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$185+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Midway to Costa Rica

Keep the following information in mind while searching for Midway to Costa Rica flight deals. Data was last updated June 12, 2025.

Round-trip from

$407
(Southwest)

One-way from

$185
(Southwest)

Popular in

December

Cheapest in

July

Average price

$559
From Chicago Midway to Costa Rica
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One-way flight from Chicago Midway to Costa Rica
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Highest demand for flights based on searches. 9% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
Mon 9/228:05 amMDW - SJO
2 stops11h 50mSouthwest
Sun 9/2812:35 pmSJO - MDW
1 stop7h 40mSouthwest
Deal found 6/11$407
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/319:12 pmMDW - SJO
1 stop14h 17mMultiple Airlines
Fri 8/88:50 amSJO - MDW
2 stops13h 27mMultiple Airlines
Deal found 6/11$454
This Southwest deal was found by Cheapflights users on 6/11. 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 7/95:20 amMDW - LIR
2 stops8h 50mSouthwest
Wed 7/232:10 pmLIR - MDW
1 stop8h 00mSouthwest
Deal found 6/11$530
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 10/246:00 amMDW - LIR
1 stop7h 00mDelta
Sun 11/22:12 pmLIR - MDW
1 stop7h 32mDelta
Deal found 6/11$534
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/85:20 pmMDW - LIR
1 stop20h 04mMultiple Airlines
Thu 7/241:25 pmLIR - MDW
1 stop18h 20mMultiple Airlines
Deal found 6/10$574
This Delta deal was found by Cheapflights users on 6/9. 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.
Sun 11/96:00 amMDW - SJO
1 stop6h 52mDelta
Sun 11/162:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 6/9$691

Cheapflights Fare Finder

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 June 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Costa Rica that are best for you.

Fly from

Midway

Fly to

Costa Rica

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/22

8:05 am-6:55 pm

2 stops11h 50m

San José Juan Santamaria Intl

Sun 9/28

12:35 pm-9:15 pm

1 stop7h 40m

$407

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 7/31

9:12 pm-10:29 am

1 stop14h 17m

San José Juan Santamaria Intl

Fri 8/8

8:50 am-11:17 pm

2 stops13h 27m

$454

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Wed 7/9

5:20 am-1:10 pm

2 stops8h 50m

Liberia

Wed 7/23

2:10 pm-11:10 pm

1 stop8h 00m

$530

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 7/8

5:20 pm-12:24 pm

1 stop20h 04m

Liberia

Thu 7/24

1:25 pm-8:45 am

1 stop18h 20m

$574

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 11/9

6:00 am-12:52 pm

1 stop6h 52m

San José Juan Santamaria Intl

Sun 11/16

2:17 pm-9:44 pm

1 stop7h 27m

$691

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 7/29

6:00 am-12:00 pm

1 stop7h 00m

Liberia

Sat 8/2

1:05 pm-9:42 pm

1 stop7h 37m

$719

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 7/8

9:24 am-12:24 pm

2 stops28h 00m

Liberia

Thu 7/17

1:25 pm-5:39 pm

2 stops27h 14m

$3,227

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 6/29

5:15 am-11:35 am

1 stop7h 20m

$185

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 7/5

9:12 pm-10:36 am

1 stop14h 24m

$232

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Thu 7/31

5:15 am-1:10 pm

2 stops8h 55m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 14 results
1
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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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Costa Rica

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.

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 June 12, 2025.

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 June 12, 2025.
Read through reviews of airlines operating flights from Chicago to Costa Rica, such as Southwest, Delta and WestJet. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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?

    $185 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and WestJet, with prices starting from $338 and $1,330, 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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$682FlexibilityNo cancel feeOn-time63%
DeltaCheapest$544Average$779FlexibilityNo cancel feeOn-timeN/A

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