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$133+ Cheap flights from Costa Rica to Midway (MDW)

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 12/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
déc. 12 — déc. 191
ven. 12/12
ven. 12/19
1 adult, Economy
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Cheap flight deals from Costa Rica to Midway

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$315
(Kiwi.com)

One-way from

$133
(Trip.com)

Popular in

June

Cheapest in

January

Average price

$429
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago (CHI) flights.
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From Costa Rica to Chicago Midway
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One-way flight from Costa Rica to Chicago Midway
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Highest demand for flights based on searches. 4% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 Costa Rica to Midway

Cheapest flights from Costa Rica to Midway
Explore the most affordable flight options available from Costa Rica to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on novembre 12, 2025.

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.
ven. 11/2111:24 amSJO - MDW
1 stop12h 05mMultiple Airlines
jeu. 11/275:30 pmMDW - SJO
1 stop16h 49mMultiple Airlines
Deal found 11/9$296
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.
jeu. 12/412:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
jeu. 12/112:16 pmMDW - SJO
1 stop25h 14mMultiple Airlines
Deal found 11/9$315
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.
jeu. 12/47:45 amSJO - MDW
1 stop14h 08mMultiple Airlines
sam. 12/62:59 pmMDW - SJO
2 stops20h 26mMultiple Airlines
Deal found 11/12$316
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.
jeu. 12/1812:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
dim. 1/42:16 pmMDW - SJO
1 stop21h 26mMultiple Airlines
Deal found 11/11$329
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.
ven. 12/262:57 pmSJO - MDW
1 stop31h 15mMultiple Airlines
jeu. 1/16:12 amMDW - SJO
2 stops21h 38mMultiple Airlines
Deal found 11/11$333
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. 12/1512:39 pmSJO - MDW
2 stops9h 33mMultiple Airlines
dim. 1/42:16 pmMDW - SJO
1 stop21h 26mMultiple Airlines
Deal found 11/11$344
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.
mar. 12/91:31 pmSJO - MDW
2 stops19h 15mMultiple Airlines
lun. 12/153:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
Deal found 11/10$345
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.
dim. 12/2112:39 pmSJO - MDW
1 stop8h 25mMultiple Airlines
mer. 12/313:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
Deal found 11/10$349
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.
mar. 12/2312:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
mer. 12/313:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
Deal found 11/10$352
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.
mer. 12/2412:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
mer. 12/313:32 pmMDW - SJO
2 stops19h 53mMultiple Airlines
Deal found 11/11$358

Cheapflights Fare Finder

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

Fly from

Costa Rica

Fly to

Midway

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

sam. 1/17

7:00 am-10:09 pm

1 stop15h 09m

Chicago Midway

sam. 1/24

6:00 am-1:00 pm

1 stop7h 00m

$400

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mer. 1/14

7:00 am-10:09 pm

1 stop15h 09m

Chicago Midway

mer. 1/28

12:48 pm-10:15 pm

1 stop9h 27m

$400

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

jeu. 1/15

7:00 am-10:09 pm

1 stop15h 09m

Chicago Midway

mar. 1/20

9:34 am-10:15 pm

2 stops12h 41m

$400

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

jeu. 2/5

7:00 am-10:26 pm

1 stop15h 26m

Chicago Midway

dim. 2/22

10:53 am-10:15 pm

1 stop11h 22m

$411

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

ven. 1/23

7:00 am-10:26 pm

1 stop15h 26m

Chicago Midway

ven. 1/30

12:48 pm-10:15 pm

1 stop9h 27m

$440

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

ven. 1/30

9:40 am-10:55 pm

1 stop13h 15m

Chicago Midway

jeu. 2/5

5:55 am-7:30 pm

1 stop13h 35m

$466

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

lun. 12/22

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

jeu. 1/1

9:50 am-9:55 pm

1 stop12h 05m

$470

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mer. 12/3

7:00 am-6:00 pm

2 stops11h 00m

Chicago Midway

lun. 12/8

10:49 am-10:20 pm

1 stop11h 31m

$470

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

sam. 12/20

2:21 pm-10:22 pm

1 stop8h 01m

Chicago Midway

mar. 1/20

10:53 am-10:15 pm

1 stop11h 22m

$470

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

sam. 12/20

10:36 am-9:04 pm

1 stop10h 28m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 18 results
1
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Best time to book a flight from Costa Rica to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Costa Rica 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 Costa Rica to Chicago Midway Airport

What is the cheapest month to book a flight from Costa Rica to Chicago Midway Airport?

Currently, August is the cheapest month in which you can book a flight from Costa Rica to Chicago Midway Airport (average of $292). Flying from Costa Rica to Chicago Midway Airport in November is currently the most expensive (average of $639). 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated novembre 12, 2025.
Read reviews from past customers who have flown Southwest from Costa Rica to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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 Costa Rica to Midway. 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 Costa Rica to Chicago Midway Airport?

    Delta can get you from Costa Rica to Chicago Midway Airport in just under 15h 09m. Your travel time can differ by up to . Costa Rica and Chicago Midway Airport are separated by a distance of 2206 mi.

  • Can I find deals for flights from Costa Rica to Midway that include hotel bookings?

    Yes. In addition to deals on Costa Rica to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Costa Rica to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Costa Rica to Midway.

  • Can I find deals for business class flights from Costa Rica to Midway?

    Yes. Cheapflights offers flight deals from Costa Rica to Midway 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 Costa Rica to Chicago Midway Airport?

    Currently, August is the cheapest month in which you can book a flight from Costa Rica to Chicago Midway Airport (average of $292). Flying from Costa Rica to Chicago Midway Airport in November is currently the most expensive (average of $639). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Costa Rica to Midway

Discover the top airline that operate flights from Costa Rica to Midway. 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 novembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$463Average$523FlexibilityNo cancel feeOn-time63%

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