Flight from Chicago to San Juan
SouthwestWN 2320, WN 3764
Class: Economy
$282.46
Per Adult
11:25 AMChicago17, Jul 2025
10h 40m
ORDMCOSJU
11:05 PM San Juan17, Jul 2025
$282.46
Per Adult
American AirlinesAA 2323, AA 1341
Class: Economy
$255.2
Per Adult
04:49 PMChicago17, Jul 2025
17h 15m
ORDMIASJU
11:04 AM +1 DAYSan Juan18, Jul 2025
$255.2
Per Adult
DeltaDL 1264, DL 1882
Class: Economy
$781.77
Per Adult
05:35 AMChicago17, Jul 2025
6h 54m
ORDATLSJU
01:29 PM San Juan17, Jul 2025
$781.77
Per Adult
American AirlinesAA 2896, AA 702
Class: Economy
$446.17
Per Adult
06:00 AMChicago17, Jul 2025
16h 25m
ORDDFWSJU
11:25 PM San Juan17, Jul 2025
$446.17
Per Adult
SouthwestWN 2987, WN 2291
Class: Economy
$301.33
Per Adult
07:45 AMChicago17, Jul 2025
9h 15m
MDWMCOSJU
06:00 PM San Juan17, Jul 2025
$301.33
Per Adult
American AirlinesAA 1555, AA 702
Class: Economy
$560.55
Per Adult
08:25 AMChicago17, Jul 2025
14h 0m
ORDDFWSJU
11:25 PM San Juan17, Jul 2025
$560.55
Per Adult
SouthwestWN 2320, WN 2604
Class: Economy
$282.46
Per Adult
11:25 AMChicago17, Jul 2025
7h 25m
ORDMCOSJU
07:50 PM San Juan17, Jul 2025
$282.46
Per Adult
UnitedUA 1634, UA 2021
Class: Economy
$538.62
Per Adult
02:24 PMChicago17, Jul 2025
21h 10m
ORDIADSJU
12:34 PM +1 DAYSan Juan18, Jul 2025
$538.62
Per Adult
American AirlinesAA 760, AA 702
Class: Economy
$446.17
Per Adult
05:00 AMChicago17, Jul 2025
17h 25m
ORDDFWSJU
11:25 PM San Juan17, Jul 2025
$446.17
Per Adult
DeltaDL 1247, DL 1861
Class: Economy
$1,817.44
Per Adult
07:00 AMChicago17, Jul 2025
14h 23m
ORDATLSJU
10:23 PM San Juan17, Jul 2025
$1,817.44
Per Adult
DeltaDL 1147, DL 1757
Class: Economy
$1,877.25
Per Adult
11:20 AMChicago17, Jul 2025
23h 36m
ORDATLSJU
11:56 AM +1 DAYSan Juan18, Jul 2025
$1,877.25
Per Adult
UnitedUA 2362, UA 1556
Class: Economy
$623.3
Per Adult
07:35 PMChicago17, Jul 2025
17h 10m
ORDEWRSJU
01:45 PM +1 DAYSan Juan18, Jul 2025
$623.3
Per Adult
UnitedUA 2362, UA 2143
Class: Economy
$623.3
Per Adult
07:35 PMChicago17, Jul 2025
15h 22m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$623.3
Per Adult
DeltaDL 1264, DL 1861
Class: Economy
$1,817.44
Per Adult
05:35 AMChicago17, Jul 2025
15h 48m
ORDATLSJU
10:23 PM San Juan17, Jul 2025
$1,817.44
Per Adult
DeltaDL 1264, DL 1946
Class: Economy
$579
Per Adult
05:35 AMChicago17, Jul 2025
10h 0m
ORDATLSJU
04:35 PM San Juan17, Jul 2025
$579
Per Adult
SouthwestWN 1375, WN 2604
Class: Economy
$301.33
Per Adult
10:30 AMChicago17, Jul 2025
8h 20m
MDWMCOSJU
07:50 PM San Juan17, Jul 2025
$301.33
Per Adult
DeltaDL 2879, DL 1882
Class: Economy
$1,871.03
Per Adult
07:59 PMChicago17, Jul 2025
16h 30m
ORDATLSJU
01:29 PM +1 DAYSan Juan18, Jul 2025
$1,871.03
Per Adult
DeltaDL 1178, DL 1791
Class: Economy
$781.77
Per Adult
09:50 AMChicago17, Jul 2025
9h 49m
ORDATLSJU
08:39 PM San Juan17, Jul 2025
$781.77
Per Adult
American AirlinesAA 2984, AA 967
Class: Economy
$300.52
Per Adult
05:00 AMChicago17, Jul 2025
12h 10m
ORDMIASJU
06:10 PM San Juan17, Jul 2025
$300.52
Per Adult
American AirlinesAA 1380, AA 1364
Class: Economy
$446.17
Per Adult
06:00 AMChicago17, Jul 2025
14h 55m
ORDMIASJU
09:55 PM San Juan17, Jul 2025
$446.17
Per Adult
DeltaDL 2358, DL 1913
Class: Economy
$1,854.56
Per Adult
05:00 PMChicago17, Jul 2025
19h 26m
ORDDTWSJU
01:26 PM +1 DAYSan Juan18, Jul 2025
$1,854.56
Per Adult
DeltaDL 2738, DL 1882
Class: Economy
$1,877.25
Per Adult
05:59 PMChicago17, Jul 2025
18h 30m
ORDATLSJU
01:29 PM +1 DAYSan Juan18, Jul 2025
$1,877.25
Per Adult
SouthwestWN 4752, WN 4751
Class: Economy
$257.97
Per Adult
05:15 PMChicago17, Jul 2025
6h 40m
MDWMCOSJU
12:55 AM +1 DAYSan Juan18, Jul 2025
$257.97
