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Flights from San Juan to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

SJU to MDW flights and routes map SJU to MDW – All flight route options from Luis Munoz Marin International, Puerto Rico to Chicago Midway International, Illinois, USA. These flights are operated by 4 airlines. Fly non-stop with Southwest Airlines or choose from 9 different transit flights. The shortest flight time is 5 hours and 15 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
Puerto Rico SJU Luis Munoz Marin San Juan, Puerto Rico
USA MDW Chicago Midway , IL, USA
SJU
Luis Munoz Marin
Puerto RicoSan Juan, Puerto Rico
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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12 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 0-1 flights per day.
Sat & Sun

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5h 15m

Sat & Sun
Southwest Airlines
Non-stop with Southwest Airlines.
5h 15m
0-1 flights per day.
Sat & Sun
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1 stop route options with the same airline:

Duration

Via Philadelphia PHL
1 stop with Frontier Airlines. 0-1 flights per day.
Begins in 22/8

SHOW SCHEDULE
7h 57m

Begins in 22/8
Via Philadelphia PHL
1 stop with Frontier Airlines.
7h 57m
0-1 flights per day.
Begins in 22/8
SHOW SCHEDULE
Via Fort Lauderdale FLL
1 stop with Southwest Airlines. 0-1 flights per day.

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8h 20m

Via Fort Lauderdale FLL
1 stop with Southwest Airlines.
8h 20m
0-1 flights per day.
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Via Tampa TPA
1 stop with Southwest Airlines. 1-2 flights per day.

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8h 33m

Via Tampa TPA
1 stop with Southwest Airlines.
8h 33m
1-2 flights per day.
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Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.

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9h 03m

Via Atlanta ATL
1 stop with Frontier Airlines.
9h 03m
0-1 flights per day.
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Via Saint Louis STL
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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9h 08m

Only saturdays
Via Saint Louis STL
1 stop with Southwest Airlines.
9h 08m
0-1 flights per day.
Only saturdays
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Via Orlando MCO
1 stop with Southwest Airlines. 6 flights per day.

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9h 10m

Via Orlando MCO
1 stop with Southwest Airlines.
9h 10m
6 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 4 flights per day.

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9h 11m

Via Atlanta ATL
1 stop with Delta Air Lines.
9h 11m
4 flights per day.
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Via Orlando MCO
1 stop with Frontier Airlines. 0-1 flights per day.
Only saturdays

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9h 14m

Only saturdays
Via Orlando MCO
1 stop with Frontier Airlines.
9h 14m
0-1 flights per day.
Only saturdays
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Via Nashville BNA
1 stop with Southwest Airlines. 0-1 flights per day.
Sat & Sun

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9h 20m

Sat & Sun
Via Nashville BNA
1 stop with Southwest Airlines.
9h 20m
0-1 flights per day.
Sat & Sun
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Via Baltimore BWI
1 stop with Southwest Airlines. 2-3 flights per day.

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9h 25m

Via Baltimore BWI
1 stop with Southwest Airlines.
9h 25m
2-3 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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12h 45m

Only saturdays
Via Kansas City MCI
1 stop with Southwest Airlines.
12h 45m
0-1 flights per day.
Only saturdays
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1 stop route options with codeshare or different airlines:

Duration

Via Atlanta ATL With WestJet & Delta Air Lines 0-3 flights per day.
CODESHARE

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9h 11m

Via Atlanta ATL
9h 11m
With WestJet & Delta Air Lines 0-3 flights per day.
CODESHARE
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Find the best prices on hotels and car rental near Chicago Midway

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San Juan to Chicago flights

With over 204 flights every week and 10 different airlines you have a wide range of options. You can fly non-stop to Chicago (MDW) from San Juan (SJU) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Philadelphia, Fort Lauderdale or any other of the 9 alternatives with connectiing airports.

San Juan to Chicago with Southwest Airlines

Southwest Airlines has non-stop every Saturday or Sunday at 1:00 pm, 2:00 pm or 3:00 pm. You can also catch a transit flight via Fort Lauderdale or Tampa.

With Delta Air Lines

If you fly from San Juan with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching Chicago. This flight trip will take 9 hours and 11 minutes and you can fly every weekday with departures between 6:00 am and 3:00 pm. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Luis Munoz Marin International to Midway International Airport

The shortest flight time between SJU and MDW is 5 hours and 15 minutes.

ViaTotal flight timeLayover timeDistance
Direct5h 15m-2070 miles (3331 km)
PHL Philadelphia7h 57m1h 34m2258 miles (3633 km)
FLL Fort Lauderdale8h 20m3h 40m2227 miles (3583 km)
TPA Tampa8h 33m1h 0m2248 miles (3617 km)
STL Saint Louis9h 8m3h 20m2288 miles (3681 km)
ATL Atlanta9h 11m1h 8m2150 miles (3459 km)
MCO Orlando9h 14m3h 18m2192 miles (3527 km)
BNA Nashville9h 20m2h 55m2161 miles (3477 km)
BWI Baltimore9h 25m1h 35m2189 miles (3522 km)
MCI Kansas City12h 45m4h 50m2658 miles (4277 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.SJU-MDW flight routesSan Juan to Chicago flight routes illustrated on a map.
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San Juan - Chicago route map and flight paths
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Show all destinations from SJU Show all destinations from MDW
From San Juan to USA

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

From Puerto Rico to Chicago

We have found another destination to USA from Luis Munoz Marin International as well.

You can fly non-stop from San Juan (SJU) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 5 hours and 15 minutes. If you travel with a connecting flight instead, for example via Philadelphia, the total flight time will be 7 hours and 57 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Frontier Airlines, Southwest Airlines or Delta Air Lines is also an option.

The flight time between Luis Munoz Marin (SJU) and Chicago Midway International (MDW) is approximately 5 hours and 15 minutes. The distance between the two airports is 2150 miles (or 3459 kilometers).

Yes, you can fly non-stop to MDW from SJU with Southwest Airlines.

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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