Cheap flights from Chicago to San Juan from $0
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Discover deals on Chicago to San Juan flights
Typical range $0–$0•Cheapest found $0
Checking latest prices...Find cheap flights from Chicago to San Juan
Best
8 Feb
DEP
12:17
ORD
18:49
SJU
4h 32m
8 Feb
DEPARTURE
12:17 - 18:49
4h 32m
ORD
SJU
1 stop
8 Feb
DEP
07:20
ORD
1×
15:35
SJU
6h 15m
8 Feb
DEPARTURE
07:20 - 15:35
6h 15m
ORD
1 stop
SJU
Spirit Airlines flights from Chicago to San Juan
Our best Spirit Airlines deals on Chicago to San Juan tickets
Best
8 Feb
DEP
12:17
ORD
18:49
SJU
4h 32m
8 Feb
DEPARTURE
12:17 - 18:49
4h 32m
ORD
SJU
1 stop
8 Feb
DEP
07:20
ORD
1×
15:35
SJU
6h 15m
8 Feb
DEPARTURE
07:20 - 15:35
6h 15m
ORD
1 stop
SJU
American Airlines flights from Chicago to San Juan
Our best American Airlines deals on Chicago to San Juan tickets
Best
8 Feb
DEP
15:00
ORD
21:39
SJU
4h 39m
8 Feb
DEPARTURE
15:00 - 21:39
4h 39m
ORD
SJU
1 stop
8 Feb
DEP
05:00
ORD
1×
17:01
SJU
10h 1m
8 Feb
DEPARTURE
05:00 - 17:01
10h 1m
ORD
1 stop
SJU
Frontier Airlines flights from Chicago to San Juan
Our best Frontier Airlines deals on Chicago to San Juan tickets
Best
1 stop
8 Feb
DEP
05:40
ORD
1×
15:12
SJU
7h 32m
8 Feb
DEPARTURE
05:40 - 15:12
7h 32m
ORD
1 stop
SJU
1 stop
8 Feb
DEP
05:40
ORD
1×
15:12
SJU
7h 32m
8 Feb
DEPARTURE
05:40 - 15:12
7h 32m
ORD
1 stop
SJU
What's the cheapest day of the week to fly from Chicago to San Juan?
If your flying dates are flexible, you should consider flying to San Juan on a Wed, as we generally find the cheapest rates on that day. On the other hand, Fri is the most expensive day to fly.
What is the cheapest month to fly from Chicago to San Juan?
The cheapest month for flights from Chicago to San Juan is Sep, where tickets cost $116 on average. The most expensive months are Dec.
JanFebMarAprMayJunJulAugSepOctNovDec
$183$150$116
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Everything you should know
Cheapest one-way flight
$129
Typical prices: $129–$258
When to book
3 weeks
in advance to save around 25%
Good to know
💰
Save money
Compare prices across airlines to find the best deal. Prices can vary significantly.
📅
Be flexible
Flying midweek or in off-peak seasons can save you up to 30% on airfare.
⏰
Book early
Booking 3+ weeks in advance typically offers the best prices.
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Frequently asked questions
The cheapest flight from Chicago to San Juan currently costs AUD $129. Prices typically range from $129 to $129. Prices change frequently, so we recommend booking early and being flexible with your travel dates.