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$151+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$387
(Southwest)

One-way from

$151
(Orbitz)

Popular in

December

Cheapest in

September

Average price

$536
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. 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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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 agosto 14, 2025.

This Priceline deal was found by Cheapflights users on 8/12. 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.
sáb. 10/116:15 amMDW - SJO
1 stop7h 19mFrontier
sáb. 10/181:49 pmSJO - MDW
1 stop8h 36mFrontier
Deal found 8/12$367
This Southwest deal was found by Cheapflights users on 8/14. 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.
mar. 9/99:10 amMDW - SJO
1 stop10h 45mSouthwest
mié. 9/171:40 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 8/14$387
This Delta deal was found by Cheapflights users on 8/14. 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.
jue. 11/66:00 amMDW - SJO
1 stop6h 50mDelta
mar. 11/112:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 8/14$394
This Delta deal was found by Cheapflights users on 8/14. 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.
mié. 11/199:30 amMDW - SJO
2 stops12h 45mDelta
mar. 11/252:17 pmSJO - MDW
1 stop7h 27mDelta
Deal found 8/14$398
This Southwest deal was found by Cheapflights users on 8/13. 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.
lun. 9/85:05 amMDW - SJO
1 stop8h 40mSouthwest
sáb. 9/131:15 pmSJO - MDW
1 stop8h 30mSouthwest
Deal found 8/13$417
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
sáb. 9/1310:51 amMDW - SJO
1 stop24h 36mMultiple Airlines
vie. 9/192:55 pmSJO - MDW
2 stops17h 56mMultiple Airlines
Deal found 8/13$430
This Southwest deal was found by Cheapflights users on 8/13. 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.
mar. 9/26:15 amMDW - SJO
1 stop7h 30mSouthwest
mar. 9/98:50 amSJO - MDW
1 stop8h 35mSouthwest
Deal found 8/13$432
This Delta deal was found by Cheapflights users on 8/13. 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.
jue. 12/116:00 amMDW - SJO
1 stop16h 15mDelta
mar. 12/232:10 pmSJO - MDW
1 stop7h 55mDelta
Deal found 8/13$435
This Delta deal was found by Cheapflights users on 8/13. 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.
jue. 12/111:05 pmMDW - SJO
1 stop9h 10mDelta
mié. 12/242:10 pmSJO - MDW
2 stops18h 42mDelta
Deal found 8/13$439
This Southwest deal was found by Cheapflights users on 8/12. 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.
mié. 11/128:20 pmMDW - LIR
2 stops17h 30mSouthwest
mié. 11/192:45 pmLIR - MDW
2 stops18h 30mSouthwest
Deal found 8/12$447
This Southwest deal was found by Cheapflights users on 8/12. 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.
mié. 11/57:00 amMDW - LIR
1 stop6h 50mSouthwest
mié. 11/122:45 pmLIR - MDW
1 stop7h 25mSouthwest
Deal found 8/12$449
This Southwest deal was found by Cheapflights users on 8/13. 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.
dom. 11/95:10 amMDW - LIR
1 stop8h 40mSouthwest
vie. 11/142:45 pmLIR - MDW
2 stops16h 45mSouthwest
Deal found 8/13$475

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 agosto 14, 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

sáb. 10/11

6:15 am-12:34 pm

1 stop7h 19m

San José Juan Santamaria Intl

sáb. 10/18

1:49 pm-11:25 pm

1 stop8h 36m

$367

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mié. 9/10

6:25 am-6:55 pm

1 stop13h 30m

San José Juan Santamaria Intl

mar. 9/23

1:40 pm-11:20 pm

1 stop8h 40m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 11/11

10:15 am-8:30 pm

1 stop10h 15m

San José Juan Santamaria Intl

mar. 11/18

9:00 am-4:35 pm

1 stop7h 35m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 9/9

9:10 am-6:55 pm

1 stop10h 45m

San José Juan Santamaria Intl

mar. 9/16

8:50 am-6:25 pm

1 stop8h 35m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 9/9

9:10 am-6:55 pm

1 stop10h 45m

San José Juan Santamaria Intl

mié. 9/17

1:40 pm-11:20 pm

1 stop8h 40m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

lun. 9/8

5:05 am-12:45 pm

1 stop8h 40m

San José Juan Santamaria Intl

jue. 9/18

8:50 am-7:25 pm

1 stop9h 35m

$387

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

lun. 9/8

5:05 am-12:45 pm

1 stop8h 40m

San José Juan Santamaria Intl

mié. 9/10

8:50 am-9:40 pm

1 stop11h 50m

$387

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

mié. 11/12

8:20 pm-1:50 pm

2 stops17h 30m

Liberia

mié. 11/19

2:45 pm-9:15 am

2 stops18h 30m

$447

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

mié. 11/5

7:00 am-1:50 pm

1 stop6h 50m

Liberia

mié. 11/12

2:45 pm-10:10 pm

1 stop7h 25m

$449

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

dom. 11/9

5:10 am-1:50 pm

1 stop8h 40m

Liberia

vie. 11/14

2:45 pm-7:30 am

2 stops16h 45m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 30 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.

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 agosto 14, 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.

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 agosto 14, 2025.
See what other customers who have flown with Southwest from Chicago Midway Airport to Costa Rica have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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 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.

  • 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 airline flying from Midway to Costa Rica

Discover the top airline 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$431Average$665FlexibilityNo cancel feeOn-time63%

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