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$168+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$324
(Kiwi.com)

One-way from

$168
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$446
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. 3% potential increase in price ($17 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 September 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 September 29, 2025.

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 11/72:15 pmSJO - MDW
1 stop7h 59mDelta
Thu 11/1312:47 pmMDW - SJO
1 stop9h 20mDelta
Deal found 9/26$326
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.
Fri 11/72:15 pmSJO - MDW
1 stop7h 59mDelta
Fri 11/1412:47 pmMDW - SJO
1 stop9h 20mDelta
Deal found 9/28$332
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:55 pmSJO - MDW
1 stop9h 30mSouthwest
Mon 10/205:30 amMDW - SJO
1 stop8h 05mSouthwest
Deal found 9/26$335
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.
Fri 11/217:00 amSJO - MDW
1 stop9h 38mDelta
Fri 11/286:00 amMDW - SJO
1 stop7h 05mDelta
Deal found 9/28$337
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/171:30 pmSJO - MDW
1 stop10h 15mSouthwest
Tue 10/218:05 pmMDW - SJO
2 stops16h 35mSouthwest
Deal found 9/26$340
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.
Sat 11/89:00 amSJO - MDW
1 stop12h 22mMultiple Airlines
Sat 11/152:05 pmMDW - SJO
1 stop10h 45mMultiple Airlines
Deal found 9/26$342
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 10/2912:35 pmSJO - MDW
2 stops23h 02mMultiple Airlines
Sun 11/210:12 amMDW - SJO
1 stop25h 27mMultiple Airlines
Deal found 9/26$353
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 11/72:15 pmSJO - MDW
1 stop7h 59mDelta
Mon 11/1712:47 pmMDW - SJO
1 stop9h 20mDelta
Deal found 9/26$360
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 10/166:10 pmSJO - MDW
2 stops14h 23mMultiple Airlines
Mon 10/2010:33 amMDW - SJO
2 stops22h 17mMultiple Airlines
Deal found 9/26$363
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.
Fri 11/72:15 pmSJO - MDW
1 stop7h 59mDelta
Tue 11/1812:47 pmMDW - SJO
1 stop9h 20mDelta
Deal found 9/28$367

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 September 29, 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

Thu 11/6

2:15 pm-12:28 pm

2 stops22h 13m

Chicago Midway

Sun 11/16

6:00 am-10:07 pm

1 stop16h 07m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 11/10

2:31 pm-11:40 pm

1 stop9h 09m

Chicago Midway

Sat 11/15

6:00 am-10:07 pm

1 stop16h 07m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 11/6

2:15 pm-12:28 pm

2 stops22h 13m

Chicago Midway

Thu 11/13

12:47 pm-10:07 pm

1 stop9h 20m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 10/24

1:23 pm-10:14 pm

1 stop7h 51m

Chicago Midway

Mon 10/27

6:00 am-11:58 am

1 stop6h 58m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 10/21

1:23 pm-10:14 pm

1 stop7h 51m

Chicago Midway

Tue 10/28

6:00 am-11:58 am

1 stop6h 58m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 11/10

2:31 pm-8:54 am

2 stops18h 23m

Chicago Midway

Thu 11/13

6:00 am-10:07 pm

1 stop16h 07m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 11/10

2:31 pm-8:54 am

2 stops18h 23m

Chicago Midway

Sun 11/16

6:48 pm-1:06 pm

2 stops18h 18m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/16

12:55 pm-11:25 pm

1 stop9h 30m

Chicago Midway

Mon 10/20

5:30 am-12:35 pm

1 stop8h 05m

$335

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 10/17

1:30 pm-12:45 am

1 stop10h 15m

Chicago Midway

Sun 10/26

6:25 am-12:05 pm

1 stop6h 40m

$335

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 11/21

7:00 am-4:38 pm

1 stop9h 38m

Chicago Midway

Fri 11/28

6:00 am-1:05 pm

1 stop7h 05m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Showing 1-10 of 21 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
No data available for this route at this time. Please check back soon.

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 September 29, 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
4,246 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

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 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 22h 13m. 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, 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

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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$463Average$523FlexibilityNo cancel feeOn-time63%

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