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$203+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$384
(Kiwi.com)

One-way from

$203
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$504
Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.
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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. 10% potential increase in price ($73 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sun 6/19:12 pmMDW - SJO
1 stop14h 15mMultiple Airlines
Sun 6/86:05 pmSJO - MDW
2 stops25h 12mMultiple Airlines
Deal found 4/30$392
This Southwest deal was found by Cheapflights users on 4/29. 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.
Thu 9/259:15 amMDW - SJO
2 stops10h 40mSouthwest
Tue 9/301:40 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 4/29$451
This Delta deal was found by Cheapflights users on 4/30. 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 9/36:00 amMDW - SJO
1 stop6h 48mDelta
Mon 9/81:18 pmSJO - MDW
1 stop7h 26mDelta
Deal found 4/30$484
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 6/285:10 amMDW - LIR
1 stop8h 55mSouthwest
Sat 7/511:50 amLIR - MDW
1 stop7h 30mSouthwest
Deal found 4/29$536
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 8/196:00 amMDW - LIR
1 stop7h 00mDelta
Tue 8/261:25 pmLIR - MDW
1 stop19h 26mDelta
Deal found 4/29$616
This LATAM Airlines deal was found by Cheapflights users on 4/30. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/54:59 pmMDW - SJO
2 stops23h 36mLATAM Airlines
Tue 5/135:00 pmSJO - MDW
2 stops15h 40mLATAM Airlines
Deal found 4/30$2,887
This WestJet deal was found by Cheapflights users on 4/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/139:21 amMDW - LIR
2 stops28h 03mWestJet
Fri 6/201:25 pmLIR - MDW
2 stops26h 47mWestJet
Deal found 4/29$3,213

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 May 1, 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

Sun 6/1

9:12 pm-10:27 am

1 stop14h 15m

San José Juan Santamaria Intl

Sun 6/8

6:05 pm-8:17 pm

2 stops25h 12m

$392

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 5/6

5:55 am-12:10 pm

1 stop7h 15m

San José Juan Santamaria Intl

Wed 5/14

8:45 am-6:25 pm

1 stop8h 40m

$482

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sat 6/28

5:10 am-1:05 pm

1 stop8h 55m

Liberia

Sat 7/5

11:50 am-8:20 pm

1 stop7h 30m

$536

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 5/27

6:00 am-12:00 pm

1 stop7h 00m

Liberia

Wed 6/4

1:25 pm-8:40 am

2 stops18h 15m

$669

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 5/6

6:04 am-11:55 am

1 stop6h 51m

San José Juan Santamaria Intl

Thu 5/15

1:24 pm-6:45 pm

2 stops28h 21m

$705

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 5/5

4:59 pm-3:35 pm

2 stops23h 36m

San José Juan Santamaria Intl

Tue 5/13

5:00 pm-9:40 am

2 stops15h 40m

$2,887

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Fri 6/13

9:21 am-12:24 pm

2 stops28h 03m

Liberia

Fri 6/20

1:25 pm-5:12 pm

2 stops26h 47m

$3,213

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/14

2:12 pm-10:27 am

2 stops21h 15m

$203

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 5/13

6:00 am-11:59 am

1 stop6h 59m

$205

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 5/4

7:00 am-7:40 pm

2 stops13h 40m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 12 results
1
2

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 May 1, 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 May 1, 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
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $205 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and Frontier, with prices starting from $213 and $319, 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$692FlexibilityNo cancel feeOn-time63%
DeltaCheapest$544Average$886FlexibilityNo cancel feeOn-timeN/A

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