Flight Deals from Chicago to Caribbean from $215
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Top Deals on flights from Chicago to Panama City
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 17
Jun 17
Jun 22
Jun 23
as low as
$694
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 17
Jun 17
Jun 22
Jun 23
as low as
$709
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 9
Jun 10
Jul 10
Jul 10
as low as
$735
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 25
Jun 26
Jun 28
Jun 29
as low as
$737
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 17
Jun 17
Jun 22
Jun 23
as low as
$754
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 18
Jun 18
Jul 3
Jul 3
as low as
$794
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 14
Jun 14
Jun 17
Jun 17
as low as
$809
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 12
Jun 13
Jun 19
Jun 19
as low as
$813
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 17
Jun 18
Jun 22
Jun 23
as low as
$813
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 18
Jun 19
Jul 3
Jul 3
as low as
$936
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 21
Jun 21
Jun 24
Jun 24
as low as
$1008
Chicago, US (CHI) - Panama City, PA (PTY)
Jun 18
Jun 19
Jul 3
Jul 4
as low as
$1033
Top Deals on flights from Chicago to San Salvador
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 10
Sep 10
Sep 23
Sep 23
as low as
$386
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$386
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 6
Sep 6
Sep 9
Sep 9
as low as
$386
Chicago, US (CHI) - San Salvador, SV (SAL)
Aug 22
Aug 23
Sep 4
Sep 5
as low as
$390
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 10
Sep 10
Sep 23
Sep 24
as low as
$390
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$426
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 1
Sep 1
Sep 6
Sep 6
as low as
$452
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 1
Sep 1
Sep 6
Sep 6
as low as
$462
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 17
Sep 17
Sep 20
Sep 21
as low as
$507
Chicago, US (CHI) - San Salvador, SV (SAL)
Aug 30
Aug 30
Sep 8
Sep 9
as low as
$541
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 7
Sep 7
Sep 14
Sep 15
as low as
$545
Chicago, US (CHI) - San Salvador, SV (SAL)
Sep 7
Sep 7
Sep 14
Sep 14
as low as
$634
Top Deals on flights from Chicago to Bridgetown
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 6
Jun 7
Jun 13
Jun 14
as low as
$459
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 5
Jun 6
Jun 15
Jun 16
as low as
$464
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 16
Jun 17
Jun 24
Jun 25
as low as
$491
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 5
Jun 6
Jun 15
Jun 16
as low as
$575
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 16
Jun 16
Jun 23
Jun 23
as low as
$671
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 11
Jun 12
Jun 16
Jun 17
as low as
$711
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 10
Jun 11
Jun 15
Jun 16
as low as
$720
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 4
Jun 5
Jun 8
Jun 9
as low as
$744
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 5
Jun 6
Jun 13
Jun 13
as low as
$789
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 16
Jun 16
Jun 23
Jun 24
as low as
$791
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 8
Jun 9
Jun 23
Jun 24
as low as
$791
Chicago, US (CHI) - Bridgetown, BB (BGI)
Jun 17
Jun 17
Jun 23
Jun 23
as low as
$801
Top Deals on flights from Chicago to Punta Cana
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 3
Aug 3
Aug 13
Aug 13
as low as
$354
