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$130+ Cheap flights from Wisconsin to Costa Rica

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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
jun. 18 — jun. 251
jue. 6/18
jue. 6/25
1 adult, Economy
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Cheap flight deals from Wisconsin to Costa Rica

Cheapest flights from Wisconsin to Costa Rica
Explore the most affordable flight options available from Wisconsin to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 19, 2026.

This Justfly.com deal was found by Cheapflights users on 5/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/267:00 am
ORD
-
LIR
1 stop7h 01m
JetBlue
mié. 9/22:06 pm
LIR
-
ORD
1 stop8h 38m
JetBlue
Deal found 5/14$342
This Air Canada deal was found by Cheapflights users on 5/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/168:40 pm
ORD
-
LIR
1 stop16h 10m
Air Canada
sáb. 10/241:00 pm
LIR
-
ORD
1 stop20h 58m
Air Canada
Deal found 5/15$364
This Justfly.com deal was found by Cheapflights users on 5/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/27:00 am
ORD
-
LIR
1 stop7h 01m
JetBlue
mié. 9/92:05 pm
LIR
-
ORD
1 stop8h 39m
JetBlue
Deal found 5/18$371
This Air Canada deal was found by Cheapflights users on 5/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/169:50 am
ORD
-
LIR
1 stop27h 00m
Air Canada
mar. 10/271:55 pm
LIR
-
ORD
1 stop22h 01m
Air Canada
Deal found 5/15$374
This Air Canada deal was found by Cheapflights users on 5/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/169:50 am
ORD
-
LIR
1 stop27h 00m
Air Canada
dom. 10/251:55 pm
LIR
-
ORD
2 stops29h 15m
Air Canada
Deal found 5/15$377
This Air Canada deal was found by Cheapflights users on 5/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/247:50 am
MSP
-
LIR
1 stop30h 05m
Air Canada
vie. 10/301:55 pm
LIR
-
MSP
1 stop30h 25m
Air Canada
Deal found 5/17$404
This JetBlue deal was found by Cheapflights users on 5/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/117:00 am
ORD
-
LIR
1 stop7h 01m
JetBlue
jue. 8/132:06 pm
LIR
-
ORD
1 stop8h 38m
JetBlue
Deal found 5/17$420
This KAYAK deal was found by Cheapflights users on 5/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/226:21 pm
ORD
-
LIR
2 stops42h 29m
Copa Airlines
dom. 10/251:55 pm
LIR
-
ORD
2 stops20h 15m
Copa Airlines
Deal found 5/16$424
This Cheapflightsfares deal was found by Cheapflights users on 5/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/317:00 am
ORD
-
SJO
1 stop6h 57m
JetBlue
mar. 9/82:02 pm
SJO
-
ORD
1 stop8h 42m
JetBlue
Deal found 5/14$430
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
mar. 8/111:50 pm
ORD
-
SJO
2 stops43h 30m
Frontier
vie. 8/219:35 am
SJO
-
ORD
1 stop12h 39m
Frontier
Deal found 5/15$431
This Air Canada deal was found by Cheapflights users on 5/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/148:45 am
ORD
-
SJO
1 stop12h 50m
Air Canada
lun. 6/227:15 am
SJO
-
ORD
1 stop23h 35m
Air Canada
Deal found 5/17$434
This JetBlue deal was found by Cheapflights users on 5/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/117:00 am
ORD
-
SJO
1 stop6h 57m
JetBlue
lun. 8/172:02 pm
SJO
-
ORD
1 stop8h 42m
JetBlue
Deal found 5/15$435

Find flight deals from Wisconsin to Costa Rica

Keep the following information in mind while searching for Wisconsin to Costa Rica flight deals. Data was last updated mayo 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(Justfly.com)

One-way from

$130
(JetBlue)

Popular in

December

Cheapest in

May

Average price

$559
Provider with most accurate pricing for Milwaukee-Mitchell-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-San José Juan Santamaria Intl flights.
Search Deals
From Wisconsin to Costa Rica
Search Deals
One-way flight from Wisconsin to Costa Rica
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 2,558,603 searches. Data last updated mayo 19, 2026.
Use the filters below to find and compare flights from Wisconsin to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

dom. 6/14

3:21 pm-11:06 am

1 stop20h 45m

San José Juan Santamaria Intl

dom. 6/21

6:19 pm-4:00 am

1 stop8h 41m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

dom. 7/12

3:21 pm-9:06 am

1 stop18h 45m

San José Juan Santamaria Intl

mié. 7/15

10:03 am-4:00 am

1 stop16h 57m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

dom. 8/16

3:21 pm-7:10 am

1 stop16h 49m

San José Juan Santamaria Intl

mié. 8/19

4:08 am-1:59 pm

1 stop8h 51m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mié. 7/1

3:21 pm-8:21 am

1 stop18h 00m

San José Juan Santamaria Intl

lun. 7/6

4:08 am-1:57 pm

1 stop8h 49m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 7/9

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

jue. 7/16

10:03 am-4:00 am

1 stop16h 57m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mié. 7/22

3:21 pm-9:06 am

1 stop18h 45m

San José Juan Santamaria Intl

lun. 7/27

8:30 am-4:00 am

1 stop18h 30m

$505

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 8/6

3:21 pm-7:10 am

1 stop16h 49m

San José Juan Santamaria Intl

lun. 8/10

5:55 pm-1:59 pm

1 stop19h 04m

$505

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

vie. 7/24

1:30 am-1:15 am

1 stop24h 45m

San José Juan Santamaria Intl

sáb. 8/1

2:20 am-11:55 pm

1 stop20h 35m

$506

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

dom. 8/30

5:34 am-11:49 am

1 stop7h 15m

San José Juan Santamaria Intl

jue. 9/3

1:21 pm-11:25 pm

1 stop9h 04m

$520

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

dom. 7/5

6:21 am-11:59 pm

1 stop18h 38m

San José Juan Santamaria Intl

dom. 7/12

4:15 pm-12:09 pm

1 stop18h 54m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Wisconsin to Costa Rica

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

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Costa Rica

How far ahead should I book a flight from Wisconsin to Costa Rica?

Booking 31 days in advance of your planned departure date is, on average, the best time to get cheap flights from Wisconsin to Costa Rica. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Wisconsin to Costa Rica?

Currently, August is the cheapest month in which you can book a flight from Wisconsin to Costa Rica (average of $179). Flying from Wisconsin to Costa Rica in July is currently the most expensive (average of $515). 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.

Related info for your journey

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

  • How long is the flight from Wisconsin to Costa Rica?

    Airlines like Copa Airlines, Delta, and Southwest fly from Wisconsin to Costa Rica in about 7h 15m. The time it takes to get you to your destination can typically vary by up to 13h 30m. Airlines will cover a distance of 2286 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Wisconsin 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.

  • What is the cheapest month to book a flight from Wisconsin to Costa Rica?

    Currently, August is the cheapest month in which you can book a flight from Wisconsin to Costa Rica (average of $179). Flying from Wisconsin to Costa Rica in July is currently the most expensive (average of $515). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
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Atlanta to Panama City flights
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Top 4 airlines flying from Wisconsin to Costa Rica

Discover the top 4 airlines that operate flights from Wisconsin 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 2,558,603 searches. Data last updated mayo 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$179Average$770FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$206Average$640FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$378Average$671FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$707FlexibilityNo cancel feeOn-time63%

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