Per Adult
DeltaDL 2039, DL 1913
Class: Economy
$1,854.56
Per Adult
07:10 AMChicago17, Jul 2025
29h 16m
ORDDTWSJU
01:26 PM +1 DAYSan Juan18, Jul 2025
$1,854.56
Per Adult
UnitedUA 276, UA 2021
Class: Economy
$532.4
Per Adult
09:31 PMChicago17, Jul 2025
14h 3m
ORDIADSJU
12:34 PM +1 DAYSan Juan18, Jul 2025
$532.4
Per Adult
SouthwestWN 1734, WN 2509
Class: Economy
$212.32
Per Adult
01:50 PMChicago17, Jul 2025
9h 40m
ORDBWISJU
12:30 AM +1 DAYSan Juan18, Jul 2025
$212.32
Per Adult
American AirlinesAA 1277, AA 1613
Class: Economy
$300.52
Per Adult
06:57 PMChicago17, Jul 2025
16h 47m
ORDMIASJU
12:44 PM +1 DAYSan Juan18, Jul 2025
$300.52
Per Adult
UnitedUA 2133, UA 2143
Class: Economy
$753.61
Per Adult
03:40 PMChicago17, Jul 2025
19h 17m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$753.61
Per Adult
American AirlinesAA 3544, AA 514
Class: Economy
$618.8
Per Adult
07:03 PMChicago17, Jul 2025
9h 3m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$618.8
Per Adult
SouthwestWN 4831, WN 1122
Class: Economy
$301.33
Per Adult
05:00 AMChicago17, Jul 2025
7h 40m
MDWMCOSJU
01:40 PM San Juan17, Jul 2025
$301.33
Per Adult
SouthwestWN 2489, WN 1133
Class: Economy
$274.2
Per Adult
07:35 AMChicago17, Jul 2025
8h 25m
MDWHOUSJU
05:00 PM San Juan17, Jul 2025
$274.2
Per Adult
UnitedUA 2691, UA 1543
Class: Economy
$470.5
Per Adult
08:47 AMChicago17, Jul 2025
14h 15m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$470.5
Per Adult
SouthwestWN 4679, WN 1133
Class: Economy
$301.33
Per Adult
06:05 AMChicago17, Jul 2025
9h 55m
MDWHOUSJU
05:00 PM San Juan17, Jul 2025
$301.33
Per Adult
UnitedUA 1785, UA 2143
Class: Economy
$665.4
Per Adult
04:46 PMChicago17, Jul 2025
18h 11m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$665.4
Per Adult
UnitedUA 695
Class: Economy
$243.64
Per Adult
06:03 PMChicago17, Jul 2025
4h 51m
ORDSJU
11:54 PM San Juan17, Jul 2025
$243.64
Per Adult
FrontierF9 3854, F9 2250
Class: Economy
$288.76
Per Adult
09:12 PMChicago17, Jul 2025
10h 52m
MDWMCOSJU
09:04 AM +1 DAYSan Juan18, Jul 2025
$288.76
Per Adult
UnitedUA 534, UA 1556
Class: Economy
$671.62
Per Adult
05:55 PMChicago17, Jul 2025
18h 50m
ORDEWRSJU
01:45 PM +1 DAYSan Juan18, Jul 2025
$671.62
Per Adult
American AirlinesAA 2530, AA 2830
Class: Economy
$343.67
Per Adult
08:30 AMChicago17, Jul 2025
14h 25m
ORDCLTSJU
11:55 PM San Juan17, Jul 2025
$343.67
Per Adult
UnitedUA 1205, UA 1543
Class: Economy
$518.84
Per Adult
11:46 AMChicago17, Jul 2025
11h 16m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$518.84
Per Adult
DeltaDL 1456, DL 1861
Class: Economy
$781.77
Per Adult
01:26 PMChicago17, Jul 2025
7h 57m
ORDATLSJU
10:23 PM San Juan17, Jul 2025
$781.77
Per Adult
American AirlinesAA 1380, AA 967
Class: Economy
$300.52
Per Adult
06:00 AMChicago17, Jul 2025
11h 10m
ORDMIASJU
06:10 PM San Juan17, Jul 2025
$300.52
Per Adult
American AirlinesAA 1193, AA 514
Class: Economy
$446.17
Per Adult
03:52 PMChicago17, Jul 2025
12h 14m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$446.17
Per Adult
American AirlinesAA 2279, AA 2830
Class: Economy
$446.17
Per Adult
12:37 PMChicago17, Jul 2025
10h 18m
ORDCLTSJU
11:55 PM San Juan17, Jul 2025
$446.17
Per Adult
DeltaDL 1264, DL 1791
Class: Economy
$1,817.44
Per Adult
05:35 AMChicago17, Jul 2025
14h 4m
ORDATLSJU
08:39 PM San Juan17, Jul 2025
$1,817.44
Per Adult
American AirlinesAA 1290, AA 514
Class: Economy
$446.17
Per Adult
01:23 PMChicago17, Jul 2025
14h 43m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$446.17
Per Adult
DeltaDL 1147, DL 1861
Class: Economy
$781.77
Per Adult
11:20 AMChicago17, Jul 2025
10h 3m
ORDATLSJU
10:23 PM San Juan17, Jul 2025
