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$132+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
dic. 12 — dic. 191
vie. 12/12
vie. 12/19
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 noviembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$304
(Kiwi.com)

One-way from

$132
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$511
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 ($69 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 November 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 noviembre 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
jue. 12/112:16 pmMDW - SJO
1 stop25h 14mMultiple Airlines
dom. 12/141:31 pmSJO - MDW
2 stops20h 21mMultiple Airlines
Deal found 11/10$338
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
mié. 12/313:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
sáb. 1/102:58 pmSJO - MDW
1 stop8h 27mMultiple Airlines
Deal found 11/11$342
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/83:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
jue. 12/1812:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Deal found 11/12$345
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
lun. 12/293:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
lun. 1/122:58 pmSJO - MDW
1 stop8h 27mMultiple Airlines
Deal found 11/11$351
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
mié. 12/313:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
vie. 1/1612:33 pmSJO - MDW
1 stop8h 12mMultiple Airlines
Deal found 11/11$373
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:15 amMDW - SJO
2 stops30h 10mMultiple Airlines
jue. 12/1812:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Deal found 11/9$380
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
lun. 12/293:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
vie. 1/1612:33 pmSJO - MDW
1 stop8h 12mMultiple Airlines
Deal found 11/11$382
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
dom. 11/1610:12 amMDW - SJO
1 stop25h 27mMultiple Airlines
mar. 11/181:30 pmSJO - MDW
2 stops23h 11mMultiple Airlines
Deal found 11/10$386
This Frontier deal was found by Cheapflights users on 11/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/316:12 amMDW - SJO
1 stop7h 30mFrontier
sáb. 1/102:58 pmSJO - MDW
2 stops18h 15mFrontier
Deal found 11/10$427
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
jue. 12/47:23 pmMDW - SJO
2 stops41h 02mMultiple Airlines
mié. 12/3112:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Deal found 11/11$428
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/61:50 pmMDW - LIR
2 stops24h 39mWestJet
sáb. 12/1312:50 pmLIR - MDW
2 stops29h 28mWestJet
Deal found 11/11$682
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
sáb. 11/226:02 pmMDW - LIR
2 stops18h 48mMultiple Airlines
jue. 11/273:20 pmLIR - MDW
1 stop18h 45mMultiple Airlines
Deal found 11/10$685

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 noviembre 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

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

dom. 2/1

8:50 pm-2:15 pm

2 stops17h 25m

Liberia

vie. 2/6

2:55 pm-9:00 am

2 stops18h 05m

$403

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

dom. 2/1

8:50 pm-2:15 pm

2 stops17h 25m

Liberia

jue. 2/5

2:55 pm-10:25 pm

1 stop7h 30m

$403

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

vie. 1/30

6:00 am-1:00 pm

1 stop7h 00m

San José Juan Santamaria Intl

sáb. 2/7

7:00 am-10:26 pm

1 stop15h 26m

$410

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mié. 1/28

9:55 am-7:30 pm

2 stops9h 35m

San José Juan Santamaria Intl

mié. 2/4

9:40 am-10:55 pm

1 stop13h 15m

$413

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

sáb. 2/7

9:34 am-10:15 pm

2 stops12h 41m

San José Juan Santamaria Intl

mar. 2/10

2:31 pm-10:26 pm

1 stop7h 55m

$414

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

jue. 1/29

8:55 am-7:30 pm

1 stop10h 35m

San José Juan Santamaria Intl

mar. 2/3

9:40 am-10:55 pm

1 stop13h 15m

$438

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

sáb. 1/3

6:00 am-9:55 pm

1 stop15h 55m

San José Juan Santamaria Intl

jue. 1/15

7:00 am-10:09 pm

1 stop15h 09m

$443

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

jue. 1/29

9:34 am-10:15 pm

2 stops12h 41m

San José Juan Santamaria Intl

mar. 2/3

7:00 am-10:26 pm

1 stop15h 26m

$444

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mié. 12/10

10:15 am-8:30 pm

1 stop10h 15m

San José Juan Santamaria Intl

sáb. 12/13

2:15 pm-10:35 pm

1 stop8h 20m

$449

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

sáb. 1/10

6:45 am-1:50 pm

1 stop7h 05m

Liberia

jue. 1/15

2:05 pm-10:09 pm

1 stop8h 04m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 26 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 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 noviembre 12, 2025.

It’s optimal to fly from Chicago Midway Airport to Costa Rica in the evening. By choosing this option you can save up to 59% on the cost of your flight, compared to a flight at noon.

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 noviembre 12, 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
4,235 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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 7h. Airlines will cover a distance of 2206 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.

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 noviembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$394Average$662FlexibilityNo cancel feeOn-time63%

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