Cheap Flights From Chicago To Caribbean

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

St Thomas Island $321
St Thomas Island
Carrier Departure Date Return Date Lowest Price
Spirit Jul 18, 2022 Jul 26, 2022 $321
Multiple Airlines Jul 28, 2022 Jul 31, 2022 $942
British Airways Jun 3, 2022 Jun 9, 2022 $593
00 May 10, 2022 May 17, 2022 $152
00 Apr 24, 2022 Apr 28, 2022 $148
00 May 2, 2022 May 6, 2022 $154

Cheap Last Minute Flights from Chicago to Caribbean

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Caribbean. The chart below shows the best last minute deals and cheap flights this weekend we could find.

DestinationDepartingReturningPrice
Antigua 12/9/21 12/13/21 $350
Kingston, Jamaica 1/27/22 1/31/22 $270
St Croix Island 1/28/22 1/31/22 $133
Santo Domingo, Dominican Republic 2/24/22 2/28/22 $197
St Thomas Island 3/10/22 3/13/22 $132

Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI Last modified: May 21, 2022 13:23 -04:00

FlightsLowest Price
Chicago to Montego Bay$893
Chicago to St Thomas Island$321
Chicago to St Maarten$486
Chicago to Aruba$661
Chicago to St Lucia$15,194
Chicago to St Croix Island$949
Chicago to Barbados$664
Chicago to Kingston, Jamaica$674
Chicago to Antigua$340
Chicago to Bermuda$459
Chicago to Curacao$1,706
Chicago to Providenciales$345
Chicago to St Kitts$709
Chicago to Port au Prince$207
Chicago to Port of Spain$376
Chicago to Grenada, Grenada$574
Chicago to Bonaire$582
Chicago to Dominica$534
Chicago to Havana$1,332
Chicago to Tobago$463
Chicago to Nevis$3,168
Chicago to Anguilla, Anguilla$615
Chicago to St Vincent$3,782
Chicago to Fort de France$1,105
Chicago to Pointe-a-Pitre$915
Chicago to Georgetown, Guyana$553
Chicago to St Barts$1,273
Chicago to Tortola$516
Chicago to Punta Cana$695
Chicago to Nassau$733

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Cheap Flights from Chicago to Caribbean, from $148 Round trip from CHI to Caribbean