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Flight Deals from San Juan to Illinois 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 San Juan to Peoria

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

United Airlines Logo
United Airlines

May 30

SJU
16h 41m
EWR
ORD

May 31

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$626

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

United Airlines Logo
United Airlines

May 30

SJU
16h 41m
EWR
ORD

May 31

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
26h 13m
ORD
IAH

Jun 7

SJU

as low as

$754

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

United Airlines Logo
United Airlines

May 30

SJU
16h 41m
EWR
ORD

May 31

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
27h 45m
ORD
IAH

Jun 7

SJU

as low as

$799

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

United Airlines Logo
United Airlines

May 30

SJU
20h 26m
IAH
ORD

May 31

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$895

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

United Airlines Logo
United Airlines

May 30

SJU
15h 13m
EWR
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$908

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

United Airlines Logo
United Airlines

May 30

SJU
16h 37m
EWR
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$908

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

American Airlines Logo
American Airlines

May 30

SJU
8h 6m
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$4139

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

American Airlines Logo
American Airlines

May 30

SJU
9h 6m
CLT

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$4139

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

American Airlines Logo
American Airlines

May 30

SJU
9h 46m
CLT
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$4139

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

American Airlines Logo
American Airlines

May 30

SJU
10h 19m
CLT
ORD

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$4139

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

American Airlines Logo
American Airlines

May 30

SJU
9h 33m
CLT

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
7h 1m
ORD

Jun 6

SJU

as low as

$4139

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

American Airlines Logo
American Airlines

May 30

SJU
9h 33m
CLT

May 30

PIA
United Airlines Logo
United Airlines

Jun 6

PIA
26h 13m
ORD
IAH

Jun 7

SJU

as low as

$4203

Top Deals on flights from San Juan to Moline

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

American Airlines Logo
American Airlines

May 30

SJU
6h 55m
ORD

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
28h 21m
ORD
CLT

Jun 7

SJU

as low as

$355

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

American Airlines Logo
American Airlines

May 30

SJU
8h 35m
CLT
ORD

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
28h 21m
ORD
CLT

Jun 7

SJU

as low as

$425

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

United Airlines Logo
United Airlines

May 30

SJU
15h 40m
EWR
ORD

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
10h 49m
ORD

Jun 6

SJU

as low as

$541

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

American Airlines Logo
American Airlines

May 30

SJU
6h 55m
ORD

May 30

MLI
American Airlines Logo
American Airlines

Jun 6

MLI
7h 48m
CLT

Jun 7

SJU

as low as

$561

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

United Airlines Logo
United Airlines

May 30

SJU
15h 40m
EWR
ORD

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
27h 3m
ORD
IAH

Jun 7

SJU

as low as

$754

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

United Airlines Logo
United Airlines

May 30

SJU
19h 25m
IAH
ORD

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
10h 49m
ORD

Jun 6

SJU

as low as

$830

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

United Airlines Logo
United Airlines

May 30

SJU
19h 25m
IAH
ORD

May 31

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
27h 3m
ORD
IAH

Jun 7

SJU

as low as

$1085

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

United Airlines Logo
United Airlines

May 30

SJU
6h 24m
CLT

May 30

MLI
United Airlines Logo
United Airlines

Jun 6

MLI
8h 7m
ORD

Jun 6

SJU

as low as

$4139

Top Deals on flights from San Juan to Bloomington

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

American Airlines Logo
American Airlines

May 30

SJU
10h 20m
CLT
ORD

May 30

BMI
American Airlines Logo
American Airlines

Jun 6

BMI
8h 40m
ORD
CLT

Jun 7

SJU

as low as

$574

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

