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Cheap flights from Midway (MDW) to Costa Rica from $135

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 6/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SJO
May 18 — May 251
From?
To?
Sat 5/18
Sat 5/25
1 adult, Economy
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How far in advance should I book a flight from Chicago Midway Airport to Costa Rica?

Find a great deal and save up to 29% by booking at least 34 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago Midway Airport to Costa Rica within the next two weeks, with the cheapest ticket starting at $349.

What is the cheapest month to fly from Chicago Midway Airport to Costa Rica?

August is one of the best times of the year to fly to Costa Rica from Chicago Midway Airport. Prices for August average $540 per person but you can even find prices for as low as $288. The most expensive prices can be found in the month of December. Opting for a August flight can save you 38% on your journey compared to booking in December

When is the cheapest time to fly from Chicago Midway Airport to Costa Rica (MDW - CR)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Costa Rica as you normally would.

Cheap Frontier flights from Midway to Costa Rica

Explore cheap flight options specifically provided by Frontier for the route between Midway and Costa Rica. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Find some of the cheapest Frontier flights traveling from Chicago to Costa Rica. Deals update often to give you more flight options matching your criteria
Sat 8/106:00 amMDW - SJO
1 stop27h 25mFrontier
Sun 8/189:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 5/12$316
Wed 7/317:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 8/89:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/13$390
Wed 8/77:27 amMDW - SJO
1 stop25h 58mFrontier
Sun 8/119:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/12$405
Sat 8/106:00 amMDW - SJO
1 stop27h 25mFrontier
Sun 8/189:40 amSJO - MDW
2 stops33h 28mFrontier
Deal found 5/12$452
Wed 7/247:27 amMDW - SJO
1 stop25h 58mFrontier
Sun 7/289:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/12$455
Sat 7/276:00 amMDW - SJO
1 stop27h 25mFrontier
Thu 8/19:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 5/11$467
Sat 7/276:00 amMDW - SJO
1 stop27h 25mFrontier
Sun 8/49:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 5/13$495
Wed 5/297:53 amMDW - SJO
1 stop25h 23mFrontier
Thu 6/69:19 amSJO - MDW
1 stop28h 15mFrontier
Deal found 5/12$505
Sat 6/157:00 amMDW - SJO
1 stop26h 10mFrontier
Thu 8/89:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/11$515

Cheap Delta flights from Midway to Costa Rica

Explore cheap flight options specifically provided by Delta for the route between Midway and Costa Rica. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Browse through some of the cheapest Delta flights traveling from Chicago to Costa Rica. Check back soon if you're not seeing flights that suit your needs.
Sun 8/256:00 amMDW - LIR
1 stop6h 43mDelta
Sun 9/11:13 pmLIR - MDW
1 stop7h 34mDelta
Deal found 5/13$647
Sat 8/246:00 amMDW - LIR
1 stop6h 43mDelta
Sun 9/11:13 pmLIR - MDW
1 stop7h 34mDelta
Deal found 5/13$667
Fri 7/1912:35 pmMDW - SJO
1 stop9h 02mDelta
Sat 7/277:00 amSJO - MDW
1 stop13h 46mDelta
Deal found 5/12$676
Fri 8/96:00 amMDW - SJO
1 stop6h 53mDelta
Tue 8/131:13 pmSJO - MDW
1 stop7h 34mDelta
Deal found 5/12$760
Thu 6/131:24 pmMDW - LIR
2 stops23h 16mDelta
Sat 6/152:32 pmLIR - MDW
2 stops17h 16mDelta
Deal found 5/12$771
Tue 8/276:00 amMDW - LIR
1 stop6h 43mDelta
Tue 9/31:13 pmLIR - MDW
1 stop18h 59mDelta
Deal found 5/13$779
Thu 6/133:45 pmMDW - LIR
1 stop20h 55mDelta
Sat 6/152:32 pmLIR - MDW
2 stops17h 16mDelta
Deal found 5/12$783
Wed 6/58:45 amMDW - SJO
1 stop12h 28mDelta
Wed 6/127:00 amSJO - MDW
1 stop13h 46mDelta
Deal found 5/12$794
Wed 6/59:32 amMDW - SJO
2 stops11h 41mDelta
Wed 6/127:00 amSJO - MDW
1 stop9h 59mDelta
Deal found 5/12$799

