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 $282, but on average you can expect to pay $357.

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.

Which airlines flying from Chicago Midway to Costa Rica have flexible changes due to COVID-19?

Some of our airline partners flying from Chicago Midway to Costa Rica have new flexible policies in place due to COVID-19. Delta is one of the carriers where you may find flexible change policies. You can use our site to filter for airlines like Delta with this kind of flexibility.

How far in advance should I book a flight from Chicago Midway Airport to Costa Rica?

Find a great deal and save up to 18% by booking at least 61 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 $648.

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 $585 per person but you can even find prices for as low as $349. The most expensive prices can be found in the month of December. Opting for a September flight can save you 48% 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 Flights from Chicago Midway Airport (MDW) to Costa Rica from $118 - Find Tickets & Airfare Deals at Cheapflights.com

Cheap flights from Midway to Costa Rica in June, July 2023

The lowest fares we've come across on flights traveling from Chicago to Costa Rica in June and July 2023. For more flight deals, be sure to check back very soon.

Jun 21 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 50m

$341

Multiple Airlines

Deal found 6/6

Jun 21 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

11h 40m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 50m

$345

Multiple Airlines

Deal found 6/6

Jul 22 - Jul 31

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

14h 27m

$368

Multiple Airlines

Deal found 6/6

Jun 18 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

13h 20m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 50m

$370

Frontier

Deal found 6/6

Jun 21 - Jun 27

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

13h 19m

$372

Multiple Airlines

Deal found 6/6

Jun 25 - Jul 6

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

8h 39m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

22h 45m

$380

Multiple Airlines

Deal found 6/6

Jun 21 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

15h 19m

$393

Multiple Airlines

Deal found 6/6

Jul 4 - Jul 10

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

19h 13m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 45m

$403

Multiple Airlines

Deal found 6/6

Jun 17 - Jun 19

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

24h 15m

$408

Multiple Airlines

Deal found 6/6

Midway to Costa Rica 2023 flight deals

The lowest fares we've come across on flights traveling from Chicago to Costa Rica in June and July 2023. For more flight deals, be sure to check back very soon.

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$282

Frontier

Deal found 6/6

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

35h 20m

$310

Frontier

Deal found 6/6

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$312

Frontier

Deal found 6/7

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$314

Frontier

Deal found 6/7

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

35h 20m

$338

Frontier

Deal found 6/6

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$339

Frontier

Deal found 6/7

Jun 21 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 50m

$341

Multiple Airlines

Deal found 6/6

Jun 21 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

11h 40m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 50m

$345

Multiple Airlines

Deal found 6/6

Jul 22 - Jul 31

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

14h 27m

$368

Multiple Airlines

Deal found 6/6

Cheap Frontier flights from Midway to Costa Rica

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

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$282

Frontier

Deal found 6/6

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$287

Frontier

Deal found 6/7

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

35h 20m

$310

Frontier

Deal found 6/6

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$312

Frontier

Deal found 6/7

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$314

Frontier

Deal found 6/7

Aug 23 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

35h 20m

$338

Frontier

Deal found 6/6

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$339

Frontier

Deal found 6/7

Jun 18 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

13h 20m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 50m

$370

Frontier

Deal found 6/6

Aug 13 - Aug 17

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

13h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

8h 19m

$385

Frontier

Deal found 6/7

Cheap Delta flights from Midway to Costa Rica

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.