$781.77
Per Adult
UnitedUA 396, UA 1543
Class: Economy
$389.66
Per Adult
09:25 PMChicago17, Jul 2025
25h 37m
ORDEWRSJU
12:02 AM +2 DAYSSan Juan19, Jul 2025
$389.66
Per Adult
American AirlinesAA 1250, AA 967
Class: Economy
$343.67
Per Adult
08:25 AMChicago17, Jul 2025
8h 45m
ORDMIASJU
06:10 PM San Juan17, Jul 2025
$343.67
Per Adult
SouthwestWN 1643, WN 3594
Class: Economy
$206.71
Per Adult
02:55 PMChicago17, Jul 2025
7h 20m
MDWTPASJU
11:15 PM San Juan17, Jul 2025
$206.71
Per Adult
American AirlinesAA 1784, AA 783
Class: Economy
$446.17
Per Adult
07:05 AMChicago17, Jul 2025
6h 49m
ORDCLTSJU
02:54 PM San Juan17, Jul 2025
$446.17
Per Adult
American AirlinesAA 550, AA 514
Class: Economy
$560.55
Per Adult
06:20 PMChicago17, Jul 2025
9h 46m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$560.55
Per Adult
American AirlinesAA 3311, AA 514
Class: Economy
$560.55
Per Adult
05:08 PMChicago17, Jul 2025
10h 58m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$560.55
Per Adult
American AirlinesAA 1854, AA 3065
Class: Economy
$446.17
Per Adult
07:00 AMChicago17, Jul 2025
14h 50m
ORDPHLSJU
10:50 PM San Juan17, Jul 2025
$446.17
Per Adult
American AirlinesAA 2257, AA 514
Class: Economy
$560.55
Per Adult
03:00 PMChicago17, Jul 2025
13h 6m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$560.55
Per Adult
SouthwestWN 2602, WN 2509
Class: Economy
$206.71
Per Adult
02:50 PMChicago17, Jul 2025
8h 40m
MDWBWISJU
12:30 AM +1 DAYSan Juan18, Jul 2025
$206.71
Per Adult
American AirlinesAA 835, AA 967
Class: Economy
$343.67
Per Adult
06:57 AMChicago17, Jul 2025
10h 13m
ORDMIASJU
06:10 PM San Juan17, Jul 2025
$343.67
Per Adult
American AirlinesAA 1380, AA 1329
Class: Economy
$446.17
Per Adult
06:00 AMChicago17, Jul 2025
8h 35m
ORDMIASJU
03:35 PM San Juan17, Jul 2025
$446.17
Per Adult
DeltaDL 2879, DL 1757
Class: Economy
$1,871.03
Per Adult
07:59 PMChicago17, Jul 2025
14h 57m
ORDATLSJU
11:56 AM +1 DAYSan Juan18, Jul 2025
$1,871.03
Per Adult
American AirlinesAA 2984, AA 1329
Class: Economy
$446.17
Per Adult
05:00 AMChicago17, Jul 2025
9h 35m
ORDMIASJU
03:35 PM San Juan17, Jul 2025
$446.17
Per Adult
American AirlinesAA 1250, AA 1364
Class: Economy
$560.55
Per Adult
08:25 AMChicago17, Jul 2025
12h 30m
ORDMIASJU
09:55 PM San Juan17, Jul 2025
$560.55
Per Adult
American AirlinesAA 2842, AA 783
Class: Economy
$446.17
Per Adult
05:15 AMChicago17, Jul 2025
8h 39m
ORDCLTSJU
02:54 PM San Juan17, Jul 2025
$446.17
Per Adult
UnitedUA 1996
Class: Economy
$306.45
Per Adult
08:49 AMChicago17, Jul 2025
4h 55m
ORDSJU
02:44 PM San Juan17, Jul 2025
$306.45
Per Adult
SouthwestWN 4154, WN 2291
Class: Economy
$310.09
Per Adult
06:00 AMChicago17, Jul 2025
11h 0m
ORDMCOSJU
06:00 PM San Juan17, Jul 2025
$310.09
Per Adult
UnitedUA 2668, UA 1543
Class: Economy
$475.9
Per Adult
10:40 AMChicago17, Jul 2025
12h 22m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$475.9
Per Adult
DeltaDL 1178, DL 1861
Class: Economy
$781.77
Per Adult
09:50 AMChicago17, Jul 2025
11h 33m
ORDATLSJU
10:23 PM San Juan17, Jul 2025
$781.77
Per Adult
American AirlinesAA 1747, AA 514
Class: Economy
$560.55
Per Adult
09:50 AMChicago17, Jul 2025
18h 16m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$560.55
Per Adult
American AirlinesAA 2080, AA 2830
Class: Economy
$343.67
Per Adult
09:17 AMChicago17, Jul 2025
13h 38m
ORDCLTSJU
11:55 PM San Juan17, Jul 2025
$343.67
Per Adult
American AirlinesAA 1109, AA 514
Class: Economy
$560.55
Per Adult
11:53 AMChicago17, Jul 2025
16h 13m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$560.55
Per Adult
American AirlinesAA 1290, AA 702
Class: Economy
$446.17
