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Cheap Flights From Chicago To Caribbean Last modified: Jun 27, 2016 6:37 AM

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

Aruba
Carrier Departure Date Return Date Lowest Price
United Aug 2, 2016 Aug 6, 2016 $391
United Jul 30, 2016 Aug 6, 2016 $394
United Jul 30, 2016 Aug 3, 2016 $394
United Jul 19, 2016 Jul 23, 2016 $399
United Jul 7, 2016 Jul 13, 2016 $399
United Jul 13, 2016 Jul 18, 2016 $399
United Jul 6, 2016 Jul 11, 2016 $399
United Jul 11, 2016 Jul 13, 2016 $399
United Jul 25, 2016 Aug 1, 2016 $399
United Jul 23, 2016 Aug 1, 2016 $399
Grand Cayman
Carrier Departure Date Return Date Lowest Price
United Aug 20, 2016 Aug 27, 2016 $388
United Jul 30, 2016 Aug 3, 2016 $429
United Aug 5, 2016 Aug 10, 2016 $429
United Jul 23, 2016 Jul 27, 2016 $429
United Jul 29, 2016 Aug 2, 2016 $429
United Aug 2, 2016 Aug 12, 2016 $429
United Jul 15, 2016 Jul 22, 2016 $429
United Jul 26, 2016 Aug 2, 2016 $429
United Aug 5, 2016 Aug 9, 2016 $429
United Jul 23, 2016 Jul 26, 2016 $429
Montego Bay
Carrier Departure Date Return Date Lowest Price
Spirit Sep 9, 2016 Sep 16, 2016 $378
Spirit Sep 8, 2016 Sep 10, 2016 $378
Spirit Sep 6, 2016 Sep 10, 2016 $378
Spirit Sep 10, 2016 Sep 15, 2016 $378
Spirit Sep 8, 2016 Sep 15, 2016 $378
Spirit Sep 7, 2016 Sep 10, 2016 $378
Spirit Sep 10, 2016 Sep 16, 2016 $378
Spirit Sep 10, 2016 Sep 17, 2016 $378
Spirit Sep 9, 2016 Sep 17, 2016 $378
Spirit Sep 8, 2016 Sep 19, 2016 $378
Nassau
Carrier Departure Date Return Date Lowest Price
United Jul 14, 2016 Jul 18, 2016 $397
United May 4, 2017 May 9, 2017 $397
United Nov 12, 2016 Nov 16, 2016 $402
United Nov 26, 2016 Dec 3, 2016 $402
United Nov 21, 2016 Nov 24, 2016 $402
United Nov 5, 2016 Nov 12, 2016 $402
United Jul 23, 2016 Jul 30, 2016 $402
United Nov 25, 2016 Nov 30, 2016 $402
United Nov 30, 2016 Dec 7, 2016 $402
United Nov 12, 2016 Nov 19, 2016 $402
Puerto Plata
Carrier Departure Date Return Date Lowest Price
American Sep 13, 2016 Sep 20, 2016 $608
American Jul 24, 2016 Jul 28, 2016 $608
American Aug 4, 2016 Aug 11, 2016 $608
American Sep 14, 2016 Sep 28, 2016 $608
American Jul 28, 2016 Aug 5, 2016 $608
American Aug 15, 2016 Aug 24, 2016 $608
American Sep 19, 2016 Sep 27, 2016 $608
American Sep 13, 2016 Sep 22, 2016 $608
American Jul 27, 2016 Aug 2, 2016 $608
American Aug 24, 2016 Sep 2, 2016 $608
Punta Cana
Carrier Departure Date Return Date Lowest Price
American Feb 14, 2017 Feb 21, 2017 $316
American Feb 4, 2017 Feb 11, 2017 $316
American Feb 7, 2017 Feb 8, 2017 $318
American Feb 4, 2017 Feb 7, 2017 $318
American Jan 7, 2017 Jan 14, 2017 $318
American Feb 14, 2017 Feb 15, 2017 $318
American Feb 4, 2017 Feb 8, 2017 $318
American Apr 4, 2017 Apr 13, 2017 $318
Santo Domingo
Carrier Departure Date Return Date Lowest Price
United Oct 24, 2016 Oct 30, 2016 $387
United Oct 3, 2016 Oct 17, 2016 $387
United Oct 22, 2016 Oct 25, 2016 $392
United Sep 30, 2016 Oct 4, 2016 $392
United Oct 20, 2016 Oct 27, 2016 $392
United Oct 4, 2016 Oct 20, 2016 $392
United Oct 21, 2016 Oct 27, 2016 $392
United Oct 4, 2016 Oct 19, 2016 $392
United Oct 6, 2016 Oct 21, 2016 $392
United Oct 18, 2016 Oct 25, 2016 $392
St Lucia
Carrier Departure Date Return Date Lowest Price
JetBlue Sep 21, 2016 Sep 29, 2016 $548
United Feb 25, 2017 Mar 4, 2017 $574
United May 13, 2017 May 20, 2017 $589
United Aug 27, 2016 Sep 3, 2016 $589
United Feb 11, 2017 Feb 25, 2017 $594
American Dec 10, 2016 Dec 17, 2016 $596
American Jul 26, 2016 Aug 2, 2016 $596
St Maarten
Carrier Departure Date Return Date Lowest Price
Spirit Feb 11, 2017 Feb 18, 2017 $472
Spirit Jan 14, 2017 Jan 28, 2017 $472
Spirit Feb 4, 2017 Feb 18, 2017 $472
Spirit Jan 28, 2017 Feb 4, 2017 $472
Spirit Jan 14, 2017 Jan 21, 2017 $472
Spirit Jan 28, 2017 Feb 11, 2017 $472
Spirit Jan 21, 2017 Jan 28, 2017 $472
United Jan 8, 2017 Jan 14, 2017 $481
United Jan 8, 2017 Jan 15, 2017 $481
United Nov 5, 2016 Nov 12, 2016 $481
St Thomas Island
Carrier Departure Date Return Date Lowest Price
JetBlue Nov 4, 2016 Nov 11, 2016 $325
JetBlue Dec 8, 2016 Dec 12, 2016 $325
JetBlue Jan 10, 2017 Jan 17, 2017 $325
JetBlue Nov 29, 2016 Dec 3, 2016 $325
JetBlue Dec 9, 2016 Dec 16, 2016 $325
JetBlue Jan 31, 2017 Feb 7, 2017 $325
American Aug 10, 2016 Aug 25, 2016 $326
American Sep 9, 2016 Sep 16, 2016 $326
American Aug 25, 2016 Aug 29, 2016 $326
American Sep 8, 2016 Sep 12, 2016 $326