Cheap Midway to Costa Rica flights in May & June 2024

Find cheap flight options from Midway to Costa Rica specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,633,403 searches. Prices were last updated on May 13, 2024.
The lowest fares we've come across on flights traveling from Chicago to Costa Rica in May and June 2024. For more flight deals, be sure to check back very soon.
Thu 5/307:45 amMDW - SJO
1 stop26h 01mMultiple Airlines
Mon 6/1012:59 amSJO - MDW
2 stops13h 37mMultiple Airlines
Deal found 5/12$309
Wed 5/297:49 amMDW - SJO
1 stop29h 58mMultiple Airlines
Tue 6/1112:59 amSJO - MDW
2 stops12h 35mMultiple Airlines
Deal found 5/12$310
Thu 6/68:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Tue 6/115:10 amSJO - MDW
2 stops25h 21mMultiple Airlines
Deal found 5/12$368
Wed 5/297:49 amMDW - SJO
2 stops17h 15mMultiple Airlines
Wed 6/121:42 pmSJO - MDW
1 stop18h 49mMultiple Airlines
Deal found 5/12$373
Wed 5/297:49 amMDW - SJO
1 stop26h 32mMultiple Airlines
Wed 6/121:42 pmSJO - MDW
1 stop18h 49mMultiple Airlines
Deal found 5/12$380
Sun 6/98:53 pmMDW - SJO
2 stops28h 16mMultiple Airlines
Sun 6/161:42 pmSJO - MDW
1 stop20h 28mMultiple Airlines
Deal found 5/12$415
Sun 6/98:53 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Sun 6/161:42 pmSJO - MDW
1 stop20h 28mMultiple Airlines
Deal found 5/12$434
Sat 5/2510:33 pmMDW - SJO
2 stops13h 59mMultiple Airlines
Tue 5/281:42 pmSJO - MDW
1 stop16h 12mMultiple Airlines
Deal found 5/11$444
Thu 5/168:55 pmMDW - SJO
2 stops36h 51mMultiple Airlines
Fri 5/249:36 amSJO - MDW
1 stop26h 45mMultiple Airlines
Deal found 5/13$451

Midway to Costa Rica 2024 flight deals

Discover exclusive flight deals for travel between Midway and Costa Rica in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
The lowest fares we've come across on flights traveling from Chicago to Costa Rica in May and June 2024. For more flight deals, be sure to check back very soon.
Thu 5/307:45 amMDW - SJO
1 stop26h 01mMultiple Airlines
Mon 6/1012:59 amSJO - MDW
2 stops13h 37mMultiple Airlines
Deal found 5/12$309
Wed 5/297:49 amMDW - SJO
1 stop29h 58mMultiple Airlines
Tue 6/1112:59 amSJO - MDW
2 stops12h 35mMultiple Airlines
Deal found 5/12$310
Sat 8/106:00 amMDW - SJO
1 stop27h 25mFrontier
Sun 8/189:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 5/12$316
Wed 8/147:27 amMDW - SJO
1 stop25h 58mFrontier
Sun 8/189:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 5/13$322
Wed 8/147:27 amMDW - SJO
1 stop25h 58mFrontier
Sun 8/189:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 5/12$342
Thu 6/68:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Tue 6/115:10 amSJO - MDW
2 stops25h 21mMultiple Airlines
Deal found 5/12$368
Wed 5/297:49 amMDW - SJO
2 stops17h 15mMultiple Airlines
Wed 6/121:42 pmSJO - MDW
1 stop18h 49mMultiple Airlines
Deal found 5/12$373
Wed 5/297:49 amMDW - SJO
1 stop26h 32mMultiple Airlines
Wed 6/121:42 pmSJO - MDW
1 stop18h 49mMultiple Airlines
Deal found 5/12$380
Wed 7/317:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 8/89:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/13$390

