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$157+ 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 12 — Nov 191
1 adult
Tue 11/12
Tue 11/19
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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 7, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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.
Fri 12/61:24 pmSJO - ORD
1 stop7h 43mSpirit Airlines
Mon 12/95:00 amORD - SJO
1 stop7h 19mSpirit Airlines
Deal found 11/7$308
This Copa Airlines deal was found by Cheapflights users on 11/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/95:20 pmSJO - ORD
1 stop18h 56mCopa Airlines
Sun 11/176:54 amORD - SJO
1 stop8h 54mCopa Airlines
Deal found 11/7$318
This Priceline deal was found by Cheapflights users on 11/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/41:24 pmSJO - ORD
1 stop7h 43mMultiple Airlines
Wed 1/291:35 pmORD - SJO
1 stop19h 45mMultiple Airlines
Deal found 11/6$341
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2112:26 pmSJO - MDW
1 stop19h 44mMultiple Airlines
Mon 11/252:55 pmMDW - SJO
2 stops20h 36mMultiple Airlines
Deal found 11/7$354
This Priceline deal was found by Cheapflights users on 11/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/92:15 amSJO - ORD
1 stop10h 00mAvianca
Tue 11/121:35 pmORD - SJO
1 stop19h 45mAvianca
Deal found 11/6$399
This Gotogate deal was found by Cheapflights users on 11/6. 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 Gotogate 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 1/12:20 pmMDW - SJO
1 stop19h 58mFrontier
Deal found 11/6$468
This Southwest deal was found by Cheapflights users on 11/5. 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 12/61:40 pmSJO - MDW
2 stops17h 40mSouthwest
Wed 12/119:00 amMDW - SJO
2 stops11h 40mSouthwest
Deal found 11/5$505
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 25mAlaska Airlines
Sun 12/88:00 amORD - LIR
2 stops23h 31mAlaska Airlines
Deal found 11/6$610
This Delta deal was found by Cheapflights users on 11/6. 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.
Sat 12/72:13 pmSJO - MDW
1 stop7h 53mDelta
Thu 2/271:05 pmMDW - SJO
1 stop9h 21mDelta
Deal found 11/6$628
This Justfly.com deal was found by Cheapflights users on 11/6. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/53:30 pmLIR - ORD
1 stop21h 41mAir Canada
Sun 12/87:19 amORD - LIR
1 stop31h 11mAir Canada
Deal found 11/6$635
This United Airlines deal was found by Cheapflights users on 11/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/52:14 pmLIR - ORD
1 stop8h 30mUnited Airlines
Sun 12/87:45 amORD - LIR
Nonstop5h 10mUnited Airlines
Deal found 11/6$788
This Mytrip deal was found by Cheapflights users on 11/7. 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.
Sun 12/16:40 amLIR - ORD
2 stops21h 57mMultiple Airlines
Mon 12/94:00 pmORD - LIR
1 stop22h 30mMultiple Airlines
Deal found 11/7$905

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 2,537,365 searches. Data last updated November 7, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 12/6

1:49 am-4:06 pm

1 stop14h 17m

$185

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 11/20

12:26 pm-7:55 am

1 stop19h 29m

$193

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 11/17

4:55 pm-12:15 pm

1 stop19h 20m

$234

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 12/14

3:40 pm-11:35 am

1 stop19h 55m

$255

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 11/27

3:30 pm-10:05 am

1 stop18h 35m

$272

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 4/9

11:15 pm-10:16 am

1 stop10h 01m

$286

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 12/6

7:34 pm-11:47 pm

2 stops28h 13m

$293

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 12/29

11:38 am-1:24 pm

1 stop25h 46m

$330

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 11/24

2:05 pm-7:30 pm

Nonstop5h 25m

$335

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 12/3

4:08 am-12:16 pm

1 stop8h 08m

$337

Flights are sorted by cheapest first

Deals found on 11/6

Showing 1-10 of 37 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 7, 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 7, 2024.
Read through reviews of airlines operating flights from Costa Rica to Chicago, such as Spirit Airlines, Alaska Airlines and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,083 reviews

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,083 reviews
Southwest
8.1
Very good
5,083 reviews

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,828 reviews
Southwest
8.1
Very good
5,083 reviews

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,428 reviews
Southwest
8.1
Very good
5,083 reviews

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Copa Airlines
7.8
Good
1,850 reviews
Southwest
8.1
Very good
5,083 reviews

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Aeromexico
7.5
Good
2,022 reviews
Southwest
8.1
Very good
5,083 reviews

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.7

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?

    $157 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Avianca and Sun Country Air, with prices starting from $234 and $255, 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 $1,027, our data shows the cheapest flight currently is $210. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $266 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.
Guatemala City to O'Hare Intl flights
San José to O'Hare Intl flights
Panama City to O'Hare Intl flights
San Salvador to O'Hare Intl flights
Guatemala City to Midway flights
San José to Midway flights
San Pedro Sula to O'Hare Intl flights
San José to St. Louis flights
Philip S.W.Goldson to O'Hare Intl flights
Managua to O'Hare Intl flights
San Pedro Sula to Midway flights
San Pedro Sula to St. Louis flights
Liberia to O'Hare Intl flights
Philip S.W.Goldson to Midway flights
Guatemala City to St. Louis flights
Managua to Midway flights
Tegucigalpa to St. Louis flights
Panama City to St. Louis flights
Tegucigalpa to Midway flights
Tegucigalpa to O'Hare Intl flights
Coxen Hole to O'Hare Intl 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 2,537,365 searches. Data last updated November 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$365FlexibilityNo cancel feeOn-time65%
AviancaCheapest$262Average$403FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$393Average$561FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$438Average$676FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$476Average$668FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$680FlexibilityNo cancel feeOn-timeN/A
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