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 30m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

What airlines fly to Chicago?

United Airlines, American Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from Costa Rica according to our data. United Airlines is the first choice among our users, with 33% 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.

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 12% 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 167 minutes.

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

As of November 2025, 1 flights take off from Costa Rica and land in Chicago each day. The most common flight departure time for this route is 1:00PM, with 100% of daily flights taking off in the afternoon.

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

As of November 2025, 7 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.

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

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

$130 Cheap Flights from Costa Rica to Chicago in 2025/26

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Find the cheapest flights from Costa Rica to Chicago

Round-trip

One-way

Last minute

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Recent round-trip flight deals from Costa Rica to Chicago

Enter your travel dates to find the best prices.

11:24 am - 11:06 pmSJO-ORD

11h 42m1 stop

5:32 pm - 11:37 amORD-SJO

18h 05m2 stops

$258Spirit Airlines

Find Deal

lun., nov. 24 - mar., feb. 10

1:31 pm - 12:09 amSJO-ORD

10h 38m1 stop

8:22 pm - 3:20 pmORD-SJO

18h 58m2 stops

$265Multiple Airlines

Find Deal

mar., dic. 16 - dom., ene. 11

1:31 pm - 12:09 amSJO-ORD

10h 38m1 stop

5:00 am - 12:25 pmORD-SJO

7h 25m1 stop

$267Spirit Airlines

Find Deal

sáb., dic. 13 - mié., ene. 7

1:31 pm - 12:30 amSJO-ORD

10h 59m1 stop

3:26 pm - 12:25 pmORD-SJO

20h 59m1 stop

$268Spirit Airlines

Find Deal

mié., dic. 24 - mié., dic. 31

1:35 pm - 10:17 pmSJO-MDW

8h 42m1 stop

6:10 am - 1:50 pmMDW-SJO

7h 40m1 stop

$346Frontier

Find Deal

sáb., ene. 10 - sáb., ene. 17

2:45 pm - 9:10 amLIR-ORD

17h 25m1 stop

8:20 pm - 1:30 pmORD-LIR

18h 10m1 stop

$353Air Canada

Find Deal

mar., abr. 14 - mar., abr. 21

3:45 pm - 10:05 pmLIR-ORD

30h 20m1 stop

10:00 am - 2:45 pmORD-LIR

28h 45m1 stop

$365Air Canada

Find Deal

mar., ene. 13 - jue., ene. 15

2:00 pm - 9:52 pmLIR-ORD

31h 52m2 stops

7:00 am - 12:55 pmORD-LIR

29h 55m2 stops

$440JetBlue

Find Deal

mar., dic. 9 - sáb., dic. 13

2:01 pm - 7:20 pmLIR-ORD

5h 19mnonstop

7:49 am - 12:55 pmORD-LIR

5h 06mnonstop

$461United Airlines

Find Deal

jue., feb. 5 - dom., feb. 8

2:01 pm - 7:20 pmLIR-ORD

5h 19mnonstop

5:40 am - 1:10 pmORD-LIR

7h 30m1 stop

$466United Airlines

Find Deal

jue., feb. 5 - dom., feb. 8

Spirit Airlines flights from Costa Rica to Chicago

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

Spirit Airlines

Nov 24

SJO11:24 amSan José Juan Santamaria Intl

11h 42m

1 stop

ORD11:06 pmChicago O'Hare Intl

Feb 10

ORD5:32 pmChicago O'Hare Intl

18h 05m

2 stops

SJO11:37 amSan José Juan Santamaria Intl

$258

Find similar

Spirit Airlines

Dec 13

SJO1:31 pmSan José Juan Santamaria Intl

10h 38m

1 stop

ORD12:09 amChicago O'Hare Intl

Jan 7

ORD5:00 amChicago O'Hare Intl

7h 25m

1 stop

SJO12:25 pmSan José Juan Santamaria Intl

$267

Find similar

Spirit Airlines

Dec 24

SJO1:31 pmSan José Juan Santamaria Intl

10h 59m

1 stop

ORD12:30 amChicago O'Hare Intl

Dec 31

ORD3:26 pmChicago O'Hare Intl

20h 59m

1 stop

SJO12:25 pmSan José Juan Santamaria Intl

$268

Find similar

Air Canada flights from Costa Rica to Chicago

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

Air Canada

Apr 14

LIR2:45 pmLiberia

17h 25m

1 stop

ORD9:10 amChicago O'Hare Intl

Apr 21

ORD8:20 pmChicago O'Hare Intl

18h 10m

1 stop

LIR1:30 pmLiberia

$353

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

$365

Find similar

Air Canada

Nov 27

LIR3:45 pmLiberia

17h 28m

1 stop

ORD9:13 amChicago O'Hare Intl

Dec 1

ORD3:35 pmChicago O'Hare Intl

22h 15m

1 stop

LIR1:50 pmLiberia

$410

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

lun. 11/24

11:24 am-11:06 pm

1 stop11h 42m

Chicago O'Hare Intl

mar. 2/10

5:32 pm-11:37 am

2 stops18h 05m

$258

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

mar. 12/16

1:31 pm-12:09 am

1 stop10h 38m

Chicago O'Hare Intl

dom. 1/11

8:22 pm-3:20 pm

2 stops18h 58m

$265

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

sáb. 12/13

1:31 pm-12:09 am

1 stop10h 38m

