How long is the flight from Chicago to Costa Rica?

Airlines like Copa Airlines, Delta, and Southwest fly from Chicago to Costa Rica in about 9h 14m. The time it takes to get you to your destination can typically vary by up to 1h 21m. The distance from Chicago to Costa Rica is about 2220 mi. This flight may include one or multiple stops.

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 ($105), Avianca ($123), and JetBlue ($177).

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.

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).

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 $686, our data shows the cheapest flight currently is $150. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $224 for that flight.

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

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

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.

$96+ Flights from Chicago to Costa Rica

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Cheap flight deals from Chicago to Costa Rica

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$257 (Cheapflightsfares)
One-way from	$96 (Cheapflightsfares)
Popular in	December
Cheapest in	September
Average price	$377
Good round-trip deal	$437 or less
Good one-way deal	$214 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. 12% potential increase in price ($79 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 October 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 October 23, 2025.

Wed 11/1210:52 amORD - SJO

2 stops24h 47mSpirit Airlines

Wed 11/191:30 pmSJO - ORD

1 stop10h 57mSpirit Airlines

Deal found 10/21

$257

Sun 11/95:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Fri 11/141:30 pmSJO - ORD

1 stop10h 57mSpirit Airlines

Deal found 10/21

$258

Tue 11/255:00 amORD - SJO

1 stop7h 15mSpirit Airlines

Thu 11/271:20 pmSJO - ORD

1 stop9h 53mSpirit Airlines

Deal found 10/23

$259

Thu 11/1310:52 amORD - SJO

1 stop25h 33mMultiple Airlines

Wed 11/191:30 pmSJO - ORD

1 stop26h 55mMultiple Airlines

Deal found 10/22

$260

Tue 11/118:28 amORD - SJO

2 stops27h 11mSpirit Airlines

Mon 11/171:30 pmSJO - ORD

1 stop20h 17mSpirit Airlines

Deal found 10/22

$261

Wed 11/123:26 pmORD - SJO

2 stops20h 13mMultiple Airlines

Wed 11/191:30 pmSJO - ORD

1 stop26h 55mMultiple Airlines

Deal found 10/22

$263

Mon 11/105:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Fri 11/141:30 pmSJO - ORD

1 stop10h 57mSpirit Airlines

Deal found 10/22

$264

Tue 11/185:10 amORD - SJO

1 stop7h 15mMultiple Airlines

Fri 11/212:20 amSJO - ORD

1 stop12h 50mMultiple Airlines

Deal found 10/23

$265

Tue 11/185:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Mon 11/2411:24 amSJO - ORD

1 stop11h 42mSpirit Airlines

Deal found 10/23

$266

Wed 11/55:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Thu 12/41:31 pmSJO - ORD

1 stop10h 48mSpirit Airlines

Deal found 10/22

$267

Sat 12/63:21 pmORD - SJO

1 stop21h 04mSpirit Airlines

Sat 12/131:31 pmSJO - ORD

1 stop10h 48mSpirit Airlines

Deal found 10/23

$268

Wed 11/52:06 pmMDW - SJO

2 stops22h 19mMultiple Airlines

Thu 12/412:39 pmSJO - MDW

1 stop9h 19mMultiple Airlines

Deal found 10/22

$321

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 October 23, 2025.

