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Flight Deals from Chicago to Jamaica from $327

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Top Deals on flights from Chicago to Montego Bay

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Spirit Airlines Logo
Spirit Airlines

Jun 7

ORD
5h 57m
FLL

Jun 7

MBJ
Spirit Airlines Logo
Spirit Airlines

Jun 11

MBJ
10h 57m
FLL

Jun 11

ORD

as low as

$327

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Frontier Airlines Logo
Frontier Airlines

May 30

MDW
7h 23m
ATL

May 30

MBJ
Frontier Airlines Logo
Frontier Airlines

Jun 2

MBJ
13h 3m
ATL

Jun 2

MDW

as low as

$446

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Frontier Airlines Logo
Frontier Airlines

May 29

ORD
13h 24m
ATL

May 30

MBJ
Frontier Airlines Logo
Frontier Airlines

Jun 2

MBJ
13h 3m
ATL

Jun 2

ORD

as low as

$446

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Frontier Airlines Logo
Frontier Airlines

May 23

MDW
14h 58m
PHL

May 24

MBJ
Frontier Airlines Logo
Frontier Airlines

Jun 6

MBJ
16h 54m
ATL

Jun 7

MDW

as low as

$446

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Frontier Airlines Logo
Frontier Airlines

May 25

MDW
22h
ATL

May 26

MBJ
Frontier Airlines Logo
Frontier Airlines

May 28

MBJ
31h 41m
ATL
TPA

May 29

MDW

as low as

$479

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Delta Air Lines Logo
Delta Air Lines

May 25

MDW
5h 37m
ATL

May 25

MBJ
Delta Air Lines Logo
Delta Air Lines

May 28

MBJ
8h 25m
ATL

May 28

MDW

as low as

$491

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Air Canada Logo
Air Canada

May 26

ORD
14h 50m
YYZ

May 27

MBJ
Air Canada Logo
Air Canada

Jun 4

MBJ
24h 50m
YYZ

Jun 5

ORD

as low as

$496

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Air Canada Logo
Air Canada

Jun 12

ORD
19h 20m
YYZ

Jun 13

MBJ
Air Canada Logo
Air Canada

Jun 19

MBJ
21h 47m
YYZ
YUL

Jun 20

ORD

as low as

$520

Chicago, US (CHI) - Montego Bay, JM (MBJ)

Frontier Airlines Logo
Frontier Airlines

May 25

MDW
24h 5m
DFW
ATL

May 26

MBJ
Frontier Airlines Logo
Frontier Airlines

May 28

MBJ
31h 41m
ATL
TPA

May 29

MDW

as low as

$522

Chicago, US (CHI) - Montego Bay, JM (MBJ)

United Airlines Logo
United Airlines

May 25

ORD
4h 7m
Direct

May 25

MBJ
United Airlines Logo
United Airlines

May 28

MBJ
7h 18m
IAD

May 28

ORD

as low as

$523

Chicago, US (CHI) - Montego Bay, JM (MBJ)

American Airlines Logo
American Airlines

May 25

ORD
6h 35m
CLT

May 25

MBJ
American Airlines Logo
American Airlines

May 28

MBJ
4h 35m
Direct

May 28

ORD

as low as

$524

Chicago, US (CHI) - Montego Bay, JM (MBJ)

American Airlines Logo
American Airlines

Jun 7

ORD
15h 30m
DCA
CLT

Jun 8

MBJ
American Airlines Logo
American Airlines

Jun 11

MBJ
9h 22m
MIA

Jun 11

ORD

as low as

$530

Top Deals on flights from Chicago to Kingston

Chicago, US (CHI) - Kingston, JM (KIN)

Spirit Airlines Logo
Spirit Airlines

May 27

ORD
7h 24m
FLL

May 27

KIN
Spirit Airlines Logo
Spirit Airlines

Jun 3

KIN
9h 30m
FLL

Jun 3

ORD

as low as

$366

Chicago, US (CHI) - Kingston, JM (KIN)

Delta Air Lines Logo
Delta Air Lines

May 20

ORD
12h 50m
DTW
ATL

May 20

KIN
Delta Air Lines Logo
Delta Air Lines

Jun 3

KIN
11h 21m
ATL
DTW

Jun 3

ORD

as low as

$465

Chicago, US (CHI) - Kingston, JM (KIN)

