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$199+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$375
(Kiwi.com)

One-way from

$199
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$443
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 ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sun 6/84:10 amSJO - MDW
2 stops15h 07mMultiple Airlines
Thu 6/129:12 pmMDW - SJO
1 stop14h 25mMultiple Airlines
Deal found 4/30$375
This Southwest deal was found by Cheapflights users on 4/30. 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 9/111:40 pmSJO - MDW
1 stop9h 25mSouthwest
Mon 9/155:05 amMDW - SJO
1 stop8h 40mSouthwest
Deal found 4/30$426
This Delta deal was found by Cheapflights users on 4/30. 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 5/31:20 pmSJO - MDW
1 stop8h 02mDelta
Sat 5/106:00 amMDW - SJO
1 stop8h 05mDelta
Deal found 4/30$435

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 May 1, 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

Sun 6/8

4:10 am-8:17 pm

2 stops15h 07m

Chicago Midway

Thu 6/12

9:12 pm-10:37 am

1 stop14h 25m

$375

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/11

1:40 pm-12:05 am

1 stop9h 25m

Chicago Midway

Mon 9/15

5:05 am-12:45 pm

1 stop8h 40m

$426

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/15

1:18 pm-9:44 pm

1 stop7h 26m

Chicago Midway

Fri 9/19

6:00 am-11:53 am

1 stop6h 53m

$478

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 6/5

11:32 am-2:03 pm

2 stops25h 31m

$199

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 6/5

1:40 pm-1:05 am

1 stop10h 25m

$247

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 10/28

1:13 pm-9:44 pm

1 stop7h 31m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May 1, 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.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Costa Rica to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Costa Rica?

Book flights to Costa Rica if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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