American Airlines Logo
American Airlines

May 30

SJU
8h 40m
ORD

May 30

BMI
American Airlines Logo
American Airlines

Jun 6

BMI
8h 40m
ORD
CLT

Jun 7

SJU

as low as

$574

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

American Airlines Logo
American Airlines

May 30

SJU
16h 15m
CLT
ORD

May 30

BMI
American Airlines Logo
American Airlines

Jun 6

BMI
8h 40m
ORD
CLT

Jun 7

SJU

as low as

$574

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

American Airlines Logo
American Airlines

May 30

SJU
15h 24m
CLT
DFW

May 30

BMI
American Airlines Logo
American Airlines

Jun 6

BMI
8h 40m
ORD
CLT

Jun 7

SJU

as low as

$619

Top Deals on flights from San Juan to Champaign

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

American Airlines Logo
American Airlines

May 29

SJU
7h 39m
ORD

May 29

CMI
American Airlines Logo
American Airlines

Jun 5

CMI
26h 46m
ORD
CLT

Jun 7

SJU

as low as

$482

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

American Airlines Logo
American Airlines

May 29

SJU
16h
CLT
DFW

May 29

CMI
American Airlines Logo
American Airlines

Jun 5

CMI
26h 46m
ORD
CLT

Jun 7

SJU

as low as

$482

Top Deals on flights from San Juan to Springfield

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

American Airlines Logo
American Airlines

May 29

SJU
18h 51m
CLT
ORD

May 30

SPI
American Airlines Logo
American Airlines

Jun 5

SPI
28h 44m
ORD
CLT

Jun 7

SJU

as low as

$351

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

American Airlines Logo
American Airlines

May 29

SJU
20h 11m
CLT
ORD

May 30

SPI
American Airlines Logo
American Airlines

Jun 5

SPI
28h 44m
ORD
CLT

Jun 7

SJU

as low as

$351

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

American Airlines Logo
American Airlines

May 29

SJU
21h 31m
CLT
ORD

May 30

SPI
American Airlines Logo
American Airlines

Jun 5

SPI
28h 44m
ORD
CLT

Jun 7

SJU

as low as

$351

Top Deals on flights from San Juan to Decatur

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

United Airlines Logo
United Airlines

May 29

SJU
17h 52m
ORD

May 30

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
27h 59m
ORD

Jun 6

SJU

as low as

$599

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

United Airlines Logo
United Airlines

May 29

SJU
11h 8m
ORD

May 29

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
27h 59m
ORD

Jun 6

SJU

as low as

$599

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

United Airlines Logo
United Airlines

May 29

SJU
17h 52m
ORD

May 30

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
13h 9m
ORD

Jun 5

SJU

as low as

$609

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

United Airlines Logo
United Airlines

May 29

SJU
11h 8m
ORD

May 29

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
13h 9m
ORD

Jun 5

SJU

as low as

$609

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

United Airlines Logo
United Airlines

May 29

SJU
16h 48m
IAH
ORD

May 29

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
13h 9m
ORD

Jun 5

SJU

as low as

$612

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

United Airlines Logo
United Airlines

May 29

SJU
16h 48m
IAH
ORD

May 29

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
27h 59m
ORD

Jun 6

SJU

as low as

$632

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

United Airlines Logo
United Airlines

May 29

SJU
16h 48m
IAH
ORD

May 29

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
18h 49m
ORD

Jun 6

SJU

as low as

$632

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

United Airlines Logo
United Airlines

May 29

SJU
16h 48m
IAH
ORD

May 29

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
27h 59m
ORD

Jun 6

SJU

as low as

$632

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

United Airlines Logo
United Airlines

May 29

SJU
25h 58m
IAD
ORD

May 30

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
13h 9m
ORD

Jun 5

SJU

as low as

$697

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

United Airlines Logo
United Airlines

May 29

SJU
16h 53m
IAD
ORD

May 30

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
13h 9m
ORD

Jun 5

SJU

as low as

$730

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

United Airlines Logo
United Airlines

May 29

SJU
11h 8m
ORD

May 29

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
16h 39m
ORD
IAD

Jun 6

SJU

as low as

$737

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

United Airlines Logo
United Airlines

May 29

SJU
17h 52m
ORD

May 30

DEC
United Airlines Logo
United Airlines

Jun 5

DEC
16h 39m
ORD
IAD

Jun 6

SJU

