HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$188+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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

Keep the following information in mind while searching for Costa Rica to Midway flight deals. Data was last updated April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$426
(Southwest)

One-way from

$188
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$500
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago (CHI) flights.
Search Deals
From Costa Rica to Chicago Midway
Search Deals
One-way flight from Costa Rica to Chicago Midway
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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 April 2, 2025.

This Southwest deal was found by Cheapflights users on 4/1. 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 4/1$426
This Delta deal was found by Cheapflights users on 4/1. 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.
Thu 4/37:00 amSJO - MDW
2 stops10h 02mDelta
Sun 4/612:48 pmMDW - SJO
1 stop9h 38mDelta
Deal found 4/1$435
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/311:15 pmSJO - MDW
1 stop18h 48mFrontier
Sat 6/146:00 amMDW - SJO
1 stop7h 37mFrontier
Deal found 4/1$486
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Tue 4/81:55 amSJO - MDW
2 stops18h 38mMultiple Airlines
Sat 4/197:25 amMDW - SJO
1 stop16h 15mMultiple Airlines
Deal found 4/1$609

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 April 2, 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

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

Sat 5/31

1:15 pm-9:03 am

1 stop18h 48m

Chicago Midway

Sat 6/14

6:00 am-12:37 pm

1 stop7h 37m

$486

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/3

1:20 pm-10:22 pm

1 stop8h 02m

Chicago Midway

Sat 5/10

6:00 am-11:59 am

1 stop6h 59m

$502

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 4/12

12:55 am-7:35 pm

2 stops17h 40m

Chicago Midway

Mon 4/21

1:23 pm-10:24 am

1 stop22h 01m

$622

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 4/30

12:23 pm-12:24 pm

2 stops23h 01m

$188

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/10

1:24 pm-1:34 pm

1 stop23h 10m

$208

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/1

1:20 pm-10:22 pm

1 stop8h 02m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 April 2, 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 April 2, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Frontier 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
4,272 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,276 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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.