What are the cheapest airlines to fly from Chicago to Costa Rica one-way?

The cheapest airlines for a one-way flight from Chicago to Costa Rica are Spirit Airlines ($150), Avianca ($176), and Frontier ($196).

What are the most popular routes from Chicago to Costa Rica?

While some choose either Chicago O'Hare Intl - Liberia or Chicago Midway - San José Juan Santamaria Intl, Chicago O'Hare Intl - San José Juan Santamaria Intl is the most popular route from Chicago to Costa Rica.

What are the cheapest flights from Chicago to Costa Rica?

While on average a flight from Chicago to Costa Rica is generally $498, our data shows the cheapest flight currently is $200. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $246 for that flight.

What are the most popular airlines that fly from Chicago to Costa Rica?

American Airlines, Avianca and JetBlue are the most popular airlines when flying from Chicago to Costa Rica.

What is the cheapest day to fly round-trip from Chicago to Costa Rica?

Flying to your destination on a Sunday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Costa Rica. Check prices with Cheapflights to find a great deal for your trip.

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

Find a great deal and save up to 56% by booking at least 27 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Costa Rica within the next two weeks, with the cheapest ticket starting at $392.

What is the cheapest month to fly from Chicago to Costa Rica?

Flights from Chicago to Costa Rica lean towards being more expensive in December. Prices are generally better when you fly from Chicago to Costa Rica in May, with the cheapest ticket starting at $225.

Can I find deals for flights from Chicago to Costa Rica that include hotel bookings?

Yes. In addition to deals on Chicago to Costa Rica flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to Costa Rica?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Costa Rica.

Can I find deals for business class flights from Chicago to Costa Rica?

Yes. Cheapflights offers flight deals from Chicago to Costa Rica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$473+ Flights from Chicago to Costa Rica - Compare & Save Big

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Cheap flight deals from Chicago to Costa Rica

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$325 (Booking.com)
One-way from	$147 (Avianca Connect)
Popular in	December
Cheapest in	May
Average price	$504
Good round-trip deal	$559 or less
Good one-way deal	$225 or less

Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.

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Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.

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From Chicago (CHI) to Costa Rica

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One-way flight from Chicago (CHI) to Costa Rica

Search Deals

Highest demand for flights based on searches. 10% potential increase in price ($73 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in May 2025

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Price to beat on a round-trip flight from Chicago (CHI) to Costa Rica.

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Price to beat on a one-way flight from Chicago (CHI) to Costa Rica.

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Find flight deals from Chicago to Costa Rica

Cheapest flights from Chicago to Costa Rica
Explore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Sat 8/233:07 pmORD - SJO

1 stop7h 46mCopa Airlines

Sun 8/318:09 amSJO - ORD

1 stop15h 13mCopa Airlines

Deal found 4/30

$325

Tue 5/275:05 amORD - SJO

1 stop7h 28mSpirit Airlines

Sun 6/112:28 pmSJO - ORD

2 stops10h 01mSpirit Airlines

Deal found 4/29

$331

Mon 5/125:05 amORD - SJO

1 stop7h 28mMultiple Airlines

Thu 5/2211:32 amSJO - ORD

1 stop11h 48mMultiple Airlines

Deal found 4/28

$332

Wed 6/43:45 pmORD - SJO

2 stops17h 55mAvianca

Sat 7/268:00 pmSJO - ORD

2 stops17h 25mAvianca

Deal found 4/29

$340

Sun 6/19:12 pmMDW - SJO

1 stop14h 15mMultiple Airlines

Sun 6/86:05 pmSJO - MDW

2 stops25h 12mMultiple Airlines

Deal found 4/30

$392

Sat 6/145:01 amORD - SJO

1 stop8h 30mFrontier

Sat 6/211:47 pmSJO - ORD

1 stop9h 27mFrontier

Deal found 4/30

$440

Sat 5/35:00 amORD - SJO

1 stop9h 19mAmerican Airlines

Mon 5/51:50 pmSJO - ORD

1 stop9h 06mAmerican Airlines

Deal found 4/29

$443

Tue 11/256:00 amORD - SJO

1 stop6h 52mDelta

Wed 11/262:17 pmSJO - ORD

1 stop9h 36mDelta

Deal found 4/29

$446

Sun 6/87:52 amORD - LIR

Nonstop5h 01mUnited Airlines

Sat 6/141:03 pmLIR - ORD

Nonstop5h 25mUnited Airlines

Deal found 4/30

$450

Thu 9/259:15 amMDW - SJO

2 stops10h 40mSouthwest

Tue 9/301:40 pmSJO - MDW

1 stop8h 40mSouthwest

Deal found 4/29

$451

Sat 5/317:16 pmORD - LIR

1 stop17h 29mAmerican Airlines

Sat 6/71:25 pmLIR - ORD

Nonstop5h 30mAmerican Airlines

Deal found 4/30

$455

Mon 6/165:35 amORD - LIR

1 stop7h 25mDelta

Thu 6/191:25 pmLIR - ORD

1 stop9h 33mDelta

Deal found 4/30

$465

Best flights from Chicago to Costa Rica
Discover carefully curated flight deals from Chicago to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 1, 2025.

