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Cheap flights from Midway (MDW) to Costa Rica from $119

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 6/5. 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
Jun 4 — Jun 111
From?
To?
Tue 6/4
Tue 6/11
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 $344.

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

September is one of the best times of the year to fly to Costa Rica from Chicago Midway Airport. Prices for September average $542 per person but you can even find prices for as low as $222. The most expensive prices can be found in the month of December. Opting for a September flight can save you 38% on your journey compared to booking in December

What is the cheapest time of day to fly from MDW to 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 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 2,784,634 searches. Data last updated May 30, 2024.
Find some of the cheapest Delta flights traveling from Chicago to Costa Rica. Deals update often to give you more flight options matching your criteria
Tue 10/296:00 amMDW - LIR
1 stop6h 43mDelta
Sun 11/32:08 pmLIR - MDW
1 stop7h 36mDelta
Deal found 5/29$647
Fri 8/96:00 amMDW - SJO
1 stop6h 43mDelta
Tue 8/201:08 pmSJO - MDW
1 stop7h 38mDelta
Deal found 5/28$661
Sun 8/116:55 pmMDW - LIR
1 stop17h 44mDelta
Tue 8/201:04 pmLIR - MDW
1 stop7h 42mDelta
Deal found 5/29$667
Sun 8/111:24 pmMDW - LIR
2 stops23h 15mDelta
Tue 8/201:04 pmLIR - MDW
1 stop7h 42mDelta
Deal found 5/29$671
Mon 8/56:00 amMDW - LIR
1 stop6h 39mDelta
Fri 8/161:04 pmLIR - MDW
1 stop21h 40mDelta
Deal found 5/29$677
Tue 8/61:24 pmMDW - LIR
2 stops23h 15mDelta
Fri 8/161:04 pmLIR - MDW
1 stop21h 40mDelta
Deal found 5/29$682
Thu 8/156:55 pmMDW - LIR
1 stop17h 44mDelta
Tue 8/201:04 pmLIR - MDW
1 stop7h 42mDelta
Deal found 5/29$687
Sat 8/105:45 pmMDW - LIR
2 stops18h 54mDelta
Tue 8/201:04 pmLIR - MDW
1 stop7h 42mDelta
Deal found 5/29$691
Sun 8/116:00 amMDW - LIR
1 stop6h 39mDelta
Wed 8/211:04 pmLIR - MDW
1 stop7h 42mDelta
Deal found 5/29$697

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 2,784,634 searches. Data last updated May 30, 2024.
Browse through some of the cheapest Frontier flights traveling from Chicago to Costa Rica. Check back soon if you're not seeing flights that suit your needs.
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/99:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$296
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Thu 6/139:19 amSJO - MDW
1 stop28h 15mFrontier
Deal found 5/29$325
Wed 8/287:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 9/59:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/30$359
Wed 6/121:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/169:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$370
Wed 8/147:27 amMDW - SJO
1 stop25h 58mFrontier
Sun 8/189:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 5/29$398
Sat 6/87:00 amMDW - SJO
1 stop26h 10mFrontier
Sun 6/169:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$429
Fri 8/1612:15 pmMDW - SJO
2 stops45h 10mFrontier
Sun 8/259:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/29$443
Wed 8/71:43 pmMDW - SJO
1 stop19h 17mFrontier
Sun 8/119:10 amSJO - MDW
1 stop28h 27mFrontier
Deal found 5/29$454
Wed 6/121:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/169:23 amSJO - MDW
2 stops33h 44mFrontier
Deal found 5/29$455

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 2,784,634 searches. Prices were last updated on May 30, 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.
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/99:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$296
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Thu 6/139:19 amSJO - MDW
1 stop28h 15mFrontier
Deal found 5/29$325
Wed 6/121:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/169:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$370
Sat 6/17:53 amMDW - SJO
1 stop25h 23mFrontier
Sun 6/99:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$373
Thu 6/138:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Mon 6/171:42 pmSJO - MDW
2 stops27h 57mMultiple Airlines
Deal found 5/28$394
Sat 6/17:53 amMDW - SJO
1 stop25h 23mFrontier
Thu 6/139:19 amSJO - MDW
1 stop28h 15mFrontier
Deal found 5/29$403
Wed 5/297:53 amMDW - SJO
1 stop25h 23mFrontier
Sun 6/29:40 amSJO - MDW
1 stop10h 17mFrontier
Deal found 5/28$416
Thu 6/138:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Sun 6/161:42 pmSJO - MDW
1 stop20h 28mMultiple Airlines
Deal found 5/28$423
Sat 6/87:00 amMDW - SJO
1 stop26h 10mFrontier
Sun 6/169:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$429

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 2,784,634 searches. Data last updated May 30, 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.
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/99:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$296
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Thu 6/139:19 amSJO - MDW
1 stop28h 15mFrontier
Deal found 5/29$325
Wed 9/119:44 pmMDW - SJO
1 stop11h 41mFrontier
Thu 9/199:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/29$348
Wed 9/1810:00 amMDW - SJO
1 stop23h 25mFrontier
Sun 9/229:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/29$357
Wed 9/49:44 pmMDW - SJO
1 stop11h 41mFrontier
Thu 9/129:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/29$358
Wed 8/287:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 9/59:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/30$359
Wed 6/121:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/169:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$370
Sat 6/17:53 amMDW - SJO
1 stop25h 23mFrontier
Sun 6/99:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$373
Sat 9/79:44 pmMDW - SJO
1 stop11h 41mFrontier
Sun 9/159:40 amSJO - MDW
1 stop10h 09mFrontier
Deal found 5/29$378

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 2,784,634 searches. Data last updated May 30, 2024.
Book one of these great deals on flights from Chicago to Costa Rica. Tip: verify your flight details before completing your reservation.
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Sun 6/99:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$296
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Thu 6/139:19 amSJO - MDW
1 stop28h 15mFrontier
Deal found 5/29$325
Sat 6/87:00 amMDW - SJO
1 stop26h 10mFrontier
Sun 6/169:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/29$429
Tue 6/48:45 amMDW - SJO
1 stop12h 28mDelta
Fri 6/141:07 pmSJO - MDW
1 stop7h 39mDelta
Deal found 5/29$1,084
Tue 6/49:32 amMDW - SJO
2 stops11h 41mDelta
Fri 6/141:07 pmSJO - MDW
1 stop7h 39mDelta
Deal found 5/29$1,089
Sat 6/812:45 pmMDW - SJO
1 stop8h 42mDelta
Wed 6/127:00 amSJO - MDW
1 stop13h 46mDelta
Deal found 5/30$1,206
Sat 6/83:45 pmMDW - SJO
2 stops14h 33mDelta
Wed 6/127:00 amSJO - MDW
1 stop13h 46mDelta
Deal found 5/30$1,211
Thu 6/66:00 amMDW - LIR
1 stop7h 00mDelta
Mon 6/101:05 pmLIR - MDW
1 stop7h 41mDelta
Deal found 5/29$1,307
Sun 6/99:34 amMDW - SJO
2 stops11h 53mDelta
Wed 6/127:00 amSJO - MDW
1 stop9h 59mDelta
Deal found 5/29$1,559

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 2,784,634 searches. Data last updated May 30, 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.
Wed 6/51:43 pmMDW - SJO
1 stop19h 23mFrontier
Deal found 5/29$119
Thu 8/229:44 pmMDW - SJO
2 stops16h 03mMultiple Airlines
Deal found 5/29$161
Wed 6/512:57 pmMDW - SJO
2 stops12h 12mMultiple Airlines
Deal found 5/29$172
Mon 7/229:31 amMDW - SJO
3 stops14h 44mMultiple Airlines
Deal found 5/29$197
Sat 6/227:00 amMDW - SJO
1 stop26h 10mFrontier
Deal found 5/28$200
Fri 6/218:27 amMDW - SJO
2 stops24h 03mMultiple Airlines
Deal found 5/29$202
Thu 6/278:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Deal found 5/30$224
Tue 6/410:16 amMDW - SJO
2 stops26h 21mMultiple Airlines
Deal found 5/29$239
Thu 6/277:40 amMDW - SJO
2 stops17h 29mMultiple Airlines
Deal found 5/30$240

