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$162+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Delta deal was found by Cheapflights users on 12/25. 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 12/272:21 pmSJO - MDW
1 stop8h 01mDelta
Fri 1/29:29 amMDW - SJO
2 stops12h 26mDelta
Deal found 12/25$470
This Delta deal was found by Cheapflights users on 12/26. 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.
Mon 12/297:00 amSJO - MDW
1 stop15h 22mDelta
Sun 1/49:50 amMDW - SJO
1 stop12h 05mDelta
Deal found 12/26$569
This Booking.com deal was found by Cheapflights users on 12/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2710:36 amSJO - MDW
1 stop10h 28mFrontier
Sat 1/36:12 amMDW - SJO
1 stop7h 30mFrontier
Deal found 12/26$593
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 12/3112:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Sun 1/410:50 pmMDW - SJO
2 stops36h 52mMultiple Airlines
Deal found 12/25$599
This Delta deal was found by Cheapflights users on 12/26. 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 12/277:00 amSJO - MDW
1 stop15h 22mDelta
Sat 1/39:29 amMDW - SJO
2 stops12h 26mDelta
Deal found 12/26$640
This KAYAK deal was found by Cheapflights users on 12/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:52 pmSJO - MDW
1 stop26h 46mFrontier
Sat 1/36:12 amMDW - SJO
1 stop7h 30mFrontier
Deal found 12/25$655
This Delta deal was found by Cheapflights users on 12/26. 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 12/272:21 pmSJO - MDW
1 stop8h 01mDelta
Sun 1/49:50 amMDW - SJO
1 stop12h 05mDelta
Deal found 12/26$668
This Southwest deal was found by Cheapflights users on 12/26. 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.
Sat 12/279:00 amSJO - MDW
1 stop7h 55mSouthwest
Sun 1/48:05 amMDW - SJO
1 stop12h 25mSouthwest
Deal found 12/26$683
This Southwest deal was found by Cheapflights users on 12/26. 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.
Sat 12/279:00 amSJO - MDW
2 stops10h 30mSouthwest
Sat 1/39:40 pmMDW - SJO
2 stops15h 35mSouthwest
Deal found 12/26$688
This Southwest deal was found by Cheapflights users on 12/26. 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.
Wed 12/312:15 pmSJO - MDW
1 stop7h 55mSouthwest
Sun 1/45:20 amMDW - SJO
1 stop7h 55mSouthwest
Deal found 12/26$696

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$307
(Kiwi.com)

One-way from

$162
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$469
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago (CHI) flights.
Search Deals
From Costa Rica to Chicago Midway
Search Deals
One-way flight from Costa Rica to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
Search Deals

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 December 28, 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

Wed 2/11

2:31 pm-10:22 pm

1 stop7h 51m

Chicago Midway

Wed 2/18

9:34 am-10:02 pm

2 stops12h 28m

$346

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 2/5

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Tue 2/24

12:45 pm-10:02 pm

1 stop9h 17m

$346

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 2/10

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Tue 2/17

10:49 am-10:02 pm

1 stop11h 13m

$346

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 2/18

2:25 pm-10:31 pm

1 stop8h 06m

Chicago Midway

Sat 2/21

11:06 am-10:02 pm

1 stop10h 56m

$373

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 3/4

2:25 pm-10:31 pm

1 stop8h 06m

Chicago Midway

Sun 3/8

6:25 am-9:15 pm

1 stop15h 50m

$400

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 3/25

1:20 pm-12:29 pm

2 stops22h 09m

Chicago Midway

Thu 4/9

6:25 am-9:15 pm

1 stop15h 50m

$412

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 3/25

1:20 pm-8:53 am

2 stops18h 33m

Chicago Midway

Fri 4/10

12:47 pm-9:15 pm

1 stop9h 28m

$412

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 3/12

7:45 am-12:49 am

2 stops16h 04m

$230

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 3/13

7:30 am-8:53 pm

1 stop12h 23m

$247

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

8:05 pm-7:09 pm

3 stops23h 04m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 12 results
1
2

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

How often are flights from Costa Rica to Chicago delayed?

About 0% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.

What is the most punctual flight time for Costa Rica to Chicago flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

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 December 28, 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
4,256 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 7h 51m. 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.

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
Merrillville
Hammond
Porter
Benton Harbor

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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$463Average$523FlexibilityNo cancel feeOn-time63%

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