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Flight Deals from Chicago O Hare Airport to Puerto Rico from $175

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Top Deals on flights from Chicago O Hare Airport to San Juan

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

Jan 20

ORD
6h 32m
Direct

Jan 20

SJU
Spirit Airlines Logo
Spirit Airlines

Jan 22

SJU
6h 24m
MIA

Jan 22

ORD

as low as

$175

Chicago, US (CHI) - San Juan, PR (SJU)

Frontier Airlines Logo
Frontier Airlines

Jan 8

ORD
17h 22m
MCO

Jan 9

SJU
Frontier Airlines Logo
Frontier Airlines

Jan 15

SJU
12h 5m
MCO

Jan 16

ORD

as low as

$189

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

Jan 20

ORD
10h 20m
FLL

Jan 20

SJU
Spirit Airlines Logo
Spirit Airlines

Jan 22

SJU
6h 24m
MIA

Jan 22

ORD

as low as

$192

Chicago, US (CHI) - San Juan, PR (SJU)

JetBlue Logo
JetBlue

Jan 13

ORD
10h 20m
BOS

Jan 13

SJU
JetBlue Logo
JetBlue

Jan 17

SJU
9h 11m
JFK

Jan 17

ORD

as low as

$195

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

Jan 10

ORD
6h 32m
Direct

Jan 10

SJU
Spirit Airlines Logo
Spirit Airlines

Jan 17

SJU
3h 15m
Direct

Jan 17

ORD

as low as

$197

Chicago, US (CHI) - San Juan, PR (SJU)

Frontier Airlines Logo
Frontier Airlines

Jan 1

ORD
21h 55m
MCO

Jan 2

SJU
Frontier Airlines Logo
Frontier Airlines

Jan 15

SJU
5h 44m
ATL

Jan 15

ORD

as low as

$209

Chicago, US (CHI) - San Juan, PR (SJU)

Delta Air Lines Logo
Delta Air Lines

Jan 22

ORD
11h 3m
ATL

Jan 22

SJU
Delta Air Lines Logo
Delta Air Lines

Jan 29

SJU
10h 45m
JFK

Jan 29

ORD

as low as

$225

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

Jan 8

ORD
23h 44m
EWR

Jan 9

SJU
Spirit Airlines Logo
Spirit Airlines

Jan 15

SJU
6h 24m
MIA

Jan 15

ORD

as low as

$231

Chicago, US (CHI) - San Juan, PR (SJU)

Frontier Airlines Logo
Frontier Airlines

Jan 8

ORD
18h 34m
TPA

Jan 9

SJU
Frontier Airlines Logo
Frontier Airlines

Jan 11

SJU
15h 22m
MCO

Jan 11

ORD

as low as

$236

Chicago, US (CHI) - San Juan, PR (SJU)

Frontier Airlines Logo
Frontier Airlines

Jan 15

ORD
15h 55m
RDU

Jan 15

SJU
Frontier Airlines Logo
Frontier Airlines

Jan 21

SJU
18h 5m
MCO

Jan 22

ORD

as low as

$269

Chicago, US (CHI) - San Juan, PR (SJU)

American Airlines Logo
American Airlines

Jan 22

ORD
6h 39m
Direct

Jan 22

SJU
American Airlines Logo
American Airlines

Jan 29

SJU
3h 35m
Direct

Jan 29

ORD

as low as

$276

Chicago, US (CHI) - San Juan, PR (SJU)

American Airlines Logo
American Airlines

Jan 22

ORD
6h 39m
Direct

Jan 22

SJU
American Airlines Logo
American Airlines

Jan 29

SJU
5h 32m
CLT

Jan 29

ORD

as low as

$280

Top Deals on flights from Chicago O Hare Airport to Aguadilla

Chicago, US (CHI) - Aguadilla, PR (BQN)

JetBlue Logo
JetBlue

Jan 9

ORD
14h 43m
BOS
JFK

Jan 9

BQN
JetBlue Logo
JetBlue

Jan 15

BQN
13h 21m
JFK

Jan 15

ORD

as low as

$465

Chicago, US (CHI) - Aguadilla, PR (BQN)

JetBlue Logo
JetBlue

Jan 9

ORD
13h 13m
JFK

Jan 9

BQN
JetBlue Logo
JetBlue

Jan 15

BQN
13h 21m
JFK

Jan 15

ORD

as low as

$497

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Jan 9

ORD
9h 30m
EWR

Jan 9

BQN
United Airlines Logo
United Airlines

Jan 15

BQN
6h 45m
EWR

Jan 15

ORD

as low as

$620

Chicago, US (CHI) - Aguadilla, PR (BQN)

