Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.
Flights
Hotels
Round-trip
One-way
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.

Cheap Flights From Chicago To Caribbean Last modified: Aug 27, 2016 12:42 AM

Cheap flights from Chicago (CHI) to popular destinations in Caribbean

Aruba
Carrier Departure Date Return Date Lowest Price
Copa Oct 22, 2016 Oct 29, 2016 $383
Spirit Sep 10, 2016 Sep 17, 2016 $410
Spirit Sep 17, 2016 Sep 24, 2016 $413
Spirit Sep 16, 2016 Sep 24, 2016 $423
Spirit Apr 29, 2017 May 6, 2017 $429
Spirit May 6, 2017 May 13, 2017 $429
Spirit Apr 21, 2017 Apr 29, 2017 $440
Spirit Jan 28, 2017 Feb 4, 2017 $469
United Dec 8, 2016 Dec 15, 2016 $484
American Feb 24, 2017 Mar 5, 2017 $484
Grand Cayman
Carrier Departure Date Return Date Lowest Price
United Nov 26, 2016 Dec 3, 2016 $360
United Dec 3, 2016 Dec 10, 2016 $368
American Sep 28, 2016 Oct 3, 2016 $370
American Oct 10, 2016 Oct 17, 2016 $370
American Oct 13, 2016 Oct 17, 2016 $370
American Oct 19, 2016 Oct 26, 2016 $372
American Sep 29, 2016 Oct 4, 2016 $372
Montego Bay
Carrier Departure Date Return Date Lowest Price
Spirit Feb 4, 2017 Feb 7, 2017 $405
Spirit Sep 29, 2016 Oct 2, 2016 $405
Spirit Feb 1, 2017 Feb 11, 2017 $405
Spirit Jan 12, 2017 Jan 21, 2017 $405
Spirit Jan 11, 2017 Jan 21, 2017 $405
Spirit Jan 14, 2017 Jan 16, 2017 $405
American Sep 13, 2016 Sep 16, 2016 $406
American Sep 24, 2016 Sep 27, 2016 $407
Nassau
Carrier Departure Date Return Date Lowest Price
JetBlue Jan 17, 2017 Jan 24, 2017 $326
JetBlue Jan 25, 2017 Jan 30, 2017 $345
JetBlue Jan 18, 2017 Jan 26, 2017 $345
Copa Oct 4, 2016 Oct 8, 2016 $355
Copa Nov 11, 2016 Nov 13, 2016 $358
Copa Nov 5, 2016 Nov 12, 2016 $358
Copa Oct 22, 2016 Oct 29, 2016 $358
Copa Oct 18, 2016 Oct 23, 2016 $358
Copa Sep 27, 2016 Oct 1, 2016 $358
Copa Oct 22, 2016 Oct 26, 2016 $358
Providenciales
Carrier Departure Date Return Date Lowest Price
American Sep 29, 2016 Oct 7, 2016 $424
American Sep 9, 2016 Sep 11, 2016 $434
American Sep 9, 2016 Sep 18, 2016 $434
American Sep 23, 2016 Oct 2, 2016 $434
American Sep 30, 2016 Oct 3, 2016 $434
American Oct 21, 2016 Oct 28, 2016 $434
American Sep 17, 2016 Sep 24, 2016 $434
American Sep 10, 2016 Sep 18, 2016 $434
American Sep 5, 2016 Sep 9, 2016 $434
Punta Cana
Carrier Departure Date Return Date Lowest Price
Copa Oct 3, 2016 Oct 7, 2016 $297
Copa Oct 29, 2016 Nov 3, 2016 $297
Copa Nov 1, 2016 Nov 9, 2016 $297
Copa Oct 24, 2016 Oct 27, 2016 $297
Copa Sep 29, 2016 Oct 7, 2016 $297
Copa Oct 3, 2016 Oct 12, 2016 $297
Copa Nov 4, 2016 Nov 9, 2016 $297
Copa Oct 31, 2016 Nov 9, 2016 $297
Copa Oct 18, 2016 Oct 22, 2016 $297
Copa Sep 27, 2016 Oct 1, 2016 $297
Santo Domingo
Carrier Departure Date Return Date Lowest Price
AeroMexico Sep 29, 2016 Oct 5, 2016 $356
AeroMexico Sep 3, 2016 Sep 10, 2016 $356
AeroMexico Sep 30, 2016 Oct 5, 2016 $356
AeroMexico Sep 30, 2016 Oct 2, 2016 $359
AeroMexico Sep 23, 2016 Sep 28, 2016 $359
AeroMexico Sep 27, 2016 Sep 30, 2016 $359
AeroMexico Sep 29, 2016 Oct 3, 2016 $359
St Lucia
Carrier Departure Date Return Date Lowest Price
American Nov 11, 2016 Nov 19, 2016 $490
American Nov 12, 2016 Nov 19, 2016 $490
United Nov 11, 2016 Nov 19, 2016 $490
American Nov 3, 2016 Nov 10, 2016 $495
American Nov 28, 2016 Dec 3, 2016 $501
American Oct 29, 2016 Nov 5, 2016 $501
American Nov 26, 2016 Dec 3, 2016 $501
St Maarten
Carrier Departure Date Return Date Lowest Price
Copa Nov 12, 2016 Nov 19, 2016 $416
Copa Oct 22, 2016 Oct 29, 2016 $416
Copa Oct 14, 2016 Oct 23, 2016 $416
Copa Nov 20, 2016 Dec 4, 2016 $416
Copa Sep 30, 2016 Oct 9, 2016 $416
Copa Nov 4, 2016 Nov 14, 2016 $416
Copa Oct 28, 2016 Oct 31, 2016 $416
Copa Oct 1, 2016 Oct 8, 2016 $416
Copa Nov 5, 2016 Nov 19, 2016 $416
Copa Nov 25, 2016 Dec 4, 2016 $416
St Thomas Island
Carrier Departure Date Return Date Lowest Price
Spirit Nov 1, 2016 Nov 7, 2016 $304
Spirit Sep 7, 2016 Sep 13, 2016 $304
Spirit Sep 25, 2016 Oct 2, 2016 $304
Spirit Sep 21, 2016 Oct 5, 2016 $307
Spirit Sep 15, 2016 Sep 19, 2016 $307
Spirit Sep 18, 2016 Sep 21, 2016 $307
Spirit Sep 25, 2016 Sep 29, 2016 $307
Spirit Sep 6, 2016 Sep 9, 2016 $307
Spirit Sep 7, 2016 Sep 14, 2016 $307
Spirit Sep 12, 2016 Sep 16, 2016 $307

