Cheap Flights From Chicago To Caribbean

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

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