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

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

Spirit Airlines

Jan 15

11:52am

SJU

6h 24m

MIA

Jan 15

6:16pm

ORD

Spirit Airlines

Jan 21

12:17pm

ORD

6h 32m

Direct

Jan 21

6:49pm

SJU

as low as

^$185

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

Spirit Airlines

Jan 15

11:52am

SJU

6h 24m

MIA

Jan 15

6:16pm

ORD

Spirit Airlines

Jan 21

5:15am

ORD

10h 20m

FLL

Jan 21

3:35pm

SJU

as low as

^$192

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

Spirit Airlines

Jan 23

1:22pm

SJU

3h 15m

Direct

Jan 23

4:37pm

ORD

Spirit Airlines

Jan 26

12:17pm

ORD

6h 32m

Direct

Jan 26

6:49pm

SJU

as low as

^$197

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

JetBlue

Jan 22

11:06am

SJU

8h 30m

JFK

Jan 22

7:36pm

ORD

JetBlue

Jan 27

7:45am

ORD

10h 17m

BOS

Jan 27

6:02pm

SJU

as low as

^$210

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

Delta Air Lines

Jan 22

7:30am

SJU

6h 10m

ATL

Jan 22

1:40pm

ORD

Delta Air Lines

Jan 27

7:00am

ORD

9h 50m

JFK

Jan 27

4:50pm

SJU

as low as

^$225

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

Frontier Airlines

Jan 8

6:15am

SJU

13h 2m

MCO

Jan 8

7:17pm

ORD

Frontier Airlines

Jan 15

7:45am

ORD

15h 55m

RDU

Jan 15

11:40pm

SJU

as low as

^$261

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

American Airlines

Jan 22

6:00am

SJU

3h 35m

Direct

Jan 22

9:35am

ORD

American Airlines

Jan 27

3:00pm

ORD

6h 39m

Direct

Jan 27

9:39pm

SJU

as low as

^$276

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

American Airlines

Jan 22

5:55pm

SJU

5h 32m

CLT

Jan 22

11:27pm

ORD

American Airlines

Jan 27

3:00pm

ORD

6h 39m

Direct

Jan 27

9:39pm

SJU

as low as

^$280

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

United Airlines

Jan 28

8:35am

SJU

3h 22m

Direct

Jan 28

11:57am

ORD

United Airlines

Feb 1

8:55am

ORD

6h 45m

Direct

Feb 1

3:40pm

SJU

as low as

^$326

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

United Airlines

Jan 14

8:10am

SJU

6h 15m

IAD

Jan 14

2:25pm

ORD

United Airlines

Jan 20

2:20pm

ORD

6h 40m

Direct

Jan 20

9:00pm

SJU

as low as

^$405

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

United Airlines

Feb 6

4:52pm

SJU

3h 28m

Direct

Feb 6

8:20pm

ORD

United Airlines

Feb 8

8:54am

ORD

12h 32m

IAH

Feb 8

9:26pm

SJU

as low as

^$405

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

United Airlines

Jan 15

2:05am

SJU

8h 48m

EWR

Jan 15

10:53am

ORD

United Airlines

Jan 19

2:20pm

ORD

6h 40m

Direct

Jan 19

9:00pm

SJU

as low as

^$405

Top Deals on flights from Aguadilla to Chicago O Hare Airport

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

Frontier Airlines

Jan 10

11:52am

BQN

7h 25m

MCO

Jan 10

7:17pm

ORD

Frontier Airlines

Jan 24

9:25am

ORD

26h 36m

MCO

Jan 25

12:01pm

BQN

as low as

^$218

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

Frontier Airlines

Jan 18

3:48am

BQN

16h 3m

MCO

Jan 18

7:51pm

ORD

Frontier Airlines

Jan 25

12:21pm

ORD

23h 55m

MCO

Jan 26

12:16pm

BQN

as low as

^$268

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

United Airlines

Jan 14

1:09am

BQN

6h 45m

EWR

Jan 14

7:54am

ORD

United Airlines

Jan 20

9:02am

ORD

14h 55m

EWR

Jan 20

11:57pm

BQN

as low as

^$481

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

United Airlines

Jan 18

1:09am

BQN

6h 45m

EWR

Jan 18

7:54am

ORD