Tue 2/107:34 amORD - SJO

1 stop9h 14mCopa Airlines

Mon 2/164:09 amSJO - ORD

1 stop8h 22mCopa Airlines

Deal found 10/21

$330

Mon 11/1712:47 pmMDW - SJO

1 stop9h 20mDelta

Thu 11/202:31 pmSJO - MDW

1 stop9h 09mDelta

Deal found 10/21

$342

Tue 1/138:55 amMDW - SJO

1 stop10h 35mSouthwest

Tue 1/209:40 amSJO - MDW

1 stop13h 15mSouthwest

Deal found 10/20

$373

Fri 12/56:00 amORD - LIR

1 stop7h 10mUnited Airlines

Wed 12/1012:50 pmLIR - ORD

1 stop11h 09mUnited Airlines

Deal found 10/23

$469

Mon 1/128:00 amORD - LIR

3 stops22h 39mAlaska Airlines

Thu 1/2211:20 amLIR - ORD

2 stops25h 50mAlaska Airlines

Deal found 10/20

$478

Wed 11/126:56 amORD - SJO

1 stop15h 00mCopa Airlines

Sun 11/166:07 pmSJO - ORD

1 stop18h 39mCopa Airlines

Deal found 10/21

$330

Fri 11/282:07 pmORD - SJO

1 stop18h 12mCopa Airlines

Tue 12/24:08 amSJO - ORD

1 stop8h 44mCopa Airlines

Deal found 10/23

$330

Sat 12/611:05 amMDW - SJO

1 stop11h 15mDelta

Sat 12/137:00 amSJO - MDW

2 stops11h 06mDelta

Deal found 10/22

$372

Mon 1/126:15 amMDW - LIR

1 stop8h 15mSouthwest

Thu 1/223:25 pmLIR - MDW

1 stop7h 30mSouthwest

Deal found 10/20

$398

Thu 11/272:07 pmORD - SJO

1 stop7h 49mCopa Airlines

Mon 12/15:53 pmSJO - ORD

1 stop18h 59mCopa Airlines

Deal found 10/23

$330

Wed 11/262:07 pmORD - SJO

1 stop17h 26mCopa Airlines

Mon 12/16:07 pmSJO - ORD

1 stop18h 45mCopa Airlines

Deal found 10/23

$330

Mon 11/109:25 amMDW - SJO

2 stops11h 05mSouthwest

Thu 11/132:10 pmSJO - MDW

1 stop10h 00mSouthwest

Deal found 10/21

$416

Sat 12/62:05 pmORD - LIR

2 stops16h 15mAlaska Airlines

Mon 12/157:17 pmLIR - ORD

3 stops24h 37mAlaska Airlines

Deal found 10/21

$481

Wed 11/192:07 pmORD - SJO

1 stop17h 26mCopa Airlines

Mon 11/244:08 amSJO - ORD

1 stop8h 38mCopa Airlines

Deal found 10/22

$330

Wed 11/196:00 amMDW - SJO

1 stop16h 07mDelta

Mon 12/87:00 amSJO - MDW

1 stop9h 34mDelta

Deal found 10/21

$444

Wed 1/146:15 amMDW - SJO

1 stop13h 15mSouthwest

Wed 1/219:40 amSJO - MDW

2 stops12h 25mSouthwest

Deal found 10/23

$417

Tue 11/182:07 pmORD - SJO

1 stop7h 49mCopa Airlines

Sun 11/234:08 amSJO - ORD

1 stop8h 38mCopa Airlines

Deal found 10/21

$330

Wed 11/1912:47 pmMDW - SJO

1 stop9h 20mDelta

Sat 12/62:31 pmSJO - MDW

1 stop9h 16mDelta

Deal found 10/21

$444

Wed 3/187:35 amORD - LIR

1 stop11h 02mUnited Airlines

Wed 3/251:01 pmLIR - ORD

Nonstop5h 19mUnited Airlines

Deal found 10/22

$545

Sat 1/105:10 amMDW - LIR

1 stop9h 45mSouthwest

Thu 1/152:55 pmLIR - MDW

1 stop7h 30mSouthwest

Deal found 10/22

$438

Thu 2/192:22 pmORD - SJO

1 stop17h 59mCopa Airlines

Mon 2/2310:08 amSJO - ORD

1 stop13h 56mCopa Airlines

Deal found 10/22

$330

Mon 2/237:45 amORD - LIR

2 stops23h 00mAlaska Airlines

Sat 2/287:45 pmLIR - ORD

2 stops28h 14mAlaska Airlines

Deal found 10/23

$536

Wed 11/1910:47 amMDW - SJO

1 stop11h 20mDelta

Tue 11/252:31 pmSJO - MDW

1 stop9h 09mDelta

Deal found 10/23

$444

Wed 1/2110:05 amMDW - SJO

2 stops9h 25mSouthwest

Fri 1/301:45 pmSJO - MDW

2 stops17h 50mSouthwest

Deal found 10/23

$440

Fri 11/72:07 pmORD - SJO

1 stop18h 12mCopa Airlines

Sun 11/94:08 amSJO - ORD

1 stop8h 38mCopa Airlines

Deal found 10/21

$332

Fri 2/277:45 amORD - LIR

2 stops23h 00mAlaska Airlines

Wed 3/411:00 amLIR - ORD

3 stops26h 04mAlaska Airlines

Deal found 10/22

$542

Fri 1/26:45 amORD - LIR

1 stop7h 05mDelta

Thu 1/83:55 pmLIR - ORD

1 stop18h 11mDelta

Deal found 10/20

$477

Tue 1/136:15 amMDW - LIR

1 stop8h 15mSouthwest

Wed 1/213:25 pmLIR - MDW

2 stops17h 50mSouthwest

Deal found 10/21

$443

Thu 1/16:00 amMDW - LIR

1 stop7h 50mDelta

Thu 1/83:55 pmLIR - MDW

1 stop18h 01mDelta

Deal found 10/21

$477

Wed 11/1210:15 amMDW - SJO

1 stop10h 15mSouthwest

Mon 11/172:15 pmSJO - MDW

1 stop7h 55mSouthwest

Deal found 10/21

$451

Last-minute flights from Chicago to Costa Rica
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated October 23, 2025 and is based on user searches.

