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$182+ Cheap flights from Midway (MDW) 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Midway to Costa Rica

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Costa Rica (CR0). 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 December 22, 2024.

Round-trip from

$377
(Trip.com)

One-way from

$182
(Kiwi.com)
From Chicago Midway to Costa Rica
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One-way flight from Chicago Midway to Costa Rica
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Find flight deals from Midway to Costa Rica

Cheapest flights from Midway to Costa Rica
Explore the most affordable flight options available from Midway to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 22, 2024.

This Delta deal was found by Cheapflights users on 12/21. 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 12/306:00 amMDW - SJO
1 stop6h 50mDelta
Tue 12/312:15 pmSJO - MDW
1 stop7h 51mDelta
Deal found 12/21$813
This Southwest deal was found by Cheapflights users on 12/21. 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.
Sun 12/2210:40 pmMDW - LIR
2 stops15h 25mSouthwest
Wed 12/253:00 pmLIR - MDW
2 stops18h 15mSouthwest
Deal found 12/21$870
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/252:20 pmMDW - SJO
1 stop19h 58mMultiple Airlines
Sat 1/1112:25 pmSJO - MDW
1 stop21h 30mMultiple Airlines
Deal found 12/21$876
This Southwest deal was found by Cheapflights users on 12/21. 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.
Wed 12/2511:15 amMDW - SJO
2 stops9h 25mSouthwest
Fri 12/279:55 amSJO - MDW
1 stop12h 00mSouthwest
Deal found 12/21$960
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/252:20 pmMDW - SJO
1 stop19h 58mFrontier
Thu 1/211:38 amSJO - MDW
1 stop25h 46mFrontier
Deal found 12/21$1,050
This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:00 amMDW - LIR
1 stop8h 32mDelta
Tue 12/312:19 pmLIR - MDW
1 stop7h 47mDelta
Deal found 12/20$1,397
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Wed 12/2511:48 amMDW - LIR
3 stops19h 16mMultiple Airlines
Fri 12/275:20 pmLIR - MDW
2 stops23h 20mMultiple Airlines
Deal found 12/21$1,662
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Thu 12/2611:48 amMDW - LIR
3 stops19h 16mWestJet
Thu 1/28:05 amLIR - MDW
3 stops33h 39mWestJet
Deal found 12/21$2,769

Find flights from Midway to Costa Rica within your budget

Customize your flight search to find flights from Midway 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 December 22, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 2/14

6:48 pm-11:31 am

1 stop16h 43m

San José Juan Santamaria Intl

Sat 2/22

12:55 pm-10:04 pm

1 stop9h 09m

$377

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 2/22

10:43 am-10:06 pm

2 stops11h 23m

San José Juan Santamaria Intl

Sat 3/1

12:55 pm-10:04 pm

1 stop9h 09m

$481

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 4/30

5:55 am-12:10 pm

1 stop7h 15m

San José Juan Santamaria Intl

Sat 5/10

1:35 pm-11:30 pm

1 stop8h 55m

$583

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 1/11

6:00 am-12:54 pm

1 stop6h 54m

San José Juan Santamaria Intl

Sat 1/18

2:19 pm-10:20 pm

1 stop8h 01m

$636

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Fri 4/4

6:10 am-1:05 pm

1 stop7h 55m

Liberia

Sun 4/13

2:05 pm-11:00 pm

1 stop7h 55m

$701

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Mon 2/3

10:19 am-2:01 pm

3 stops27h 42m

Liberia

Thu 2/6

2:55 pm-5:43 pm

2 stops26h 48m

$793

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 3/25

6:00 am-11:41 am

1 stop6h 41m

Liberia

Tue 4/1

1:06 pm-10:27 pm

1 stop8h 21m

$795

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sat 2/15

1:05 pm-2:01 pm

1 stop24h 56m

Liberia

Sat 2/22

6:40 am-10:04 pm

2 stops15h 24m

$858

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 2/4

5:31 pm-12:59 am

2 stops31h 28m

$182

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 3/6

5:55 am-1:55 pm

1 stop8h 00m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 13 results
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Best time to book a flight from Midway to Costa Rica

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

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

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

Find hourly flight availability from Midway 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 December 22, 2024.

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

Rainfall in Costa Rica by month

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

Plan your trip to Costa Rica by taking into account the average temperature totals 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 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 December 22, 2024.
Read through reviews of airlines operating flights from Chicago to Costa Rica, such as Frontier, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.3
Good
2,812 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,472 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

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

    $269 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $281 and $299, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Costa Rica?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Costa Rica (average of $398). Flying from Chicago Midway Airport 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

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Top 2 airlines flying from Midway to Costa Rica

Discover the top 2 airlines that operate flights from Midway 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$613FlexibilityNo cancel feeOn-time63%
DeltaCheapest$584Average$1,005FlexibilityNo cancel feeOn-timeN/A
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