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.

In terms of precipitation, rainfall in Costa Rica ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit Costa Rica when rainfall is around 0.0 in.

If weather is an important factor for your trip to Costa Rica, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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.

$139+ Flights from Chicago Midway Airport to Costa Rica

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Cheap 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 December 26, 2025.

Wed 12/316:12 amMDW - SJO

1 stop7h 30mFrontier

Wed 1/73:10 pmSJO - MDW

1 stop20h 21mFrontier

Deal found 12/26

$512

Wed 12/319:50 amMDW - SJO

1 stop12h 05mDelta

Thu 1/82:31 pmSJO - MDW

1 stop7h 36mDelta

Deal found 12/26

$591

Wed 12/319:50 amMDW - SJO

1 stop12h 05mDelta

Tue 1/67:00 amSJO - MDW

1 stop15h 07mDelta

Deal found 12/26

$691

Mon 12/296:15 amMDW - SJO

1 stop9h 15mMultiple Airlines

Wed 12/3110:45 pmSJO - MDW

3 stops23h 27mMultiple Airlines

Deal found 12/25

$697

Thu 12/256:00 amMDW - LIR

1 stop7h 50mDelta

Thu 1/12:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/24

$1,092

Fri 12/266:00 amMDW - LIR

1 stop6h 50mDelta

Tue 12/302:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/24

$1,755

Sun 12/286:00 amMDW - LIR

1 stop7h 50mDelta

Sun 1/42:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/24

$2,568

Sat 12/276:00 amMDW - LIR

1 stop7h 50mDelta

Sun 1/42:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/25

$2,693

Sat 12/276:00 amMDW - LIR

1 stop7h 50mDelta

Sat 1/312:35 pmLIR - MDW

1 stop9h 47mDelta

Deal found 12/25

$2,940

Best flights from Midway to Costa Rica
Discover carefully curated flight deals from Midway to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 26, 2025.

