From
To
City
Select sites to compare prices

Find Flights

Search

Enter your destination to continue
Enter your travel dates to continue
Select at least 3 sites to continue
Select your depart date
Select your return date

Cheap Flights From Chicago To Caribbean

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

Nassau
Carrier Departure Date Return Date Lowest Price
JetBlue May 10, 2017 May 17, 2017 $291
JetBlue May 6, 2017 May 10, 2017 $307
JetBlue May 31, 2017 Jun 7, 2017 $331
JetBlue May 17, 2017 May 24, 2017 $335
JetBlue May 2, 2017 May 5, 2017 $335
JetBlue May 14, 2017 May 17, 2017 $335
JetBlue May 16, 2017 May 23, 2017 $342
JetBlue May 9, 2017 May 16, 2017 $345
JetBlue May 30, 2017 Jun 3, 2017 $351
JetBlue May 1, 2017 May 5, 2017 $351

Cheap Last Minute Flights from Chicago to Caribbean Prices shown were found by travelers like you over the past 30 days

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
Punta Cana 3/31/17 4/3/17 $321
Santo Domingo, Dominican Republic 4/22/17 4/24/17 $408
Nassau 4/27/17 5/2/17 $379
Havana 4/27/17 5/2/17 $415
Montego Bay 4/29/17 5/2/17 $397

Flight Schedule Summaries Last modified: Mar 24, 2017 0:38 -04:00Number of routes searched: 1,132Number of itineraries searched: 1,571,704

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Frontier -
United -
American BOS
American CLT
American DCA
American DFW
Air Berlin TXL
Air Canada YOW
Air Canada YUL
Air Canada YYZ
Air France CDG
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines JFK
Swiss ZRH
Spirit FLL
United EWR
United IAD
United IAH

Cheap Flights from Chicago to Caribbean Countries

Cheap Flights from Chicago to Caribbean, from $291 Round trip from CHI to Caribbean