Midway to Costa Rica flights leaving soon

Find last-minute flight options from Midway to Costa Rica for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Book one of these great deals on flights from Chicago to Costa Rica. Tip: verify your flight details before completing your reservation.
Thu 5/232:28 pmMDW - SJO
2 stops34h 36mMultiple Airlines
Tue 5/281:42 pmSJO - MDW
1 stop16h 12mMultiple Airlines
Deal found 5/13$545
Wed 5/2211:05 amMDW - LIR
1 stop26h 27mMultiple Airlines
Mon 5/276:30 pmLIR - MDW
2 stops35h 24mMultiple Airlines
Deal found 5/13$746
Mon 5/208:45 amMDW - SJO
1 stop12h 28mDelta
Mon 6/177:00 amSJO - MDW
1 stop13h 46mDelta
Deal found 5/13$1,000
Wed 5/226:00 amMDW - SJO
1 stop6h 44mDelta
Wed 5/297:00 amSJO - MDW
1 stop7h 50mDelta
Deal found 5/13$1,084
Wed 5/229:32 amMDW - SJO
2 stops11h 41mDelta
Wed 5/297:00 amSJO - MDW
1 stop7h 50mDelta
Deal found 5/13$1,089
Sat 5/186:00 amMDW - SJO
1 stop15h 13mDelta
Tue 5/217:00 amSJO - MDW
1 stop14h 01mDelta
Deal found 5/11$1,206
Sat 5/185:47 pmMDW - SJO
2 stops18h 57mDelta
Tue 5/217:00 amSJO - MDW
1 stop7h 50mDelta
Deal found 5/11$1,211
Thu 5/238:45 amMDW - SJO
1 stop12h 28mDelta
Wed 5/291:11 pmSJO - MDW
1 stop7h 50mDelta
Deal found 5/13$1,233
Thu 5/239:32 amMDW - SJO
2 stops11h 41mDelta
Tue 5/287:00 amSJO - MDW
1 stop7h 50mDelta
Deal found 5/12$1,238

One-way flights to Costa Rica from Midway

Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Take a look at some of the one-way flights we've detected from Chicago to Costa Rica. Users needing a return flight from Chicago to Costa Rica should utilize the search form above.
Mon 6/248:27 amMDW - SJO
3 stops15h 48mMultiple Airlines
Deal found 5/13$135
Sat 8/36:00 amMDW - SJO
1 stop27h 25mFrontier
Deal found 5/12$168
Mon 6/1712:06 pmMDW - SJO
2 stops37h 03mMultiple Airlines
Deal found 5/13$190
Mon 6/1712:57 pmMDW - SJO
3 stops36h 12mMultiple Airlines
Deal found 5/13$195
Mon 6/248:27 amMDW - SJO
2 stops26h 35mMultiple Airlines
Deal found 5/13$206
Mon 6/1712:06 pmMDW - SJO
1 stop25h 39mMultiple Airlines
Deal found 5/13$207
Sat 6/151:02 pmMDW - SJO
2 stops12h 07mMultiple Airlines
Deal found 5/12$210
Fri 6/148:27 amMDW - SJO
3 stops15h 48mMultiple Airlines
Deal found 5/12$220
Sat 7/66:00 amMDW - SJO
1 stop27h 25mFrontier
Deal found 5/12$236

Find flights from Midway to Costa Rica within your budget

Customize your flight search to find flights from Midway to Costa Rica 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 2,633,403 searches. Data last updated May 13, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$309 - $647

