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Flight Deals from Puerto Rico to Chicago from $221

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Top Deals on flights from San Juan to Chicago

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

Spirit Airlines Logo
Spirit Airlines

May 16

SJU
4h 16m
Direct

May 16

ORD
Spirit Airlines Logo
Spirit Airlines

May 19

ORD
5h 46m
Direct

May 19

SJU

as low as

$221

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

Spirit Airlines Logo
Spirit Airlines

May 16

SJU
4h 16m
Direct

May 16

ORD
Spirit Airlines Logo
Spirit Airlines

May 19

ORD
8h 55m
MIA

May 19

SJU

as low as

$269

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

Frontier Airlines Logo
Frontier Airlines

May 16

SJU
6h 53m
MCO

May 16

ORD
Frontier Airlines Logo
Frontier Airlines

May 19

ORD
10h 36m
MCO

May 20

SJU

as low as

$307

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

Frontier Airlines Logo
Frontier Airlines

May 9

SJU
8h 58m
MCO

May 9

ORD
Frontier Airlines Logo
Frontier Airlines

May 23

ORD
10h 5m
ATL

May 23

SJU

as low as

$317

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

United Airlines Logo
United Airlines

May 8

SJU
9h 20m
IAH

May 9

ORD
United Airlines Logo
United Airlines

May 9

ORD
5h 51m
Direct

May 9

SJU

as low as

$380

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

JetBlue Logo
JetBlue

May 10

SJU
9h 56m
JFK

May 10

ORD
JetBlue Logo
JetBlue

May 24

ORD
9h 46m
JFK

May 25

SJU

as low as

$410

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

Delta Air Lines Logo
Delta Air Lines

May 17

SJU
10h 49m
ATL

May 17

ORD
Delta Air Lines Logo
Delta Air Lines

May 24

ORD
9h 17m
ATL

May 24

SJU

as low as

$420

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

Spirit Airlines Logo
Spirit Airlines

May 6

SJU
7h 41m
DFW

May 6

ORD
Spirit Airlines Logo
Spirit Airlines

May 13

ORD
5h 46m
Direct

May 13

SJU

as low as

$420

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

American Airlines Logo
American Airlines

May 15

SJU
9h 55m
MIA

May 15

ORD
American Airlines Logo
American Airlines

May 19

ORD
14h 8m
PHL

May 19

SJU

as low as

$460

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

United Airlines Logo
United Airlines

May 17

SJU
7h 9m
IAD

May 17

ORD
United Airlines Logo
United Airlines

May 24

ORD
5h 51m
Direct

May 24

SJU

as low as

$468

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

Delta Air Lines Logo
Delta Air Lines

May 10

SJU
10h 29m
JFK

May 10

ORD
Delta Air Lines Logo
Delta Air Lines

May 24

ORD
8h 41m
MSP

May 24

SJU

as low as

$475

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

United Airlines Logo
United Airlines

May 11

SJU
8h 40m
EWR

May 11

ORD
United Airlines Logo
United Airlines

May 18

ORD
5h 51m
Direct

May 18

SJU

as low as

$476

Top Deals on flights from Aguadilla to Chicago

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

Frontier Airlines Logo
Frontier Airlines

May 30

BQN
21h 21m
MCO

May 31

ORD
Frontier Airlines Logo
Frontier Airlines

Jun 6

ORD
8h 51m
MCO

Jun 7

BQN

as low as

$337

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

JetBlue Logo
JetBlue

Jun 10

BQN
9h 6m
JFK

Jun 10

ORD
JetBlue Logo
JetBlue

Jun 13

ORD
15h 17m
JFK
FLL

Jun 13

BQN

as low as

$456

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

JetBlue Logo
JetBlue

Jun 10

BQN
13h 31m
JFK
BOS

Jun 10

ORD
JetBlue Logo
JetBlue

Jun 13

ORD
15h 17m
JFK
FLL

Jun 13

BQN

as low as

$490

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

JetBlue Logo
JetBlue

Jun 9

BQN
12h 8m
JFK

Jun 9

ORD
JetBlue Logo
JetBlue

Jun 13

ORD
15h 17m
JFK
FLL

Jun 13

BQN

as low as

$498

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

JetBlue Logo
JetBlue

May 30

BQN
12h 8m
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
10h 55m
JFK

Jun 7

BQN

as low as

$520

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

JetBlue Logo
JetBlue

May 30

BQN
32h 59m
MCO
JFK

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
10h 55m
JFK

Jun 7

BQN

as low as

$530

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

JetBlue Logo
JetBlue

Jun 10

BQN
9h 6m
JFK

Jun 10

ORD
JetBlue Logo
JetBlue

Jun 13

ORD
15h 51m
JFK

Jun 14

BQN

as low as

$593

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

JetBlue Logo
JetBlue

Jun 9

BQN
12h 8m
JFK

Jun 9

ORD
JetBlue Logo
JetBlue

Jun 13

ORD
15h 51m
JFK

Jun 14

BQN

as low as

$645

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

JetBlue Logo
JetBlue

Jun 9

BQN
13h 31m
JFK
BOS

Jun 9

ORD
JetBlue Logo
JetBlue

Jun 13

ORD
15h 17m
JFK
FLL

Jun 13

BQN

as low as

$675

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

JetBlue Logo
JetBlue