Mon 2/26:00 amMDW - SJO

1 stop7h 00mDelta

Tue 2/242:25 pmSJO - MDW

1 stop8h 08mDelta

Deal found 12/25

$358

Fri 5/15:35 amMDW - SJO

1 stop7h 35mSouthwest

Fri 5/81:10 pmSJO - MDW

1 stop7h 45mSouthwest

Deal found 12/23

$423

Tue 2/2410:49 amMDW - SJO

1 stop11h 13mDelta

Tue 3/32:25 pmSJO - MDW

1 stop8h 08mDelta

Deal found 12/24

$384

Thu 2/510:48 amMDW - SJO

1 stop11h 27mDelta

Tue 2/247:00 amSJO - MDW

1 stop15h 33mDelta

Deal found 12/25

$384

Wed 1/288:15 amMDW - SJO

2 stops11h 15mSouthwest

Thu 2/59:40 amSJO - MDW

1 stop13h 00mSouthwest

Deal found 12/25

$423

Tue 3/316:00 amMDW - SJO

1 stop7h 55mSouthwest

Tue 4/71:10 pmSJO - MDW

1 stop8h 55mSouthwest

Deal found 12/23

$423

Fri 2/279:34 amMDW - SJO

2 stops12h 28mDelta

Tue 3/32:25 pmSJO - MDW

1 stop8h 08mDelta

Deal found 12/25

$415

Wed 2/46:15 amMDW - SJO

1 stop13h 15mSouthwest

Wed 2/259:40 amSJO - MDW

1 stop13h 15mSouthwest

Deal found 12/25

$439

Sat 2/710:53 amMDW - SJO

1 stop11h 22mDelta

Tue 2/242:25 pmSJO - MDW

1 stop8h 08mDelta

Deal found 12/25

$420

Sun 1/1811:21 amMDW - SJO

1 stop10h 54mDelta

Fri 1/237:00 amSJO - MDW

1 stop15h 22mDelta

Deal found 12/23

$438

Sun 1/256:35 pmMDW - SJO

2 stops27h 40mDelta

Tue 2/32:31 pmSJO - MDW

1 stop7h 51mDelta

Deal found 12/25

$443

Mon 1/198:45 pmMDW - LIR

2 stops17h 45mSouthwest

Fri 1/233:10 pmLIR - MDW

1 stop7h 45mSouthwest

Deal found 12/25

$540

Mon 3/28:45 pmMDW - LIR

2 stops17h 45mSouthwest

Tue 3/102:05 pmLIR - MDW

2 stops13h 55mSouthwest

Deal found 12/25

$541

Mon 1/196:00 amMDW - LIR

1 stop7h 50mDelta

Fri 1/232:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/25

$473

Fri 2/276:15 amMDW - LIR

1 stop8h 00mSouthwest

Tue 3/33:25 pmLIR - MDW

1 stop7h 30mSouthwest

Deal found 12/25

$557

Fri 1/236:00 amMDW - LIR

1 stop7h 50mDelta

Wed 1/283:05 pmLIR - MDW

1 stop7h 17mDelta

Deal found 12/23

$503

Sat 1/246:25 amMDW - LIR

1 stop7h 25mDelta

Thu 1/292:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/24

$503

Sat 2/76:25 amMDW - LIR

1 stop7h 25mDelta

Sat 2/143:05 pmLIR - MDW

1 stop7h 26mDelta

Deal found 12/24

$533

Mon 1/196:00 amMDW - LIR

1 stop7h 50mDelta

Sat 1/2412:35 pmLIR - MDW

1 stop9h 47mDelta

Deal found 12/25

$543

Thu 1/226:00 amMDW - LIR

1 stop7h 50mDelta

Wed 1/282:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/24

$543

Sun 2/16:00 amMDW - LIR

1 stop7h 50mDelta

Sat 2/72:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/24

$543

Thu 1/226:00 amMDW - LIR

1 stop7h 50mDelta

Tue 1/272:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/24

$543

Last-minute flights from Midway to Costa Rica
Discover last-minute flight deals from Midway to Costa Rica. Data last updated December 26, 2025 and is based on user searches.

Mon 1/124:31 pmMDW - SJO

1 stop19h 06mMultiple Airlines

Thu 1/158:05 pmSJO - MDW

2 stops22h 49mMultiple Airlines

Deal found 12/25

$407

Sun 1/1811:21 amMDW - SJO

1 stop10h 54mDelta

Fri 1/237:00 amSJO - MDW

1 stop15h 22mDelta

Deal found 12/23

$438

Mon 1/1910:46 amMDW - SJO

1 stop11h 29mAir France

Tue 1/277:00 amSJO - MDW

1 stop15h 22mAir France

Deal found 12/24

$356

Mon 1/191:26 pmMDW - SJO

2 stops8h 49mDelta

Tue 1/277:00 amSJO - MDW

1 stop10h 29mDelta

Deal found 12/24

$363

Mon 1/196:00 amMDW - LIR

1 stop7h 50mDelta

Fri 1/232:05 pmLIR - MDW

1 stop8h 17mDelta

Deal found 12/25

$473

Fri 1/238:55 amMDW - SJO

1 stop10h 35mSouthwest

Wed 1/289:40 amSJO - MDW

1 stop13h 15mSouthwest

Deal found 12/23

$385

Fri 1/236:00 amMDW - SJO

1 stop7h 00mDelta

Fri 1/302:31 pmSJO - MDW

1 stop7h 51mDelta

Deal found 12/25

$428

Fri 1/236:00 amMDW - LIR

1 stop7h 50mDelta

Wed 1/283:05 pmLIR - MDW

1 stop7h 17mDelta

Deal found 12/23

$503

Sat 1/246:25 amMDW - LIR

1 stop7h 25mDelta

Sat 1/313:05 pmLIR - MDW

1 stop7h 17mDelta

Deal found 12/25

$533

Sun 1/256:35 pmMDW - SJO

2 stops27h 40mDelta

Thu 2/57:00 amSJO - MDW

1 stop10h 29mDelta

Deal found 12/25

$443

Mon 1/266:00 amMDW - SJO

1 stop16h 15mDelta

Fri 2/67:00 amSJO - MDW

1 stop15h 22mDelta

Deal found 12/25

$384

Mon 1/266:00 amMDW - SJO

1 stop16h 15mDelta

Sat 2/73:54 pmSJO - MDW

1 stop17h 59mDelta

Deal found 12/25

$410

One-way flights from Midway to Costa Rica
Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated December 26, 2025.