Route

Depart

Return

Price

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Thu 5/30

1 stop26h 01m

San José Juan Santamaria Intl

Mon 6/10

2 stops13h 37m

$309

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/29

1 stop29h 58m

San José Juan Santamaria Intl

Tue 6/11

2 stops12h 35m

$310

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sat 8/10

1 stop27h 25m

San José Juan Santamaria Intl

Sun 8/18

1 stop24h 15m

$316

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Thu 6/6

1 stop16h 54m

San José Juan Santamaria Intl

Tue 6/11

2 stops25h 21m

$368

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/29

2 stops17h 15m

San José Juan Santamaria Intl

Wed 6/12

1 stop18h 49m

$373

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/29

1 stop26h 32m

San José Juan Santamaria Intl

Wed 6/12

1 stop18h 49m

$380

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 7/31

1 stop25h 58m

San José Juan Santamaria Intl

Thu 8/8

1 stop10h 09m

$390

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/7

1 stop25h 58m

San José Juan Santamaria Intl

Sun 8/11

1 stop10h 09m

$405

Chicago MidwayLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sun 8/25

1 stop6h 43m

Liberia

Sun 9/1

1 stop7h 34m

$647

Flights are sorted by cheapest first

Deals found on 5/12

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated May 13, 2024.
Read through reviews of airlines operating flights from Chicago to Costa Rica, such as Frontier, Delta and WestJet. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,736 reviews
Check prices

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,736 reviews
Delta
8.0
Very good
10,736 reviews
Check prices

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

LATAM Airlines
7.6
Good
2,423 reviews
Delta
8.0
Very good
10,736 reviews
Check prices

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.6
Good
2,926 reviews
Delta
8.0
Very good
10,736 reviews
Check prices

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,081 reviews
Delta
8.0
Very good
10,736 reviews
Check prices

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

7.9

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Midway to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago Midway Airport to Costa Rica for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Costa Rica for under $400. The cheapest flight booked recently is on Multiple Airlines for just $309, but on average you can expect to pay $416.

  • Are there last-minute flights available from Chicago Midway Airport to Costa Rica for under $600?

    There are currently 20+ open flights from Chicago Midway Airport to Costa Rica within the next 7 days for less than $600.

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

    $168 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on WestJet and Delta, with prices starting from $355 and $448, respectively.

  • What does MDW to SJO mean?

    This is defined as Chicago Midway Airport (MDW) and San José Juan Santamaria Intl Airport (SJO). Codes like San José Juan Santamaria Intl Airport are often used to just call airports uniquely. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Liberia Airport (LIR), Limon Airport (LIO), San José Tobias Bolanos Intl Airport (SYQ), Tamarindo Airport (TNO), Buenos Aires Airport (BAI).

  • Can I find deals for flights from Midway to Costa Rica that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Costa Rica flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Costa Rica with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Costa Rica flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Costa Rica that include hotel bookings?

    Yes. In addition to deals on Midway to Costa Rica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Costa Rica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Costa Rica.

  • Can I find deals for business class flights from Midway to Costa Rica?

    Yes. Cheapflights offers flight deals from Midway to Costa Rica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Costa Rica that allow pets onboard?

    Many airlines flying from Midway to Costa Rica offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Costa Rica?

    Yes, you can often find last-minute deals on Midway to Costa Rica flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Costa Rica flight deals updated?

    The Chicago Midway Airport to Costa Rica flight deals you see on this page were last updated on 5/13.

See more FAQs

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Alternative routes for Midway to Costa Rica
See prices for flight routes from nearby airports that may be better suited for you.

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Top airline flying from Midway to Costa Rica

Discover the top airline that operate flights from Midway to Costa Rica. 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 2,633,403 searches. Data last updated May 13, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$497Average$972FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to Costa Rica by cabin class

Find flights from Midway to Costa Rica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

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How does Cheapflights help users find flights from Midway to Costa Rica?

Cheapflights makes it easy to find Midway to Costa Rica flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Midway to Costa Rica?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Midway to Costa Rica.

Can Cheapflights find flights from Midway to Costa Rica with no change fees?

Yes! Cheapflights helps users easily find flights from Midway to Costa Rica with no change fees.

Can Cheapflights notify me if prices for flights from Midway to Costa Rica become cheaper?

Of course! You can now track prices for flights from Midway to Costa Rica and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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