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Top Deals on flights from San Juan to Chicago

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

Spirit Airlines

Oct 24

7:43pm

SJU

5h 14m

Direct

Oct 24

11:57pm

ORD

Spirit Airlines

Oct 31

9:06pm

ORD

4h 45m

Direct

Nov 1

2:51am

SJU

as low as

^$167

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

Spirit Airlines

Oct 24

7:43pm

SJU

5h 14m

Direct

Oct 24

11:57pm

ORD

Spirit Airlines

Oct 31

7:51pm

ORD

28h 3m

MCO

Nov 2

12:54am

SJU

as low as

^$220

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

Spirit Airlines

Oct 24

7:43pm

SJU

5h 14m

Direct

Oct 24

11:57pm

ORD

Spirit Airlines

Oct 31

6:00am

ORD

7h 12m

MCO

Oct 31

2:12pm

SJU

as low as

^$235

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

Frontier Airlines

Oct 24

12:02pm

SJU

12h 1m

PHL

Oct 24

11:03pm

MDW

Frontier Airlines

Oct 31

9:32am

MDW

10h 52m

MCO

Oct 31

9:24pm

SJU

as low as

^$285

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

Frontier Airlines

Oct 24

3:05pm

SJU

9h 41m

ATL

Oct 24

11:46pm

MDW

Frontier Airlines

Oct 31

9:32am

MDW

15h 22m

MCO

Nov 1

1:54am

SJU

as low as

^$285

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

Frontier Airlines

Oct 24

9:19pm

SJU

14h 2m

MCO

Oct 25

10:21am

MDW

Frontier Airlines

Oct 31

6:20am

MDW

6h 59m

ATL

Oct 31

2:19pm

SJU

as low as

^$285

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

Frontier Airlines

Oct 24

12:02pm

SJU

12h 1m

PHL

Oct 24

11:03pm

MDW

Frontier Airlines

Oct 31

6:20am

MDW

6h 59m

ATL

Oct 31

2:19pm

SJU

as low as

^$285

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

JetBlue

Oct 24

9:25pm

SJU

22h

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

6:55pm

ORD

27h 48m

BOS

Nov 1

11:43pm

SJU

as low as

^$342

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

JetBlue

Oct 24

2:25pm

SJU

29h

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

6:55pm

ORD

27h 48m

BOS

Nov 1

11:43pm

SJU

as low as

^$342

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

American Airlines

Oct 24

3:00pm

SJU

5h 20m

Direct

Oct 24

7:20pm

ORD

American Airlines

Oct 31

10:00am

ORD

4h 40m

Direct

Oct 31

3:40pm

SJU

as low as

^$430

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

American Airlines

Oct 24

7:00pm

SJU

14h 53m

MIA

Oct 25

8:53am

ORD

American Airlines

Oct 31

10:00am

ORD

4h 40m

Direct

Oct 31

3:40pm

SJU

as low as

^$459

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

American Airlines

Oct 24

3:00pm

SJU

5h 20m

Direct

Oct 24

7:20pm

ORD

American Airlines

Oct 31

7:05pm

ORD

16h 34m

MIA

Nov 1

12:39pm

SJU

as low as

^$459

Top Deals on flights from Aguadilla to Chicago

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

Frontier Airlines

Oct 24

2:59am

BQN

14h 21m

MCO

Oct 24

4:20pm

MDW

Frontier Airlines

Oct 31

9:32am

MDW

15h 45m

MCO

Nov 1

2:17am

BQN

as low as

^$345

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

Frontier Airlines

Oct 24

2:59am

BQN

14h 21m

MCO

Oct 24

4:20pm

MDW

Frontier Airlines

Oct 31

5:25am

ORD

19h 52m

MCO

Nov 1

2:17am

BQN

as low as

^$354

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

United Airlines

Oct 24

12:15am

BQN

9h 23m

EWR

Oct 24

8:38am

ORD

United Airlines

Oct 31

2:22pm

ORD

7h 35m

EWR

Oct 31

10:57pm

BQN

as low as

^$472

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

United Airlines

Oct 24

12:15am

BQN

8h 23m

EWR

Oct 24

7:38am

ORD

United Airlines

Oct 31

2:22pm

ORD

7h 35m

EWR

Oct 31

10:57pm

BQN

as low as

^$472

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

United Airlines

Oct 24

12:15am

BQN

10h 24m

EWR

Oct 24

9:39am

ORD

United Airlines

Oct 31

2:22pm

ORD

7h 35m

EWR

Oct 31

10:57pm

BQN

as low as

^$472

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

JetBlue

Oct 24

5:01am

BQN

16h 49m

JFK

Oct 24

8:50pm

ORD

JetBlue

Oct 31

6:45am

ORD

13h 57m

JFK

Oct 31

9:42pm

BQN

as low as

^$483

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

United Airlines

Oct 24

12:15am

BQN

24h 15m

EWR

Oct 24

11:30pm

ORD

United Airlines

Oct 31

2:22pm

ORD

7h 35m

EWR

Oct 31

10:57pm

BQN

as low as

^$517

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

United Airlines

Oct 24

12:15am

BQN

8h 23m

EWR

Oct 24

7:38am

ORD

United Airlines

Oct 31

1:33pm

ORD

8h 24m

EWR

Oct 31

10:57pm

BQN

as low as

^$535

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

United Airlines

Oct 24

12:15am

BQN

9h 23m

EWR

Oct 24

8:38am

ORD

United Airlines

Oct 31

1:33pm

ORD

8h 24m

EWR

Oct 31

10:57pm

BQN

as low as

^$535

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

JetBlue

Oct 24

5:01am

BQN

16h 49m

JFK

Oct 24

8:50pm

ORD

JetBlue

Oct 31

6:45am

ORD

16h 55m

JFK

MCO

Nov 1

12:40am

