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Cheap flights from Chicago (CHI) to Caribbean

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Cheap flights from Chicago to Caribbean in April 2020

The best prices found for ORD to Caribbean flights for April
14 Apr - 27 Apr
$42pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
7 Apr - 20 Apr
$43pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
17 Apr - 20 Apr
$45pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Caribbean 2020 flight deals

Cheap flights to Caribbean from Chicago found for this year
18 May - 26 May
$41pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
2 May - 9 May
$42pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
26 May - 9 Jun
$43pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Caribbean

Late deals on round-trip flights to Caribbean from Chicago, departing today and this week
5 Apr - 30 Apr
$41pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
6 Apr - 20 Apr
$42pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Apr - 22 Apr
$44pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Caribbean from Chicago

The cheapest one-way flights from Chicago to Caribbean
4:37 am - 12:16 pm
Major Airline
Nonstop
6h 39m
ORD - SJU
Major Airline
$24
FlightNetwork
4:37 am - 12:16 pm
Major Airline
Nonstop
6h 39m
ORD - SJU
Major Airline
$42
FlightNetwork

Destination information for Caribbean

Things to know before you go. Useful info for your trip from Chicago to Caribbean
Today's exchange rate
$1 = $1.00
Flight duration
4h 55m

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)

Related info for your journey

Useful info, stats and facts about Chicago to Caribbean flights.

Flight FAQs

From Chicago to Caribbean

Are flight prices decreasing from Chicago to Caribbean due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Caribbean for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Chicago to Caribbean for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Caribbean for under $100. The cheapest flight booked recently is on Spirit Airlines for just $42, but on average you can expect to pay $43.

Are there nonstop flights from Chicago to Caribbean for under $0 on Cheapflights?

There are no nonstop flights from Chicago to Caribbean, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Chicago to Caribbean for under $100?

There are currently just 3 open flights from Chicago to Caribbean within the next 7 days for less than $100.

What days are nonstop flights available from Chicago to Caribbean?

Nonstop flights can be found on the following days: Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

How popular is this flight route?

Flights from Chicago to Caribbean have been viewed 555 times in the past calendar month.

What are the most popular airlines that fly from Chicago to Caribbean?

Consider American Airlines, JetBlue or Delta when booking your flight. These represent the most popular airlines when flying from Chicago to Caribbean.

What are the most popular routes from Chicago to Caribbean?

Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Oranjestad Reina Beatrix or Chicago O'Hare Intl - Montego Bay Sangster Intl when deciding on the best route from Chicago to Caribbean.

What are the cheapest Flights from Chicago to Caribbean?

The cheapest flight price from Chicago to Caribbean is $21. On average you can expect to pay $166. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $42.

What are the most reliable airlines from Chicago to Caribbean?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Caribbean on time: Air Canada(96%), United Airlines(96%), Air New Zealand(96%.)