Flights from Chicago Airport (MDW) to San José Airport Airport (SJO)
Direct flights to Juan Santamaría International from Midway are only offered by Flexjet as this route is in low demand, so the options are limited. If this route is not ideal, the only other option is to get a flight with a stop over. The flight time is approximately 4 Hours 59 Minutes.
The cost of the flights varies significantly so we can’t provide you an estimate. Prices can be 50% cheaper if you book more than a month in advance. The cheapest flights available will generally be mid week or late in the evening, so if you are on a budget then these are the flight times you should consider. Alternatively, you could book well in advance and you flight could be up to 50% cheaper, especially with budget airliners. The ticket prices for most airliners will increase the closer you get the departure date, so as soon as you know the date you will travel you should book your flights.
If you are planning a trip to Juan Santamaría International Airport from Midway Airport you can pre-arrange short or long term parking at Midway Airport.
If you chose to rent a car at Juan Santamaría International Airport and need to return it, find the nearest fuel station along your route to Juan Santamaría International Airport in order to avoid incurring additional cost when you return your vehicle.
We suggest pre-booking your transport to Midway Airport. The following options are available:
- Private Transfers to Midway Airport
- Buses to Midway Airport
- Taxis to Midway Airport
- Train Services to/near Midway Airport
Ensure your arrival at Juan Santamaría International Airport is as smooth as possible by pre-booking your transport - which in many cases will also save you money:
- Car rental at Juan Santamaría International Airport (SJO)
- Private transfers at Juan Santamaría International Airport (SJO)
- Buses from Juan Santamaría International Airport (SJO)
- Taxis from Juan Santamaría International Airport (SJO)
- Train services at or near Juan Santamaría International Airport (SJO)
Find hotels close to Juan Santamaría International Airport many hotels offer airport transfers directly from the airport to your hotel.
For a full summary of all the airliners that fly from Midway to Juan Santamaría International, please see the table below.

Airliner | Mo | Tu | We | Th | Fr | Sa | Su | First Flight | Last Flight | Flights |
---|---|---|---|---|---|---|---|---|---|---|
Flexjet | 0 | 0 | 1 | 0 | 0 | 0 | 0 | 10:53 | 10:53 | VIEW FLIGHTS |
Flexjet offer the highest number of flights for this route with departures times between 10:53 and 10:53.
You can find the latest flight availability and prices from Flexjet at www.flexjet.com/. You can also book direct and get their latest discounts.
Flight times for the route are summarised in the table below. These time were correct at the time of writing, but please be aware that times may vary from time to time so please check their website for exact times and the dates you wish to fly.

Day | Flight Times | Flights | ||||
---|---|---|---|---|---|---|
Wednesday | 10:53
| VIEW FLIGHTS |
If you are flexible on the airport you depart from, then there are other airports that offer direct flights to Juan Santamaría International. You can see full details of these below.

Route | Stops | Distance | Flying Time |
---|---|---|---|
Chicago O'Hare to San José Juan Santamaría | 0 | 5 Hours 1 Minute |
Before you start your journey remember to check you have all your documents; in particular, your passport and flight tickets. You will be surprised at the amount of people of forget these!
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Other Airports Connecting To San José Airport in united states
- airplanemode_active Miami International Airport to San José 41 flights per week
- airplanemode_active Orlando International Airport to San José 24 flights per week
- airplanemode_active Fort Lauderdale hollywood International Airport to San José 19 flights per week
- airplanemode_active Atlanta Airport to San José 16 flights per week
- airplanemode_active Houston William P Hobby Airport to San José 8 flights per week
- airplanemode_active New York John F Kennedy International Airport to San José 7 flights per week
- airplanemode_active Baltimore Washington International Thurgood Marshall Airport to San José 2 flights per week
- airplanemode_active Chicago OHare International Airport to San José 2 flights per week
- airplanemode_active Punta Gorda Charlotte County Airport to San José 1 flights per week
- airplanemode_active Houston Airport to San José 25 flights per week
- airplanemode_active Newark Airport to San José 21 flights per week
- airplanemode_active Los Angeles Airport to San José 17 flights per week
- airplanemode_active Dallas Fort Worth International Airport to San José 14 flights per week
- airplanemode_active Charlotte Douglas Airport to San José 7 flights per week
- airplanemode_active Denver International Airport to San José 4 flights per week
- airplanemode_active Washington Dulles International Airport to San José 2 flights per week
- airplanemode_active Naples Airport to San José 1 flights per week
- airplanemode_active Clearwater St Petersburg Clearwater International Airport to San José 1 flights per week
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Useful Information about San José Airport

See all the airport lounges, locations and opening times available at San José Airport
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See all bars and restaurants at San José Airport, including locations and if they are before or after check-in
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See all shops available at San José Airport - plan your duty free shopping in advance
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Things to see and do in and around San José City in Costa Rica.
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