$173+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Mar 13 — Mar 201
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
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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 February 11, 2026.
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 February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Fri 3/612:35 pm
SJO
- MDW
1 stop8h 18m
Multiple Airlines
Tue 3/1011:19 am
MDW
- SJO
1 stop24h 21m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Mon 3/911:35 am
SJO
- MDW
1 stop8h 18m
Multiple Airlines
Mon 3/169:51 pm
MDW
- SJO
1 stop13h 51m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Fri 3/612:35 pm
SJO
- MDW
1 stop11h 16m
Multiple Airlines
Wed 3/1111:19 am
MDW
- SJO
1 stop24h 23m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/8. 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.
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Tue 3/1012:47 pm
MDW
- SJO
1 stop9h 28m
Delta
Deal found 2/8![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 2/9. 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 2/192:25 pm
SJO
- MDW
1 stop8h 06m
Delta
Tue 2/249:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/9![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 2/107:00 am
SJO
- MDW
1 stop10h 29m
Delta
Fri 2/209:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/9![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 3/107:00 am
SJO
- MDW
1 stop14h 31m
Delta
Tue 3/179:35 am
MDW
- SJO
2 stops12h 40m
Delta
Deal found 2/8![Delta logo]()
$378
Best flights from Costa Rica to MidwayDiscover carefully curated flight deals from Costa Rica to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
Discover carefully curated flight deals from Costa Rica to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
This Delta deal was found by Cheapflights users on 2/8. 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.
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Wed 3/1112:47 pm
MDW
- SJO
1 stop9h 28m
Delta
Deal found 2/8![Delta logo]()
$334
This Southwest deal was found by Cheapflights users on 2/10. 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.
Fri 5/89:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Sun 5/175:00 am
MDW
- SJO
2 stops9h 00m
Southwest
Deal found 2/10![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 2/9. 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 5/61:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Thu 5/285:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Deal found 2/9![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 2/9. 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 2/282:25 pm
SJO
- MDW
1 stop8h 06m
Delta
Wed 3/49:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/9![Delta logo]()
$472
This Southwest deal was found by Cheapflights users on 2/8. 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.
Fri 2/279:40 am
SJO
- MDW
2 stops11h 15m
Southwest
Tue 3/35:00 am
MDW
- SJO
1 stop7h 50m
Southwest
Deal found 2/8![Southwest logo]()
$464
This Southwest deal was found by Cheapflights users on 2/8. 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 2/261:50 pm
SJO
- MDW
1 stop8h 25m
Southwest
Sun 3/18:00 am
MDW
- SJO
2 stops11h 30m
Southwest
Deal found 2/8![Southwest logo]()
$469
This Southwest deal was found by Cheapflights users on 2/7. 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.
Fri 2/279:40 am
SJO
- MDW
1 stop10h 45m
Southwest
Tue 3/316:00 am
MDW
- SJO
1 stop7h 55m
Southwest
Deal found 2/7![Southwest logo]()
$485
This Southwest deal was found by Cheapflights users on 2/8. 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 5/71:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Sun 5/105:00 am
MDW
- SJO
2 stops9h 00m
Southwest
Deal found 2/8![Southwest logo]()
$490
This Southwest deal was found by Cheapflights users on 2/10. 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 5/219:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Tue 5/266:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Deal found 2/10![Southwest logo]()
$492
Last-minute flights from Costa Rica to MidwayDiscover last-minute flight deals from Costa Rica to Midway. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Costa Rica to Midway. Data last updated February 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 2/107:00 am
SJO
- MDW
1 stop10h 29m
Delta
Fri 2/209:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/9![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 2/9. 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 2/192:25 pm
SJO
- MDW
1 stop8h 06m
Delta
Tue 2/249:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/9![Delta logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Fri 3/612:35 pm
SJO
- MDW
1 stop8h 18m
Multiple Airlines
Tue 3/1011:19 am
MDW
- SJO
1 stop24h 21m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Fri 3/612:35 pm
SJO
- MDW
1 stop11h 16m
Multiple Airlines
Wed 3/1111:19 am
MDW
- SJO
1 stop24h 23m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/8. 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.
