$236 Flight Deals from Illinois to San Juan

Top flight deals from leading airlines:

... and +100s more

Incredible Deals

Save up to 50% on select flights with Priceline

Bundle & Save

Save an average of $240 per person when bundling your flight and hotel together with Priceline

Best Price Guarantee

If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference

Help 24/7

We’re always here for you - reach us 24 hours a day, 7 days a week

Priceline Phone Deals

Book with an agent for great rates!

Call now!

1 (888) 775-6158

Top Deals on flights from Chicago to San Juan

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

Spirit Airlines

May 12

11:30am

ORD

5h 46m

Direct

May 12

5:16pm

SJU

Spirit Airlines

May 29

6:09am

SJU

4h 16m

Direct

May 29

10:25am

ORD

as low as

$236

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

Spirit Airlines

May 19

9:55am

ORD

8h 55m

MIA

May 19

6:50pm

SJU

Spirit Airlines

May 23

6:09am

SJU

4h 16m

Direct

May 23

10:25am

ORD

as low as

$253

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

Spirit Airlines

May 17

4:35pm

ORD

8h 19m

MCO

May 18

12:54am

SJU

Spirit Airlines

May 25

6:09am

SJU

4h 16m

Direct

May 25

10:25am

ORD

as low as

$269

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

Spirit Airlines

May 13

11:30am

ORD

5h 46m

Direct

May 13

5:16pm

SJU

Spirit Airlines

May 27

4:05pm

SJU

6h 59m

FLL

May 27

11:04pm

ORD

as low as

$284

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

Frontier Airlines

May 9

4:15pm

ORD

10h 36m

MCO

May 10

2:51am

SJU

Frontier Airlines

May 23

4:31pm

SJU

7h 46m

ATL

May 24

12:17am

ORD

as low as

$317

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

Frontier Airlines

May 15

1:19pm

MDW

8h 12m

MCO

May 15

9:31pm

SJU

Frontier Airlines

May 19

3:56am

SJU

8h 28m

MCO

May 19

12:24pm

MDW

as low as

$317

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

Frontier Airlines

May 16

4:15pm

ORD

10h 36m

MCO

May 17

2:51am

SJU

Frontier Airlines

May 22

4:55pm

SJU

7h 25m

MCO

May 23

12:20am

ORD

as low as

$317

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

Frontier Airlines

May 5

12:58pm

ORD

12h 52m

PHL

May 6

1:50am

SJU

Frontier Airlines

May 9

2:34pm

SJU

8h 58m

MCO

May 9

11:32pm

ORD

as low as

$337

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

JetBlue

May 4

6:20am

ORD

9h 40m

JFK

May 4

4:00pm

SJU

JetBlue

May 14

7:01am

SJU

8h 3m

JFK

May 14

3:04pm

ORD

as low as

$355

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

Delta Air Lines

May 17

6:00am

MDW

7h 16m

ATL

May 17

1:16pm

SJU

Delta Air Lines

May 31

7:30am

SJU

7h 50m

ATL

May 31

3:20pm

MDW

as low as

$383

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

JetBlue

May 8

6:15am

ORD

19h 34m

JFK

May 9

1:49am

SJU

JetBlue

May 12

6:00am

SJU

26h

BOS

May 13

8:00am

ORD

as low as

$436

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

American Airlines

May 26

7:00am

ORD

13h 33m

CLT

May 26

8:33pm

SJU

American Airlines

May 29

2:50pm

SJU

4h 20m

Direct

May 29

7:10pm

ORD

as low as

$452

Top Deals on flights from Peoria to San Juan

Peoria, US (PIA) - San Juan, PR (SJU)

United Airlines

May 27

3:53pm

PIA

7h 1m

ORD

May 27

11:54pm

SJU

United Airlines

Jun 3

7:45am

SJU

8h 33m

ORD

Jun 3

3:18pm

PIA

as low as

$372

Peoria, US (PIA) - San Juan, PR (SJU)

United Airlines

May 27

3:53pm

PIA

7h 1m

ORD

May 27

11:54pm

SJU

United Airlines

Jun 3

7:45am

SJU

9h 57m

ORD

Jun 3

4:42pm

PIA

as low as

$443

Peoria, US (PIA) - San Juan, PR (SJU)

American Airlines

May 27

5:05pm

PIA

26h 28m

ORD

CLT

May 28

8:33pm

SJU

American Airlines

Jun 3

2:50pm

SJU

8h 6m

ORD

Jun 3

9:56pm

PIA

as low as

$446

Peoria, US (PIA) - San Juan, PR (SJU)