as low as

$737

Top Deals on flights from San Juan to Marion

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

United Airlines Logo
United Airlines

May 29

SJU
20h 44m
ORD

May 30

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
8h 54m
ORD

Jun 5

SJU

as low as

$616

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

United Airlines Logo
United Airlines

May 29

SJU
27h 54m
ORD

May 30

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
8h 54m
ORD

Jun 5

SJU

as low as

$616

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

United Airlines Logo
United Airlines

May 29

SJU
12h 5m
ORD

May 29

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
8h 54m
ORD

Jun 5

SJU

as low as

$616

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

United Airlines Logo
United Airlines

May 29

SJU
12h 5m
ORD

May 29

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
15h 39m
ORD

Jun 5

SJU

as low as

$625

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

United Airlines Logo
United Airlines

May 29

SJU
27h 54m
ORD

May 30

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
15h 39m
ORD

Jun 5

SJU

as low as

$625

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

United Airlines Logo
United Airlines

May 29

SJU
12h 5m
ORD

May 29

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
23h 44m
ORD

Jun 6

SJU

as low as

$625

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

United Airlines Logo
United Airlines

May 29

SJU
20h 44m
ORD

May 30

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
15h 39m
ORD

Jun 5

SJU

as low as

$625

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

United Airlines Logo
United Airlines

May 29

SJU
27h 54m
ORD

May 30

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
23h 44m
ORD

Jun 6

SJU

as low as

$626

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

United Airlines Logo
United Airlines

May 29

SJU
20h 44m
ORD

May 30

MWA
CONTOUR AIRLINES Logo
CONTOUR AIRLINES

Jun 5

MWA
23h 44m
ORD

Jun 6

SJU

as low as

$626

Top Deals on flights from San Juan to Quincy

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

United Airlines Logo
United Airlines

May 29

SJU
24h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
12h 19m
ORD

Jun 5

SJU

as low as

$572

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

United Airlines Logo
United Airlines

May 29

SJU
24h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
8h 19m
ORD

Jun 5

SJU

as low as

$572

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

United Airlines Logo
United Airlines

May 29

SJU
28h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
8h 19m
ORD

Jun 5

SJU

as low as

$572

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

United Airlines Logo
United Airlines

May 29

SJU
28h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
12h 19m
ORD

Jun 5

SJU

as low as

$572

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

United Airlines Logo
United Airlines

May 29

SJU
24h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
17h 14m
ORD

Jun 5

SJU

as low as

$572

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

United Airlines Logo
United Airlines

May 29

SJU
28h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
17h 14m
ORD

Jun 5

SJU

as low as

$572

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

United Airlines Logo
United Airlines

May 29

SJU
24h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
23h 9m
ORD

Jun 6

SJU

as low as

$576

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

United Airlines Logo
United Airlines

May 29

SJU
28h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
27h 9m
ORD

Jun 6

SJU

as low as

$576

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

United Airlines Logo
United Airlines

May 29

SJU
24h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
27h 9m
ORD

Jun 6

SJU

as low as

$576

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

United Airlines Logo
United Airlines

May 29

SJU
28h 9m
ORD

May 30

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
23h 9m
ORD

Jun 6

SJU

as low as

$576

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

United Airlines Logo
United Airlines

May 29

SJU
8h 20m
ORD

May 29

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
12h 19m
ORD

Jun 5

SJU

as low as

$588

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

United Airlines Logo
United Airlines

May 29

SJU
12h 20m
ORD

May 29

UIN
Southern Airways Express Logo
Southern Airways Express

Jun 5

UIN
8h 19m
ORD

Jun 5

SJU

as low as

$588

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