Menu
Menu
New York

Cheap flights from Chicago (CHI) to Puerto Rico

Know your dates, get live prices in seconds:

From
To
Depart
–
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
Add another flight clear all

We work with more than 300 partners to bring you better travel deals

CHI
Chicago
PR0
Puerto Rico
 Add details to search for flights
Cheap flights from Chicago to Puerto Rico

Cheap flights from Chicago to Puerto Rico in June 2019

The best prices found for CHI to Puerto Rico flights for June
27 Jun - 4 Jul
$324pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BQN
Aguadilla Borinquen
BQN
Aguadilla Borinquen
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
24 Jun - 18 Jul
$384pp
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
BQN
Aguadilla Borinquen
BQN
Aguadilla Borinquen
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
30 Jun - 27 Jul
$410pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Puerto Rico 2019 flight deals

Cheap flights to Puerto Rico from Chicago found for this year
13 Nov - 18 Nov
$280pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BQN
Aguadilla Borinquen
BQN
Aguadilla Borinquen
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
20 Aug - 26 Aug
$283pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
9 Sep - 14 Sep
$285pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BQN
Aguadilla Borinquen
BQN
Aguadilla Borinquen
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Puerto Rico

Late deals on round-trip flights to Puerto Rico from Chicago, departing today and this week
20 Jun - 4 Jul
$436pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
19 Jun - 25 Jun
$437pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
18 Jun - 20 Jun
$460pp
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Destination information for Puerto Rico

Things to know before you go. Useful info for your trip from Chicago to Puerto Rico
Today's exchange rate
$1.00 = $1.00
Flight duration
4h 59m

Airports servicing Chicago

Chicago Midway (MDW)
Chicago-O'Hare Intl (ORD)
Rockford (RFD)