American Airlines

May 27

5:05pm

PIA

26h 28m

ORD

CLT

May 28

8:33pm

SJU

American Airlines

Jun 3

1:10pm

SJU

22h 54m

CLT

DFW

Jun 4

11:04am

PIA

as low as

$446

Peoria, US (PIA) - San Juan, PR (SJU)

American Airlines

May 27

5:05pm

PIA

26h 28m

ORD

CLT

May 28

8:33pm

SJU

American Airlines

Jun 3

1:10pm

SJU

22h 35m

CLT

ORD

Jun 4

10:45am

PIA

as low as

$446

Peoria, US (PIA) - San Juan, PR (SJU)

United Airlines

May 27

6:45am

PIA

6h 59m

ORD

May 27

2:44pm

SJU

United Airlines

Jun 3

7:45am

SJU

8h 33m

ORD

Jun 3

3:18pm

PIA

as low as

$447

Peoria, US (PIA) - San Juan, PR (SJU)

United Airlines

May 27

6:45am

PIA

6h 59m

ORD

May 27

2:44pm

SJU

United Airlines

Jun 3

7:45am

SJU

9h 57m

ORD

Jun 3

4:42pm

PIA

as low as

$518

Peoria, US (PIA) - San Juan, PR (SJU)

American Airlines

May 27

3:37pm

PIA

18h 33m

DFW

CLT

May 28

11:10am

SJU

American Airlines

Jun 3

2:50pm

SJU

8h 6m

ORD

Jun 3

9:56pm

PIA

as low as

$583

Peoria, US (PIA) - San Juan, PR (SJU)

American Airlines

May 27

3:37pm

PIA

18h 33m

DFW

CLT

May 28

11:10am

SJU

American Airlines

Jun 3

1:10pm

SJU

22h 35m

CLT

ORD

Jun 4

10:45am

PIA

as low as

$583

Peoria, US (PIA) - San Juan, PR (SJU)

United Airlines

May 27

5:25pm

PIA

26h 13m

ORD

IAH

May 28

8:38pm

SJU

United Airlines

Jun 3

7:45am

SJU

8h 33m

ORD

Jun 3

3:18pm

PIA

as low as

$642

Peoria, US (PIA) - San Juan, PR (SJU)

United Airlines

May 27

6:45am

PIA

16h 12m

ORD

EWR

May 27

11:57pm

SJU

United Airlines

Jun 3

7:45am

SJU

8h 33m

ORD

Jun 3

3:18pm

PIA

as low as

$668

Peoria, US (PIA) - San Juan, PR (SJU)

United Airlines

May 27

5:25pm

PIA

26h 13m

ORD

IAH

May 28

8:38pm

SJU

United Airlines

Jun 3

7:45am

SJU

9h 57m

ORD

Jun 3

4:42pm

PIA

as low as

$715

Top Deals on flights from Moline to San Juan

Moline, US (MLI) - San Juan, PR (SJU)

United Airlines

May 29

3:47pm

MLI

8h 7m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

1:05am

SJU

9h 15m

EWR

ORD

Jun 5

10:20am

MLI

as low as

$417

Moline, US (MLI) - San Juan, PR (SJU)

United Airlines

May 29

5:40pm

MLI

18h 17m

ORD

EWR

May 30

11:57am

SJU

United Airlines

Jun 5

1:05am

SJU

9h 15m

EWR

ORD

Jun 5

10:20am

MLI

as low as

$437

Moline, US (MLI) - San Juan, PR (SJU)

United Airlines

May 29

3:47pm

MLI

8h 7m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

9h 2m

ORD

Jun 5

4:47pm

MLI

as low as

$465

Moline, US (MLI) - San Juan, PR (SJU)

American Airlines

May 29

6:32pm

MLI

26h 1m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

6:15am

SJU

16h 54m

DFW

Jun 5

11:09pm

MLI

as low as

$476

Moline, US (MLI) - San Juan, PR (SJU)

United Airlines

May 29

5:40pm

MLI

18h 17m

ORD

EWR

May 30

11:57am

SJU

United Airlines

Jun 5

7:45am

SJU

9h 2m

ORD

Jun 5

4:47pm

MLI

as low as

$487

Moline, US (MLI) - San Juan, PR (SJU)

American Airlines

May 29

6:32pm

MLI

26h 1m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

3:45pm

SJU

19h 9m

CLT

ORD

Jun 6

10:54am

MLI

as low as

$596

Moline, US (MLI) - San Juan, PR (SJU)

American Airlines

May 29

5:00am

MLI

10h

CLT

May 29

3:00pm

SJU

American Airlines

Jun 5

6:15am

SJU

16h 54m

DFW

Jun 5

11:09pm

MLI

as low as

$633

Moline, US (MLI) - San Juan, PR (SJU)

