Flight Deals from Caribbean to Chicago from $226
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Top Deals on flights from Panama City to Chicago
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 15
Jun 16
Jun 30
Jun 30
as low as
$714
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 16
Jun 17
Jun 29
Jun 29
as low as
$729
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 27
Jun 27
Jun 30
Jul 1
as low as
$738
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 5
Jun 6
Jun 19
Jun 21
as low as
$755
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 1
Jun 2
Jun 5
Jun 6
as low as
$765
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 1
Jun 2
Jun 5
Jun 5
as low as
$765
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 12
Jun 13
Jun 18
Jun 18
as low as
$779
Panama City, PA (PTY) - Chicago, US (CHI)
May 31
May 31
Jun 12
Jun 13
as low as
$810
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 6
Jun 6
Jun 13
Jun 14
as low as
$835
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 15
Jun 15
Jun 28
Jun 29
as low as
$1001
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 12
Jun 12
Jun 18
Jun 18
as low as
$1032
Panama City, PA (PTY) - Chicago, US (CHI)
Jun 27
Jun 27
Jun 30
Jul 1
as low as
$1133
Top Deals on flights from San Salvador to Chicago
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 14
Sep 14
Sep 21
Sep 21
as low as
$381
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 25
Sep 25
Sep 29
Sep 29
as low as
$381
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 5
Sep 6
Sep 13
Sep 13
as low as
$381
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 14
Sep 14
Sep 21
Sep 22
as low as
$385
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 4
Sep 4
Sep 11
Sep 11
as low as
$385
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 25
Sep 26
Sep 29
Sep 29
as low as
$390
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 4
Sep 5
Sep 11
Sep 11
as low as
$452
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 5
Sep 5
Sep 13
Sep 13
as low as
$460
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 14
Sep 14
Sep 21
Sep 21
as low as
$461
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 5
Sep 6
Sep 13
Sep 14
as low as
$479
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 4
Sep 5
Sep 11
Sep 11
as low as
$514
San Salvador, SV (SAL) - Chicago, US (CHI)
Sep 4
Sep 5
Sep 11
Sep 12
as low as
$543
Top Deals on flights from Bridgetown to Chicago
Bridgetown, BB (BGI) - Chicago, US (CHI)
May 22
May 23
May 29
May 30
as low as
$702
Bridgetown, BB (BGI) - Chicago, US (CHI)
Jun 11
Jun 11
Jun 17
Jun 18
as low as
$755
Bridgetown, BB (BGI) - Chicago, US (CHI)
Jun 11
Jun 12
Jun 17
Jun 18
as low as
$784
Bridgetown, BB (BGI) - Chicago, US (CHI)
Jun 11
Jun 12
Jun 17
Jun 17
as low as
$902
Bridgetown, BB (BGI) - Chicago, US (CHI)
Jun 8
Jun 9
Jun 15
Jun 15
as low as
$1061
Bridgetown, BB (BGI) - Chicago, US (CHI)
May 13
May 14
May 18
May 19
as low as
$1069
Bridgetown, BB (BGI) - Chicago, US (CHI)
Jun 8
Jun 9
Jun 15
Jun 16
as low as
$1374
Bridgetown, BB (BGI) - Chicago, US (CHI)
May 13
May 13
May 18
May 19
as low as
$6682
Bridgetown, BB (BGI) - Chicago, US (CHI)
May 13
May 13
May 18
May 19
as low as
$6818
Top Deals on flights from Punta Cana to Chicago
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 7
May 7
May 11
May 11
as low as
$444
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 1
May 1
May 3
May 4
as low as
$449
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 1
May 1
May 3
May 4
as low as
$459
Punta Cana, DO (PUJ) - Chicago, US (CHI)
Apr 29
Apr 29
May 6
May 6
as low as
$506
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 6
May 6
May 10
May 10
as low as
$522
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 13
May 13
May 17
May 17
as low as
$642
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 13
May 13
May 17
May 18
as low as
$686
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 13
May 13
May 17
May 17
as low as
$770
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 13
May 14
May 17
May 17
as low as
$780
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 2
May 2
May 25
May 25
as low as
$803
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 13
May 14
May 17
May 18
as low as
$804
Punta Cana, DO (PUJ) - Chicago, US (CHI)
May 1
May 2
May 3
May 3
as low as
$857
Top Deals on flights from San Juan to Chicago
San Juan, PR (SJU) - Chicago, US (CHI)
Sep 2
Sep 2
Sep 6
Sep 6
as low as
$226
San Juan, PR (SJU) - Chicago, US (CHI)
Sep 3
Sep 3
Sep 6
Sep 6
as low as
$291
San Juan, PR (SJU) - Chicago, US (CHI)
May 8
May 8
May 12
May 12
as low as
$332
San Juan, PR (SJU) - Chicago, US (CHI)
Jun 23
Jun 23
Jul 14
Jul 14
as low as
$401
San Juan, PR (SJU) - Chicago, US (CHI)
May 9
May 9
May 10
May 10
as low as
$425
Top Deals on flights from Beacon Hill to Chicago
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jun 4