Flight Schedule Summaries Number of flights searched: 1,240Last modified: Aug 27, 2016 12:42 AM

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
Air Canada YYZ X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X X X
Delta ATL X X X X X X X
Spirit FLL X X X
United IAH X X X X X X X
Southwest - X X X
Southwest BWI X X X X X X X
Chicago to Aruba
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American MCO / MIA X X X X X X
Air Canada YYZ X
Avianca SAL / BOG X X X X X
JetBlue BOS X X X X X X X
Copa PTY X X X X X X
Delta ATL X X X X X X X
Spirit FLL X X
United EWR X X X X X X X
Southwest MCO X X X X X X X
Chicago to Puerto Plata
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American CVG / MIA X X X X X X X
Air Canada YUL X X X
JetBlue JFK X X X X X X X
Chicago to Grand Cayman
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X
Air Canada YYZ X
JetBlue JFK X X X
Delta ATL X X X X X X X
United IAH X X
Chicago to Montego Bay
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
Air Canada YYZ X X X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X
Delta ATL X X X X X X X
Spirit FLL X X X X X X
United EWR X X
Southwest - X X X X
Southwest BWI X X X X X X X
Chicago to Nassau
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American CVG / CLT X X X X X X
Air Canada YYZ X X X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X
Delta ATL X X X X X X X
United EWR X X
Southwest FLL X X X X X X X
Chicago to St Lucia
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American CVG / MIA X X X X X X X
Air Canada YYZ X
JetBlue JFK X X X X X X X
Delta ATL X X X X X
Chicago to St Thomas Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X
JetBlue SJU X X X X X X X
Delta ATL X X X X X X X
Spirit FLL X X X X X X X
Spirit LGA / FLL X X X X X X X
Chicago to St Croix Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
JetBlue SJU X X X X X X X
Chicago to St Maarten
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American CVG / CLT X X X X X X X
JetBlue BOS X X X X X
Copa PTY X X X X
Delta JFK X X X X X X
Spirit FLL X X

Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Montego Bay American, Air Canada, JetBlue, British Airways, Copa, Delta, Spirit, United, Virgin Atlantic, WestJet $405
Chicago to St Thomas Island American, JetBlue, Delta, Spirit, United $304
Chicago to St Maarten American, Air Canada, Air France, AeroMexico, JetBlue, Copa, Delta, Spirit, United, WestJet $416
Chicago to Aruba American, Air Canada, Avianca, JetBlue, British Airways, Copa, Delta, Spirit, United, WestJet $383
Chicago to St Lucia American, Air Canada, JetBlue, British Airways, Delta, United, WestJet $490
Chicago to St Croix Island American, JetBlue, Delta, United $333
Chicago to Barbados American, Air Berlin, Air Canada, Avianca, JetBlue, British Airways, Delta, WestJet $531
Chicago to Kingston American, Air Canada, JetBlue, Copa, Delta, Cayman, Spirit, United, WestJet $607
Chicago to Antigua American, Air Canada, JetBlue, British Airways, Delta, United, WestJet $607
Chicago to Bermuda American, Air Canada, JetBlue, British Airways, Delta, United, WestJet $325
Chicago to Curacao American, Air Berlin, Air Canada, Avianca, JetBlue, British Airways, Copa, United $548
Chicago to Providenciales American, Air Canada, JetBlue, British Airways, Delta, United, WestJet $424
Chicago to St Kitts American, Air Canada, JetBlue, British Airways, Delta, United $618
Chicago to Port au Prince American, Air Canada, JetBlue, Copa, Delta, Spirit $354
Chicago to Port of Spain American, Air Canada, JetBlue, British Airways, Copa, United, WestJet $427
Chicago to Grenada American, Air Canada, JetBlue, British Airways, Delta $503
Chicago to Bonaire Delta, United $451
Chicago to Dominica American $814
Chicago to Havana Air Berlin, Air France, AeroMexico, Avianca, Copa, Cayman, Swiss, Austrian $526
Chicago to Tobago British Airways Check Dates
Chicago to Nevis Air France, JetBlue Check Dates
Chicago to Anguilla American, JetBlue $772
Chicago to St VincentCheck Dates
Chicago to Fort de France American, Air Canada, Air France $784
Chicago to Pointe-a-Pitre American, Air Canada, Air France $784
Chicago to Georgetown Copa $1,495
Chicago to St BarthelemyCheck Dates
Chicago to Beef Island American, JetBlue $588
Chicago to Punta Cana LAN Argentina, American, Air Berlin, Air Canada, Air France, Avianca, JetBlue, British Airways, Copa, Delta, Frontier, Spirit, United, WestJet $297
Chicago to Nassau American, Air Berlin, Air Canada, JetBlue, British Airways, Copa, Delta, United, WestJet $355
Cheap Flights from Chicago to Caribbean, from $297 Round trip from CHI to caribbean