Thu 1/812:41 pmMDW - SJO

1 stop24h 55mFrontier

Deal found 12/24

$139

Mon 1/56:12 amMDW - SJO

1 stop7h 30mFrontier

Deal found 12/24

$143

Fri 1/96:10 amMDW - SJO

1 stop7h 26mFrontier

Deal found 12/24

$157

Thu 2/127:30 amMDW - SJO

1 stop28h 10mMultiple Airlines

Deal found 12/25

$202

Sun 1/255:01 pmMDW - SJO

2 stops19h 21mMultiple Airlines

Deal found 12/24

$209

Thu 1/86:10 amMDW - SJO

2 stops33h 07mMultiple Airlines

Deal found 12/26

$212

Sat 1/106:10 amMDW - SJO

2 stops21h 40mMultiple Airlines

Deal found 12/24

$230

Mon 1/58:15 amMDW - SJO

2 stops27h 27mMultiple Airlines

Deal found 12/24

$238

Sat 1/36:12 amMDW - SJO

1 stop7h 30mFrontier

Deal found 12/24

$271

Wed 2/116:15 amMDW - SJO

1 stop13h 15mSouthwest

Deal found 12/25

$273

Fri 1/1611:05 amMDW - LIR

2 stops30h 00mPorter Airlines

Deal found 12/25

$323

Sun 1/114:15 pmMDW - LIR

2 stops22h 45mPorter Airlines

Deal found 12/24

$327

Find flight deals from Midway to Costa Rica

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$347 (Orbitz)
One-way from	$139 (Priceline)
Popular in	December
Cheapest in	September
Average price	$660

Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.

Search Deals

From Chicago Midway to Costa Rica

Search Deals

One-way flight from Chicago Midway to Costa Rica

Search Deals

Highest demand for flights based on searches. 7% potential increase in price ($45 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/2

6:00 am-1:00 pm

1 stop7h 00m

San José Juan Santamaria Intl

Tue 2/24

2:25 pm-10:33 pm

1 stop8h 08m

$358

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 2/24

10:49 am-10:02 pm

1 stop11h 13m

San José Juan Santamaria Intl

Tue 3/3

2:25 pm-10:33 pm

1 stop8h 08m

$384

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/5

10:48 am-10:15 pm

1 stop11h 27m

San José Juan Santamaria Intl

Tue 2/24

7:00 am-10:33 pm

1 stop15h 33m

$384

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 2/27

9:34 am-10:02 pm

2 stops12h 28m

San José Juan Santamaria Intl

Tue 3/3

2:25 pm-10:33 pm

1 stop8h 08m

$415

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 2/7

10:53 am-10:15 pm

1 stop11h 22m

San José Juan Santamaria Intl

Tue 2/24

2:25 pm-10:33 pm

1 stop8h 08m

$420

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 5/1

5:35 am-12:10 pm

1 stop7h 35m

San José Juan Santamaria Intl

Fri 5/8

1:10 pm-9:55 pm

1 stop7h 45m

$423

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 1/28

8:15 am-7:30 pm

2 stops11h 15m

San José Juan Santamaria Intl

Thu 2/5

9:40 am-10:40 pm

1 stop13h 00m

$423

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 3/31

6:00 am-12:55 pm

1 stop7h 55m

San José Juan Santamaria Intl

Tue 4/7

1:10 pm-11:05 pm

1 stop8h 55m

$423

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 1/18

11:21 am-10:15 pm

1 stop10h 54m

San José Juan Santamaria Intl

Fri 1/23

7:00 am-10:22 pm

1 stop15h 22m

$438

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 2/4

6:15 am-7:30 pm

1 stop13h 15m

San José Juan Santamaria Intl

Wed 2/25

9:40 am-10:55 pm

1 stop13h 15m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

Showing 1-10 of 43 results

...

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?

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.

How often are flights from Chicago to Costa Rica delayed?

About 100% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 97 minutes.

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

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

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

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

Reviews of airlines servicing Costa Rica

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

4,258 reviews

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

4,258 reviews

Southwest

8.0

Very good

4,258 reviews

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

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

Alternative routes for Midway to Costa Rica

Top airline flying from Midway to Costa Rica

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$394	Average$651	FlexibilityNo cancel fee	On-time63%

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$139+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Costa Rica with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Costa Rica

Cheapest flights from Midway to Costa RicaExplore 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 December 26, 2025.

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 December 26, 2025.

Find 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 December 26, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Costa Rica that are best for you.

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.

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 December 26, 2025.

How often are flights from Chicago to Costa Rica delayed?

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

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

Reviews of airlines servicing Costa Rica

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.

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?

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Midway to Costa Rica

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Book with Flexibility

Travel Smart

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 December 26, 2025.