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$201+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Costa Rica to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Costa Rica (CR0) to Midway (MDW). 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 January 21, 2025.

Round-trip from

$398
(Kiwi.com)

One-way from

$201
(Kiwi.com)
From Costa Rica to Chicago Midway
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One-way flight from Costa Rica to Chicago Midway
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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 January 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Wed 2/124:09 amSJO - MDW
2 stops11h 04mMultiple Airlines
Thu 2/2012:43 pmMDW - SJO
1 stop22h 41mMultiple Airlines
Deal found 1/20$431
This Southwest deal was found by Cheapflights users on 1/20. 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.
Tue 5/61:10 pmSJO - MDW
1 stop8h 40mSouthwest
Sun 5/189:35 amMDW - SJO
2 stops11h 05mSouthwest
Deal found 1/20$548
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 10/11:18 pmSJO - MDW
1 stop7h 29mDelta
Wed 10/86:00 amMDW - SJO
1 stop6h 48mDelta
Deal found 1/21$651
This eDestinos deal was found by Cheapflights users on 1/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/71:42 pmSJO - MDW
1 stop27h 07mFrontier
Fri 6/136:44 pmMDW - SJO
1 stop18h 38mFrontier
Deal found 1/20$659

Find flights from Costa Rica to Midway within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 2/12

4:09 am-3:13 pm

2 stops11h 04m

Chicago Midway

Thu 2/20

12:43 pm-11:24 am

1 stop22h 41m

$431

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 5/6

1:10 pm-10:50 pm

1 stop8h 40m

Chicago Midway

Sun 5/18

9:35 am-7:40 pm

2 stops11h 05m

$548

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 3/18

7:00 am-6:02 pm

2 stops10h 02m

Chicago Midway

Wed 3/26

12:51 pm-9:24 pm

1 stop9h 33m

$651

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 6/7

1:42 pm-5:49 pm

1 stop27h 07m

Chicago Midway

Fri 6/13

6:44 pm-12:22 pm

1 stop18h 38m

$659

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 3/17

11:24 am-11:58 pm

2 stops11h 34m

$201

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 2/15

12:55 pm-10:04 pm

1 stop9h 09m

$241

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/15

1:10 pm-10:50 pm

1 stop8h 40m

$325

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 4/9

7:00 am-6:02 pm

2 stops10h 02m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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.

Travel insights for flights from Costa Rica to Midway

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

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 January 21, 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 January 21, 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
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Volaris
6.7
Okay
1,249 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

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

    One-way options have recently been found by users for as low as $256 on Frontier. Other airlines that offer cheap prices include Southwest from $336 and Delta from $452 one-way.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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