Delta Air Lines Logo
Delta Air Lines

May 20

MDW
10h 44m
DTW
ATL

May 20

KIN
Delta Air Lines Logo
Delta Air Lines

Jun 3

KIN
7h 47m
ATL

Jun 3

MDW

as low as

$465

Chicago, US (CHI) - Kingston, JM (KIN)

American Airlines Logo
American Airlines

Jun 1

ORD
5h 59m
MIA

Jun 1

KIN
American Airlines Logo
American Airlines

Jun 5

KIN
12h
MIA

Jun 5

ORD

as low as

$490

Chicago, US (CHI) - Kingston, JM (KIN)

American Airlines Logo
American Airlines

Jun 1

ORD
14h 40m
CLT
MIA

Jun 1

KIN
American Airlines Logo
American Airlines

Jun 5

KIN
17h 58m
MIA
DCA

Jun 6

ORD

as low as

$495

Chicago, US (CHI) - Kingston, JM (KIN)

American Airlines Logo
American Airlines

Jun 11

ORD
12h 54m
PHL
MIA

Jun 11

KIN
American Airlines Logo
American Airlines

Jun 18

KIN
9h 48m
MIA
CLT

Jun 18

ORD

as low as

$495

Chicago, US (CHI) - Kingston, JM (KIN)

COPA Airlines Logo
COPA Airlines

Jun 11

ORD
29h 59m
PTY

Jun 12

KIN
COPA Airlines Logo
COPA Airlines

Jun 18

KIN
9h 37m
PTY

Jun 19

ORD

as low as

$522

Chicago, US (CHI) - Kingston, JM (KIN)

Air Canada Logo
Air Canada

May 26

ORD
18h 20m
YOW
YYZ

May 27

KIN
Air Canada Logo
Air Canada

Jun 13

KIN
20h 14m
YYZ

Jun 14

ORD

as low as

$534

Chicago, US (CHI) - Kingston, JM (KIN)

Air Canada Logo
Air Canada

May 18

ORD
20h 45m
YYZ

May 19

KIN
Air Canada Logo
Air Canada

May 29

KIN
20h 7m
YYZ
YUL

May 30

ORD

as low as

$592

Chicago, US (CHI) - Kingston, JM (KIN)

JetBlue Logo
JetBlue

May 17

ORD
10h 3m
JFK

May 18

KIN
JetBlue Logo
JetBlue

Jun 4

KIN
16h 53m
JFK

Jun 4

ORD

as low as

$659

Chicago, US (CHI) - Kingston, JM (KIN)

United Airlines Logo
United Airlines

Jun 11

ORD
29h 59m
PTY

Jun 12

KIN
United Airlines Logo
United Airlines

Jun 18

KIN
9h 37m
PTY

Jun 19

ORD

as low as

$798

Chicago, US (CHI) - Kingston, JM (KIN)

United Airlines Logo
United Airlines

Jun 11

ORD
29h 1m
IAD
PTY

Jun 12

KIN
United Airlines Logo
United Airlines

Jun 18

KIN
9h 37m
PTY

Jun 19

ORD

as low as

$803

Top Deals on flights from Chicago to Ocho Rios

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
15h 55m
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 35m
MIA

Jun 6

ORD

as low as

$801

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
15h 55m
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
7h 21m
MIA

Jun 5

ORD

as low as

$801

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
16h 36m
CLT
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 46m
MIA
JFK

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
16h 36m
CLT
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
14h 55m
MIA
DFW

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
14h 26m
PHL
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 2m
MIA
DCA

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
16h 36m
CLT
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 35m
MIA

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
14h 26m
PHL
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
7h 21m
MIA

Jun 5

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
14h 26m
PHL
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 20m
MIA
DFW

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
16h 36m
CLT
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 30m
MIA
PHL

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
14h 26m
PHL
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 46m
MIA
JFK

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
14h 26m
PHL
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
14h 55m
MIA
DFW

Jun 6

ORD

as low as

$806

Chicago, US (CHI) - Ocho Rios, JM (OCJ)

American Airlines Logo
American Airlines

May 29

ORD
15h 55m
MIA

May 30

OCJ
American Airlines Logo
American Airlines

Jun 5

OCJ
16h 2m
MIA
DCA

Jun 6

ORD

as low as

$806

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