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Flights from San Jose to Chicago – Airlines & connecting routes

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SJO to MDW flights and routes map SJO to MDW – All flight route options from Juan Santamaria International, Costa Rica to Chicago Midway International, Illinois, USA. These flights are operated by 3 different airlines through 4 different connections. The shortest flight time is 7 hours and 31 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
Costa Rica SJO Juan Santamaria San Jose, Costa Rica
USA MDW Chicago Midway , IL, USA
SJO
Juan Santamaria
Costa RicaSan Jose, Costa Rica
Chicago Midway
USAChicago, IL, USA
MDW
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. 2 flights per day.
Begins in 11/9

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7h 31m

Begins in 11/9
Via Atlanta ATL
1 stop with Delta Air Lines.
7h 31m
2 flights per day.
Begins in 11/9
SHOW SCHEDULE
Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.
Begins in 11/10

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8h 20m

Begins in 11/10
Via Atlanta ATL
1 stop with Frontier Airlines.
8h 20m
0-1 flights per day.
Begins in 11/10
SHOW SCHEDULE
Via Houston HOU
1 stop with Southwest Airlines. 0-1 flights per day.

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9h 10m

Via Houston HOU
1 stop with Southwest Airlines.
9h 10m
0-1 flights per day.
SHOW SCHEDULE
Via Orlando MCO
1 stop with Southwest Airlines.

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9h 35m

Via Orlando MCO
1 stop with Southwest Airlines.
9h 35m
SHOW SCHEDULE
Via Baltimore BWI
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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9h 40m

Only sundays
Via Baltimore BWI
1 stop with Southwest Airlines.
9h 40m
0-1 flights per day.
Only sundays
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San Jose to Chicago flights

With over 30 flights every week and 4 different airlines you have a wide range of options. While flying to Chicago from San Jose you will be doing a stopover in Atlanta, Houston or any other of the 4 alternatives with flight connections.

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

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

San Jose to Chicago with Delta Air Lines

If you fly from San Jose with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching Chicago. This flight trip will take 7 hours and 31 minutes and you can fly every weekday with departures at 7:00 am, 1:00 pm or 2:00 pm. Delta Air Lines is a member of SkyTeam.

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

The shortest flight time between SJO and MDW is 7 hours and 31 minutes.

ViaTotal flight timeLayover timeDistance
ATL Atlanta7h 31m3h 22m2236 miles (3598 km)
HOU Houston9h 10m4h 45m2485 miles (3998 km)
MCO Orlando9h 35m1h 40m2290 miles (3685 km)
BWI Baltimore9h 40m2h 50m2692 miles (4331 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.SJO-MDW flight routesSan Jose to Chicago flight routes illustrated on a map.
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San Jose - Chicago route map and flight paths
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From San Jose to USA

Below is a list of other destinations to USA from Juan Santamaria International with either direct flights or 1 stop connections.

From Costa Rica to Chicago

We have found another destination to USA from Juan Santamaria International as well.

The fastest way to fly from San Jose (SJO) to Chicago (MDW) is via Atlanta and it will take about 7 hours and 31 minutes. The second fastest route is via Houston and will take 9 hours and 10 minutes.

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

The flight time between Juan Santamaria (SJO) and Chicago Midway International (MDW) via Hartsfield–Jackson Atlanta International Airport, ATL is 7 hours and 31 minutes.

No. But you can still purchase a 1 stop flight via Atlanta, Houston or any other route to Chicago (MDW).

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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