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 28
Aug 29
Sep 1
Sep 2
as low as
$397
Chicago, US (CHI) - Punta Cana, DO (PUJ)
May 18
May 18
May 23
May 23
as low as
$419
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 3
Aug 4
Aug 12
Aug 13
as low as
$445
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 3
Aug 4
Aug 12
Aug 13
as low as
$452
Chicago, US (CHI) - Punta Cana, DO (PUJ)
May 10
May 10
May 15
May 16
as low as
$459
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 2
Aug 2
Aug 12
Aug 13
as low as
$506
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Jul 17
Jul 17
Jul 24
Jul 24
as low as
$551
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 11
Aug 11
Aug 18
Aug 19
as low as
$575
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Jul 14
Jul 15
Jul 18
Jul 19
as low as
$623
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 11
Aug 12
Aug 18
Aug 19
as low as
$624
Chicago, US (CHI) - Punta Cana, DO (PUJ)
Aug 11
Aug 12
Aug 18
Aug 19
as low as
$631
Top Deals on flights from Chicago to San Juan
Chicago, US (CHI) - San Juan, PR (SJU)
May 5
May 5
May 8
May 8
as low as
$215
Chicago, US (CHI) - San Juan, PR (SJU)
Aug 18
Aug 18
Aug 18
Aug 18
as low as
$220
Chicago, US (CHI) - San Juan, PR (SJU)
May 10
May 10
May 13
May 13
as low as
$236
Chicago, US (CHI) - San Juan, PR (SJU)
May 10
May 10
May 13
May 13
as low as
$287
Chicago, US (CHI) - San Juan, PR (SJU)
Aug 16
Aug 16
Aug 19
Aug 19
as low as
$296
Chicago, US (CHI) - San Juan, PR (SJU)
Oct 1
Oct 1
Oct 10
Oct 10
as low as
$340
Chicago, US (CHI) - San Juan, PR (SJU)
May 15
May 15
May 29
May 29
as low as
$381
Chicago, US (CHI) - San Juan, PR (SJU)
May 29
May 30
Jun 3
Jun 3
as low as
$395
Chicago, US (CHI) - San Juan, PR (SJU)
Jul 16
Jul 16
Jul 28
Jul 28
as low as
$401
Chicago, US (CHI) - San Juan, PR (SJU)
May 11
May 11
May 14
May 14
as low as
$427
Chicago, US (CHI) - San Juan, PR (SJU)
Oct 30
Oct 31
Nov 7
Nov 8
as low as
$461
Top Deals on flights from Chicago to Beacon Hill
Chicago, US (CHI) - Beacon Hill, SX (SXM)
Jul 16
Jul 16
Jul 23
Jul 24
as low as
$434
Chicago, US (CHI) - Beacon Hill, SX (SXM)
May 30
May 31
Jun 6
Jun 6
as low as
$526
Chicago, US (CHI) - Beacon Hill, SX (SXM)
Jun 12
Jun 12
Jun 15
Jun 16
as low as
$714
Chicago, US (CHI) - Beacon Hill, SX (SXM)
May 30
May 31
Jun 3
Jun 4
as low as
$744
Chicago, US (CHI) - Beacon Hill, SX (SXM)
May 21
May 22
May 24
May 25
as low as
$760
Chicago, US (CHI) - Beacon Hill, SX (SXM)
Jun 12
Jun 13
Jun 15
Jun 15
as low as
$769
Chicago, US (CHI) - Beacon Hill, SX (SXM)
May 30
May 31
Jun 5
Jun 6
as low as
$874
Chicago, US (CHI) - Beacon Hill, SX (SXM)
Sep 10
Sep 11
Sep 24
Sep 25
as low as
$1177
Top Deals on flights from Chicago to Santo Domingo
Chicago, US (CHI) - Santo Domingo, DO (SDQ)
Jun 4
Jun 5
Jun 7
Jun 8
as low as
$486
Chicago, US (CHI) - Santo Domingo, DO (SDQ)
Jul 30
Jul 30
Aug 6
Aug 6
as low as
$495
Chicago, US (CHI) - Santo Domingo, DO (SDQ)
May 30
May 31
Jun 2
Jun 3
as low as
$878
Chicago, US (CHI) - Santo Domingo, DO (SDQ)
Nov 21
Nov 22
Nov 29
Nov 29
as low as
$1041
Chicago, US (CHI) - Santo Domingo, DO (SDQ)
Dec 3
Dec 3
Dec 11
Dec 11
as low as
$2006
Top Deals on flights from Chicago to Curacao Island
Chicago, US (CHI) - Curacao Island, CW (CUR)
Nov 11
Nov 12
Nov 25
Nov 25
as low as
$617
Chicago, US (CHI) - Curacao Island, CW (CUR)
Nov 11
Nov 12
Nov 25
Nov 25
as low as
$617
Chicago, US (CHI) - Curacao Island, CW (CUR)
Nov 14
Nov 15
Nov 25
Nov 26
as low as
$632
Chicago, US (CHI) - Curacao Island, CW (CUR)
Sep 18
Sep 18
Sep 25
Sep 25
as low as
$667
Chicago, US (CHI) - Curacao Island, CW (CUR)
Nov 14
Nov 15
Nov 25
Nov 26