BQN

as low as

^$539

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

JetBlue

Oct 24

5:01am

BQN

8h 22m

JFK

Oct 24

12:23pm

ORD

JetBlue

Oct 31

6:45am

ORD

13h 57m

JFK

Oct 31

9:42pm

BQN

as low as

^$585

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

JetBlue

Oct 24

5:01am

BQN

16h 49m

JFK

Oct 24

8:50pm

ORD

JetBlue

Oct 31

6:45am

ORD

33h 33m

JFK

MCO

Nov 1

5:18pm

BQN

as low as

^$874

Top Deals on flights from Ponce to Chicago

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

Frontier Airlines

Oct 24

10:13am

PSE

7h 7m

MCO

Oct 24

4:20pm

MDW

Frontier Airlines

Oct 31

5:25am

ORD

28h 55m

MCO

Nov 1

11:20am

PSE

as low as

^$412

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

Frontier Airlines

Oct 24

10:13am

PSE

7h 7m

MCO

Oct 24

4:20pm

MDW

Frontier Airlines

Oct 31

9:32am

MDW

24h 48m

MCO

Nov 1

11:20am

PSE

as low as

^$412

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

JetBlue

Oct 24

5:20am

PSE

38h 5m

MCO

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

6:45am

ORD

15h 14m

JFK

MCO

Oct 31

10:59pm

PSE

as low as

^$563

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

JetBlue

Oct 24

5:20am

PSE

38h 5m

MCO

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

6:55pm

ORD

28h 2m

BOS

MCO

Nov 1

11:57pm

PSE

as low as

^$629

Top Deals on flights from Culebra to Chicago

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

JetBlue

Oct 24

12:31pm

CPX

30h 54m

SJU

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

11:20am

ORD

21h 50m

BOS

SJU

Nov 1

10:10am

CPX

as low as

^$736

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

JetBlue

Oct 24

12:31pm

CPX

30h 54m

SJU

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

6:55pm

ORD

18h 48m

BOS

SJU

Nov 1

2:43pm

CPX

as low as

^$740

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

JetBlue

Oct 24

12:31pm

CPX

30h 54m

SJU

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

6:45am

ORD

30h 58m

JFK

SJU

Nov 1

2:43pm

CPX

as low as

^$745

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

JetBlue

Oct 24

12:31pm

CPX

30h 54m

SJU

JFK

Oct 25

6:25pm

ORD

JetBlue

Oct 31

6:45am

ORD

26h 25m

JFK

SJU

Nov 1

10:10am

CPX

as low as

^$745

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

JetBlue

Oct 24

12:31pm

CPX

21h 51m

SJU

BOS

Oct 25

9:22am

ORD

JetBlue

Oct 31

11:20am

ORD

21h 50m

BOS

SJU

Nov 1

10:10am

CPX

as low as

^$753

Top Deals on flights from Mayagueez to Chicago

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

2:20pm

ORD

18h 22m

SJU

Nov 1

9:42am

MAZ

as low as

^$1055

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

United Airlines

Oct 24

1:23pm

MAZ

10h 52m

SJU

IAD

Oct 24

11:15pm

ORD

United Airlines

Oct 31

2:20pm

ORD

18h 22m

SJU

Nov 1

9:42am

MAZ

as low as

^$1059

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

8:55am

ORD

8h 48m

SJU

Oct 31

6:43pm

MAZ

as low as

^$1075

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

United Airlines

Oct 24

1:23pm

MAZ

10h 52m

SJU

IAD

Oct 24

11:15pm

ORD

United Airlines

Oct 31

9:08pm

ORD

18h 3m

EWR

SJU

Nov 1

4:11pm

MAZ

as low as

^$1652

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

9:08pm

ORD

18h 3m

EWR

SJU

Nov 1

4:11pm

MAZ

as low as

^$1652

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

7:47pm

ORD

19h 24m

EWR

SJU

Nov 1

4:11pm

MAZ

as low as

^$1652

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

United Airlines

Oct 24

1:23pm

MAZ

10h 52m

SJU

IAD

Oct 24

11:15pm

ORD

United Airlines

Oct 31

7:47pm

ORD

19h 24m

EWR

SJU

Nov 1

4:11pm

MAZ

as low as

^$1652

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

6:20pm

ORD

20h 51m

IAD

SJU

Nov 1

4:11pm

MAZ

as low as

^$1694

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

9:10pm

ORD

18h 1m

IAD

SJU

Nov 1

4:11pm

MAZ

as low as

^$1694

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

2:20pm

ORD

24h 51m

SJU

Nov 1

4:11pm

MAZ

as low as

^$1702

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

United Airlines

Oct 24

1:23pm

MAZ

10h 52m

SJU

IAD

Oct 24

11:15pm

ORD

United Airlines

Oct 31

10:35am

ORD

28h 36m

IAH

SJU

Nov 1

4:11pm

MAZ

as low as

^$1707

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

United Airlines

Oct 24

1:23pm

MAZ

7h 40m

SJU

Oct 24

8:03pm

ORD

United Airlines

Oct 31

8:50am

ORD

30h 21m

IAH

SJU

Nov 1

4:11pm

MAZ

as low as

^$1707

Flights to Chicago

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Flight Deals from Puerto Rico to Chicago from $167

Top Deals on flights from San Juan to Chicago

Top Deals on flights from Aguadilla to Chicago

Top Deals on flights from Ponce to Chicago

Top Deals on flights from Culebra to Chicago

Top Deals on flights from Mayagueez to Chicago

Flights to Chicago