Per Adult
01:23 PMChicago17, Jul 2025
9h 2m
ORDDFWSJU
11:25 PM San Juan17, Jul 2025
$446.17
Per Adult
DeltaDL 2738, DL 1757
Class: Economy
$1,871.03
Per Adult
05:59 PMChicago17, Jul 2025
16h 57m
ORDATLSJU
11:56 AM +1 DAYSan Juan18, Jul 2025
$1,871.03
Per Adult
UnitedUA 1413, UA 1543
Class: Economy
$442.65
Per Adult
08:55 AMChicago17, Jul 2025
14h 7m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$442.65
Per Adult
DeltaDL 1716, DL 1913
Class: Economy
$1,854.56
Per Adult
02:00 PMChicago17, Jul 2025
22h 26m
ORDDTWSJU
01:26 PM +1 DAYSan Juan18, Jul 2025
$1,854.56
Per Adult
UnitedUA 293, UA 1543
Class: Economy
$475.9
Per Adult
11:00 AMChicago17, Jul 2025
12h 2m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$475.9
Per Adult
UnitedUA 2668, UA 2143
Class: Economy
$503.19
Per Adult
10:40 AMChicago17, Jul 2025
24h 17m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$503.19
Per Adult
DeltaDL 1085, DL 1913
Class: Economy
$1,854.56
Per Adult
09:00 AMChicago17, Jul 2025
27h 26m
ORDDTWSJU
01:26 PM +1 DAYSan Juan18, Jul 2025
$1,854.56
Per Adult
SouthwestWN 4154, WN 1762
Class: Economy
$301.33
Per Adult
06:00 AMChicago17, Jul 2025
9h 35m
ORDMCOSJU
04:35 PM San Juan17, Jul 2025
$301.33
Per Adult
UnitedUA 396, UA 1556
Class: Economy
$437.98
Per Adult
09:25 PMChicago17, Jul 2025
15h 20m
ORDEWRSJU
01:45 PM +1 DAYSan Juan18, Jul 2025
$437.98
Per Adult
SouthwestWN 2883, WN 2604
Class: Economy
$301.33
Per Adult
09:00 AMChicago17, Jul 2025
9h 50m
MDWMCOSJU
07:50 PM San Juan17, Jul 2025
$301.33
Per Adult
American AirlinesAA 2842, AA 2830
Class: Economy
$300.52
Per Adult
05:15 AMChicago17, Jul 2025
17h 40m
ORDCLTSJU
11:55 PM San Juan17, Jul 2025
$300.52
Per Adult
UnitedUA 758, UA 2021
Class: Economy
$538.62
Per Adult
10:50 AMChicago17, Jul 2025
24h 44m
ORDIADSJU
12:34 PM +1 DAYSan Juan18, Jul 2025
$538.62
Per Adult
UnitedUA 534, UA 2143
Class: Economy
$665.4
Per Adult
05:55 PMChicago17, Jul 2025
17h 2m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$665.4
Per Adult
SouthwestWN 2883, WN 2291
Class: Economy
$301.33
Per Adult
09:00 AMChicago17, Jul 2025
8h 0m
MDWMCOSJU
06:00 PM San Juan17, Jul 2025
$301.33
Per Adult
SouthwestWN 2236, WN 3764
Class: Economy
$257.82
Per Adult
01:25 PMChicago17, Jul 2025
8h 40m
MDWMCOSJU
11:05 PM San Juan17, Jul 2025
$257.82
Per Adult
American AirlinesAA 2984, AA 1613
Class: Economy
$446.17
Per Adult
05:00 AMChicago17, Jul 2025
6h 44m
ORDMIASJU
12:44 PM San Juan17, Jul 2025
$446.17
Per Adult
American AirlinesAA 2852
Class: Economy
$296.98
Per Adult
08:43 AMChicago17, Jul 2025
4h 50m
ORDSJU
02:33 PM San Juan17, Jul 2025
$296.98
Per Adult
American AirlinesAA 1277, AA 1341
Class: Economy
$206.65
Per Adult
06:57 PMChicago17, Jul 2025
15h 7m
ORDMIASJU
11:04 AM +1 DAYSan Juan18, Jul 2025
$206.65
Per Adult
DeltaDL 1654, DL 1913
Class: Economy
$1,854.56
Per Adult
11:01 AMChicago17, Jul 2025
25h 25m
ORDDTWSJU
01:26 PM +1 DAYSan Juan18, Jul 2025
$1,854.56
Per Adult
SouthwestWN 3882, WN 1948
Class: Economy
$296.03
Per Adult
07:15 AMChicago17, Jul 2025
10h 35m
MDWBWISJU
06:50 PM San Juan17, Jul 2025
$296.03
Per Adult
American AirlinesAA 1743, AA 3065
Class: Economy
$446.17
Per Adult
11:52 AMChicago17, Jul 2025
9h 58m
ORDPHLSJU
10:50 PM San Juan17, Jul 2025
$446.17
Per Adult
American AirlinesAA 835, AA 1329
Class: Economy
$446.17
Per Adult
06:57 AMChicago17, Jul 2025
7h 38m
ORDMIASJU
03:35 PM San Juan17, Jul 2025
$446.17
Per Adult
FrontierF9 3854, F9 1746
Class: Economy
$226.52
Per Adult
09:12 PMChicago17, Jul 2025
26h 20m
MDWMCOSJU
12:32 AM +2 DAYSSan Juan19, Jul 2025
$226.52
Per Adult
SouthwestWN 4154, WN 1122
Class: Economy
$301.33
