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$140+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(Delta)

One-way from

$140
(Southwest)

Popular in

December

Cheapest in

September

Average price

$338
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. 11% potential increase in price ($73 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 September 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 September 29, 2025.

This Delta deal was found by Cheapflights users on 9/28. 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 12/86:00 amMDW - LIR
1 stop6h 40mDelta
Thu 12/183:55 pmLIR - MDW
1 stop7h 54mDelta
Deal found 9/28$311
This Delta deal was found by Cheapflights users on 9/28. 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 12/86:00 amMDW - LIR
1 stop6h 40mDelta
Sun 12/142:05 pmLIR - MDW
2 stops22h 29mDelta
Deal found 9/28$335
This Southwest deal was found by Cheapflights users on 9/27. 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 10/185:05 amMDW - SJO
1 stop7h 55mSouthwest
Tue 10/211:00 pmSJO - MDW
1 stop9h 35mSouthwest
Deal found 9/27$340
This Delta deal was found by Cheapflights users on 9/26. 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 11/189:34 amMDW - SJO
2 stops12h 33mDelta
Mon 11/242:31 pmSJO - MDW
2 stops22h 03mDelta
Deal found 9/26$344
This Southwest deal was found by Cheapflights users on 9/28. 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 10/185:05 amMDW - SJO
1 stop7h 55mSouthwest
Wed 10/221:00 pmSJO - MDW
2 stops10h 05mSouthwest
Deal found 9/28$345
This Delta deal was found by Cheapflights users on 9/28. 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 11/36:00 amMDW - LIR
1 stop6h 40mDelta
Thu 11/62:05 pmLIR - MDW
1 stop8h 09mDelta
Deal found 9/28$355
This Delta deal was found by Cheapflights users on 9/28. 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 11/36:00 amMDW - LIR
1 stop6h 40mDelta
Tue 11/42:05 pmLIR - MDW
2 stops18h 35mDelta
Deal found 9/28$359
This Delta deal was found by Cheapflights users on 9/26. 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 11/1412:47 pmMDW - SJO
1 stop9h 20mDelta
Tue 11/257:00 amSJO - MDW
1 stop9h 38mDelta
Deal found 9/26$367
This Delta deal was found by Cheapflights users on 9/26. 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 11/156:48 pmMDW - SJO
2 stops27h 19mDelta
Mon 11/247:00 amSJO - MDW
1 stop9h 39mDelta
Deal found 9/26$371
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/309:15 amMDW - SJO
2 stops16h 35mMultiple Airlines
Fri 11/712:34 pmSJO - MDW
1 stop9h 46mMultiple Airlines
Deal found 9/26$373
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/158:05 amMDW - SJO
3 stops24h 45mMultiple Airlines
Sat 10/181:49 pmSJO - MDW
1 stop7h 58mMultiple Airlines
Deal found 9/27$376
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/88:05 amMDW - SJO
2 stops28h 25mMultiple Airlines
Sat 10/111:49 pmSJO - MDW
1 stop7h 58mMultiple Airlines
Deal found 9/26$377

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 September 29, 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

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Mon 12/8

6:00 am-12:40 pm

1 stop6h 40m

Liberia

Thu 12/18

3:55 pm-11:49 pm

1 stop7h 54m

$311

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Mon 12/8

6:00 am-12:40 pm

1 stop6h 40m

Liberia

Sun 12/14

2:05 pm-12:34 pm

2 stops22h 29m

$335

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 11/17

10:47 am-10:07 pm

1 stop11h 20m

San José Juan Santamaria Intl

Sat 11/22

2:31 pm-11:40 pm

1 stop9h 09m

$340

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 1/21

10:35 am-10:15 pm

1 stop11h 40m

San José Juan Santamaria Intl

Sat 1/31

7:00 am-3:25 pm

1 stop8h 25m

$340

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 11/18

9:34 am-10:07 pm

2 stops12h 33m

San José Juan Santamaria Intl

Tue 11/25

2:31 pm-8:54 am

2 stops18h 23m

$344

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 10/18

5:05 am-12:00 pm

1 stop7h 55m

San José Juan Santamaria Intl

Wed 10/22

1:00 pm-12:05 am

2 stops10h 05m

$345

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 10/21

8:05 pm-11:40 am

2 stops16h 35m

San José Juan Santamaria Intl

Sat 10/25

1:00 pm-10:25 pm

1 stop8h 25m

$345

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sat 1/10

6:00 am-2:30 pm

1 stop8h 30m

Liberia

Sat 1/17

2:15 pm-9:46 pm

1 stop7h 31m

$351

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Mon 11/3

6:00 am-12:40 pm

1 stop6h 40m

Liberia

Thu 11/6

2:05 pm-8:40 am

2 stops18h 35m

$359

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 11/16

6:00 am-10:07 pm

1 stop16h 07m

San José Juan Santamaria Intl

Tue 11/25

7:00 am-4:38 pm

1 stop9h 38m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Showing 1-10 of 39 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 $553). 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 September 29, 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 September 29, 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
4,246 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago Midway Airport to Costa Rica?

    Departing from Chicago Midway Airport to Costa Rica will take you 6h 40m. Airlines will cover a distance of 2158 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $553). 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$394Average$672FlexibilityNo cancel feeOn-time63%

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