HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$209+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Costa Rica to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 22, 2024.

Round-trip from

$384
(Kiwi.com)

One-way from

$209
(Kiwi.com)
From Costa Rica to Chicago Midway
Search Deals
One-way flight from Costa Rica to Chicago Midway
Search Deals

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 December 22, 2024.

This eDestinos deal was found by Cheapflights users on 12/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2911:38 amSJO - MDW
1 stop25h 46mFrontier
Wed 1/12:20 pmMDW - SJO
1 stop19h 55mFrontier
Deal found 12/21$619
This Delta deal was found by Cheapflights users on 12/21. 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.
Sat 12/282:15 pmSJO - MDW
1 stop7h 51mDelta
Wed 1/89:34 amMDW - SJO
2 stops12h 38mDelta
Deal found 12/21$639
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Sat 12/211:08 pmSJO - MDW
2 stops19h 37mMultiple Airlines
Sat 12/282:20 pmMDW - SJO
1 stop19h 58mMultiple Airlines
Deal found 12/20$745
This Southwest deal was found by Cheapflights users on 12/20. 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 12/259:55 amSJO - MDW
1 stop8h 55mSouthwest
Wed 1/19:00 amMDW - SJO
2 stops11h 40mSouthwest
Deal found 12/20$784

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/21

12:29 pm-7:29 pm

1 stop31h 00m

Chicago Midway

Wed 2/26

7:25 am-6:55 pm

2 stops11h 30m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 3/7

9:45 am-8:05 pm

1 stop10h 20m

Chicago Midway

Mon 3/10

5:55 am-12:55 pm

1 stop8h 00m

$580

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 3/11

7:00 am-4:14 pm

1 stop8h 14m

Chicago Midway

Tue 3/25

12:51 pm-9:24 pm

1 stop9h 33m

$708

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 1/27

5:05 am-3:23 pm

2 stops10h 18m

$209

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 2/22

12:55 pm-10:04 pm

1 stop9h 09m

$294

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 2/4

1:55 pm-10:40 pm

1 stop8h 45m

$298

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 12/31

2:15 pm-10:06 pm

1 stop7h 51m

$346

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 12/31

12:27 pm-8:45 am

2 stops20h 18m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 December 22, 2024.

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 December 22, 2024.
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
4,804 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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
1,264 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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
3,472 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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 $294 on Frontier. Other airlines that offer cheap prices include Southwest from $298 and Delta from $346 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

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.
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.