Flights from Chicago to San Juan (Puerto Rico)

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Our cheapest offers for flights from Chicago to San Juan (Puerto Rico)

Here you can compare cheap flights from Chicago (CHI) to San Juan (Puerto Rico) (SJU) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to San Juan (Puerto Rico). Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
San Juan (Puerto Rico)
Outbound
02/19/25
1 Stopover (MIA)
NK1843, NK1193
08h 38min
Return
03/10/25
1 Stopover (CLT)
AA2218, AA1668
17h 21min
Spirit Airlines ?
$325
Best option
Chicago
San Juan (Puerto Rico)
Outbound
03/02/25
direct
NK0491
04h 47min
Return
03/07/25
direct
UA2088
05h 21min
Spirit Airlines ?
$405
Chicago
San Juan (Puerto Rico)
Outbound
12/13/24
1 Stopover (MCO)
F93044, F92250
16h 09min
Return
12/31/24
1 Stopover (ATL)
F92081, AA0780
11h 54min
Frontier Airlines ?
$373
Chicago
San Juan (Puerto Rico)
Outbound
02/19/25
direct
AA0388
04h 25min
Return
03/10/25
1 Stopover (CLT)
AA2218, AA1668
17h 21min
American Airlines ?
$399
Chicago
San Juan (Puerto Rico)
Outbound
02/19/25
1 Stopover (IAH)
UA0307, UA0701
10h 06min
Return
03/10/25
direct
UA2089
05h 19min
United Airlines ?
$406
Chicago
San Juan (Puerto Rico)
Outbound
03/02/25
direct
AA2268
04h 25min
Return
03/07/25
direct
AA2268
05h 25min
American Airlines ?
$407
Chicago
San Juan (Puerto Rico)
Outbound
12/13/24
1 Stopover (MCO)
F93044, F92250
16h 09min
Return
12/31/24
1 Stopover (MCO)
F93505, F93043
14h 14min
Frontier Airlines
$439
Chicago
San Juan (Puerto Rico)
Outbound
02/19/25
1 Stopover (MIA)
NK1843, NK1193
08h 38min
Return
03/10/25
1 Stopover (ATL)
F92081, F91441
12h 21min
Spirit Airlines
$440
Chicago
San Juan (Puerto Rico)
Outbound
02/19/25
1 Stopover (MIA)
NK1843, NK1193
08h 38min
Return
03/10/25
1 Stopover (ATL)
F92081, F91441
12h 21min
Spirit Airlines
$444
Chicago
San Juan (Puerto Rico)
Outbound
02/19/25
1 Stopover (CLT)
AA0285, AA2830
06h 32min
Return
03/10/25
2 Stopovers (CLT, DFW)
AA2218, AA0430, AA2754
19h 38min
American Airlines ?
$449
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to San Juan (Puerto Rico)

Favorite airline: American Airlines
79 % of flights booked on the route from Chicago to San Juan (Puerto Rico) are booked with American Airlines, Spirit Airlines and United Airlines.
American Airlines
29 %
Spirit Airlines
27 %
United Airlines
23 %
Direct flights are the cheapest connection
On this route, direct flights are $ 2.00 cheaper than flights with a stopover.
non stop flight
1 stop
2 stops
04h 39min
13h 20min
15h 45min
$194
$196
$451
The favorite connection is non-stop
Flights from Chicago to San Juan (Puerto Rico) are most often booked as a direct flight.
Route
bookings
Direct flights
04h 39min, from $194
39 %
1 stopover Orlando International Airport, FL
07h 00min, from $221
18 %
1 stopover Charlotte Douglas International Airport, NC
13h 01min, from $338
15 %

Flight information: Chicago - San Juan (Puerto Rico)

Roundtrip from $324.65
Flight duration min. 04:30 / max. 07:00
Return flight duration min. 05:10/ max. 06:05
Distance 3318 km
Flights per week 28
Departure airport Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI)
Arrival airport Airport San Juan - Luis Muñoz Marín International Airport (SJU)
Destination country Flights to Puerto Rico
Alternative flights to San Juan (Puerto Rico)
Flight destinations with a similar price
Flight destinations with a similar price
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.