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Wed 3/1112:47 pm
MDW
- SJO
1 stop9h 28m
Delta
Deal found 2/8![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Mon 3/911:35 am
SJO
- MDW
1 stop8h 18m
Multiple Airlines
Mon 3/169:51 pm
MDW
- SJO
1 stop13h 51m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 3/107:00 am
SJO
- MDW
1 stop14h 31m
Delta
Tue 3/1710:45 am
MDW
- SJO
1 stop11h 30m
Delta
Deal found 2/8![Delta logo]()
$378
One-way flights from Costa Rica to MidwaySearch for one-way flight options from Costa Rica to Midway. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
Search for one-way flight options from Costa Rica to Midway. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Fri 3/61:31 pm
SJO
- MDW
2 stops32h 53m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/187:45 am
SJO
- MDW
1 stop28h 56m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/227:50 pm
SJO
- MDW
3 stops47h 17m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$203
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1411:45 am
SJO
- MDW
1 stop9h 24m
Frontier
Deal found 2/10![Frontier logo]()
$204
This Southwest deal was found by Cheapflights users on 2/10. 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 5/61:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 2/10![Southwest logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/57:48 pm
SJO
- MDW
2 stops16h 12m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 3/37:00 am
SJO
- MDW
1 stop15h 33m
Delta
Deal found 2/8![Delta logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/1511:38 am
SJO
- MDW
1 stop25h 43m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 5/155:05 am
SJO
- MDW
2 stops34h 08m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$222
Find 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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (Kiwi.com) |
One-way from | $173 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $382 |
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 February 11, 2026.
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
Fri 3/6
7:00 am-10:31 pm
1 stop15h 31m
Chicago Midway
Wed 3/11
12:47 pm-9:15 pm
1 stop9h 28m
$334
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 5/8
9:00 am-10:20 pm
2 stops12h 20m
Chicago Midway
Sun 5/17
5:00 am-1:00 pm
2 stops9h 00m
$444
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 5/6
1:10 pm-11:05 pm
1 stop8h 55m
Chicago Midway
Thu 5/28
5:35 am-12:10 pm
1 stop7h 35m
$449
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 2/27
9:40 am-8:55 pm
2 stops11h 15m
Chicago Midway
Tue 3/3
5:00 am-12:50 pm
1 stop7h 50m
$464
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 2/26
1:50 pm-10:15 pm
1 stop8h 25m
Chicago Midway
Sun 3/1
8:00 am-7:30 pm
2 stops11h 30m
$469
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 2/28
2:25 pm-10:31 pm
1 stop8h 06m
Chicago Midway
Wed 3/4
9:34 am-10:02 pm
2 stops12h 28m
$472
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 2/27
9:40 am-8:25 pm
1 stop10h 45m
Chicago Midway
Tue 3/31
6:00 am-12:55 pm
1 stop7h 55m
$485
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 5/7
1:10 pm-9:55 pm
1 stop7h 45m
Chicago Midway
Sun 5/10
5:00 am-1:00 pm
2 stops9h 00m
$490
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 5/21
9:00 am-10:20 pm
2 stops12h 20m
Chicago Midway
Tue 5/26
6:00 am-12:10 pm
1 stop7h 10m
$492
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 3/6
12:35 pm-8:53 pm
1 stop8h 18m
$173
Showing 1-10 of 20 results
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.
SJO-MDW
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
CR0-MDW
SJO-MDW
How often are flights from Costa Rica to Chicago delayed?
About 0% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.
What is the most punctual flight time for Costa Rica to Chicago flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
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 February 11, 2026.
Read reviews from past customers who have flown Southwest 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.
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 11, 2026.
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Browse other Costa Rica and Midway flight options. Last updated on February 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Costa Rica to Midway
Discover the top airline that operate flights from Costa Rica to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |