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Flights from Chicago to San Juan – Direct & connecting routes

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MDW to SJU flights and routes map MDW to SJU – All flight route options from Chicago Midway International, Illinois, USA to Luis Munoz Marin International, Puerto Rico. These flights are operated by 3 airlines. Fly non-stop with Southwest Airlines or choose from 9 different transit flights. The shortest flight time is 4 hours and 40 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
USA MDW Chicago Midway Chicago, IL, USA
Puerto Rico SJU Luis Munoz Marin , Puerto Rico
MDW
Chicago Midway
USAChicago, IL, USA
Luis Munoz Marin
Puerto RicoSan Juan, Puerto Rico
SJU
1 direct route found »
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13 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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4h 40m

Sat & Sun
Southwest Airlines
Non-stop with Southwest Airlines.
4h 40m
0-1 flights per day.
Sat & Sun
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1 stop route options with the same airline:

Duration

Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.

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7h 00m

Via Atlanta ATL
1 stop with Frontier Airlines.
7h 00m
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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7h 00m

Only saturdays
Via Saint Louis STL
1 stop with Southwest Airlines.
7h 00m
0-1 flights per day.
Only saturdays
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Via Fort Lauderdale FLL
1 stop with Southwest Airlines. 0-1 flights per day.
Mon,Thu & Fri

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8h 00m

Mon,Thu & Fri
Via Fort Lauderdale FLL
1 stop with Southwest Airlines.
8h 00m
0-1 flights per day.
Mon,Thu & Fri
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Via Philadelphia PHL
1 stop with Frontier Airlines. 0-1 flights per day.
Begins in 21/8

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8h 04m

Begins in 21/8
Via Philadelphia PHL
1 stop with Frontier Airlines.
8h 04m
0-1 flights per day.
Begins in 21/8
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Via Tampa TPA
1 stop with Frontier Airlines. 0-1 flights per day.
Begins in 5/9

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8h 16m

Begins in 5/9
Via Tampa TPA
1 stop with Frontier Airlines.
8h 16m
0-1 flights per day.
Begins in 5/9
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Via Atlanta ATL
1 stop with Delta Air Lines. 3 flights per day.

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8h 27m

Via Atlanta ATL
1 stop with Delta Air Lines.
8h 27m
3 flights per day.
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Via Orlando MCO
1 stop with Southwest Airlines. 6-13 flights per day.

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8h 50m

Via Orlando MCO
1 stop with Southwest Airlines.
8h 50m
6-13 flights per day.
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Via Tampa TPA
1 stop with Southwest Airlines. 1-3 flights per day.

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8h 58m

Via Tampa TPA
1 stop with Southwest Airlines.
8h 58m
1-3 flights per day.
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Via Miami MIA
1 stop with Frontier Airlines.
Begins in 16/10

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9h 07m

Begins in 16/10
Via Miami MIA
1 stop with Frontier Airlines.
9h 07m
Begins in 16/10
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Via Nashville BNA
1 stop with Southwest Airlines. 0-2 flights per day.
Sat & Sun

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9h 10m

Sat & Sun
Via Nashville BNA
1 stop with Southwest Airlines.
9h 10m
0-2 flights per day.
Sat & Sun
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Via Baltimore BWI
1 stop with Southwest Airlines. 2-7 flights per day.

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9h 15m

Via Baltimore BWI
1 stop with Southwest Airlines.
9h 15m
2-7 flights per day.
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Via Orlando MCO
1 stop with Frontier Airlines. 0-1 flights per day.
Mon,Fri & Sun

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9h 26m

Mon,Fri & Sun
Via Orlando MCO
1 stop with Frontier Airlines.
9h 26m
0-1 flights per day.
Mon,Fri & Sun
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1 stop route options with codeshare or different airlines:

Duration

Via Atlanta ATL With Delta Air Lines & WestJet 0-2 flights per day.
Tue & Sat
CODESHARE

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8h 27m

Tue & Sat
Via Atlanta ATL
8h 27m
With Delta Air Lines & WestJet 0-2 flights per day.
Tue & Sat
CODESHARE
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Find the best prices on hotels and car rental near Luis Munoz Marin

We got great deals on hotels and car rentals near the airport.

Luis Munoz Marin HOTEL PRICES
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Chicago to San Juan flights

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

Chicago to San Juan with Southwest Airlines

Southwest Airlines has non-stop every Saturday or Sunday at 08 in the morning. You can also catch a transit flight via Saint Louis or Fort Lauderdale.

With Frontier Airlines

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

The shortest flight time between MDW and SJU is 4 hours and 40 minutes.

ViaTotal flight timeLayover timeDistance
Direct4h 40m-2070 miles (3331 km)
STL Saint Louis7h 0m1h 20m2288 miles (3681 km)
FLL Fort Lauderdale8h 0m45m2227 miles (3583 km)
PHL Philadelphia8h 4m2h 46m2258 miles (3633 km)
ATL Atlanta8h 27m4h 5m2150 miles (3459 km)
TPA Tampa8h 58m1h 40m2248 miles (3617 km)
MIA Miami9h 7m3h 27m2241 miles (3606 km)
BNA Nashville9h 10m1h 45m2161 miles (3477 km)
BWI Baltimore9h 15m1h 10m2189 miles (3522 km)
MCO Orlando9h 26m4h 30m2192 miles (3527 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-SJU flight routesChicago to San Juan flight routes illustrated on a map.
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Chicago - San Juan route map and flight paths
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From Chicago to Puerto Rico

Below is a list of other destinations to Puerto Rico from Chicago Midway International with either direct flights or 1 stop connections.

From USA to San Juan

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

You can fly non-stop from Chicago (MDW) to San Juan (SJU) with Southwest Airlines. The flight takes approximately 4 hours and 40 minutes. If you travel with a connecting flight instead, for example via Saint Louis, the total flight time will be 7 hours.

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

The flight time between Chicago Midway (MDW) and Luis Munoz Marin International (SJU) is approximately 4 hours and 40 minutes. The distance between the two airports is 2150 miles (or 3459 kilometers).

Yes, you can fly non-stop to SJU from MDW 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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