Wed 11/55:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Thu 12/41:31 pmSJO - ORD

1 stop10h 48mSpirit Airlines

Deal found 10/22

$267

Sun 11/95:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Fri 11/141:30 pmSJO - ORD

1 stop10h 57mSpirit Airlines

Deal found 10/21

$258

Mon 11/105:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Fri 11/141:30 pmSJO - ORD

1 stop10h 57mSpirit Airlines

Deal found 10/22

$264

Mon 11/105:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Thu 11/131:30 pmSJO - ORD

1 stop21h 42mSpirit Airlines

Deal found 10/21

$268

Tue 11/118:28 amORD - SJO

2 stops27h 11mSpirit Airlines

Mon 11/171:30 pmSJO - ORD

1 stop20h 17mSpirit Airlines

Deal found 10/22

$261

Wed 11/125:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Tue 11/181:30 pmSJO - ORD

1 stop10h 57mSpirit Airlines

Deal found 10/22

$257

Wed 11/125:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Thu 11/201:20 pmSJO - ORD

1 stop9h 53mSpirit Airlines

Deal found 10/23

$262

Wed 11/123:26 pmORD - SJO

2 stops20h 13mMultiple Airlines

Wed 11/191:30 pmSJO - ORD

1 stop26h 55mMultiple Airlines

Deal found 10/22

$263

Thu 11/1310:52 amORD - SJO

1 stop25h 33mMultiple Airlines

Wed 11/191:30 pmSJO - ORD

1 stop26h 55mMultiple Airlines

Deal found 10/21

$260

Tue 11/185:10 amORD - SJO

1 stop7h 15mMultiple Airlines

Fri 11/212:20 amSJO - ORD

1 stop12h 50mMultiple Airlines

Deal found 10/23

$265

Tue 11/185:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Mon 11/2411:24 amSJO - ORD

1 stop11h 42mSpirit Airlines

Deal found 10/23

$266

Tue 11/255:00 amORD - SJO

1 stop7h 15mSpirit Airlines

Thu 11/271:20 pmSJO - ORD

1 stop9h 53mSpirit Airlines

Deal found 10/23

$259

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 October 23, 2025.

