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 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.

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

As of January 2026, 21 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Mon, with 19% 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 24m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

How often are flights from Costa Rica to Chicago delayed?

Historically, on average around 11% 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 168 minutes.

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

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

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

As of January 2026, 3 flights take off from Costa Rica and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 69% of daily flights taking off in the afternoon.

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 6% 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 39% 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.

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 January 2026.

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.

$128 Cheap Flights from Costa Rica to Chicago in 2026

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.

1:30 pm - 11:47 pm

SJO

ORD

10h 17m

1 stop

7:00 am - 12:22 pm

ORD

SJO

29h 22m

1 stop

$257Spirit Airlines

Fri, Feb 6 - Sun, Feb 15

1:31 pm - 11:47 pm

SJO

ORD

10h 16m

1 stop

8:59 am - 11:40 am

ORD

SJO

26h 41m

2 stops

$261Spirit Airlines

Fri, Feb 13 - Sun, Mar 1

1:31 pm - 11:47 pm

SJO

ORD

10h 16m

1 stop

5:15 am - 12:22 pm

ORD

SJO

7h 07m

1 stop

$262Spirit Airlines

Sat, Feb 14 - Sun, Mar 1

1:30 pm - 11:47 pm

SJO

ORD

10h 17m

1 stop

3:40 pm - 11:40 am

ORD

SJO

20h 00m

2 stops

$272Multiple Airlines

Fri, Feb 6 - Sun, Feb 15

7:00 am - 10:31 pm

SJO

MDW

15h 31m

1 stop

10:49 am - 10:02 pm

MDW

SJO

11h 13m

1 stop

$346Delta

Fri, Feb 13 - Tue, Feb 17

12:35 pm - 1:08 pm

SJO

MDW

24h 33m

1 stop

6:00 am - 3:30 pm

MDW

SJO

10h 30m

1 stop

$355Multiple Airlines

Thu, Mar 5 - Mon, Mar 9

9:00 am - 10:45 pm

SJO

MDW

12h 45m

2 stops

7:30 am - 7:00 pm

MDW

SJO

12h 30m

2 stops

$384Southwest

Fri, May 8 - Mon, May 11

9:00 am - 8:15 pm

SJO

MDW

10h 15m

2 stops

12:10 pm - 7:00 pm

MDW

SJO

7h 50m

1 stop

$392Southwest

Thu, Apr 16 - Mon, Apr 20

2:01 pm - 7:20 pm

LIR

ORD

5h 19mnonstop

7:49 am - 11:55 am

ORD

LIR

5h 06mnonstop

$617United Airlines

Fri, Mar 6 - Fri, Mar 13

8:35 am - 11:08 pm

LIR

ORD

14h 33m

1 stop

7:49 am - 11:55 am

ORD

LIR

5h 06mnonstop

$623United Airlines

Fri, Mar 6 - Fri, Mar 13

Spirit Airlines flights from Costa Rica to Chicago

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

Spirit Airlines

Feb 6

SJO1:30 pmSan José Juan Santamaria Intl

10h 17m

1 stop

ORD11:47 pmChicago O'Hare Intl

Feb 15

ORD7:00 amChicago O'Hare Intl

29h 22m

1 stop

SJO12:22 pmSan José Juan Santamaria Intl

$257

Spirit Airlines

Feb 13

SJO1:31 pmSan José Juan Santamaria Intl

10h 16m

1 stop

ORD11:47 pmChicago O'Hare Intl

Mar 1

ORD8:59 amChicago O'Hare Intl

26h 41m

2 stops

SJO11:40 amSan José Juan Santamaria Intl

$261

Spirit Airlines

Feb 14

SJO1:31 pmSan José Juan Santamaria Intl

10h 16m

1 stop

ORD11:47 pmChicago O'Hare Intl

Mar 1

ORD5:15 amChicago O'Hare Intl

7h 07m

1 stop

SJO12:22 pmSan José Juan Santamaria Intl

$262

American Airlines flights from Costa Rica to Chicago

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

American Airlines

Feb 3

SJO7:09 amSan José Juan Santamaria Intl

5h 29m

ORD12:38 pmChicago O'Hare Intl

Feb 6

ORD5:30 pmChicago O'Hare Intl

5h 00m

SJO10:30 pmSan José Juan Santamaria Intl

$340

American Airlines

Feb 3

SJO6:00 amSan José Juan Santamaria Intl

10h 20m

1 stop

ORD4:20 pmChicago O'Hare Intl

Feb 6

ORD5:30 pmChicago O'Hare Intl

5h 00m

SJO10:30 pmSan José Juan Santamaria Intl

$350

American Airlines

Jan 30

SJO7:09 amSan José Juan Santamaria Intl

5h 29m

ORD12:38 pmChicago O'Hare Intl

Mar 1

ORD6:01 amChicago O'Hare Intl

14h 32m

1 stop

SJO8:33 pmSan José Juan Santamaria Intl

$360

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/6

1:30 pm-11:47 pm

1 stop10h 17m

Chicago O'Hare Intl

Sun 2/15

7:00 am-12:22 pm

1 stop29h 22m

$257

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/13

1:31 pm-11:47 pm

1 stop10h 16m

Chicago O'Hare Intl

Sun 3/1

8:59 am-11:40 am

2 stops26h 41m

$261

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 2/14

1:31 pm-11:47 pm

1 stop10h 16m

Chicago O'Hare Intl

Sun 3/1

5:15 am-12:22 pm

1 stop7h 07m

$262

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/6