Mon 5/264:35 pmORD - SJO

2 stops19h 58mSpirit Airlines

Sat 5/3112:28 pmSJO - ORD

2 stops10h 01mSpirit Airlines

Deal found 4/30

$325

Sun 6/14:35 pmORD - SJO

2 stops19h 58mMultiple Airlines

Sun 6/82:48 pmSJO - ORD

1 stop13h 54mMultiple Airlines

Deal found 4/30

$326

Sat 6/75:25 pmORD - SJO

2 stops15h 15mAvianca

Sat 6/143:05 pmSJO - ORD

2 stops22h 20mAvianca

Deal found 4/30

$340

Tue 8/1910:10 pmORD - LIR

2 stops14h 34mAmerican Airlines

Tue 8/2612:50 pmLIR - ORD

1 stop10h 07mAmerican Airlines

Deal found 4/29

$416

Tue 8/196:00 amORD - LIR

1 stop7h 00mDelta

Tue 8/261:25 pmLIR - ORD

1 stop9h 30mDelta

Deal found 4/29

$425

Wed 5/77:54 amORD - SJO

1 stop9h 28mCopa Airlines

Mon 5/122:29 pmSJO - ORD

1 stop9h 05mCopa Airlines

Deal found 4/30

$430

Wed 9/36:15 amMDW - SJO

1 stop7h 30mSouthwest

Mon 9/81:40 pmSJO - MDW

1 stop9h 25mSouthwest

Deal found 4/30

$437

Sat 6/145:01 amORD - SJO

1 stop8h 30mFrontier

Sat 6/211:47 pmSJO - ORD

1 stop9h 27mFrontier

Deal found 4/30

$440

Sat 5/177:45 amORD - LIR

Nonstop5h 01mUnited Airlines

Sat 5/2412:53 pmLIR - ORD

Nonstop5h 25mUnited Airlines

Deal found 4/29

$450

Wed 5/287:00 amORD - LIR

2 stops24h 20mAlaska Airlines

Wed 6/411:20 amLIR - ORD

2 stops17h 20mAlaska Airlines

Deal found 4/30

$597

Fri 6/202:16 pmORD - LIR

2 stops22h 44mAir Canada

Sat 6/281:00 pmLIR - ORD

1 stop22h 54mAir Canada

Deal found 4/29

$603

Sat 5/319:12 pmMDW - SJO

1 stop14h 15mMultiple Airlines

Sat 6/75:52 amSJO - MDW

2 stops12h 33mMultiple Airlines

Deal found 4/30

$384

Last-minute flights from Chicago to Costa Rica
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated May 1, 2025 and is based on user searches.