United Airlines

May 29

3:47pm

MLI

28h 51m

ORD

IAH

May 30

8:38pm

SJU

United Airlines

Jun 5

1:05am

SJU

9h 15m

EWR

ORD

Jun 5

10:20am

MLI

as low as

$658

Moline, US (MLI) - San Juan, PR (SJU)

American Airlines

May 29

6:32pm

MLI

26h 1m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

3:45pm

SJU

24h 3m

CLT

Jun 6

3:48pm

MLI

as low as

$722

Moline, US (MLI) - San Juan, PR (SJU)

American Airlines

May 29

6:32pm

MLI

26h 1m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

3:45pm

SJU

26h 19m

CLT

ORD

Jun 6

6:04pm

MLI

as low as

$874

Moline, US (MLI) - San Juan, PR (SJU)

American Airlines

May 29

5:00am

MLI

10h

CLT

May 29

3:00pm

SJU

American Airlines

Jun 5

3:45pm

SJU

24h 3m

CLT

Jun 6

3:48pm

MLI

as low as

$886

Top Deals on flights from Bloomington to San Juan

Bloomington, US (BMI) - San Juan, PR (SJU)

American Airlines

May 29

4:24pm

BMI

27h 9m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

3:00pm

SJU

9h 42m

ORD

Jun 5

11:42pm

BMI

as low as

$506

Bloomington, US (BMI) - San Juan, PR (SJU)

American Airlines

May 29

4:24pm

BMI

27h 9m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

6:15am

SJU

17h 37m

DFW

Jun 5

10:52pm

BMI

as low as

$574

Bloomington, US (BMI) - San Juan, PR (SJU)

American Airlines

May 29

4:24pm

BMI

27h 9m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

3:45pm

SJU

8h 57m

CLT

ORD

Jun 5

11:42pm

BMI

as low as

$656

Bloomington, US (BMI) - San Juan, PR (SJU)

American Airlines

May 29

4:24pm

BMI

27h 9m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

6:15am

SJU

10h 4m

DFW

Jun 5

3:19pm

BMI

as low as

$656

Bloomington, US (BMI) - San Juan, PR (SJU)

American Airlines

May 29

6:00am

BMI

13h 33m

ORD

CLT

May 29

8:33pm

SJU

American Airlines

Jun 5

6:15am

SJU

17h 37m

DFW

Jun 5

10:52pm

BMI

as low as

$771

Top Deals on flights from Champaign to San Juan

Champaign, US (CMI) - San Juan, PR (SJU)

American Airlines

May 29

4:30pm

CMI

27h 3m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

6:15am

SJU

16h 28m

DFW

Jun 5

9:43pm

CMI

as low as

$406

Champaign, US (CMI) - San Juan, PR (SJU)

American Airlines

May 29

6:01am

CMI

13h 32m

ORD

CLT

May 29

8:33pm

SJU

American Airlines

Jun 5

6:15am

SJU

16h 28m

DFW

Jun 5

9:43pm

CMI

as low as

$548

Top Deals on flights from Springfield to San Juan

Springfield, US (SPI) - San Juan, PR (SJU)

American Airlines

May 29

6:25pm

SPI

25h 8m

ORD

CLT

May 30

8:33pm

SJU

American Airlines

Jun 5

3:45pm

SJU

21h 55m

CLT

ORD

Jun 6

12:40pm

SPI

as low as

$629

Top Deals on flights from Decatur to San Juan

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 9m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

11h 8m

ORD

Jun 5

5:53pm

DEC

as low as

$589

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 9m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

17h 52m

ORD

Jun 6

8:48am

DEC

as low as

$589

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 9m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

1:05am

SJU

17h 48m

EWR

ORD

Jun 5

5:53pm

DEC

as low as

$593

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

6:55pm

DEC

27h 59m

ORD

May 30

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

11h 8m

ORD

Jun 5

5:53pm

DEC

as low as

$599

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 9m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

26h 57m

ORD

Jun 6

5:53pm

DEC

as low as

$599

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 9m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

26h 3m

ORD

Jun 6

8:48am

DEC

as low as

$599

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 9m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

