chicago from Costa Rica on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Costa Rica to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Costa Rica. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago 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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Tue 12/30

Tue 1/6

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Cheap flights from Costa Rica to Chicago from $115

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Costa Rica to Chicago departing on 12/5. 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

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Costa Rica to Chicago

Recent round-trip flight deals from Costa Rica to Chicago

Recent one-way flight deals from Costa Rica to Chicago

Recent last minute flight deals from Costa Rica to Chicago

Recent direct flight deals from Costa Rica to Chicago

Spirit Airlines flights from Costa Rica to Chicago

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

Air Canada flights from Costa Rica to Chicago

Our best Air Canada deals on Costa Rica to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.

See travel insights to Chicago from

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

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 Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Costa Rica, with most prices found around $418. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Costa Rica to Chicago during October average around $424.

What is the cheapest day to depart on your flight to Chicago?

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Costa Rica to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $506.

What is the cheapest Costa Rica to Chicago flight route?

Fly from Liberia to Chicago O'Hare Intl for the best Costa Rica - Chicago flight prices

How far in advance should I book a flight to Chicago?

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

There are 2 cabin classes available to choose from on Costa Rica to Chicago 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 Costa Rica to Chicago flights?

No. A direct flight is the cheapest option for a flight between Costa Rica to Chicago.

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

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

What airlines fly to Chicago?

How often are flights from Costa Rica to Chicago delayed?

Historically, on average around 12% of flights between Costa Rica and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 167 minutes.

What is the most punctual flight time for Costa Rica to Chicago 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. Monday has historically seen more delays on average compared to the rest of the week.

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

According to our data, American 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 Costa Rica to Chicago on average per week?

As of November 2025, 6 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Sat, with 33% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

Cheap Costa Rica to Chicago flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

What documentation or ID do you need to fly to Chicago?

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

Best airlines flying from Costa Rica to Chicago

Compare and see reviews for airlines that fly from Costa Rica to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago