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Cheap flights from Midway (MDW) to Costa Rica from $109

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 9/10. 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 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
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?

August is one of the best times of the year to fly to Costa Rica from Chicago Midway Airport. Prices for August average $541 per person but you can even find prices for as low as $284. 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

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 Midway to Costa Rica flights in June & July 2024

Find cheap flight options from Midway to Costa Rica specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Costa Rica in June and July 2024. For more flight deals, be sure to check back very soon.
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Wed 7/1712:55 amSJO - MDW
2 stops11h 43mMultiple Airlines
Deal found 6/6$383
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Sat 7/201:40 pmSJO - MDW
1 stop19h 05mMultiple Airlines
Deal found 6/5$407
Sat 6/297:00 amMDW - SJO
1 stop26h 10mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$415
Mon 7/17:30 amMDW - SJO
2 stops17h 39mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$419
Mon 7/112:06 pmMDW - SJO
1 stop25h 39mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$424
Tue 7/21:50 pmMDW - SJO
2 stops11h 19mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$437
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Sun 7/211:40 pmSJO - MDW
1 stop20h 25mMultiple Airlines
Deal found 6/5$438
Fri 6/281:11 pmMDW - SJO
1 stop24h 34mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$442
Thu 6/278:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Mon 7/112:32 pmSJO - MDW
2 stops26h 04mMultiple Airlines
Deal found 6/4$444

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 3,050,429 searches. Data last updated June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Costa Rica in June and July 2024. For more flight deals, be sure to check back very soon.
Wed 8/73:36 pmMDW - SJO
2 stops17h 24mFrontier
Sun 8/119:10 amSJO - MDW
2 stops36h 49mFrontier
Deal found 6/6$344
Wed 8/71:43 pmMDW - SJO
1 stop19h 17mFrontier
Sun 8/119:10 amSJO - MDW
2 stops36h 49mFrontier
Deal found 6/6$349
Wed 8/287:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 9/59:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 6/4$365
Wed 8/147:27 amMDW - SJO
1 stop25h 58mFrontier
Sun 8/189:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 6/5$382
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Wed 7/1712:55 amSJO - MDW
2 stops11h 43mMultiple Airlines
Deal found 6/6$383
Fri 9/67:59 pmMDW - SJO
2 stops16h 34mMultiple Airlines
Sun 9/89:40 amSJO - MDW
1 stop10h 09mMultiple Airlines
Deal found 6/6$395
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Sat 7/201:40 pmSJO - MDW
1 stop19h 05mMultiple Airlines
Deal found 6/5$407
Wed 8/287:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 9/59:40 amSJO - MDW
2 stops33h 28mFrontier
Deal found 6/4$414
Sat 6/297:00 amMDW - SJO
1 stop26h 10mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$415

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 3,050,429 searches. Data last updated June 6, 2024.
Book one of these great deals on flights from Chicago to Costa Rica. Tip: verify your flight details before completing your reservation.
Thu 6/206:56 amMDW - SJO
2 stops18h 13mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$461
Sun 6/166:01 pmMDW - SJO
2 stops31h 08mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$516
Thu 6/208:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$541
Sun 6/98:53 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Tue 6/115:10 amSJO - MDW
2 stops25h 21mMultiple Airlines
Deal found 6/5$551
Sun 6/168:53 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$580
Sun 6/98:53 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Mon 6/1012:59 amSJO - MDW
2 stops13h 37mMultiple Airlines
Deal found 6/5$589
Fri 6/72:32 pmMDW - SJO
2 stops23h 13mMultiple Airlines
Fri 6/141:42 pmSJO - MDW
1 stop17h 13mMultiple Airlines
Deal found 6/6$603
Thu 6/208:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Sat 6/2212:59 amSJO - MDW
2 stops15h 06mMultiple Airlines
Deal found 6/5$642
Fri 6/142:14 pmMDW - SJO
2 stops10h 55mMultiple Airlines
Mon 6/2412:20 pmSJO - MDW
2 stops20h 27mMultiple Airlines
Deal found 6/5$653

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 3,050,429 searches. Data last updated June 6, 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.
Tue 9/1012:34 pmMDW - SJO
2 stops23h 59mMultiple Airlines
Deal found 6/6$109
Tue 9/1710:00 amMDW - SJO
2 stops26h 33mMultiple Airlines
Deal found 6/5$118
Mon 9/169:44 pmMDW - SJO
2 stops14h 49mMultiple Airlines
Deal found 6/5$126
Wed 9/188:13 pmMDW - SJO
3 stops28h 02mMultiple Airlines
Deal found 6/5$129
Wed 9/189:44 pmMDW - SJO
1 stop11h 41mFrontier
Deal found 6/5$152
Sun 9/155:54 amMDW - SJO
2 stops13h 56mMultiple Airlines
Deal found 6/5$167
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Deal found 6/6$169
Sat 9/219:44 pmMDW - SJO
2 stops14h 49mMultiple Airlines
Deal found 6/5$177
Thu 9/192:45 pmMDW - SJO
2 stops21h 48mMultiple Airlines
Deal found 6/5$183

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 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$344 - $653

Route

Depart

Return

Price

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/7

2 stops17h 24m

San José Juan Santamaria Intl

Sun 8/11

2 stops36h 49m

$344

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/7

1 stop19h 17m

San José Juan Santamaria Intl

Sun 8/11

2 stops36h 49m

$349

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 stop24h 15m

$365

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/14

1 stop25h 58m

San José Juan Santamaria Intl

Sun 8/18

1 stop24h 15m

$382

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sun 7/14

1 stop16h 41m

San José Juan Santamaria Intl

Wed 7/17

2 stops11h 43m

$383

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Fri 9/6

2 stops16h 34m

San José Juan Santamaria Intl

Sun 9/8

1 stop10h 09m

$395

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sun 7/14

1 stop16h 41m

San José Juan Santamaria Intl

Sat 7/20

1 stop19h 05m

$407

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sat 6/29

1 stop26h 10m

San José Juan Santamaria Intl

Fri 7/12

1 stop17h 05m

$415

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sun 11/24

1 stop15h 08m

San José Juan Santamaria Intl

Mon 12/2

1 stop14h 44m

$653

Flights are sorted by cheapest first

Deals found on 6/6

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 June 6, 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
10,368 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

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
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

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
7.5
Good
2,856 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

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
6.2
Okay
3,985 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

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 Frontier for just $344, but on average you can expect to pay $417.

  • Are there last-minute flights available from Chicago Midway Airport to Costa Rica for under $500?

    There are currently 20+ open flights from Chicago Midway Airport to Costa Rica within the next 7 days for less than $500.

  • 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 6/6.

  • 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 $383). Flying from Chicago Midway Airport to Costa Rica in July is currently the most expensive (average of $519). 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 Liberia flights
O'Hare Intl to Philip S.W.Goldson flights
Midway to San José flights
O'Hare Intl to San Salvador flights
Midway to Guatemala City flights
Midway to Liberia flights
Midway to Panama City flights
O'Hare Intl to Managua flights
Midway to Philip S.W.Goldson flights
Midway to San Salvador flights
O'Hare Intl to Coxen Hole flights
O'Hare Intl to San Pedro Sula flights
Midway to San Pedro Sula flights
Midway to Managua flights
O'Hare Intl to Tegucigalpa flights
Midway to Tegucigalpa flights
O'Hare Intl to David flights
Midway to Coxen Hole 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 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$497Average$1,007FlexibilityNo 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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