Sep 18 - Sep 21

MDW

Chicago Midway

LIR

Liberia

1 stop

6h 56m

LIR

Liberia

MDW

Chicago Midway

1 stop

7h 24m

$608

Delta

Deal found 6/6

Sep 16 - Sep 23

MDW

Chicago Midway

LIR

Liberia

1 stop

6h 56m

LIR

Liberia

MDW

Chicago Midway

1 stop

7h 24m

$808

Delta

Deal found 6/6

Aug 17 - Aug 20

MDW

Chicago Midway

LIR

Liberia

1 stop

6h 40m

LIR

Liberia

MDW

Chicago Midway

1 stop

9h 47m

$1,123

Delta

Deal found 6/6

Jun 16 - Jun 19

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

6h 43m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

9h 39m

$1,184

Delta

Deal found 6/6

Jul 29 - Aug 5

MDW

Chicago Midway

LIR

Liberia

1 stop

6h 40m

LIR

Liberia

MDW

Chicago Midway

1 stop

7h 38m

$1,256

Delta

Deal found 6/7

Jun 14 - Jun 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

6h 43m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

9h 39m

$1,266

Delta

Deal found 6/6

Aug 8 - Aug 19

MDW

Chicago Midway

LIR

Liberia

1 stop

6h 40m

LIR

Liberia

MDW

Chicago Midway

1 stop

7h 38m

$1,332

Delta

Deal found 6/6

Jun 13 - Jun 19

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

6h 43m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

9h 39m

$1,333

Delta

Deal found 6/6

Jun 12 - Jun 16

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

6h 43m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

9h 39m

$1,343

Delta

Deal found 6/6

Last minute flights from Midway to Costa Rica

Book one of these great deals on flights from Chicago to Costa Rica. Tip: verify your flight details before completing your reservation.

Jun 17 - Jun 19

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

24h 15m

$408

Multiple Airlines

Deal found 6/6

Jun 17 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

22h 50m

$422

Multiple Airlines

Deal found 6/6

Jun 17 - Jun 27

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

13h 19m

$439

Multiple Airlines

Deal found 6/6

Jun 17 - Jun 25

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

10h 54m

$440

Multiple Airlines

Deal found 6/5

Jun 17 - Jun 19

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

10h 44m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

24h 15m

$460

Multiple Airlines

Deal found 6/6

Jun 17 - Jun 26

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

15h 19m

$461

Multiple Airlines

Deal found 6/6

Jun 12 - Jun 15

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

28h 43m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

8h 39m

$497

Multiple Airlines

Deal found 6/6

Jun 17 - Jun 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

12h 38m

$513

Multiple Airlines

Deal found 6/5

Jun 12 - Jun 15

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

7h 56m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

8h 39m

$561

Multiple Airlines

Deal found 6/6

One-way flights to Costa Rica from Midway

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.

Jun 18

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

13h 20m

$118

Frontier

Deal found 6/7

Oct 13

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

25h 08m

$125

Frontier

Deal found 6/6

Nov 1

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

22h 21m

$179

Multiple Airlines

Deal found 6/6

Aug 6

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

13h 58m

$189

Frontier

Deal found 6/6

Oct 30

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

16h 23m

$190

Multiple Airlines

Deal found 6/7

Aug 13

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

13h 58m

$196

Frontier

Deal found 6/6

Jul 18

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

28h 07m

$202

Multiple Airlines

Deal found 6/5

Jun 29

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

8h 39m

$204

Frontier

Deal found 6/6

Nov 1

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

23h 50m

$217

Multiple Airlines

Deal found 6/6

Find flights from Midway to Costa Rica within your budget

Fly from

Fly to

Budget

$282 - $608

Route

Depart

Return

Price

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/23

1 stop24h 58m

San José Juan Santamaria Intl

Mon 8/28

1 stop21h 21m

$282

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/23

1 stop24h 58m

San José Juan Santamaria Intl

Mon 8/28

1 stop21h 21m

$287

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/23

1 stop24h 58m

San José Juan Santamaria Intl

Mon 8/28

2 stops35h 20m

$310

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/23

2 stops20h 12m

San José Juan Santamaria Intl

Mon 8/28

1 stop21h 21m

$312

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/16

1 stop24h 58m

San José Juan Santamaria Intl

Mon 8/21

1 stop21h 21m

$314

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 6/21

1 stop7h 56m

San José Juan Santamaria Intl

Mon 6/26

1 stop22h 50m

$341

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 6/21

2 stops11h 40m

San José Juan Santamaria Intl

Mon 6/26

1 stop22h 50m

$345

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sat 7/22

1 stop7h 56m

San José Juan Santamaria Intl

Mon 7/31

2 stops14h 27m

$368

Pick Dates

Chicago MidwayLiberia

MDW - LIR

MDWLIR

Chicago Midway

Mon 9/18

1 stop6h 56m

Liberia

Thu 9/21

1 stop7h 24m

$608

Pick Dates

Flights are sorted by cheapest first

Deals found on 6/6

Reviews of airlines servicing Costa Rica

Read through reviews of airlines operating flights from Chicago to Costa Rica, such as Frontier and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