Per Adult
06:00 AMChicago17, Jul 2025
6h 40m
ORDMCOSJU
01:40 PM San Juan17, Jul 2025
$301.33
Per Adult
American AirlinesAA 1109, AA 702
Class: Economy
$446.17
Per Adult
11:53 AMChicago17, Jul 2025
10h 32m
ORDDFWSJU
11:25 PM San Juan17, Jul 2025
$446.17
Per Adult
American AirlinesAA 2970, AA 3065
Class: Economy
$300.52
Per Adult
05:00 AMChicago17, Jul 2025
16h 50m
ORDPHLSJU
10:50 PM San Juan17, Jul 2025
$300.52
Per Adult
UnitedUA 2488, UA 1543
Class: Economy
$442.65
Per Adult
12:00 PMChicago17, Jul 2025
11h 2m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$442.65
Per Adult
DeltaDL 1456, DL 1757
Class: Economy
$1,877.25
Per Adult
01:26 PMChicago17, Jul 2025
21h 30m
ORDATLSJU
11:56 AM +1 DAYSan Juan18, Jul 2025
$1,877.25
Per Adult
American AirlinesAA 1211, AA 1341
Class: Economy
$530.37
Per Adult
03:42 PMChicago17, Jul 2025
18h 22m
ORDMIASJU
11:04 AM +1 DAYSan Juan18, Jul 2025
$530.37
Per Adult
Delta, UnitedDL 2894, UA 1543
Class: Economy
$2,313.17
Per Adult
01:01 PMChicago17, Jul 2025
10h 1m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$2,313.17
Per Adult
UnitedUA 1657, UA 1543
Class: Economy
$442.65
Per Adult
07:00 AMChicago17, Jul 2025
16h 2m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$442.65
Per Adult
UnitedUA 2677, UA 2021
Class: Economy
$706.38
Per Adult
05:56 PMChicago17, Jul 2025
17h 38m
ORDIADSJU
12:34 PM +1 DAYSan Juan18, Jul 2025
$706.38
Per Adult
UnitedUA 2649, UA 2143
Class: Economy
$629.52
Per Adult
02:27 PMChicago17, Jul 2025
20h 30m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$629.52
Per Adult
American AirlinesAA 3304, AA 967
Class: Economy
$343.67
Per Adult
10:10 AMChicago17, Jul 2025
7h 0m
ORDMIASJU
06:10 PM San Juan17, Jul 2025
$343.67
Per Adult
FrontierF9 2292, F9 2082
Class: Economy
$506.03
Per Adult
06:20 AMChicago17, Jul 2025
6h 59m
MDWATLSJU
02:19 PM San Juan17, Jul 2025
$506.03
Per Adult
SouthwestWN 3794, WN 1948
Class: Economy
$296.03
Per Adult
10:50 AMChicago17, Jul 2025
7h 0m
MDWBWISJU
06:50 PM San Juan17, Jul 2025
$296.03
Per Adult
UnitedUA 2649, UA 1543
Class: Economy
$526.28
Per Adult
02:27 PMChicago17, Jul 2025
8h 35m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$526.28
Per Adult
American AirlinesAA 2323, AA 1613
Class: Economy
$423.76
Per Adult
04:49 PMChicago17, Jul 2025
18h 55m
ORDMIASJU
12:44 PM +1 DAYSan Juan18, Jul 2025
$423.76
Per Adult
American AirlinesAA 2976, AA 783
Class: Economy
$343.67
Per Adult
08:45 PMChicago17, Jul 2025
17h 9m
ORDCLTSJU
02:54 PM +1 DAYSan Juan18, Jul 2025
$343.67
Per Adult
DeltaDL 1477, DL 1882
Class: Economy
$1,877.25
Per Adult
03:29 PMChicago17, Jul 2025
21h 0m
ORDATLSJU
01:29 PM +1 DAYSan Juan18, Jul 2025
$1,877.25
Per Adult
American AirlinesAA 471, AA 3065
Class: Economy
$446.17
Per Adult
08:37 AMChicago17, Jul 2025
13h 13m
ORDPHLSJU
10:50 PM San Juan17, Jul 2025
$446.17
Per Adult
UnitedUA 2661, UA 1543
Class: Economy
$475.9
Per Adult
10:00 AMChicago17, Jul 2025
13h 2m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$475.9
Per Adult
SouthwestWN 2987, WN 1762
Class: Economy
$301.33
Per Adult
07:45 AMChicago17, Jul 2025
7h 50m
MDWMCOSJU
04:35 PM San Juan17, Jul 2025
$301.33
Per Adult
UnitedUA 563, UA 1543
Class: Economy
$506.3
Per Adult
07:10 AMChicago17, Jul 2025
15h 52m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$506.3
Per Adult
DeltaDL 1477, DL 1757
Class: Economy
$1,877.25
Per Adult
03:29 PMChicago17, Jul 2025
19h 27m
ORDATLSJU
11:56 AM +1 DAYSan Juan18, Jul 2025
$1,877.25
Per Adult
UnitedUA 1658, UA 1543
Class: Economy
$383.47
Per Adult
06:00 AMChicago17, Jul 2025
17h 2m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$383.47