May 30

BQN
32h 59m
MCO
JFK

May 31

ORD
JetBlue Logo
JetBlue

Jun 6

ORD
33h 47m
JFK
MCO

Jun 8

BQN

as low as

$730

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

United Airlines Logo
United Airlines

May 30

BQN
7h 23m
EWR

May 30

ORD
United Airlines Logo
United Airlines

Jun 6

ORD
25h 24m
EWR

Jun 7

BQN

as low as

$740

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

United Airlines Logo
United Airlines

May 30

BQN
7h 23m
EWR

May 30

ORD
United Airlines Logo
United Airlines

Jun 6

ORD
26h 4m
BNA
EWR

Jun 7

BQN

as low as

$783

Top Deals on flights from Ponce to Chicago

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

Frontier Airlines Logo
Frontier Airlines

May 29

PSE
15h 55m
MCO

May 30

ORD
Frontier Airlines Logo
Frontier Airlines

Jun 5

ORD
14h 17m
MCO

Jun 6

PSE

as low as

$417

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

Frontier Airlines Logo
Frontier Airlines

May 29

PSE
11h 52m
MCO

May 29

MDW
Frontier Airlines Logo
Frontier Airlines

Jun 5

ORD
14h 17m
MCO

Jun 6

PSE

as low as

$417

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

Frontier Airlines Logo
Frontier Airlines

May 29

PSE
15h 55m
MCO

May 30

ORD
Frontier Airlines Logo
Frontier Airlines

Jun 5

MDW
10h 13m
MCO

Jun 6

PSE

as low as

$417

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

Frontier Airlines Logo
Frontier Airlines

May 29

PSE
11h 52m
MCO

May 29

MDW
Frontier Airlines Logo
Frontier Airlines

Jun 5

MDW
10h 13m
MCO

Jun 6

PSE

as low as

$417

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

JetBlue Logo
JetBlue

May 29

PSE
41h 45m
MCO
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
14h 14m
BOS
MCO

Jun 5

PSE

as low as

$691

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

JetBlue Logo
JetBlue

May 29

PSE
41h 45m
MCO
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
16h 44m
JFK
MCO

Jun 5

PSE

as low as

$719

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

JetBlue Logo
JetBlue

May 29

PSE
41h 45m
MCO
JFK

May 30

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
38h 14m
BOS
MCO

Jun 6

PSE

as low as

$795

Top Deals on flights from Culebra to Chicago

Culebra, PR (CPX) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

CPX
7h 15m
SJU

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
21h 48m
SJU

Jun 6

CPX

as low as

$681

Culebra, PR (CPX) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

CPX
12h 21m
SJU

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
21h 48m
SJU

Jun 6

CPX

as low as

$681

Culebra, PR (CPX) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

CPX
7h 15m
SJU

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
14h 50m
SJU

Jun 6

CPX

as low as

$681

Culebra, PR (CPX) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

CPX
12h 21m
SJU

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
12h 56m
SJU

Jun 6

CPX

as low as

$681

Culebra, PR (CPX) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

CPX
7h 15m
SJU

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
12h 56m
SJU

Jun 6

CPX

as low as

$681

Culebra, PR (CPX) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

CPX
12h 21m
SJU

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
14h 50m
SJU

Jun 6

CPX

as low as

$681

Culebra, PR (CPX) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

CPX
14h
SJU
JFK

May 29

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
26h 26m
BOS
SJU

Jun 6

CPX

as low as

$785

Culebra, PR (CPX) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

CPX
14h
SJU
JFK

May 29

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
24h 8m
BOS
SJU

Jun 6

CPX

as low as

$785

Culebra, PR (CPX) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

CPX
14h
SJU
JFK

May 29

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
19h 8m
JFK
SJU

Jun 6

CPX

as low as

$811

Culebra, PR (CPX) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

CPX
14h
SJU
JFK

May 29

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
14h 56m
JFK
SJU

Jun 6

CPX

as low as

$811

Culebra, PR (CPX) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 29

CPX
14h
SJU
JFK

May 29

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
18h 13m
BOS
SJU

Jun 6

CPX

as low as

$818

Culebra, PR (CPX) - Chicago, US (CHI)

Cape Air Logo
Cape Air

May 29

CPX
7h 15m
SJU

May 29

ORD
United Airlines Logo
United Airlines

Jun 5

ORD
18h 20m
IAD
SJU

Jun 6

CPX

as low as

$1263

Top Deals on flights from Mayagueez to Chicago

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

JetBlue Logo
JetBlue

May 27

MAZ
23h 51m
SJU
JFK

May 28

ORD
JetBlue Logo
JetBlue

Jun 3

ORD
19h 56m
BOS
SJU

Jun 4

MAZ

as low as

$581

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