Wed 4/307:51 amORD - SJO

1 stop12h 09mCopa Airlines

Tue 5/68:09 amSJO - ORD

1 stop15h 25mCopa Airlines

Deal found 4/29

$430

Thu 5/19:25 amMDW - SJO

1 stop11h 15mSouthwest

Thu 5/81:10 pmSJO - MDW

1 stop9h 25mSouthwest

Deal found 4/30

$482

Thu 5/17:50 amMDW - SJO

2 stops12h 50mSouthwest

Thu 5/81:10 pmSJO - MDW

1 stop9h 25mSouthwest

Deal found 4/30

$482

Fri 5/21:19 pmMDW - SJO

1 stop22h 05mMultiple Airlines

Sat 5/312:55 amSJO - MDW

2 stops15h 35mMultiple Airlines

Deal found 4/30

$878

Sat 5/35:00 amORD - SJO

1 stop9h 19mAmerican Airlines

Mon 5/51:50 pmSJO - ORD

1 stop9h 06mAmerican Airlines

Deal found 4/29

$443

Mon 5/51:45 amORD - SJO

1 stop22h 29mMultiple Airlines

Tue 5/1312:28 pmSJO - ORD

1 stop9h 36mMultiple Airlines

Deal found 4/28

$358

Mon 5/59:50 pmORD - SJO

1 stop15h 36mUnited Airlines

Sat 5/106:35 amSJO - ORD

1 stop15h 32mUnited Airlines

Deal found 4/28

$533

Mon 5/55:15 amORD - LIR

1 stop7h 55mUnited Airlines

Mon 5/123:25 pmLIR - ORD

1 stop7h 50mUnited Airlines

Deal found 4/30

$790

Mon 5/56:58 pmORD - SJO

2 stops29h 54mAlaska Airlines

Sun 5/111:12 amSJO - ORD

2 stops27h 53mAlaska Airlines

Deal found 4/29

$794

Tue 5/67:47 pmORD - SJO

1 stop16h 46mSpirit Airlines

Tue 5/1312:28 pmSJO - ORD

1 stop9h 36mSpirit Airlines

Deal found 4/28

$368

Tue 5/67:54 amORD - SJO

1 stop9h 28mCopa Airlines

Wed 5/215:52 amSJO - ORD

1 stop17h 42mCopa Airlines

Deal found 4/29

$430

Tue 5/68:05 amORD - SJO

2 stops11h 30mAmerican Airlines

Wed 5/212:15 pmSJO - ORD

1 stop8h 41mAmerican Airlines

Deal found 4/29

$448

One-way flights from Chicago to Costa Rica
Search for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated May 1, 2025.

Sun 6/18:17 amORD - SJO

1 stop15h 23mMultiple Airlines

Deal found 4/30

$147

Wed 5/145:05 amORD - SJO

1 stop7h 28mSpirit Airlines

Deal found 4/30

$150

Sun 6/153:45 pmORD - SJO

2 stops8h 50mAvianca

Deal found 4/30

$176

Sat 6/145:01 amORD - SJO

1 stop8h 30mFrontier

Deal found 4/30

$196

Wed 5/142:12 pmMDW - SJO

2 stops21h 15mMultiple Airlines

Deal found 4/30

$203

Tue 5/136:00 amMDW - SJO

1 stop6h 59mDelta

Deal found 4/30

$205

Sun 5/119:45 amORD - SJO

2 stops9h 50mAmerican Airlines

Deal found 4/30

$205

Sat 6/218:25 amORD - LIR

Nonstop5h 00mAmerican Airlines

Deal found 4/30

$212

Fri 10/38:45 pmMDW - SJO

2 stops15h 35mSouthwest

Deal found 4/30

$213

Thu 5/295:30 amORD - LIR

1 stop7h 30mDelta

Deal found 4/30

$217

Mon 6/27:35 pmORD - LIR

2 stops20h 55mMultiple Airlines

Deal found 4/30

$244

Sat 5/107:41 amORD - SJO

Nonstop5h 14mUnited Airlines

Deal found 4/30

$246

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 8/23

3:07 pm-9:53 pm

1 stop7h 46m

San José Juan Santamaria Intl

Sun 8/31

8:09 am-12:22 am

1 stop15h 13m

$325

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 5/27

5:05 am-11:33 am

1 stop7h 28m

San José Juan Santamaria Intl

Sun 6/1

12:28 pm-11:29 pm

2 stops10h 01m

$331

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 5/12

5:05 am-11:33 am

1 stop7h 28m

San José Juan Santamaria Intl

Thu 5/22

11:32 am-12:20 am

1 stop11h 48m

$332

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 6/4

3:45 pm-8:40 am

2 stops17h 55m

San José Juan Santamaria Intl

Sat 7/26

8:00 pm-2:25 pm

2 stops17h 25m

$340

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 6/1

9:12 pm-10:27 am

1 stop14h 15m

San José Juan Santamaria Intl

Sun 6/8

6:05 pm-8:17 pm

2 stops25h 12m

$392

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 6/14

5:01 am-12:31 pm

1 stop8h 30m

San José Juan Santamaria Intl

Sat 6/21

1:47 pm-12:14 am

1 stop9h 27m

$440

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 5/14

8:22 am-6:35 pm

2 stops11h 13m

San José Juan Santamaria Intl

Tue 5/20

11:59 pm-1:22 pm

1 stop12h 23m

$447

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 6/8

7:52 am-11:53 am

Nonstop5h 01m

Liberia

Sat 6/14

1:03 pm-7:28 pm

Nonstop5h 25m

$450

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sat 5/31

7:16 pm-11:45 am

1 stop17h 29m

Liberia

Sat 6/7

1:25 pm-7:55 pm

Nonstop5h 30m

$455

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Mon 6/16

5:35 am-12:00 pm

1 stop7h 25m

Liberia

Wed 6/18

1:25 pm-11:57 pm

1 stop9h 32m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 41 results

...

Best time to book a flight from Chicago to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Chicago with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Costa Rica

What is the cheapest month to book a flight from Chicago to Costa Rica?

Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to CR?

When flying from Chicago to Costa Rica, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 46% versus a flight at noon.

What is the cheapest day to fly from Chicago to Costa Rica?

Travelers seeking maximum savings on their Chicago to Costa Rica flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Costa Rica by month

In terms of precipitation, rainfall in Costa Rica ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit Costa Rica when rainfall is around 0.0 in.

