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$187+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$310
(Priceline)

One-way from

$187
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$452
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. 0% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 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 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 August 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.
Sat 10/181:49 pmSJO - MDW
1 stop8h 36mFrontier
Sat 10/256:15 amMDW - SJO
1 stop7h 19mFrontier
Deal found 8/12$310
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2511:37 amSJO - MDW
1 stop20h 16mMultiple Airlines
Sun 10/510:13 amMDW - SJO
1 stop25h 14mMultiple Airlines
Deal found 8/12$354
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.
Wed 9/248:50 amSJO - MDW
1 stop8h 35mSouthwest
Tue 9/306:25 amMDW - SJO
1 stop13h 30mSouthwest
Deal found 8/13$384
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:19 pmSJO - MDW
2 stops43h 59mMultiple Airlines
Sun 10/510:13 amMDW - SJO
1 stop25h 14mMultiple Airlines
Deal found 8/12$387
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/72:15 pmSJO - MDW
1 stop7h 59mDelta
Sun 11/1610:35 amMDW - SJO
1 stop11h 40mDelta
Deal found 8/12$394
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.
Thu 10/95:55 pmSJO - MDW
2 stops21h 25mMultiple Airlines
Mon 10/135:28 pmMDW - SJO
1 stop18h 14mMultiple Airlines
Deal found 8/13$410
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.
Thu 10/91:30 pmSJO - MDW
1 stop10h 15mSouthwest
Tue 10/145:15 amMDW - SJO
1 stop7h 25mSouthwest
Deal found 8/12$412
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.
Thu 9/118:50 amSJO - MDW
1 stop9h 35mSouthwest
Thu 9/187:45 amMDW - SJO
1 stop12h 10mSouthwest
Deal found 8/12$415

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 August 14, 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

Sat 10/18

1:49 pm-11:25 pm

1 stop8h 36m

Chicago Midway

Sat 10/25

6:15 am-12:34 pm

1 stop7h 19m

$310

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 10/10

11:37 am-3:11 pm

1 stop26h 34m

Chicago Midway

Mon 10/13

5:28 pm-10:41 am

1 stop18h 13m

$354

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/25

11:37 am-8:53 am

1 stop20h 16m

Chicago Midway

Sun 10/5

10:13 am-10:27 am

1 stop25h 14m

$354

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/26

11:37 am-9:51 am

1 stop21h 14m

Chicago Midway

Sun 10/5

10:13 am-10:27 am

1 stop25h 14m

$354

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 10/3

11:37 am-9:51 am

1 stop21h 14m

Chicago Midway

Sun 10/12

12:39 pm-10:42 am

1 stop23h 03m

$357

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/17

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

Tue 9/23

6:25 am-6:55 pm

1 stop13h 30m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 11/6

2:10 pm-12:10 am

1 stop10h 00m

Chicago Midway

Mon 11/10

5:50 am-1:15 pm

1 stop7h 25m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/24

8:50 am-6:25 pm

1 stop8h 35m

Chicago Midway

Mon 9/29

5:05 am-12:45 pm

1 stop8h 40m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/24

8:50 am-6:25 pm

1 stop8h 35m

Chicago Midway

Tue 9/30

6:25 am-6:55 pm

1 stop13h 30m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/30

11:37 am-8:32 am

1 stop19h 55m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 14 results
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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 time of day to fly from CR to MDW?

Find hourly flight availability from Costa Rica to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Costa Rica to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

  • 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, April is the cheapest month in which you can book a flight from Costa Rica to Chicago Midway Airport (average of $160). Flying from Costa Rica to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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