Per Adult
American AirlinesAA 1747, AA 702
Class: Economy
$446.17
Per Adult
09:50 AMChicago17, Jul 2025
12h 35m
ORDDFWSJU
11:25 PM San Juan17, Jul 2025
$446.17
Per Adult
SouthwestWN 2236, WN 4751
Class: Economy
$255.69
Per Adult
01:25 PMChicago17, Jul 2025
10h 30m
MDWMCOSJU
12:55 AM +1 DAYSan Juan18, Jul 2025
$255.69
Per Adult
UnitedUA 1140, UA 2021
Class: Economy
$538.62
Per Adult
01:05 PMChicago17, Jul 2025
22h 29m
ORDIADSJU
12:34 PM +1 DAYSan Juan18, Jul 2025
$538.62
Per Adult
American AirlinesAA 2984, AA 1364
Class: Economy
$446.17
Per Adult
05:00 AMChicago17, Jul 2025
15h 55m
ORDMIASJU
09:55 PM San Juan17, Jul 2025
$446.17
Per Adult
UnitedUA 2092, UA 1543
Class: Economy
$388.34
Per Adult
08:00 AMChicago17, Jul 2025
15h 2m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$388.34
Per Adult
American AirlinesAA 481, AA 514
Class: Economy
$560.55
Per Adult
10:39 AMChicago17, Jul 2025
17h 27m
ORDDFWSJU
05:06 AM +1 DAYSan Juan18, Jul 2025
$560.55
Per Adult
DeltaDL 1147, DL 1791
Class: Economy
$781.77
Per Adult
11:20 AMChicago17, Jul 2025
8h 19m
ORDATLSJU
08:39 PM San Juan17, Jul 2025
$781.77
Per Adult
SouthwestWN 2320, WN 4751
Class: Economy
$265.87
Per Adult
11:25 AMChicago17, Jul 2025
12h 30m
ORDMCOSJU
12:55 AM +1 DAYSan Juan18, Jul 2025
$265.87
Per Adult
American AirlinesAA 3304, AA 1364
Class: Economy
$560.55
Per Adult
10:10 AMChicago17, Jul 2025
10h 45m
ORDMIASJU
09:55 PM San Juan17, Jul 2025
$560.55
Per Adult
UnitedUA 396, UA 2143
Class: Economy
$437.98
Per Adult
09:25 PMChicago17, Jul 2025
13h 32m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$437.98
Per Adult
UnitedUA 2189, UA 1543
Class: Economy
$721.89
Per Adult
01:00 PMChicago17, Jul 2025
10h 2m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$721.89
Per Adult
DeltaDL 1247, DL 1791
Class: Economy
$1,817.44
Per Adult
07:00 AMChicago17, Jul 2025
12h 39m
ORDATLSJU
08:39 PM San Juan17, Jul 2025
$1,817.44
Per Adult
American AirlinesAA 2840, AA 3065
Class: Economy
$560.55
Per Adult
02:30 PMChicago17, Jul 2025
7h 20m
ORDPHLSJU
10:50 PM San Juan17, Jul 2025
$560.55
Per Adult
UnitedUA 1785, UA 1556
Class: Economy
$671.62
Per Adult
04:46 PMChicago17, Jul 2025
19h 59m
ORDEWRSJU
01:45 PM +1 DAYSan Juan18, Jul 2025
$671.62
Per Adult
UnitedUA 1332, UA 1543
Class: Economy
$526.28
Per Adult
01:09 PMChicago17, Jul 2025
9h 53m
ORDEWRSJU
12:02 AM +1 DAYSan Juan18, Jul 2025
$526.28
Per Adult
American AirlinesAA 835, AA 1364
Class: Economy
$560.55
Per Adult
06:57 AMChicago17, Jul 2025
13h 58m
ORDMIASJU
09:55 PM San Juan17, Jul 2025
$560.55
Per Adult
DeltaDL 1084, DL 1913
Class: Economy
$1,828.23
Per Adult
07:01 PMChicago17, Jul 2025
17h 25m
ORDDTWSJU
01:26 PM +1 DAYSan Juan18, Jul 2025
$1,828.23
Per Adult
FrontierF9 3854, F9 4726
Class: Economy
$226.52
Per Adult
09:12 PMChicago17, Jul 2025
28h 27m
MDWMCOSJU
02:39 AM +2 DAYSSan Juan19, Jul 2025
$226.52
Per Adult
American AirlinesAA 1784, AA 2830
Class: Economy
$300.52
Per Adult
07:05 AMChicago17, Jul 2025
15h 50m
ORDCLTSJU
11:55 PM San Juan17, Jul 2025
$300.52
Per Adult
SouthwestWN 2613, WN 2948
Class: Economy
$206.71
Per Adult
02:10 PMChicago17, Jul 2025
8h 0m
MDWFLLSJU
11:10 PM San Juan17, Jul 2025
$206.71
Per Adult
American AirlinesAA 481, AA 702
Class: Economy
$560.55
Per Adult
10:39 AMChicago17, Jul 2025
11h 46m
ORDDFWSJU
11:25 PM San Juan17, Jul 2025
$560.55
Per Adult
DeltaDL 1247, DL 1946
Class: Economy
$579
Per Adult
07:00 AMChicago17, Jul 2025
8h 35m
ORDATLSJU
04:35 PM San Juan17, Jul 2025
$579
Per Adult
SouthwestWN 2883, WN 1762
Class: Economy
$301.33
Per Adult
09:00 AMChicago17, Jul 2025
6h 35m
MDWMCOSJU
04:35 PM San Juan17, Jul 2025