Temperature in Costa Rica by month

If weather is an important factor for your trip to Costa Rica, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

Reviews of airlines servicing Costa Rica

Get a feel of what it's like to fly with Delta, Alaska Airlines and Southwest from Chicago to Costa Rica by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,934 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Alaska Airlines

8.0

Very good

9,968 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Southwest

8.0

Very good

4,294 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Copa Airlines

7.5

Good

1,415 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Aeromexico

7.5

Good

1,698 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

What are the cheapest airlines to fly from Chicago to Costa Rica one-way?
The cheapest airlines for a one-way flight from Chicago to Costa Rica are Spirit Airlines ($150), Avianca ($176), and Frontier ($196).
What are the most popular routes from Chicago to Costa Rica?
While some choose either Chicago O'Hare Intl - Liberia or Chicago Midway - San José Juan Santamaria Intl, Chicago O'Hare Intl - San José Juan Santamaria Intl is the most popular route from Chicago to Costa Rica.
What are the cheapest flights from Chicago to Costa Rica?
While on average a flight from Chicago to Costa Rica is generally $498, our data shows the cheapest flight currently is $200. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $246 for that flight.
Can I find deals for flights from Chicago to Costa Rica that include hotel bookings?
Yes. In addition to deals on Chicago to Costa Rica flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Costa Rica?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Costa Rica.
Can I find deals for business class flights from Chicago to Costa Rica?
Yes. Cheapflights offers flight deals from Chicago to Costa Rica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago to Costa Rica?
Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Costa Rica

O'Hare Intl to Panama City flights

O'Hare Intl to San José flights

O'Hare Intl to Guatemala City flights

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O'Hare Intl to San Salvador flights

Midway to Guatemala City flights

O'Hare Intl to Philip S.W.Goldson flights

Midway to San José flights

St. Louis to San José flights

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O'Hare Intl to Managua flights

Midway to Panama City flights

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Midway to Liberia flights

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St. Louis to Panama City flights

St. Louis to Guatemala City flights

Midway to San Pedro Sula flights

St. Louis to San Pedro Sula flights

Evansville to Panama City flights

Midway to San Salvador flights

Bloomington to San José flights

St. Louis to Coxen Hole flights

O'Hare Intl to David flights

Moline to Guatemala City flights

Midway to Managua flights

Moline to San José flights

Midway to Coxen Hole flights

Moline to Philip S.W.Goldson flights

Moline to Liberia flights

Midway to Tegucigalpa flights

St. Louis to Managua flights

St. Louis to Tegucigalpa flights

Peoria to San Salvador flights

O'Hare Intl to Tegucigalpa flights

Springfield to Liberia flights

Moline to San Salvador flights

Bloomington to Philip S.W.Goldson flights

Top 8 airlines flying from Chicago to Costa Rica

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$249	Average$416	FlexibilityNo cancel fee	On-time65%
Avianca	Cheapest$337	Average$488	FlexibilityNo cancel fee	On-time71%
JetBlue	Cheapest$345	Average$635	FlexibilityNo cancel fee	On-time62%
Copa Airlines	Cheapest$416	Average$617	FlexibilityNo cancel fee	On-time70%
Delta	Cheapest$442	Average$794	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$451	Average$735	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$479	Average$666	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$544	Average$838	FlexibilityNo cancel fee	On-time69%

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$127+ Cheap flights from Chicago (CHI) to Costa Rica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/17. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Costa Rica with Cheapflights

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Cheap flight deals from Chicago to Costa Rica

Keep the following information in mind while searching for Chicago to Costa Rica flight deals. Data was last updated May 1, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Costa Rica

Cheapest flights from Chicago to Costa RicaExplore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Explore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Chicago to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Costa Rica

What is the cheapest month to book a flight from Chicago to Costa Rica?

What is the cheapest time of day to fly from CHI to CR?

Find hourly flight availability from Chicago to Costa Rica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

What is the cheapest day to fly from Chicago to Costa Rica?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Costa Rica. Price data was last updated on April 7, 2024.

Rainfall in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average rainfall totals by month.

Temperature in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average temperature totals by month.

Reviews of airlines servicing Costa Rica

Get a feel of what it's like to fly with Delta, Alaska Airlines and Southwest from Chicago to Costa Rica by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What are the cheapest airlines to fly from Chicago to Costa Rica one-way?

What are the most popular routes from Chicago to Costa Rica?

What are the cheapest flights from Chicago to Costa Rica?

Can I find deals for flights from Chicago to Costa Rica that include hotel bookings?

How can I find direct flights from Chicago to Costa Rica?

Can I find deals for business class flights from Chicago to Costa Rica?

What is the cheapest month to book a flight from Chicago to Costa Rica?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.

Top 8 airlines flying from Chicago to Costa Rica

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Cheapest flights from Chicago to Costa Rica
Explore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.