Cheap Flights from Chicago to Caribbean, from $211 Round trip from CHI to Caribbean

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

Havana
Carrier	Departure Date	Return Date	Lowest Price
Copa	Nov 24, 2018	Dec 1, 2018	$211
American	Oct 5, 2018	Oct 9, 2018	$245
American	Oct 3, 2018	Oct 17, 2018	$245
American	Sep 10, 2018	Sep 12, 2018	$245
American	Oct 4, 2018	Oct 7, 2018	$245
American	Oct 21, 2018	Oct 29, 2018	$245
American	Oct 7, 2018	Oct 18, 2018	$245
American	Sep 22, 2018	Sep 29, 2018	$245
American	Oct 19, 2018	Oct 22, 2018	$245
American	Oct 4, 2018	Oct 8, 2018	$245

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.

Destination	Departing	Returning	Price
St Thomas Island	9/13/18	9/17/18	$236
Montego Bay	9/13/18	9/16/18	$372
Havana	9/20/18	9/25/18	$248
Santiago, Dominican Republic	9/21/18	9/25/18	$366
Santo Domingo, Dominican Republic	9/22/18	9/25/18	$332

Flight Schedule Summaries Last modified: Aug 19, 2018 2:28 -04:00Number of routes searched: 1,351Number of itineraries searched: 842,786

Chicago to Punta Cana
Airline	Connections	Mon	Tue	Wed	Thu	Fri	Sat	Sun
American	-	√		√	√	√	√	√
Frontier	-	√	√	√	√	√	√	√
United	-	√	√	√	√	√	√	√
American	BOS						√
American	CLT	√	√	√	√	√	√	√
American	DFW						√
American	JFK	√	√	√	√	√	√	√
Air Canada	YOW		√		√		√
Air Canada	YUL	√	√	√	√	√	√	√
Air Canada	YYZ	√	√	√	√	√	√	√
Air France	CDG	√	√	√	√	√	√	√
AeroMexico	MEX					√	√
Avianca	BOG	√		√		√	√
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 International Flights from Chicago - CHI Last modified: Aug 19, 2018 2:28 -04:00Prices shown were found by travelers like you over the past 30 days

Flights	Lowest Price
Chicago to Montego Bay	$343
Chicago to St Thomas Island	$222
Chicago to St Maarten	$517
Chicago to Aruba	$355
Chicago to St Lucia	$641
Chicago to St Croix Island	$396
Chicago to Barbados	$368
Chicago to Kingston, Jamaica	$356
Chicago to Antigua	$625
Chicago to Bermuda	$376
Chicago to Curacao	$757
Chicago to Providenciales	$361
Chicago to St Kitts	$601
Chicago to Port au Prince	$405
Chicago to Port of Spain	$439
Chicago to Grenada, Grenada	$731
Chicago to Bonaire	$693
Chicago to Dominica	Check Dates
Chicago to Havana	$211
Chicago to Tobago	Check Dates
Chicago to Nevis	Check Dates
Chicago to Anguilla, Anguilla	Check Dates
Chicago to St Vincent	$837
Chicago to Fort de France	$1,646
Chicago to Pointe-a-Pitre	$755
Chicago to Georgetown, Guyana	Check Dates
Chicago to St Barts	Check Dates
Chicago to Tortola	Check Dates
Chicago to Punta Cana	$389
Chicago to Nassau	$380

Cheap Flights From Chicago To Caribbean