Cheap Flights From Chicago To Caribbean

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

Punta Cana
Carrier Departure Date Return Date Lowest Price
< Frontier < May 22, 2023 < May 24, 2023 $236
< Frontier < May 23, 2023 < May 27, 2023 $248
< Frontier < May 23, 2023 < May 28, 2023 $255
< Frontier < Aug 14, 2023 < Aug 19, 2023 $264
< Frontier < May 30, 2023 < Jun 6, 2023 $266
< Frontier < May 23, 2023 < May 30, 2023 $270
< Frontier < May 19, 2023 < May 22, 2023 $276
< Frontier < Aug 12, 2023 < Aug 19, 2023 $280
< Frontier < May 19, 2023 < May 23, 2023 $282
< Frontier < May 19, 2023 < May 24, 2023 $282

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
Santiago, Dominican Republic 5/5/23 5/10/23 $397
Grand Cayman 5/19/23 5/22/23 $341
Santo Domingo, Dominican Republic 6/3/23 6/7/23 $247
Montego Bay 6/3/23 6/5/23 $295
Punta Cana 6/9/23 6/14/23 $304

Cheap Flights from Chicago to Caribbean Countries

Cheap Flights from Chicago to Caribbean, from $182 Round trip from CHI to Caribbean