United Airlines

Jan 25

12:00pm

ORD

11h 57m

EWR

Jan 25

11:57pm

BQN

as low as

^$485

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

United Airlines

Jan 15

1:09am

BQN

6h 45m

EWR

Jan 15

7:54am

ORD

United Airlines

Jan 16

7:10am

ORD

16h 47m

EWR

Jan 16

11:57pm

BQN

as low as

^$540

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

United Airlines

Jan 13

1:09am

BQN

6h 45m

EWR

Jan 13

7:54am

ORD

United Airlines

Jan 16

7:10am

ORD

16h 47m

EWR

Jan 16

11:57pm

BQN

as low as

^$540

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

United Airlines

Jan 18

1:09am

BQN

6h 45m

EWR

Jan 18

7:54am

ORD

United Airlines

Jan 25

2:27pm

ORD

9h 30m

EWR

Jan 25

11:57pm

BQN

as low as

^$575

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

United Airlines

Jan 12

1:09am

BQN

6h 45m

EWR

Jan 12

7:54am

ORD

United Airlines

Jan 20

9:02am

ORD

14h 55m

EWR

Jan 20

11:57pm

BQN

as low as

^$616

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

JetBlue

Jan 18

6:15am

BQN

13h 21m

JFK

Jan 18

7:36pm

ORD

JetBlue

Jan 25

9:15am

ORD

11h 44m

JFK

Jan 25

8:59pm

BQN

as low as

^$667

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

JetBlue

Jan 18

6:15am

BQN

13h 21m

JFK

Jan 18

7:36pm

ORD

JetBlue

Jan 25

9:15am

ORD

29h 39m

JFK

FLL

Jan 26

2:54pm

BQN

as low as

^$689

Top Deals on flights from Ponce to Chicago O Hare Airport

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

JetBlue

Jan 18

4:10pm

PSE

27h 33m

MCO

BOS

Jan 19

5:43pm

ORD

JetBlue

Jan 25

7:45am

ORD

29h 28m

BOS

MCO

Jan 26

3:13pm

PSE

as low as

^$591

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

JetBlue

Jan 18

4:10pm

PSE

27h 33m

MCO

BOS

Jan 19

5:43pm

ORD

JetBlue

Jan 25

9:15am

ORD

27h 58m

JFK

MCO

Jan 26

3:13pm

PSE

as low as

^$621

Top Deals on flights from Mayagueez to Chicago O Hare Airport

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

JetBlue

Jan 9

4:36pm

MAZ

27h 7m

SJU

BOS

Jan 10

5:43pm

ORD

JetBlue

Jan 16

7:45am

ORD

23h 57m

BOS

SJU

Jan 17

9:42am

MAZ

as low as

^$458

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

JetBlue

Jan 9

4:36pm

MAZ

27h 7m

SJU

BOS

Jan 10

5:43pm

ORD

JetBlue

Jan 16

7:45am

ORD

26h 59m

BOS

SJU

Jan 17

12:44pm

MAZ

as low as

^$458

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

JetBlue

Jan 9

4:36pm

MAZ

27h 7m

SJU

BOS

Jan 10

5:43pm

ORD

JetBlue

Jan 16

9:15am

ORD

22h 27m

JFK

SJU

Jan 17

9:42am

MAZ

as low as

^$473

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

JetBlue

Jan 9

4:36pm

MAZ

29h

SJU

JFK

Jan 10

7:36pm

ORD

JetBlue

Jan 16

7:45am

ORD

23h 57m

BOS

SJU

Jan 17

9:42am

MAZ

as low as

^$562

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

JetBlue

Jan 9

4:36pm

MAZ

29h

SJU

JFK

Jan 10

7:36pm

ORD

JetBlue

Jan 16

7:45am

ORD

26h 59m

BOS

SJU

Jan 17

12:44pm

MAZ

as low as

^$562

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

JetBlue

Jan 9

4:36pm

MAZ

29h

SJU

JFK

Jan 10

7:36pm

ORD

JetBlue

Jan 16

9:15am

ORD

22h 27m

JFK

SJU

Jan 17

9:42am

MAZ

as low as

^$577

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Flight Deals from Puerto Rico to Chicago O Hare Airport from $185

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

Top Deals on flights from Aguadilla to Chicago O Hare Airport

Top Deals on flights from Ponce to Chicago O Hare Airport

Top Deals on flights from Mayagueez to Chicago O Hare Airport

Flights to Chicago