Chicago O'Hare Intl

mié. 1/7

5:00 am-12:25 pm

1 stop7h 25m

$267

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

mié. 12/24

1:31 pm-12:30 am

1 stop10h 59m

Chicago O'Hare Intl

mié. 12/31

3:26 pm-12:25 pm

1 stop20h 59m

$268

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

sáb. 1/10

1:35 pm-10:17 pm

1 stop8h 42m

Chicago Midway

sáb. 1/17

6:10 am-1:50 pm

1 stop7h 40m

$346

LiberiaChicago

LIR - ORD

LIRORD

Liberia

mar. 4/14

2:45 pm-9:10 am

1 stop17h 25m

Chicago O'Hare Intl

mar. 4/21

8:20 pm-1:30 pm

1 stop18h 10m

$353

LiberiaChicago

LIR - ORD

LIRORD

Liberia

mar. 1/13

3:45 pm-10:05 pm

1 stop30h 20m

Chicago O'Hare Intl

jue. 1/15

10:00 am-2:45 pm

1 stop28h 45m

$365

LiberiaChicago

LIR - ORD

LIRORD

Liberia

mar. 12/9

2:00 pm-9:52 pm

2 stops31h 52m

Chicago O'Hare Intl

sáb. 12/13

7:00 am-12:55 pm

2 stops29h 55m

$440

LiberiaChicago

LIR - ORD

LIRORD

Liberia

jue. 2/5

2:01 pm-7:20 pm

Nonstop5h 19m

Chicago O'Hare Intl

dom. 2/8

7:49 am-12:55 pm

Nonstop5h 06m

$461

LiberiaChicago

LIR - ORD

LIRORD

Liberia

jue. 2/5

2:01 pm-7:20 pm

Nonstop5h 19m

Chicago O'Hare Intl

dom. 2/8

5:40 am-1:10 pm

1 stop7h 30m

$466

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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 $588.

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 $540.

What is the cheapest Costa Rica to Chicago flight route?

Fly from San José Juan Santamaria Intl 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 $463 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 $391 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?

You could potentially save up to 11% on your flight if you consider stops on a Costa Rica to Chicago flight.

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	$175
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 $175. The best round-trip flight deal from Costa Rica to Chicago found on momondo in the last 72 hours is $325.

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 8, representing 38.28% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 31.16%, Airbus A320neo at 6.23%, and Airbus A330-300 at 4.15%.

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 $230	Free Cancellation	Rating 6.3 8,151 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $249	Free Cancellation	Rating 6.6 2,475 reviews	Search Avianca flights
Copa Airlines	PriceFrom $314	Free Cancellation	Rating 7.6 1,566 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $324	Free Cancellation	Rating 7.2 11,044 reviews	Search American Airlines flights
Southwest	PriceFrom $425	Free Cancellation	Rating 8.0 4,248 reviews	Search Southwest flights
United Airlines	PriceFrom $434	Free Cancellation	Rating 7.4 9,019 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

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vie. 12/19

vie. 12/26

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Cheap flights from Costa Rica to Chicago from $130

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 12/16. 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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Big names and deals

Filter for what you want

Filter for what you want

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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

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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 $540.

What is the cheapest Costa Rica to Chicago flight route?

Fly from San José Juan Santamaria Intl 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?

You could potentially save up to 11% on your flight if you consider stops on a Costa Rica to Chicago flight.

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

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

What airlines fly to Chicago?

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 12% 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 167 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 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 $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] 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 day?

As of November 2025, 1 flights take off from Costa Rica and land in Chicago each day. The most common flight departure time for this route is 1:00PM, with 100% of daily flights taking off in the afternoon.

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

As of November 2025, 7 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% 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