2:05am

SJU

16h 48m

IAH

ORD

Jun 5

5:53pm

DEC

as low as

$613

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 12m

ORD

EWR

May 29

11:57pm

SJU

United Airlines

Jun 5

3:56pm

SJU

17h 52m

ORD

Jun 6

8:48am

DEC

as low as

$614

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 12m

ORD

EWR

May 29

11:57pm

SJU

United Airlines

Jun 5

1:05am

SJU

17h 48m

EWR

ORD

Jun 5

5:53pm

DEC

as low as

$614

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

6:55pm

DEC

18h 49m

ORD

May 30

2:44pm

SJU

United Airlines

Jun 5

7:45am

SJU

11h 8m

ORD

Jun 5

5:53pm

DEC

as low as

$619

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 12m

ORD

EWR

May 29

11:57pm

SJU

United Airlines

Jun 5

2:05am

SJU

16h 48m

IAH

ORD

Jun 5

5:53pm

DEC

as low as

$634

Decatur, US (DEC) - San Juan, PR (SJU)

United Airlines

May 29

9:45am

DEC

13h 12m

ORD

EWR

May 29

11:57pm

SJU

United Airlines

Jun 5

7:00am

SJU

11h 53m

IAH

ORD

Jun 5

5:53pm

DEC

as low as

$661

Top Deals on flights from Marion to San Juan

Marion, US (MWA) - San Juan, PR (SJU)

CONTOUR AIRLINES

May 29

2:00pm

MWA

8h 54m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

12h 5m

ORD

Jun 5

6:50pm

MWA

as low as

$577

Marion, US (MWA) - San Juan, PR (SJU)

CONTOUR AIRLINES

May 29

7:15am

MWA

15h 39m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

12h 5m

ORD

Jun 5

6:50pm

MWA

as low as

$577

Marion, US (MWA) - San Juan, PR (SJU)

CONTOUR AIRLINES

May 29

7:15am

MWA

15h 39m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

27h 54m

ORD

Jun 6

6:50pm

MWA

as low as

$597

Marion, US (MWA) - San Juan, PR (SJU)

CONTOUR AIRLINES

May 29

2:00pm

MWA

8h 54m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

27h 54m

ORD

Jun 6

6:50pm

MWA

as low as

$597

Marion, US (MWA) - San Juan, PR (SJU)

CONTOUR AIRLINES

May 29

2:00pm

MWA

23h 44m

ORD

May 30

2:44pm

SJU

United Airlines

Jun 5

7:45am

SJU

12h 5m

ORD

Jun 5

6:50pm

MWA

as low as

$606

Marion, US (MWA) - San Juan, PR (SJU)

CONTOUR AIRLINES

May 29

2:00pm

MWA

23h 44m

ORD

May 30

2:44pm

SJU

United Airlines

Jun 5

3:56pm

SJU

27h 54m

ORD

Jun 6

6:50pm

MWA

as low as

$626

Top Deals on flights from Quincy to San Juan

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

2:35pm

UIN

8h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

12h 20m

ORD

Jun 5

7:05pm

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

2:35pm

UIN

8h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

19h 14m

ORD

Jun 6

10:10am

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

10:35am

UIN

12h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

8h 20m

ORD

Jun 5

3:05pm

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

5:40am

UIN

17h 14m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

8h 20m

ORD

Jun 5

3:05pm

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

2:35pm

UIN

8h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

8h 20m

ORD

Jun 5

3:05pm

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

5:40am

UIN

17h 14m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

19h 14m

ORD

Jun 6

10:10am

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

10:35am

UIN

12h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

19h 14m

ORD

Jun 6

10:10am

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

10:35am

UIN

12h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

12h 20m

ORD

Jun 5

7:05pm

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

5:40am

UIN

17h 14m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

7:45am

SJU

12h 20m

ORD

Jun 5

7:05pm

UIN

as low as

$549

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

2:35pm

UIN

8h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

28h 9m

ORD

Jun 6

7:05pm

UIN

as low as

$553

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

10:35am

UIN

12h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

24h 9m

ORD

Jun 6

3:05pm

UIN

as low as

$553

Quincy, US (UIN) - San Juan, PR (SJU)

Southern Airways Express

May 29

2:35pm

UIN

8h 19m

ORD

May 29

11:54pm

SJU

United Airlines

Jun 5

3:56pm

SJU

24h 9m

ORD

Jun 6

3:05pm

UIN

as low as

$553

Flights to San Juan

Priceline Phone Deals

Book with an agent for great rates!
Call now!

1 (888) 775-6158

Flight Deals from Illinois to San Juan from $236

Top Deals on flights from Chicago to San Juan

Top Deals on flights from Peoria to San Juan

Top Deals on flights from Moline to San Juan

Top Deals on flights from Bloomington to San Juan

Top Deals on flights from Champaign to San Juan

Top Deals on flights from Springfield to San Juan

Top Deals on flights from Decatur to San Juan

Top Deals on flights from Marion to San Juan

Top Deals on flights from Quincy to San Juan

Flights to San Juan

Return flights

Browse origins

Browse destinations

Cabin classes

Top Flight Routes Destinations

Priceline Phone Deals