1:30 pm-11:47 pm

1 stop10h 17m

Chicago O'Hare Intl

Sun 2/15

3:40 pm-11:40 am

2 stops20h 00m

$272

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/13

7:00 am-10:31 pm

1 stop15h 31m

Chicago Midway

Tue 2/17

10:49 am-10:02 pm

1 stop11h 13m

$346

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 3/5

12:35 pm-1:08 pm

1 stop24h 33m

Chicago Midway

Mon 3/9

6:00 am-3:30 pm

1 stop10h 30m

$355

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/8

9:00 am-10:45 pm

2 stops12h 45m

Chicago Midway

Mon 5/11

7:30 am-7:00 pm

2 stops12h 30m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

9:00 am-8:15 pm

2 stops10h 15m

Chicago Midway

Mon 4/20

12:10 pm-7:00 pm

1 stop7h 50m

$392

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 3/6

2:01 pm-7:20 pm

Nonstop5h 19m

Chicago O'Hare Intl

Fri 3/13

7:49 am-11:55 am

Nonstop5h 06m

$617

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 3/6

8:35 am-11:08 pm

1 stop14h 33m

Chicago O'Hare Intl

Fri 3/13

7:49 am-11:55 am

Nonstop5h 06m

$623

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 $374. 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 $412.

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 Thursday when prices can be found for as low as $416. 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 morning. Flights from Costa Rica to Chicago during this time can be as low as $460. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

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 $447 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 $380 on momondo.

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

There are 3 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 2% 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	$150
Fastest flight time	5h 19m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Costa Rica in the past 72 hours is $150. The best round-trip flight deal from Costa Rica to Chicago found on momondo in the last 72 hours is $296.

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

Direct flights go from Costa Rica to Chicago every day.

There are 3 airports in Chicago. From Costa Rica there are direct flights to 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 January 2026.
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 37.20% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 35.39%, Airbus A320neo at 7.49%, and Airbus A320-100/200 at 5.31%.

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 $206	Free Cancellation	Rating 6.3 8,364 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $249	Free Cancellation	Rating 6.6 2,496 reviews	Search Avianca flights
Copa Airlines	PriceFrom $311	Free Cancellation	Rating 7.6 1,557 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $332	Free Cancellation	Rating 7.2 11,173 reviews	Search American Airlines flights
United Airlines	PriceFrom $400	Free Cancellation	Rating 7.4 9,191 reviews	Search United Airlines flights
Southwest	PriceFrom $463	Free Cancellation	Rating 8.0 4,266 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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

Fri 2/20

Fri 2/27

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 $128

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 2/7. 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

American Airlines flights from Costa Rica to Chicago

Our best American Airlines 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

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 $374. 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 $412.

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 morning. Flights from Costa Rica to Chicago during this time can be as low as $460. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

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 3 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 2% 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, Southwest, and JetBlue 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 11% 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 168 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 6% of their flights experiencing any sort of delay.

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

As of January 2026, 3 flights take off from Costa Rica and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 69% of daily flights taking off in the afternoon.

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

As of January 2026, 21 flights take off from Costa Rica and land in Chicago each week. The most common flight departure day for this route is Mon, with 19% 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