Cheap Flights From Chicago To Caribbean

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

Santo Domingo, Dominican Republic
Carrier Departure Date Return Date Lowest Price
Spirit Jun 7, 2021 Jun 14, 2021 $308
Copa Jun 8, 2021 Jun 15, 2021 $316
Copa Jun 22, 2021 Jun 29, 2021 $316
AeroMexico Jul 6, 2021 Jul 13, 2021 $387
!! Jul 6, 2021 Jul 13, 2021 $377
Spirit Jun 8, 2021 Jun 15, 2021 $358
!! Jul 20, 2021 Jul 27, 2021 $377
!! Jul 13, 2021 Jul 20, 2021 $377

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
St Croix Island 4/15/21 4/19/21 $270
Punta Cana 4/16/21 4/20/21 $289
Port au Prince 4/17/21 4/20/21 $329
Santo Domingo, Dominican Republic 4/22/21 4/27/21 $320
St Thomas Island 4/24/21 4/27/21 $221

Flight Schedule Summaries Last modified: Apr 19, 2021 18:28 -04:00Number of routes searched: 0Number of itineraries searched: 0

Cheap Flights from Chicago to Caribbean Countries

Cheap Flights from Chicago to Caribbean, from $196 Round trip from CHI to Caribbean