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$162+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Midway to Costa Rica

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Costa Rica (CR0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Find 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 November 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Mon 12/28:50 amMDW - SJO
1 stop26h 41mMultiple Airlines
Sat 12/71:24 pmSJO - MDW
2 stops33h 21mMultiple Airlines
Deal found 11/20$514
This Southwest deal was found by Cheapflights users on 11/20. 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 12/411:00 amMDW - SJO
1 stop9h 40mSouthwest
Tue 12/109:55 amSJO - MDW
2 stops11h 30mSouthwest
Deal found 11/20$573
This Delta deal was found by Cheapflights users on 11/21. 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 12/212:43 pmMDW - SJO
1 stop9h 10mDelta
Tue 12/102:13 pmSJO - MDW
1 stop7h 53mDelta
Deal found 11/21$636
This Gurufare deal was found by Cheapflights users on 11/20. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/182:20 pmMDW - SJO
1 stop19h 58mFrontier
Thu 12/2611:38 amSJO - MDW
1 stop25h 46mFrontier
Deal found 11/20$927
This Southwest deal was found by Cheapflights users on 11/20. 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.
Sun 12/225:50 amMDW - LIR
1 stop8h 15mSouthwest
Fri 12/273:00 pmLIR - MDW
2 stops9h 20mSouthwest
Deal found 11/20$976
This Delta deal was found by Cheapflights users on 11/20. 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.
Wed 12/46:00 amMDW - LIR
1 stop6h 43mDelta
Sun 12/82:20 pmLIR - MDW
1 stop7h 46mDelta
Deal found 11/20$1,157
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/62:15 pmMDW - LIR
2 stops22h 47mWestJet
Fri 12/132:55 pmLIR - MDW
2 stops27h 37mWestJet
Deal found 11/19$1,506
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/275:04 pmMDW - LIR
3 stops22h 56mMultiple Airlines
Fri 1/35:20 pmLIR - MDW
2 stops17h 10mMultiple Airlines
Deal found 11/20$2,485

Find flights from Midway to Costa Rica within your budget

Customize your flight search to find flights from Midway to Costa Rica 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 2,629,791 searches. Data last updated November 21, 2024.

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Route

Depart

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Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/2

8:50 am-11:31 am

1 stop26h 41m

San José Juan Santamaria Intl

Sat 12/7

1:24 pm-10:45 pm

2 stops33h 21m

$514

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 2/26

5:45 am-12:55 pm

1 stop7h 10m

San José Juan Santamaria Intl

Tue 3/4

9:55 am-6:50 pm

2 stops8h 55m

$538

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/2

12:43 pm-9:53 pm

1 stop9h 10m

San José Juan Santamaria Intl

Tue 12/10

2:13 pm-10:06 pm

1 stop7h 53m

$636

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Fri 1/17

7:05 pm-12:30 pm

2 stops17h 25m

Liberia

Mon 1/27

3:05 pm-10:40 pm

1 stop7h 35m

$705

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Wed 2/12

6:00 am-12:45 pm

1 stop6h 45m

Liberia

Wed 2/19

2:10 pm-10:20 pm

1 stop8h 10m

$733

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 3/8

9:44 pm-8:25 am

1 stop10h 41m

San José Juan Santamaria Intl

Thu 3/13

9:40 am-8:49 pm

1 stop10h 09m

$808

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Wed 1/15

10:19 am-2:02 pm

3 stops27h 43m

Liberia

Sun 1/19

2:55 pm-5:47 pm

2 stops26h 52m

$1,173

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 1/4

7:55 pm-11:25 am

2 stops15h 30m

San José Juan Santamaria Intl

Sat 1/11

12:27 pm-8:45 am

2 stops20h 18m

$1,248

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Fri 12/27

5:04 pm-4:00 pm

3 stops22h 56m

Liberia

Fri 1/3

5:20 pm-10:30 am

2 stops17h 10m

$2,485

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 12/5

4:27 pm-12:53 am

2 stops32h 26m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 18 results
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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.

Travel insights for flights from Midway to Costa Rica

Get recent, data-driven insights about flights from Midway to Costa Rica including ideal travel times, pricing trends, and more.

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 November 21, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Costa Rica as you normally would.

Rainfall in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average rainfall totals by month.

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.

Temperature in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated November 21, 2024.
Read through reviews of airlines operating flights from Chicago to Costa Rica, such as Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,759 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,810 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Costa Rica one-way?

    $202 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $208 and $297, respectively.

  • 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.

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

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Costa Rica (average of $398). Flying from Chicago Midway Airport to Costa Rica in July is currently the most expensive (average of $532). 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.

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Top 2 airlines flying from Midway to Costa Rica

Discover the top 2 airlines that operate flights from Midway to Costa Rica. 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$600FlexibilityNo cancel feeOn-time63%
DeltaCheapest$584Average$1,008FlexibilityNo cancel feeOn-timeN/A
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