Jun 4
Jun 10
Jun 11
as low as
$664
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jun 4
Jun 4
Jun 10
Jun 11
as low as
$664
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jul 25
Jul 26
Jul 29
Jul 29
as low as
$689
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jun 4
Jun 4
Jun 10
Jun 10
as low as
$749
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jun 4
Jun 5
Jun 10
Jun 10
as low as
$789
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jun 4
Jun 5
Jun 10
Jun 10
as low as
$789
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jun 4
Jun 5
Jun 10
Jun 11
as low as
$819
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jul 25
Jul 26
Jul 29
Jul 30
as low as
$839
Beacon Hill, SX (SXM) - Chicago, US (CHI)
Jun 7
Jun 7
Jun 14
Jun 15
as low as
$1070
Top Deals on flights from Santo Domingo to Chicago
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jul 1
Jul 2
Jul 8
Jul 8
as low as
$744
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jun 27
Jun 28
Jul 10
Jul 10
as low as
$744
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jun 24
Jun 24
Jul 1
Jul 1
as low as
$833
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jun 24
Jun 24
Jul 1
Jul 1
as low as
$837
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jul 1
Jul 1
Jul 8
Jul 9
as low as
$854
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jul 1
Jul 2
Jul 8
Jul 9
as low as
$866
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jul 2
Jul 3
Jul 6
Jul 7
as low as
$890
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jul 1
Jul 1
Jul 8
Jul 9
as low as
$928
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jun 20
Jun 20
Jun 26
Jun 26
as low as
$960
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jun 24
Jun 24
Jul 1
Jul 2
as low as
$979
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jun 24
Jun 24
Jul 1
Jul 1
as low as
$1013
Santo Domingo, DO (SDQ) - Chicago, US (CHI)
Jul 1
Jul 1
Jul 8
Jul 8
as low as
$1025
Top Deals on flights from San Jose to Chicago
San Jose, CR (SJO) - Chicago, US (CHI)
Jul 30
Jul 30
Aug 6
Aug 6
as low as
$326
San Jose, CR (SJO) - Chicago, US (CHI)
Jan 20
Jan 20
Jan 26
Jan 26
as low as
$364
San Jose, CR (SJO) - Chicago, US (CHI)
Jul 15
Jul 15
Jul 21
Jul 22
as low as
$367
San Jose, CR (SJO) - Chicago, US (CHI)
Dec 22
Dec 22
Jan 5
Jan 5
as low as
$368
San Jose, CR (SJO) - Chicago, US (CHI)
Jun 18
Jun 19
Jun 23
Jun 23
as low as
$415
San Jose, CR (SJO) - Chicago, US (CHI)
Jul 25
Jul 26
Jul 27
Jul 28
as low as
$440
San Jose, CR (SJO) - Chicago, US (CHI)
Jan 20
Jan 20
Jan 30
Jan 31
as low as
$444
San Jose, CR (SJO) - Chicago, US (CHI)
Jun 10
Jun 11
Jun 14
Jun 14
as low as
$491
San Jose, CR (SJO) - Chicago, US (CHI)
Jul 30
Jul 31
Aug 4
Aug 5
as low as
$653
San Jose, CR (SJO) - Chicago, US (CHI)
May 7
May 7
May 7
May 8
as low as
$3625
Top Deals on flights from Montego Bay to Chicago
Montego Bay, JM (MBJ) - Chicago, US (CHI)
May 28
May 28
Jun 1
Jun 2
as low as
$330
Montego Bay, JM (MBJ) - Chicago, US (CHI)
May 28
May 28
Jun 1
Jun 1
as low as
$350
Montego Bay, JM (MBJ) - Chicago, US (CHI)
May 28
May 28
Jun 1
Jun 1
as low as
$361
Montego Bay, JM (MBJ) - Chicago, US (CHI)
May 28
May 29
Jun 1
Jun 1
as low as
$365
Montego Bay, JM (MBJ) - Chicago, US (CHI)
Jun 7
Jun 7
Jun 14
Jun 14
as low as
$413
Montego Bay, JM (MBJ) - Chicago, US (CHI)
Jun 8
Jun 9
Jun 15
Jun 16
as low as
$421
Montego Bay, JM (MBJ) - Chicago, US (CHI)
Jun 7
Jun 8
Jun 14
Jun 15
as low as
$421
Montego Bay, JM (MBJ) - Chicago, US (CHI)
Jun 5
Jun 6
Jun 12
Jun 13
as low as
$536
Montego Bay, JM (MBJ) - Chicago, US (CHI)
May 28
May 28
Jun 1
Jun 1
as low as
$585
Montego Bay, JM (MBJ) - Chicago, US (CHI)
May 28
May 28
Jun 1
Jun 1
as low as
$595
Montego Bay, JM (MBJ) - Chicago, US (CHI)
May 28
May 28
Jun 1
Jun 1
as low as
$650
Montego Bay, JM (MBJ) - Chicago, US (CHI)
Jun 7
Jun 8
Jun 14
Jun 14
as low as
$678
Good to Know
Essential information to help you plan your flight from Caribbean to Chicago
Cheapest Flight
$226
The lowest price we found in the last two weeks, departing Sep 2 and returning Sep 6
1 stop ‧ 8h 6m ‧ economyFastest Flights
$449
The fastest flight that we found in the last two weeks, departing May 1 and returning May 4
1 stop ‧ 4h 9m ‧ economyCheapest Flight Round-trip
$226
Cheapest price found in the last 14 days, departing Sep 2 and returning Sep 6
1 stop ‧ 8h 6m ‧ economyCheapest Layover airport
$291
The cheapest layover airport to Chicago is currently $291
1 stop ‧ 16h 13m ‧ economyBest Arrival airport
$330
The best arrival airport to Chicago is currently $330
2 stops ‧ 7h 14m ‧ economyBest Departure airport
$330
The best departure airport to Chicago is currently $330
2 stops ‧ 7h 14m ‧ economyCheapest Airline
$330
The cheapest airline to Chicago is currently $330
2 stops ‧ 7h 14m ‧ economyFlights to Chicago
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