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Flights from Chicago to San Jose – Airlines & connecting routes

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MDW to SJO flights and routes map MDW to SJO – All flight route options from Chicago Midway International, Illinois, USA to Juan Santamaria International, Costa Rica. These flights are operated by 3 different airlines through 4 different connections. The shortest flight time is 7 hours. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA MDW Chicago Midway Chicago, IL, USA
Costa Rica SJO Juan Santamaria , Costa Rica
MDW
Chicago Midway
USAChicago, IL, USA
Juan Santamaria
Costa RicaSan Jose, Costa Rica
SJO
No direct flights found
5 routes with 1 stop found »
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1 stop route options with the same airline:

Duration

Via Atlanta ATL
1 stop with Delta Air Lines. 1-2 flights per day.

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7h 00m

Via Atlanta ATL
1 stop with Delta Air Lines.
7h 00m
1-2 flights per day.
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Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.
Only saturdays

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7h 13m

Only saturdays
Via Atlanta ATL
1 stop with Frontier Airlines.
7h 13m
0-1 flights per day.
Only saturdays
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Via Baltimore BWI
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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7h 20m

Only sundays
Via Baltimore BWI
1 stop with Southwest Airlines.
7h 20m
0-1 flights per day.
Only sundays
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Via Orlando MCO
1 stop with Southwest Airlines. 1-2 flights per day.

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7h 30m

Via Orlando MCO
1 stop with Southwest Airlines.
7h 30m
1-2 flights per day.
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Via Houston HOU
1 stop with Southwest Airlines. 0-3 flights per day.

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8h 20m

Via Houston HOU
1 stop with Southwest Airlines.
8h 20m
0-3 flights per day.
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Chicago to San Jose flights

With over 24 flights every week and 4 different airlines you have a wide range of options. While flying to San Jose from Chicago you will be doing a stopover in Atlanta, Baltimore or any other of the 4 alternatives with flight connections.

Are there any non-stop flights from MDW to SJO?

There are no direct or non-stop flights from Chicago Midway International, MDW to Juan Santamaria International, SJO.

Chicago to San Jose with Delta Air Lines

If you fly from Chicago with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching San Jose. This flight trip will take 7 hours and you can fly every weekday with departures at 06:00, 06:04 or 13:05. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Midway International Airport to Juan Santamaria International

The shortest flight time between MDW and SJO is 7 hours.

ViaTotal flight timeLayover timeDistance
ATL Atlanta7h 0m53m2236 miles (3598 km)
BWI Baltimore7h 20m50m2692 miles (4331 km)
MCO Orlando7h 30m1h 45m2290 miles (3685 km)
HOU Houston8h 20m50m2485 miles (3998 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.MDW-SJO flight routesChicago to San Jose flight routes illustrated on a map.
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Chicago - San Jose route map and flight paths
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Show all destinations from MDW Show all destinations from SJO
From Chicago to Costa Rica

We have found another destination to Costa Rica from Chicago Midway International as well.

From USA to San Jose

Below is a list of other cities in USA with flights to San Jose with either non-stop or connecting flights.

The fastest way to fly from Chicago (MDW) to San Jose (SJO) is via Atlanta and it will take about 7 hours. The second fastest route is via Baltimore and will take 7 hours and 20 minutes.

You can fly with Delta Air Lines or Southwest Airlines from Chicago to San Jose.

The flight time between Chicago Midway (MDW) and Juan Santamaria International (SJO) via Hartsfield–Jackson Atlanta International Airport, ATL is 7 hours.

No. But you can still purchase a 1 stop flight via Atlanta, Baltimore or any other route to San Jose (SJO).

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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