Cheap flights from Illinois (IL) to Caribbean

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

How to find the cheapest flight from
Illinois to Caribbean

All the information you need to plan the best null to SJU flight in 2021: compare Illinois to Caribbean flight prices with the expected peak season, weather and rainfall in Caribbean.
How far in advance should I book a flight from Illinois to Caribbean?

Find a great deal and save up to 13% by booking at least 18 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Illinois to Caribbean within the next two weeks, with the cheapest ticket starting at $256.

When is the cheapest time to fly from Illinois to Caribbean (IL - CB)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Caribbean as you normally would.

What is the cheapest month to fly from Illinois to Caribbean?

The best pricing can be found in the month of August. Prices to Caribbean from Illinois average $307. You can even find prices in August for less than $307, as users have found deals to Caribbean from as low as $118. The month of December appears to be one of the more expensive times to travel to Caribbean from Illinois. Flying in the targeted month can save you up to 81%.

Cheap flights from Illinois to Caribbean in December, January 2022

The best prices found for Illinois to Caribbean flights for December, January
12 Dec - 14 Dec
$127pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
22 Jan - 26 Jan
$137pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
22 Jan - 29 Jan
$138pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Illinois to Caribbean 2022 flight deals

Cheap flights to Caribbean from Illinois found for this year
12 Dec - 14 Dec
$127pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
8 Dec - 13 Dec
$146pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
11 Dec - 18 Dec
$148pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Caribbean from Illinois

Save time with Illinois to Caribbean direct flight deals
20 Feb - 24 Feb
$143pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
30 Jan - 20 Feb
$148pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
PUJ
Punta Cana
PUJ
Punta Cana
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
8 Mar - 12 Mar
$164pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Illinois to Caribbean

Late deals on round-trip flights to Caribbean from Illinois, departing today and this week
12 Dec - 14 Dec
$127pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
11 Dec - 18 Dec
$148pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
14 Dec - 20 Jan
$149pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Caribbean from Illinois

The cheapest one-way flights from Illinois to Caribbean
3:38 pm - 9:50 am
American Airlines
1 Stop
16h 12m
ORD - PUJ
American Airlines
12:59 am - 9:39 pm
Frontier
1 Stop
18h 40m
ORD - SJU
Frontier
$91
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Illinois</span> to <span class="emphasized">Caribbean</span> flights.

Flight FAQs

From Illinois to Caribbean

Which airlines flying from Illinois to Caribbean have flexible cancellations due to COVID-19?

Some of our airline partners flying from Illinois to Caribbean have new flexible policies in place due to COVID-19. United Airlines, American Airlines, and Spirit Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

Can I find flights from Illinois to Caribbean for under $200 on Cheapflights?

Yes, there are multiple flights from Illinois to Caribbean for under $200. The cheapest flight booked recently is on Frontier for just $137, but on average you can expect to pay $144.

Are there nonstop flights from Illinois to Caribbean for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Illinois to Caribbean under $200. A good price for a nonstop flight from Illinois to Caribbean is less than $190.

Are there last-minute flights available from Illinois to Caribbean for under $200?

There are currently 20+ open flights from Illinois to Caribbean within the next 7 days for less than $200.

What days are nonstop flights available from Illinois to Caribbean?

Days when nonstop flights are available for this flight are: Wednesday.

How many flights depart from Illinois to Caribbean on average per day?

Per day, 2 flights depart from Illinois to Caribbean on average.
Afternoon (Noon - 6pm) - 100% of flight departures

How long is the flight from Illinois to Caribbean?

There are many flights that can get you from Illinois to Caribbean in 16h 07m. Fly via Frontier or Spirit Airlines to get the fastest option. The distance from Illinois to Caribbean is about 2085 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines to fly from Illinois to Caribbean one-way?

The cheapest airlines for a one-way flight from Illinois to Caribbean are Frontier ($63), Spirit Airlines ($69), and American Airlines ($89).

Related searches

Flights to Caribbean from Illinois
Flights to Illinois Flights to Caribbean

Rent a Car

Car Rentals in Caribbean Car Rentals at Luis Munoz Marin Intl

Destination information for Caribbean

Things to know before you go - useful duration and weather info for your trip from Illinois to Caribbean.
Today's exchange rate
$1 = $1.00

Airports servicing

Bloomington (BMI)
Champaign (CMI)
Decatur (DEC)
Moline (MLI)
Marion (MWA)

Top 10 airlines flying from Illinois to Caribbean

The chart below displays the airlines Cheapflights users traveling from Illinois to Caribbean choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$90 $386 No cancel fee 62%
Spirit Airlines
$112 $367 No cancel fee 65%
JetBlue
$151 $452 No cancel fee 62%
Delta
$163 $687 No cancel fee N/A
United Airlines
$183 $619 No cancel fee 69%
American Airlines
$185 $627 No cancel fee 71%
Copa Airlines
$199 $432 No cancel fee 70%
Aeromexico
$203 $371 No cancel fee N/A
Air Canada
$272 $608 No cancel fee 67%
Avianca
$502 $571 No cancel fee 71%
Home Caribbean Cheap flights from Illinois to Caribbean