Cheap Flights From Chicago To Caribbean

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

Santo Domingo, Dominican Republic $308
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

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Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI Last modified: Apr 19, 2021 18:28 -04:00

FlightsLowest Price
Chicago to Montego Bay$922
Chicago to St Thomas Island$335
Chicago to St Maarten$312
Chicago to Aruba$533
Chicago to St Lucia$609
Chicago to St Croix Island$210
Chicago to Barbados$644
Chicago to Kingston, Jamaica$373
Chicago to Antigua$1,187
Chicago to Bermuda$641
Chicago to Curacao$677
Chicago to Providenciales$449
Chicago to St Kitts$702
Chicago to Port au Prince$403
Chicago to Port of Spain$558
Chicago to Grenada, Grenada$881
Chicago to Bonaire$576
Chicago to Dominica$142,191
Chicago to Havana$491
Chicago to TobagoCheck Dates
Chicago to NevisCheck Dates
Chicago to Anguilla, AnguillaCheck Dates
Chicago to St Vincent$665
Chicago to Fort de France$690
Chicago to Pointe-a-Pitre$574
Chicago to Georgetown, Guyana$1,144
Chicago to St BartsCheck Dates
Chicago to TortolaCheck Dates
Chicago to Punta Cana$866
Chicago to Nassau$527

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