Wed 1/215:05 amORD - SJO

1 stop7h 09mSpirit Airlines

Deal found 10/22

$96

Sun 12/75:05 amORD - SJO

1 stop7h 20mSpirit Airlines

Deal found 10/21

$97

Tue 11/185:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Deal found 10/22

$102

Mon 11/175:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Deal found 10/22

$104

Wed 12/105:05 amORD - SJO

1 stop7h 20mSpirit Airlines

Deal found 10/22

$110

Sat 11/87:34 pmORD - SJO

2 stops16h 51mSpirit Airlines

Deal found 10/20

$111

Wed 11/125:10 amORD - SJO

1 stop7h 15mSpirit Airlines

Deal found 10/21

$114

Mon 2/233:02 pmMDW - SJO

2 stops21h 12mMultiple Airlines

Deal found 10/22

$120

Sat 11/86:30 amMDW - SJO

2 stops29h 09mMultiple Airlines

Deal found 10/20

$131

Sun 12/76:37 pmMDW - SJO

1 stop17h 05mMultiple Airlines

Deal found 10/21

$138

Mon 3/23:02 pmMDW - SJO

2 stops21h 12mMultiple Airlines

Deal found 10/23

$144

Fri 2/276:00 amMDW - SJO

3 stops30h 14mMultiple Airlines

Deal found 10/23

$149

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/10

7:34 am-4:48 pm

1 stop9h 14m

San José Juan Santamaria Intl

Mon 2/16

4:09 am-12:31 pm

1 stop8h 22m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 11/12

6:56 am-9:56 pm

1 stop15h 00m

San José Juan Santamaria Intl

Sun 11/16

6:07 pm-12:46 pm

1 stop18h 39m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 11/28

2:07 pm-8:19 am

1 stop18h 12m

San José Juan Santamaria Intl

Tue 12/2

4:08 am-12:52 pm

1 stop8h 44m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 11/27

2:07 pm-9:56 pm

1 stop7h 49m

San José Juan Santamaria Intl

Mon 12/1

5:53 pm-12:52 pm

1 stop18h 59m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 11/26

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Mon 12/1

6:07 pm-12:52 pm

1 stop18h 45m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 11/19

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Mon 11/24

4:08 am-12:46 pm

1 stop8h 38m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/18

2:07 pm-9:56 pm

1 stop7h 49m

San José Juan Santamaria Intl

Sun 11/23

4:08 am-12:46 pm

1 stop8h 38m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/19

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Mon 2/23

10:08 am-12:04 am

1 stop13h 56m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 11/7

2:07 pm-8:19 am

1 stop18h 12m

San José Juan Santamaria Intl

Sun 11/9

4:08 am-12:46 pm

1 stop8h 38m

$332

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 11/17

12:47 pm-10:07 pm

1 stop9h 20m

San José Juan Santamaria Intl

Thu 11/20

2:31 pm-11:40 pm

1 stop9h 09m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 60 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, October is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $246). Flying from Chicago to Costa Rica in December is currently the most expensive (average of $395). 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 evening, which can drop the price by up to 35% versus a flight in the morning.

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 at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Costa Rica

Read reviews from past customers who have flown Southwest, Copa Airlines, and United Airlines from Chicago to Costa Rica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,236 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Southwest

8.0

Very good

4,236 reviews

Southwest

8.0

Very good

4,236 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Copa Airlines

7.6

Good

1,560 reviews

Southwest

8.0

Very good

4,236 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

United Airlines

7.4

Good

8,995 reviews

Southwest

8.0

Very good

4,236 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

American Airlines

7.2

Good

11,033 reviews

Southwest

8.0

Very good

4,236 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Spirit Airlines

6.3

Okay

8,103 reviews

Southwest

8.0

Very good

4,236 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

How long is the flight from Chicago to Costa Rica?
Airlines like Copa Airlines, Delta, and Southwest fly from Chicago to Costa Rica in about 9h 14m. The time it takes to get you to your destination can typically vary by up to 1h 21m. The distance from Chicago to Costa Rica is about 2220 mi. This flight may include one or multiple stops.
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 ($105), Avianca ($123), and JetBlue ($177).
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 $686, our data shows the cheapest flight currently is $150. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $224 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, October is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $246). Flying from Chicago to Costa Rica in December is currently the most expensive (average of $395). 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 San José flights

O'Hare Intl to Panama City flights

O'Hare Intl to Guatemala City flights

O'Hare Intl to Liberia flights

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

Midway to San José flights

O'Hare Intl to San Salvador flights

Midway to Guatemala City flights

St. Louis to San José flights

Midway to Panama City flights

O'Hare Intl to Managua flights

Midway to Liberia flights

O'Hare Intl to Coxen Hole flights

Midway to Philip S.W.Goldson flights

O'Hare Intl to San Pedro Sula flights

St. Louis to Philip S.W.Goldson flights

St. Louis to Liberia flights

Midway to San Salvador flights

Evansville to Panama City flights

St. Louis to Panama City flights

St. Louis to Guatemala City flights

Midway to San Pedro Sula flights

St. Louis to Coxen Hole flights

Midway to Managua flights

Midway to Coxen Hole flights

Bloomington to San José flights

Moline to San Salvador flights

O'Hare Intl to David flights

St. Louis to Managua flights

Peoria to San Salvador flights

Moline to Liberia flights

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Moline to Philip S.W.Goldson flights

Midway to Tegucigalpa flights

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Moline to Guatemala City flights

Bloomington to Philip S.W.Goldson flights

St. Louis to Tegucigalpa flights

Springfield to Liberia flights

O'Hare Intl to Tegucigalpa flights

Top 9 airlines flying from Chicago to Costa Rica

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$261	Average$426	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$290	Average$748	FlexibilityNo cancel fee	On-timeN/A
Avianca	Cheapest$307	Average$460	FlexibilityNo cancel fee	On-time71%
Copa Airlines	Cheapest$314	Average$528	FlexibilityNo cancel fee	On-time70%
Frontier	Cheapest$345	Average$796	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$385	Average$697	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$394	Average$647	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$431	Average$746	FlexibilityNo cancel fee	On-time69%
JetBlue	Cheapest$432	Average$635	FlexibilityNo cancel fee	On-time62%

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$96+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.

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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 October 23, 2025.

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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 October 23, 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 October 23, 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 October 23, 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 December 16, 2024.

Reviews of airlines servicing Costa Rica

Read reviews from past customers who have flown Southwest, Copa Airlines, and United Airlines from Chicago to Costa Rica. Users can see the overall rating for each airline as well as how each is rated 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.

How long is the flight from Chicago to Costa Rica?

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?

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Alternative routes for Chicago to Costa Rica

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Top 9 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 October 23, 2025.