$301.33
Per Adult
UnitedUA 1332, UA 2143
Class: Economy
$629.52
Per Adult
01:09 PMChicago17, Jul 2025
21h 48m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$629.52
Per Adult
UnitedUA 1205, UA 2143
Class: Economy
$598.5
Per Adult
11:46 AMChicago17, Jul 2025
23h 11m
ORDEWRSJU
11:57 AM +1 DAYSan Juan18, Jul 2025
$598.5
Per Adult
SouthwestWN 1375, WN 2291
Class: Economy
$301.33
Per Adult
10:30 AMChicago17, Jul 2025
6h 30m
MDWMCOSJU
06:00 PM San Juan17, Jul 2025
$301.33
Per Adult
Do's and Don'ts at the Airport and During a Flight
Do's
- Arrive Early: Reach the airport at least 2–3 hours before your flight.
- Carry Valid ID: Keep your government-issued ID or passport handy.
- Stay Updated: Keep your phone charged and notifications on.
- Follow Cabin Crew Instructions: They’re there for your safety.
- Wear Comfortable Clothes: Layers help with varying cabin temperatures.
- Be Polite: Kindness with airline staff and others goes a long way.
Don'ts
- No Security Jokes: Don’t joke about bombs or threats.
- Don’t Recline Suddenly: Be courteous during meals or when others are using trays.
- Avoid Overpacking: Stick to cabin baggage limits.
- Don’t Rush: Allow front rows to exit first after landing.
- Be Considerate: Avoid loud conversations or using speakerphone.
Things You Can Carry in Your Flight Bag
Knowing what’s allowed in your cabin baggage can save you from surprises at security.
Essentials You Can Bring:
- Travel Documents: Boarding pass, passport, visa, hotel confirmations.
- Electronics: Laptops, tablets, smartphones, power banks (under 100Wh).
- Toiletries: Liquids under 100ml in a clear zip-lock bag.
- Medication: In original packaging, carry prescriptions if needed.
- Snacks: Packaged snacks are allowed; avoid liquids or semi-liquids.
Items to Avoid:
- Sharp objects, large liquid containers, flammable items, and restricted substances.
Tip: Always check your airline’s baggage policy for details.
Payment Methods We Support
At Travorio, we understand that flexibility is key when booking flights. That’s why we offer a wide range of secure and convenient payment options:
- Credit & Debit Cards: Visa, Mastercard, Amex, Discover, all with 3D Secure.
- Buy Now, Pay Later (BNPL): Options like Affirm and Afterpay let you split payments.
- Digital Wallets: Apple Pay, Google Pay, Amazon Pay, Link Pay, WeChat Pay.
- Cryptocurrency Payments: Bitcoin, Ethereum, and selected altcoins via secure gateways.
Your Payment Security is Guaranteed: End-to-end encryption and fraud detection keep your transactions safe and worry-free.
What to Do in Case of a Flight Emergency
Whether it's a sudden delay, lost baggage, or a missed flight, here's how you can stay calm and take the right steps:
Flight Delays or Cancellations:
- Check your airline’s mobile app or website for real-time updates.
- Speak to the airline counter at the airport or customer care if you're already at the gate.
- If you booked via Travorio, our 24/7 support team is just a click or call away.
Lost Baggage:
- Immediately report to the airline’s baggage claim or lost & found counter.
- Share your baggage tag and provide a detailed description of your luggage.
- Airlines usually deliver lost baggage within 24–72 hours.
Missed Flight:
- Contact your airline right away; some offer rescheduling with a fee.
- If your flight was missed due to an airline delay, they may rebook you at no extra cost.
Medical Emergencies:
- Inform cabin crew; all flights are equipped with basic medical kits.
- In case of a serious situation at the airport, reach out to airport medical assistance immediately.
