Cheap Flights from Chicago to San Juan
Any date
Find your flight
With a stop
16 Sep
12:11
CHI → FLL → SJU
F9 + F9 · 0d 23h stopover in Fort Lauderdale
€98
2 flights
☕ 23h in Fort Lauderdale — enough time to explore
22 Sep
14:38
CHI → FLL → SJU
B6 + F9 · 0d 18h stopover in Fort Lauderdale
€115
2 flights
☕ 18h in Fort Lauderdale — enough time to explore
24 Sep
11:25
CHI → MIA → SJU
F9 + F9 · 0d 16h stopover in Miami
€116
2 flights
☕ 16h in Miami — enough time to explore
28 Sep
12:11
CHI → FLL → SJU
F9 + F9 · 1d 1h stopover in Fort Lauderdale
€117
2 flights
☕ 25h in Fort Lauderdale — enough time to explore
3 Oct
21:49
CHI → ORL → SJU
F9 + F9 · 2h layover in ORL
€118
2 flights
5 Oct
13:05
CHI → MIA → SJU
WN + F9 · 11h layover in Miami
€119
2 flights
☕ 11h in Miami — enough time to explore
29 Sep
14:25
CHI → MIA → SJU
WN + F9 · 10h layover in Miami
€124
2 flights
☕ 10h in Miami — enough time to explore
28 Sep
10:00
CHI → MIA → SJU
AA + F9 · 0d 14h stopover in Miami
€130
2 flights
☕ 14h in Miami — enough time to explore
You might also like
More from Chicago
⭐ GREAT Direct↓27%
Baltimore
CHI → BWI·Thu 24 Sep·2h 5m
F9
€77€30
Get offer
⭐ GREAT Direct↓37%
Denver
CHI → DEN·Sat 19 Sep·2h 45m
F9
€49€31
Get offer
⭐ GREAT Direct↓55%
Fort Lauderdale
CHI → FLL·Sat 24 Oct·8h 21m
B6
€83€37
Get offerDirect↓48%
St Louis
CHI → STL·Wed 30 Sep·1h 10m
WN
€98€51
Get offer
Direct↓40%
Washington
CHI → WAS·Fri 9 Oct·2h 1m
AA
€118€71
Get offerDirect↓54%
Fort Lauderdale
CHI → FLL·Sun 4 Oct·3h 12m
F9
€119€43
Get offerFlight delayed or cancelled? You could be owed up to EUR 600 under EU261. Get your free claim letter →