United Airlines Logo
United Airlines

Jan 12

ORD
10h 57m
EWR

Jan 12

BQN
United Airlines Logo
United Airlines

Jan 19

BQN
8h 31m
EWR

Jan 19

ORD

as low as

$620

Chicago, US (CHI) - Aguadilla, PR (BQN)

JetBlue Logo
JetBlue

Jan 12

ORD
14h 8m
BOS
JFK

Jan 12

BQN
JetBlue Logo
JetBlue

Jan 19

BQN
13h 21m
JFK

Jan 19

ORD

as low as

$818

Top Deals on flights from Chicago O Hare Airport to Ponce

Chicago, US (CHI) - Ponce, PR (PSE)

Frontier Airlines Logo
Frontier Airlines

Feb 12

ORD
20h 9m
MCO

Feb 13

PSE
Frontier Airlines Logo
Frontier Airlines

Feb 27

PSE
13h 47m
MCO

Feb 27

ORD

as low as

$603

Chicago, US (CHI) - Ponce, PR (PSE)

JetBlue Logo
JetBlue

Feb 12

ORD
17h 4m
JFK
MCO

Feb 13

PSE
JetBlue Logo
JetBlue

Feb 27

PSE
31h 58m
MCO
JFK

Feb 28

ORD

as low as

$813

Top Deals on flights from Chicago O Hare Airport to Mayagueez

Chicago, US (CHI) - Mayagueez, PR (MAZ)

JetBlue Logo
JetBlue

Jan 18

ORD
25h 29m
JFK
SJU

Jan 19

MAZ
JetBlue Logo
JetBlue

Jan 25

MAZ
29h
SJU
JFK

Jan 26

ORD

as low as

$515

Chicago, US (CHI) - Mayagueez, PR (MAZ)

JetBlue Logo
JetBlue

Jan 18

ORD
22h 27m
JFK
SJU

Jan 19

MAZ
JetBlue Logo
JetBlue

Jan 25

MAZ
29h
SJU
JFK

Jan 26

ORD

as low as

$515

Chicago, US (CHI) - Mayagueez, PR (MAZ)

JetBlue Logo
JetBlue

Jan 18

ORD
23h 57m
BOS
SJU

Jan 19

MAZ
JetBlue Logo
JetBlue

Jan 25

MAZ
29h
SJU
JFK

Jan 26

ORD

as low as

$530

Chicago, US (CHI) - Mayagueez, PR (MAZ)

JetBlue Logo
JetBlue

Jan 18

ORD
22h 27m
JFK
SJU

Jan 19

MAZ
JetBlue Logo
JetBlue

Jan 25

MAZ
27h 7m
SJU
BOS

Jan 26

ORD

as low as

$661

Chicago, US (CHI) - Mayagueez, PR (MAZ)

American Airlines Logo
American Airlines

Jan 18

ORD
16h 27m
SJU

Jan 19

MAZ
United Airlines Logo
United Airlines

Jan 25

MAZ
24h 38m
SJU

Jan 26

ORD

as low as

$2949

Chicago, US (CHI) - Mayagueez, PR (MAZ)

American Airlines Logo
American Airlines

Jan 18

ORD
16h 27m
SJU

Jan 19

MAZ
United Airlines Logo
United Airlines

Jan 25

MAZ
24h 46m
SJU
EWR

Jan 26

ORD

as low as

$2953

Chicago, US (CHI) - Mayagueez, PR (MAZ)

American Airlines Logo
American Airlines

Jan 18

ORD
16h 27m
SJU

Jan 19

MAZ
United Airlines Logo
United Airlines

Jan 25

MAZ
13h 9m
SJU
IAH

Jan 26

ORD

as low as

$2953

Chicago, US (CHI) - Mayagueez, PR (MAZ)

American Airlines Logo
American Airlines

Jan 18

ORD
16h 27m
SJU

Jan 19

MAZ
United Airlines Logo
United Airlines

Jan 25

MAZ
27h 9m
SJU
EWR

Jan 26

ORD

as low as

$2953

Chicago, US (CHI) - Mayagueez, PR (MAZ)

American Airlines Logo
American Airlines

Jan 18

ORD
16h 27m
SJU

Jan 19

MAZ
United Airlines Logo
United Airlines

Jan 25

MAZ
11h 39m
SJU
IAH

Jan 25

ORD

as low as

$2953

Chicago, US (CHI) - Mayagueez, PR (MAZ)

American Airlines Logo
American Airlines

Jan 18

ORD
16h 27m
SJU

Jan 19

MAZ
United Airlines Logo
United Airlines

Jan 25

MAZ
25h 56m
SJU
EWR

Jan 26

ORD

as low as

$2953