$212+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
juil. 1 — juil. 81
1 adult, Economy
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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 juin 26, 2025.
Round-trip from | $426 (Southwest) |
|---|---|
One-way from | $212 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $524 |
Find flight deals from Costa Rica to Midway
Cheapest flights from Costa Rica to MidwayExplore 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 juin 26, 2025.
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 juin 26, 2025.
This Southwest deal was found by Cheapflights users on 6/25. 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.
mer. 9/241:40 pmSJO - MDW
1 stop8h 40mSouthwest
mar. 9/306:25 amMDW - SJO
1 stop13h 30mSouthwest
Deal found 6/25![Southwest logo]()
$426
This eDestinos deal was found by Cheapflights users on 6/24. 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.
sam. 7/127:30 amSJO - MDW
1 stop11h 52mMultiple Airlines
mer. 7/232:48 pmMDW - SJO
2 stops30h 31mMultiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 6/25. 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.
jeu. 9/251:18 pmSJO - MDW
1 stop7h 26mDelta
dim. 10/56:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 6/25![Delta logo]()
$691
This LATAM Airlines deal was found by Cheapflights users on 6/26. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 7/205:00 pmSJO - MDW
2 stops24h 02mLATAM Airlines
sam. 7/264:22 pmMDW - SJO
2 stops24h 13mLATAM Airlines
Deal found 6/26![LATAM Airlines logo]()
$2,762
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 juin 26, 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
mer. 9/24
1:40 pm-11:20 pm
1 stop8h 40m
Chicago Midway
mar. 9/30
6:25 am-6:55 pm
1 stop13h 30m
$426
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
sam. 7/12
7:30 am-8:22 pm
1 stop11h 52m
Chicago Midway
mer. 7/23
2:48 pm-8:19 pm
2 stops30h 31m
$495
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
jeu. 9/25
1:18 pm-9:44 pm
1 stop7h 26m
Chicago Midway
dim. 10/5
6:00 am-11:53 am
1 stop6h 53m
$691
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
dim. 7/20
5:00 pm-6:02 pm
2 stops24h 02m
Chicago Midway
sam. 7/26
4:22 pm-3:35 pm
2 stops24h 13m
$2,762
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
mar. 8/5
5:10 pm-7:36 pm
1 stop25h 26m
$212
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
ven. 10/10
12:55 pm-11:15 pm
1 stop9h 20m
$248
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
ven. 10/10
1:13 pm-9:44 pm
1 stop7h 31m
$765
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 juin 26, 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.
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 juin 26, 2025.
Read reviews from past customers who have flown Southwest, Delta, and LATAM Airlines from Costa Rica to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.6
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
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.
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