Cheap Flights from Chicago to Caribbean, from $243 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	Sep 1, 2018	Sep 10, 2018	$243
Copa	Aug 13, 2018	Aug 22, 2018	$243
Copa	Aug 24, 2018	Aug 27, 2018	$243
Copa	Aug 12, 2018	Aug 22, 2018	$243
Copa	Aug 23, 2018	Aug 28, 2018	$243
Copa	Aug 17, 2018	Aug 24, 2018	$243
Copa	Aug 26, 2018	Aug 31, 2018	$243
Copa	Aug 30, 2018	Sep 5, 2018	$243
Copa	Aug 30, 2018	Sep 4, 2018	$243
Copa	Aug 20, 2018	Aug 31, 2018	$243

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	7/12/18	7/17/18	$376
Freeport, Bahamas	7/13/18	7/15/18	$399
Bermuda	7/19/18	7/24/18	$357
St Croix Island	7/19/18	7/24/18	$379
Havana	7/28/18	7/31/18	$352

Flight Schedule Summaries Last modified: Jun 24, 2018 2:47 -04:00Number of routes searched: 1,301Number of itineraries searched: 809,898

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: Jun 24, 2018 2:47 -04:00Prices shown were found by travelers like you over the past 30 days

Flights	Lowest Price
Chicago to Montego Bay	$380
Chicago to St Thomas Island	$267
Chicago to St Maarten	$558
Chicago to Aruba	$379
Chicago to St Lucia	$631
Chicago to St Croix Island	$272
Chicago to Barbados	$353
Chicago to Kingston, Jamaica	$391
Chicago to Antigua	$584
Chicago to Bermuda	$348
Chicago to Curacao	$605
Chicago to Providenciales	$371
Chicago to St Kitts	$660
Chicago to Port au Prince	$405
Chicago to Port of Spain	$432
Chicago to Grenada, Grenada	$760
Chicago to Bonaire	$604
Chicago to Dominica	Check Dates
Chicago to Havana	$243
Chicago to Tobago	Check Dates
Chicago to Nevis	Check Dates
Chicago to Anguilla, Anguilla	Check Dates
Chicago to St Vincent	$1,137
Chicago to Fort de France	$812
Chicago to Pointe-a-Pitre	$707
Chicago to Georgetown, Guyana	$1,204
Chicago to St Barts	Check Dates
Chicago to Tortola	Check Dates
Chicago to Punta Cana	$436
Chicago to Nassau	$375

Cheap Flights From Chicago To Caribbean