as low as
$668
Chicago, US (CHI) - Curacao Island, CW (CUR)
Aug 13
Aug 14
Aug 17
Aug 18
as low as
$691
Chicago, US (CHI) - Curacao Island, CW (CUR)
Jun 12
Jun 13
Jun 17
Jun 18
as low as
$878
Chicago, US (CHI) - Curacao Island, CW (CUR)
Nov 9
Nov 10
Nov 25
Nov 25
as low as
$919
Chicago, US (CHI) - Curacao Island, CW (CUR)
Nov 11
Nov 12
Nov 25
Nov 26
as low as
$1132
Chicago, US (CHI) - Curacao Island, CW (CUR)
Nov 11
Nov 12
Nov 25
Nov 26
as low as
$1305
Top Deals on flights from Chicago to San Jose
Chicago, US (CHI) - San Jose, CR (SJO)
Aug 1
Aug 2
Aug 7
Aug 7
as low as
$305
Chicago, US (CHI) - San Jose, CR (SJO)
Feb 22
Feb 22
Mar 2
Mar 2
as low as
$367
Chicago, US (CHI) - San Jose, CR (SJO)
Feb 22
Feb 22
Mar 2
Mar 3
as low as
$369
Chicago, US (CHI) - San Jose, CR (SJO)
May 6
May 6
May 14
May 15
as low as
$433
Chicago, US (CHI) - San Jose, CR (SJO)
Sep 7
Sep 7
Sep 15
Sep 15
as low as
$437
Chicago, US (CHI) - San Jose, CR (SJO)
Jun 16
Jun 16
Jun 19
Jun 19
as low as
$441
Chicago, US (CHI) - San Jose, CR (SJO)
Feb 7
Feb 7
Feb 12
Feb 12
as low as
$485
Chicago, US (CHI) - San Jose, CR (SJO)
Oct 8
Oct 8
Oct 13
Oct 14
as low as
$496
Chicago, US (CHI) - San Jose, CR (SJO)
Nov 14
Nov 15
Nov 24
Nov 25
as low as
$519
Chicago, US (CHI) - San Jose, CR (SJO)
May 28
May 28
May 31
Jun 1
as low as
$540
Chicago, US (CHI) - San Jose, CR (SJO)
Jun 5
Jun 6
Jun 8
Jun 9
as low as
$570
Chicago, US (CHI) - San Jose, CR (SJO)
May 30
May 30
Jun 6
Jun 6
as low as
$955
Top Deals on flights from Chicago to Montego Bay
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Jun 28
Jun 28
Jul 4
Jul 4
as low as
$317
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Apr 24
Apr 24
Apr 29
Apr 29
as low as
$317
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Apr 24
Apr 24
Apr 29
Apr 29
as low as
$327
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Jun 13
Jun 13
Jun 17
Jun 17
as low as
$387
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Jan 18
Jan 19
Jan 22
Jan 22
as low as
$436
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Apr 24
Apr 25
Apr 29
Apr 29
as low as
$437
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Apr 24
Apr 25
Apr 29
Apr 29
as low as
$443
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Aug 14
Aug 15
Aug 19
Aug 20
as low as
$447
Chicago, US (CHI) - Montego Bay, JM (MBJ)
May 16
May 17
May 23
May 23
as low as
$449
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Feb 10
Feb 11
Feb 17
Feb 18
as low as
$515
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Nov 13
Nov 14
Nov 25
Nov 26
as low as
$602
Chicago, US (CHI) - Montego Bay, JM (MBJ)
Jun 12
Jun 13
Jun 15
Jun 16
as low as
$939
Good to Know
Essential information to help you plan your flight from Chicago to Caribbean
Cheapest Flight
$215
The lowest price we found in the last two weeks, departing May 5 and returning May 8
1 stop ‧ 7h 7m ‧ economyFastest Flights
$317
The fastest flight that we found in the last two weeks, departing Jun 28 and returning Jul 4
3h 55m ‧ economyCheapest Flight Round-trip
$215
Cheapest price found in the last 14 days, departing May 5 and returning May 8
1 stop ‧ 7h 7m ‧ economyCheapest Layover airport
$215
The cheapest layover airport to San Juan is currently $215
1 stop ‧ 7h 7m ‧ economyBest Arrival airport
$317
The best arrival airport to Montego Bay is currently $317
4h 8m ‧ economyBest Departure airport
$317
The best departure airport to Montego Bay is currently $317
4h 8m ‧ economyCheapest Airline
$317
The cheapest airline to Montego Bay is currently $317
4h 8m ‧ economyFlights to Caribbean
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