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$82+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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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 August 18, 2025.

Round-trip from

$285
(FlightHub)

One-way from

$82
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$536

Good round-trip deal

$563 or less

Good one-way deal

$268 or less
From Chicago (CHI) to Costa Rica
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One-way flight from Chicago (CHI) to Costa Rica
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Highest demand for flights based on searches. 11% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 18, 2025.

This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Fri 10/312:19 pmSJO - ORD
2 stops21h 23mSpirit Airlines
Deal found 8/17$285
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1311:37 amORD - SJO
2 stops24h 37mSpirit Airlines
Sat 9/2012:19 pmSJO - ORD
2 stops21h 23mSpirit Airlines
Deal found 8/17$286
This SmartFares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/165:17 pmORD - SJO
2 stops18h 57mSpirit Airlines
Tue 9/2312:19 pmSJO - ORD
2 stops23h 50mSpirit Airlines
Deal found 8/17$287
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/28:12 pmORD - SJO
2 stops15h 20mSpirit Airlines
Tue 9/912:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Deal found 8/17$288
This Cheapflightsfares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:29 pmORD - SJO
1 stop17h 01mSpirit Airlines
Wed 10/2911:37 amSJO - ORD
2 stops12h 26mSpirit Airlines
Deal found 8/17$291
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/255:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Thu 10/212:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Deal found 8/17$292
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/81:26 pmORD - SJO
2 stops23h 04mSpirit Airlines
Mon 10/1312:35 pmSJO - ORD
1 stop28h 49mSpirit Airlines
Deal found 8/17$293
This Cheapflightsfares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Wed 10/811:37 amSJO - ORD
2 stops11h 08mSpirit Airlines
Deal found 8/17$294
This Cheapflightsfares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:28 pmORD - SJO
1 stop18h 56mSpirit Airlines
Tue 11/41:35 pmSJO - ORD
1 stop11h 28mSpirit Airlines
Deal found 8/17$295
This Mytrip deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:56 amORD - SJO
1 stop9h 17mMultiple Airlines
Sat 8/307:30 amSJO - ORD
1 stop13h 52mMultiple Airlines
Deal found 8/18$299
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/205:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Fri 9/2612:19 pmSJO - ORD
1 stop21h 33mSpirit Airlines
Deal found 8/17$300
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:00 amMDW - SJO
1 stop6h 50mDelta
Tue 11/112:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 8/18$394

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Costa Rica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.

Fly from

Chicago

Fly to

Costa Rica

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 10/2

5:05 am-11:14 am

1 stop7h 09m

San José Juan Santamaria Intl

Wed 10/8

12:35 pm-11:45 pm

1 stop10h 10m

$292

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 9/27

5:05 am-11:14 am

1 stop7h 09m

San José Juan Santamaria Intl

Thu 10/2

12:19 pm-10:48 pm

1 stop9h 29m

$292

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 9/25

6:44 pm-11:14 am

1 stop17h 30m

San José Juan Santamaria Intl

Thu 10/2

12:19 pm-10:48 pm

1 stop9h 29m

$292

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 10/3

11:37 am-11:14 am

2 stops24h 37m

San José Juan Santamaria Intl

Sat 10/11

12:35 pm-11:45 pm

1 stop10h 10m

$298

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 12/4

10:15 am-12:21 am

2 stops14h 06m

San José Juan Santamaria Intl

Tue 12/9

1:16 am-7:16 pm

2 stops18h 00m

$300

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 12/4

7:35 am-12:21 am

2 stops16h 46m

San José Juan Santamaria Intl

Tue 12/9

1:19 pm-9:10 am

2 stops19h 51m

$300

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 9/20

6:44 pm-11:14 am

1 stop17h 30m

San José Juan Santamaria Intl

Sun 9/28

12:19 pm-10:52 am

1 stop21h 33m

$300

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 12/5

10:15 am-12:21 am

2 stops14h 06m

San José Juan Santamaria Intl

Tue 12/9

1:19 pm-9:10 am

2 stops19h 51m

$300

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 10/8

7:29 pm-11:30 am

1 stop17h 01m

San José Juan Santamaria Intl

Mon 10/13

12:35 pm-6:24 pm

1 stop28h 49m

$300

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 11/15

6:00 am-12:52 pm

1 stop6h 52m

San José Juan Santamaria Intl

Fri 11/21

7:00 am-9:44 pm

1 stop14h 44m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 60 results
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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?

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 August 18, 2025.

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 30% versus a flight in the morning.

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.

Travelers seeking maximum savings on their Chicago to Costa Rica flight should consider departing on Tuesday 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.

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Costa Rica. Reviews last updated August 18, 2025.
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
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Copa Airlines
7.5
Good
1,510 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,038 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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?

    Airlines like Spirit Airlines, Delta, and Air Canada fly from Chicago to Costa Rica in about 6h 52m. The time it takes to get you to your destination can typically vary by up to 23h 53m. The distance from Chicago to Costa Rica is about 2206 mi. This flight may include one or multiple stops.

  • 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 $509, our data shows the cheapest flight currently is $176. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $226 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

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Alternative routes for Chicago to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to San José flights
O'Hare Intl to Panama City flights
O'Hare Intl to Liberia flights
O'Hare Intl to Guatemala City flights
O'Hare Intl to Philip S.W.Goldson flights
St. Louis to Philip S.W.Goldson flights
Midway to San José flights
Midway to Guatemala City flights
St. Louis to San José flights
O'Hare Intl to San Salvador flights
O'Hare Intl to Coxen Hole flights
Midway to Liberia flights
St. Louis to Liberia flights
Midway to Panama City flights
O'Hare Intl to Managua flights
Midway to Philip S.W.Goldson flights
O'Hare Intl to San Pedro Sula flights
Evansville to Panama City flights
St. Louis to Panama City flights
Midway to San Salvador flights
Midway to San Pedro Sula flights
St. Louis to Coxen Hole flights
St. Louis to Guatemala City flights
Midway to Coxen Hole flights
Moline to Philip S.W.Goldson flights
Bloomington to San José flights
Moline to San Salvador flights
Bloomington to Philip S.W.Goldson flights
St. Louis to Managua flights
O'Hare Intl to David flights
Midway to Tegucigalpa flights
Peoria to San Salvador flights
Moline to Guatemala City flights
O'Hare Intl to Tegucigalpa flights
St. Louis to Tegucigalpa flights
Moline to San José flights
Midway to Managua flights
Springfield to Liberia flights
Moline to Liberia flights
St. Louis to San Pedro Sula flights

Top 8 airlines flying from Chicago to Costa Rica

Discover the top 8 airlines that operate flights from Chicago to Costa Rica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$275Average$456FlexibilityNo cancel feeOn-time65%
AviancaCheapest$319Average$462FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$343Average$609FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$431Average$656FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$432Average$649FlexibilityNo cancel feeOn-time62%
DeltaCheapest$438Average$778FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$444Average$710FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$470Average$799FlexibilityNo cancel feeOn-time69%

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