Favorite airline: United Airlines
The most popular airline for flights from Chicago to San Juan (Puerto Rico) is United Airlines.
United Airlines
11 %
American Airlines
7 %
Interjet
4 %
Stopover flights are the cheapest connection
Compared to direct flights, flights with a stopover on this route are on average 70 % cheaper.
non stop flight
1 stop
2 stops
04h 53min
06h 56min
13h 36min
$268
$158
$427
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 53min, from $268
36 %
1 stopover Fort Lauderdale-Hollywood International Airport, FL
06h 56min, from $158
24 %
1 stopover Orlando International Airport, FL
06h 50min, from $187
11 %

Flights from Chicago to San Juan (Puerto Rico)

IDEALO: 122 Flight Offers from $158
Outbound flight: 04/25/20
18:34 CHI
02:30 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$158
14 days ago*
Check
Outbound flight: 04/25/20
14:29 CHI
22:19 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$188
14 days ago*
Check
Outbound flight: 04/25/20
14:29 CHI
22:19 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$188
14 days ago*
Check
Outbound flight: 04/25/20
14:29 CHI
22:19 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
14:11 SJU
00:19 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$213
14 days ago*
Check
Outbound flight: 04/25/20
19:47 CHI
13:30 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
21:20 SJU
11:21 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$223
14 days ago*
Check
Outbound flight: 04/25/20
19:47 CHI
13:30 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
21:20 SJU
11:21 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$223
14 days ago*
Check
Outbound flight: 04/25/20
06:00 CHI
20:20 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Frontier Airlines, Spirit Airlines
Return flight: 04/28/20
15:30 SJU
00:47 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines, Frontier Airlines
$241
14 days ago*
Check
Outbound flight: 04/25/20
06:00 CHI
20:20 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Frontier Airlines, Spirit Airlines
Return flight: 04/28/20
15:30 SJU
00:47 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines, Frontier Airlines
$241
14 days ago*
Check
Outbound flight: 04/25/20
07:30 CHI
20:35 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
JetBlue Airways
Return flight: 04/28/20
05:50 SJU
22:30 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
JetBlue Airways
$258
14 days ago*
Check
Outbound flight: 04/25/20
07:30 CHI
20:35 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
JetBlue Airways
Return flight: 04/28/20
05:50 SJU
22:30 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
JetBlue Airways
$258
14 days ago*
Check
Outbound flight: 04/25/20
19:35 CHI
01:28 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
direct
United Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$268
14 days ago*
Check
Outbound flight: 04/25/20
22:55 CHI
04:40 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
direct
United Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$268
14 days ago*
Check
Outbound flight: 04/25/20
19:35 CHI
01:28 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
direct
United Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$268
14 days ago*
Check
Outbound flight: 04/25/20
22:55 CHI
04:40 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
direct
United Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$268
14 days ago*
Check
Outbound flight: 04/25/20
18:34 CHI
02:30 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
15:12 SJU
19:35 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$273
14 days ago*
Check
Outbound flight: 04/25/20
18:34 CHI
02:30 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
Spirit Airlines
Return flight: 04/28/20
15:12 SJU
19:35 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$273
14 days ago*
Check
Outbound flight: 04/25/20
15:56 CHI
23:44 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$276
14 days ago*
Check
Outbound flight: 04/25/20
15:56 CHI
23:44 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$276
14 days ago*
Check
Outbound flight: 07/02/20
07:07 CHI
13:04 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
direct
Frontier Airlines
Return flight: 07/20/20
14:27 SJU
18:48 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
direct
Frontier Airlines
$278
55 days ago*
Check
Outbound flight: 04/25/20
17:00 CHI
01:31 SJU
Chicago-IL all Airports (ORD, MDW, RFD)
San Juan - Luis Muñoz Marín International Airport
1 Stopover
American Airlines
Return flight: 04/28/20
03:30 SJU
10:05 CHI
San Juan - Luis Muñoz Marín International Airport
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Spirit Airlines
$278
14 days ago*
Check
Page 1 / 7
12+
2-11
under 2 years
hab
12+
2-11
under 2 years