2,394 reviews

Check prices

Reviews

1 / 10

The crew was amazing. They took such good care of us. I mistakenly thought our seats were changed and they investigated the issue. Later, I realized it was my mistake but they took great pains to rectify the issue. Also, the flight attendant that worked our section was so pleasant and helpful. Good flight

Delta

8.0

Very good

2,394 reviews

Delta

8.0

Very good

2,394 reviews

Check prices

Reviews

1 / 10

The crew was amazing. They took such good care of us. I mistakenly thought our seats were changed and they investigated the issue. Later, I realized it was my mistake but they took great pains to rectify the issue. Also, the flight attendant that worked our section was so pleasant and helpful. Good flight

WestJet

7.2

Good

647 reviews

Delta

8.0

Very good

2,394 reviews

Check prices

Reviews

1 / 10

The crew was amazing. They took such good care of us. I mistakenly thought our seats were changed and they investigated the issue. Later, I realized it was my mistake but they took great pains to rectify the issue. Also, the flight attendant that worked our section was so pleasant and helpful. Good flight

Spirit Airlines

6.5

Okay

1,068 reviews

Delta

8.0

Very good

2,394 reviews

Check prices

Reviews

1 / 10

The crew was amazing. They took such good care of us. I mistakenly thought our seats were changed and they investigated the issue. Later, I realized it was my mistake but they took great pains to rectify the issue. Also, the flight attendant that worked our section was so pleasant and helpful. Good flight

Frontier

5.9

Fair

684 reviews

Delta

8.0

Very good

2,394 reviews

Check prices

Reviews

1 / 10

The crew was amazing. They took such good care of us. I mistakenly thought our seats were changed and they investigated the issue. Later, I realized it was my mistake but they took great pains to rectify the issue. Also, the flight attendant that worked our section was so pleasant and helpful. Good flight

Related info for your journey

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), Quepos Airport (XQP).

Flights to Costa Rica from Midway

Flights to Midway

Flights to Costa Rica

Flights from Midway

Flights from Costa Rica

Rent a Car

Car Rentals in Costa Rica

Car Rentals at Liberia

Top airline flying from Midway to Costa Rica

Airline	Cheapest	Average	Flexibility	On-time	COVID-19 safety
Delta	Cheapest$739	Average$1,091	FlexibilityNo cancel fee	On-timeN/A	COVID-19 safety	Search Delta flights

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Cheap flights from Midway (MDW) to Costa Rica from $118

This is the cheapest one-way flight price, found on 6/7. Prices may vary by date and flight preferences.

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How far in advance should I book a flight from Chicago Midway Airport to Costa Rica?

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

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

Cheap flights from Midway to Costa Rica in June, July 2023

The best prices found for MDW to Costa Rica flights for June, July

The lowest fares we've come across on flights traveling from Chicago to Costa Rica in June and July 2023. For more flight deals, be sure to check back very soon.

Midway to Costa Rica 2023 flight deals

Cheap flights to Costa Rica from Midway found for this year

The lowest fares we've come across on flights traveling from Chicago to Costa Rica in June and July 2023. For more flight deals, be sure to check back very soon.

Cheap Frontier flights from Midway to Costa Rica

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

Cheap Delta flights from Midway to Costa Rica

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.

Last minute flights from Midway to Costa Rica

Late deals on return flights to Costa Rica from Midway, departing today and this week

Book one of these great deals on flights from Chicago to Costa Rica. Tip: verify your flight details before completing your reservation.

One-way flights to Costa Rica from Midway

The cheapest one-way flights from Midway to Costa Rica

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.

Find flights from Midway to Costa Rica within your budget

Use the slider to find flights from Midway to Costa Rica that fit your budget.

Reviews of airlines servicing Costa Rica

Read through reviews of airlines operating flights from Chicago to Costa Rica, such as Frontier and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Useful info, stats and facts about Midway to Costa Rica flights.

Which airlines flying from Chicago Midway to Costa Rica have flexible changes due to COVID-19?

Can I find flights from Chicago Midway Airport to Costa Rica for under $300 on Cheapflights?

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

What does MDW to SJO mean?

Flights to Costa Rica from Midway

Rent a Car

Top airline flying from Midway to Costa Rica

The chart below displays the airlines Cheapflights users traveling from Midway to Costa Rica choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2023