Stay calm, stay informed — help is always available!
Baggage Policies for Travelers
Understanding your airline’s baggage policy is essential to avoid last-minute surprises and extra fees.
Cabin (Carry-On) Baggage:
- Most airlines allow one carry-on bag (typically 7–10 kg or 15–22 lbs) and one personal item such as a laptop bag or handbag.
- Keep essentials like travel documents, electronics, and medications in your carry-on.
- Liquids must be in containers no larger than 100ml (3.4 oz) and packed in a clear resealable bag for security screening.
Checked Baggage:
- Domestic flights usually permit 15–23 kg (33–50 lbs) of checked baggage, depending on the fare class.
- International flights often include 23–32 kg (50–70 lbs) per piece, sometimes allowing two bags on long-haul routes.
- Pre-booking extra baggage online is usually cheaper than paying at the airport.
Prohibited Items:
- Power banks and spare lithium batteries must go in your cabin bag, not checked luggage.
- Sharp objects, flammable liquids, and certain tools are restricted or banned on most flights.
- Always verify with your airline’s official baggage guidelines for destination-specific rules.
Visa and Documentation Requirements
Traveling across borders requires more than just booking a ticket, documentation matters.
For International Flights:
- A valid passport (typically valid for at least 6 months beyond your intended return date) is required.
- Visa: Depending on your citizenship and destination, a visa may be required in advance or available on arrival.
- Return/onward ticket and proof of funds may be required by immigration authorities.
- Some destinations require mandatory travel insurance with health coverage.
For Domestic Flights:
- A government-issued photo ID such as a passport, national ID, or driver’s license is required at check-in and security.
- Ensure the name on your ID matches the name on your booking exactly.
Pro Tips:
- Review visa requirements for your destination and any layovers.
- Print and save copies of hotel bookings, flight details, and insurance.
- Use digital wallets or apps to store e-documents securely.
Health and Medical Assistance While Flying
Whether it’s your first trip or your fiftieth, your health in transit is a priority.
Before Your Flight:
- Consult your physician if you have any medical conditions or upcoming procedures.
- Check if vaccinations or health certificates are required for your destination.
- Carry a personal health kit: pain relievers, motion sickness meds, bandages, sanitizer, and any prescriptions in original packaging.
In-Flight:
- Stay hydrated with plenty of water and avoid excessive caffeine or alcohol.
- Move regularly during long flights to improve circulation and prevent stiffness.
- Inform the crew in advance if you need assistance or allergy accommodations.
At the Airport:
- Most major airports have a medical help desk or clinic for emergencies or minor issues.
- Look for designated assistance areas or contact the airline if mobility or health support is needed.
Important Information about Chicago to San Juan
| Lowest Fare to Travel on Date | $0 - 17 Jul |
| Highest Fare to Travel on Date | $0 - 17 Jul |
| First Departing Flight | undefined, Depart at undefined |
| Last Departing Flight | undefined, Depart at undefined |
| First Arriving Flight | undefined, Arrival at undefined |
| Last Arriving Flight | undefined, Arrival at undefined |
| Popular Airlines from Chicago to San Juan | |
| Airports Codes for Chicago and San Juan |
Customer Reviews
T
Trenton Edwards
First time using Travorio and I was honestly impressed. I used Afterpay to book a round-trip flight and it made it super manageable for my budget. The interface was simple, and I liked being able to compare different airlines without jumping between tabs.
Z
Zachariah Gonzales
I liked how clearly the flight details were presented. Everything from layovers to aircraft type was listed before booking, so I knew exactly what I was getting. No guessing or clicking through extra pages.
T
Travis Morgan
Customer support was fantastic. I had a question about baggage allowance and used their chat feature. Got a friendly, helpful response in less than five minutes. You don’t get that kind of support on most travel sites.
D
Damon Brooks
Honestly, the design of the website is top-notch. It's easy to read, loads fast, and doesn’t bombard you with pop-ups or ads. I felt like I could trust the site from the moment I landed on it.
A
Ariana Foster
What sold me on Travorio was the ability to pay with crypto. I used USDC and it processed faster than expected. Booking was easy, and I got an email confirmation almost immediately. The site felt trustworthy, which isn’t always the case with travel platforms.
H
Hailey Edwards
I’m a pretty frequent traveler and always looking for flexible ways to pay. Travorio’s selection of payment options really sets them apart. I used Affirm for a longer international trip and the experience was painless.
S
Sarah Brown
Just booked a getaway for next month and the process was seamless. I paid using Klarna to break it into smaller payments, which was perfect for my monthly budget. Got a great deal compared to other sites I checked.
M
Matthew Young
What impressed me most was the follow-up communication. After booking, I received my confirmation instantly, and they sent a pre-departure checklist a few days before my flight. Small thing, but really helpful.
M
Milo McConnell
What I liked most was how clean the whole process felt. No bait-and-switch tactics, no mystery fees. Just found the flight, confirmed the info, and checked out. It’s rare to find a travel site this transparent.
A
Anjali Menon
One of the easiest booking sites I’ve used. No need to make an account, and I got my flight confirmation right away. Everything was straightforward with no weird third-party redirects.