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Caribbean

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to Caribbean.

DestinationDepartingReturningPrice
Punta Cana 7/28/16 8/1/16 $491

Flight Schedule Summaries Number of flights searched: 1,470Last modified: Jun 27, 2016 6:37 AM

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X
American CLT X X X X X X X
Air Canada YUL X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X X X X
Delta ATL X X X X X X X
Frontier - X X X X X X X
Spirit FLL X X X X X X X
United - X X X X X X X
United EWR X X X X X X X
Southwest - X X X X X X X
Southwest ATL X X X X X X X
Chicago to Montego Bay
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X
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 X
United - X
United EWR X X X X X X X
Southwest - X X X X X X X
Southwest BWI X X X X X X X
Chicago to St Thomas 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
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
United IAD 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 IND / CLT 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
United EWR X X X
Chicago to Aruba
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American PHL X X X X X X X
American CVG / CLT X X X X X X
Air Canada YYZ X
Avianca SAL / BOG X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X X X X
Delta ATL X X X X X X X
Spirit FLL X X
United - X
United IAD X X X X X X X
Southwest MCO 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
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
United - X
United IAH X X X X X X X
Southwest BWI X X X X X X X
Chicago to Puerto Plata
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American JAX / MIA X X X X X X X
Air Canada YUL X X X
JetBlue JFK X X X X X X X
United EWR 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 X
American MCO / MIA X X X X
Air Canada YYZ X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
Cayman - X
United IAH 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 IND / CLT X X X X X X X
Air Canada YYZ X X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
United EWR 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
Delta ATL X X

Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Montego Bay Silver, American, JetBlue, Frontier, Spirit, Sun Country, United $378
Chicago to St Thomas Island American, JetBlue, Spirit, United $326
Chicago to St Maarten American, JetBlue, Spirit, United $498
Chicago to Aruba Insel Air Aruba, American, JetBlue, Spirit, United $391
Chicago to St Lucia American, JetBlue, United $548
Chicago to St Croix Island American, Alaska, JetBlue, United $404
Chicago to Barbados American, JetBlue, United $523
Chicago to Kingston American, Alaska, JetBlue, Frontier, Spirit, United $552
Chicago to Antigua American, JetBlue, LIAT, Spirit, United $612
Chicago to Bermuda American, JetBlue, United $474
Chicago to Curacao Insel Air, American, JetBlue, United $623
Chicago to Providenciales Silver, American, JetBlue, interCaribbean, United $432
Chicago to St Kitts American, JetBlue, United $633
Chicago to Port au Prince Silver, American, Alaska, JetBlue, Spirit, United $354
Chicago to Port of Spain Silver, American, JetBlue, Caribbean, United $439
Chicago to Grenada American, JetBlue, United $825
Chicago to Bonaire American, United $452
Chicago to Dominica American, JetBlue, Spirit, United $1,033
Chicago to Havana American, Cubana, Frontier, Spirit, Sun Country, United, Virgin America $570
Chicago to Tobago American, Caribbean, United $857
Chicago to Nevis American, JetBlue, Tradewind, United $631
Chicago to Anguilla American, JetBlue, Tradewind, United Check Dates
Chicago to St Vincent JetBlue $717
Chicago to Fort de France American, JetBlue, United $902
Chicago to Pointe-a-Pitre American, JetBlue, United Check Dates
Chicago to Georgetown American, United $690
Chicago to St Barthelemy Tradewind, United $1,047
Chicago to Beef Island Cape Air, American, Alaska, JetBlue, United $526
Chicago to Punta Cana American, JetBlue, Frontier, Spirit, Sun Country, United $346
Chicago to Nassau Silver, American, JetBlue, Frontier, Spirit, United, Bahamasair $397
Cheap Flights from Chicago to Caribbean, from $316 Round trip from CHI to caribbean