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$186+ Cheap flights from Costa Rica to Chicago (CHI)

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Costa Rica to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Costa Rica (CR0) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

Find flight deals from Costa Rica to Chicago

Cheapest flights from Costa Rica to Chicago
Explore the most affordable flight options available from Costa Rica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1612:23 pmSJO - ORD
1 stop8h 35mSpirit Airlines
Thu 2/204:20 pmORD - SJO
1 stop8h 39mSpirit Airlines
Deal found 11/19$315
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/151:49 amSJO - ORD
1 stop8h 43mMultiple Airlines
Wed 2/1912:48 amORD - SJO
1 stop13h 09mMultiple Airlines
Deal found 11/19$333
This Avianca deal was found by Cheapflights users on 11/19. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/254:55 pmSJO - ORD
1 stop19h 20mAvianca
Wed 12/42:35 pmORD - SJO
1 stop8h 20mAvianca
Deal found 11/19$453
This eDestinos deal was found by Cheapflights users on 11/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2611:38 amSJO - MDW
1 stop25h 46mMultiple Airlines
Mon 12/309:59 pmMDW - SJO
2 stops26h 55mMultiple Airlines
Deal found 11/18$484
This Booking.com deal was found by Cheapflights users on 11/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2911:38 amSJO - MDW
1 stop25h 46mFrontier
Wed 1/18:25 amMDW - SJO
1 stop25h 53mFrontier
Deal found 11/20$567
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/69:55 amSJO - MDW
1 stop7h 35mSouthwest
Mon 12/99:00 amMDW - SJO
2 stops11h 40mSouthwest
Deal found 11/19$579
This Air Canada deal was found by Cheapflights users on 11/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/222:45 pmLIR - ORD
1 stop20h 09mAir Canada
Fri 11/298:25 pmORD - LIR
1 stop18h 05mAir Canada
Deal found 11/18$631
This Delta deal was found by Cheapflights users on 11/19. 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.
Mon 11/252:12 pmSJO - MDW
1 stop7h 34mDelta
Sat 11/3010:41 amMDW - SJO
1 stop11h 12mDelta
Deal found 11/19$639
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Fri 11/2210:25 amLIR - ORD
3 stops28h 24mMultiple Airlines
Fri 11/298:40 pmORD - LIR
1 stop19h 02mMultiple Airlines
Deal found 11/18$665
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/233:45 pmLIR - ORD
1 stop17h 18mSun Country Air
Sun 12/298:03 pmORD - LIR
1 stop18h 41mSun Country Air
Deal found 11/19$678
This Alaska Airlines deal was found by Cheapflights users on 11/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/57:34 pmLIR - ORD
2 stops21h 20mAlaska Airlines
Sun 12/86:32 amORD - LIR
2 stops24h 59mAlaska Airlines
Deal found 11/19$833
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2311:41 amLIR - ORD
2 stops11h 56mAmerican Airlines
Sun 12/295:35 pmORD - LIR
1 stop17h 06mAmerican Airlines
Deal found 11/19$930

Find flights from Costa Rica to Chicago within your budget

Customize your flight search to find flights from Costa Rica to Chicago 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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 1/27

1:57 am-8:13 pm

1 stop18h 16m

Chicago O'Hare Intl

Mon 2/3

6:06 pm-11:18 am

1 stop17h 12m

$314

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 5/17

3:32 pm-11:05 am

1 stop18h 33m

Chicago O'Hare Intl

Sat 5/24

12:45 pm-11:15 pm

1 stop11h 30m

$317

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 2/3

1:57 am-7:06 pm

2 stops41h 09m

Chicago Midway

Mon 2/10

4:41 pm-12:59 am

3 stops32h 18m

$349

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 12/3

4:55 pm-12:15 pm

1 stop19h 20m

Chicago O'Hare Intl

Fri 12/6

2:35 pm-10:55 pm

1 stop8h 20m

$453

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 12/6

1:40 pm-7:20 am

2 stops17h 40m

Chicago Midway

Mon 12/9

7:15 am-8:40 pm

2 stops13h 25m

$515

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 12/29

11:38 am-1:24 pm

1 stop25h 46m

Chicago Midway

Wed 1/1

8:25 am-10:18 am

1 stop25h 53m

$567

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/7

7:00 am-4:12 pm

1 stop9h 12m

Chicago Midway

Thu 2/27

12:44 pm-9:52 pm

1 stop9h 08m

$639

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Mon 12/23

3:45 pm-9:03 am

1 stop17h 18m

Chicago O'Hare Intl

Sun 12/29

8:03 pm-2:44 pm

1 stop18h 41m

$678

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 1/10

8:50 am-11:25 am

1 stop26h 35m

Chicago O'Hare Intl

Sat 1/18

3:40 pm-5:57 pm

1 stop26h 17m

$706

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 4/16

10:00 am-5:04 am

2 stops18h 04m

Chicago O'Hare Intl

Sun 4/20

3:21 pm-5:25 pm

2 stops27h 04m

$724

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 41 results
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Best time to book a flight from Costa Rica to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Costa Rica 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.

Travel insights for flights from Costa Rica to Chicago

Get recent, data-driven insights about flights from Costa Rica to Chicago including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $232). Flying from Costa Rica to Chicago in June is currently the most expensive (average of $308). 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 CR to CHI?

Find hourly flight availability from Costa Rica to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Costa Rica to Chicago as you normally would.

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 20, 2024.
Read through reviews of airlines operating flights from Costa Rica to Chicago, such as Spirit Airlines, Air Canada and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Aeromexico
7.5
Good
2,004 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from Costa Rica to Chicago. 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 Costa Rica to Chicago one-way?

    $186 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on Spirit Airlines and Avianca, with prices starting from $189 and $203, respectively.

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

    When deciding which route to take from Costa Rica to Chicago consider San José Juan Santamaria Intl - Chicago O'Hare Intl, San José Juan Santamaria Intl - Chicago Midway or Liberia - Chicago O'Hare Intl as they are the most popular.

  • What are the cheapest flights from Costa Rica to Chicago?

    While on average a flight from Costa Rica to Chicago is generally $1,050, our data shows the cheapest flight currently is $280. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $278 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Costa Rica to Chicago 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 Costa Rica to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $232). Flying from Costa Rica to Chicago in June is currently the most expensive (average of $308). 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 Costa Rica to Chicago

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

Top 6 airlines flying from Costa Rica to Chicago

Discover the top 6 airlines that operate flights from Costa Rica to Chicago. 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$370FlexibilityNo cancel feeOn-time65%
AviancaCheapest$262Average$413FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$393Average$562FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$438Average$676FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$476Average$667FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$680FlexibilityNo cancel feeOn-timeN/A
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