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 2,784,634 searches. Data last updated May 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$296 - $647

Route

Depart

Return

Price

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 6/5

1 stop19h 23m

San José Juan Santamaria Intl

Sun 6/9

1 stop28h 11m

$296

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 6/5

1 stop19h 23m

San José Juan Santamaria Intl

Thu 6/13

1 stop28h 15m

$325

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/28

1 stop25h 58m

San José Juan Santamaria Intl

Thu 9/5

1 stop10h 09m

$359

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 6/12

1 stop19h 23m

San José Juan Santamaria Intl

Sun 6/16

1 stop28h 11m

$370

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Thu 6/13

1 stop16h 54m

San José Juan Santamaria Intl

Mon 6/17

2 stops27h 57m

$394

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Thu 6/13

1 stop16h 54m

San José Juan Santamaria Intl

Sun 6/16

1 stop20h 28m

$423

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Thu 6/13

2 stops15h 46m

San José Juan Santamaria Intl

Sun 6/16

1 stop20h 28m

$434

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Mon 7/1

1 stop16h 45m

San José Juan Santamaria Intl

Thu 7/4

1 stop17h 55m

$514

Chicago MidwayLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 10/29

1 stop6h 43m

Liberia

Sun 11/3

1 stop7h 36m

$647

Flights are sorted by cheapest first

Deals found on 5/29

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

Best time to book a flight from Midway to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Midway 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.

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 30, 2024.
Read through reviews of airlines operating flights from Chicago to Costa Rica, such as Delta, Frontier and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,956 reviews
Check prices

Food

7.3

Comfort

8.1

Overall

8.2

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,956 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Food

7.3

Comfort

8.1

Overall

8.2

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,457 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Food

7.3

Comfort

8.1

Overall

8.2

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

WestJet
7.5
Good
2,869 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Food

7.3

Comfort

8.1

Overall

8.2

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Frontier
6.3
Okay
4,016 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Food

7.3

Comfort

8.1

Overall

8.2

Boarding

8.3

Entertainment

7.8

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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 $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Costa Rica for under $300. The cheapest flight booked recently is on Frontier for just $296, but on average you can expect to pay $440.

  • Are there last-minute flights available from Chicago Midway Airport to Costa Rica for under $300?

    There are currently 10+ open flights from Chicago Midway Airport to Costa Rica within the next 7 days for less than $300.

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

    $119 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 $344 and $353, 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 5/30.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Costa Rica?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Costa Rica (average of $385). Flying from Chicago Midway Airport to Costa Rica in July is currently the most expensive (average of $524). 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

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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.

O'Hare Intl to San José flights
O'Hare Intl to Guatemala City flights
O'Hare Intl to Panama City flights
O'Hare Intl to Philip S.W.Goldson flights
Midway to San José flights
O'Hare Intl to Liberia flights
Midway to Guatemala City flights
O'Hare Intl to San Salvador flights
O'Hare Intl to Managua flights
Midway to Panama City flights
Midway to Liberia flights
Midway to Philip S.W.Goldson flights
O'Hare Intl to San Pedro Sula flights
Midway to San Salvador flights
O'Hare Intl to Coxen Hole flights
Midway to San Pedro Sula flights
Midway to Managua flights
Midway to Tegucigalpa flights
Midway to Coxen Hole flights
O'Hare Intl to Tegucigalpa flights
O'Hare Intl to David flights

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 2,784,634 searches. Data last updated May 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$497Average$1,004FlexibilityNo 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

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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