$92 Find Cheap Flights from Illinois to Caribbean Islands

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$92
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from Chicago O'Hare Airport to San Juan

FAQs for booking flights from Illinois to Caribbean Islands

  • How does KAYAK find such low prices on flights from Illinois to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Illinois to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Illinois to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Caribbean Islands?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean Islands is San Juan Luis Munoz Marin Intl Airport (SJU), with an average flight price of $238.

  • What is the cheapest day to fly to Caribbean Islands?

    Based on KAYAK data, the cheapest day to fly to Caribbean Islands is Monday where round-trip tickets can be as cheap as $393. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $448 on average.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $302 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $440.

  • What is the cheapest flight to Caribbean Islands?

    The cheapest ticket to Caribbean Islands from Illinois found in the last 72 hours was to Punta Cana, at $240 round-trip. The most popular route is Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $241.

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

    The cheapest month for flights from Illinois to Caribbean Islands is July, when tickets cost $555 (return) on average. On the other hand, the most expensive months are October and March, when the average cost of round-trip tickets is $938 and $933 respectively.

  • How far in advance should I book a flight from Illinois to Caribbean Islands?

    To get a below average price on the flight from Illinois to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

  • How long is the flight to Caribbean Islands?

    An average nonstop flight from Illinois to Caribbean Islands takes 6h 19m, covering a distance of 2020 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 18m.

  • What are the most popular destinations in Caribbean Islands?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (21% of total searches to Caribbean Islands). The next most popular destinations are Montego Bay (18%) and Oranjestad (10%). Searches for flights to Saint Thomas Island (10%), to Nassau (5%) and to Providenciales (4%) are also popular.

Book cheap flights from Illinois to Caribbean Islands

Recent round-trip flight deals

8/5Tue
1 stopSpirit Airlines
7h 59mORD-SJU
8/6Wed
1 stopSpirit Airlines
15h 21mSJU-ORD
$201
8/5Tue
1 stopSpirit Airlines
7h 59mORD-SJU
8/6Wed
1 stopSpirit Airlines
15h 21mSJU-ORD
$202
12/6Sat
1 stopFrontier
6h 54mMDW-SJU
12/10Wed
1 stopFrontier
7h 33mSJU-MDW
$210
8/1Fri
1 stopFrontier
27h 14mMDW-SJU
8/6Wed
1 stopFrontier
12h 21mSJU-MDW
$220
9/22Mon
1 stopSouthwest
6h 45mMDW-SJU
9/23Tue
2 stopsSouthwest
8h 05mSJU-MDW
$228
9/6Sat
nonstopUnited Airlines
4h 52mORD-SJU
9/12Fri
1 stopUnited Airlines
10h 33mSJU-ORD
$229
9/2Tue
1 stopDelta
8h 27mORD-SJU
9/5Fri
1 stopDelta
7h 19mSJU-ORD
$233
11/3Mon
1 stopDelta
9h 18mMDW-SJU
11/13Thu
1 stopDelta
9h 54mSJU-MDW
$233
10/1Wed
2 stopsSouthwest
8h 30mMDW-SJU
10/5Sun
2 stopsSouthwest
8h 05mSJU-MDW
$292
11/14Fri
nonstopUnited Airlines
4h 32mORD-PUJ
11/18Tue
nonstopUnited Airlines
5h 13mPUJ-ORD
$311

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/5Tue
1 stopSpirit Airlines
7h 59mORD-SJU
$92
7/26Sat
nonstopSpirit Airlines
4h 43mORD-SJU
$100
12/18Thu
1 stopFrontier
6h 54mMDW-SJU
$104
8/11Mon
1 stopFrontier
7h 58mORD-SJU
$109
9/22Mon
nonstopUnited Airlines
4h 52mORD-SJU
$112
11/23Sun
nonstopArajet
4h 45mORD-PUJ
$114
10/9Thu
1 stopDelta
9h 18mORD-SJU
$117
10/9Thu
1 stopDelta
9h 18mMDW-SJU
$117
11/15Sat
nonstopArajet
4h 45mORD-PUJ
$118
9/27Sat
nonstopUnited Airlines
4h 52mORD-SJU
$133

Search by stops

Search by airline

Search by price

Last minute flights from Illinois to Caribbean Islands

Last minute flight, train and bus deals

7/17Thu
multi-stopFrontier
6h 59mMDW-SJU
7/20Sun
multi-stopFrontier
18h 36mSJU-MDW
$238
7/14Mon
multi-stop
9h 13mORD-SJU
7/29Tue
multi-stop
11h 04mSJU-ORD
$243
7/17Thu
nonstopSpirit Airlines
4h 43mORD-SJU
7/26Sat
multi-stopSpirit Airlines
8h 26mSJU-ORD
$280
7/17Thu
nonstopSpirit Airlines
4h 43mORD-SJU
7/24Thu
multi-stopSpirit Airlines
11h 41mSJU-ORD
$289
7/17Thu
multi-stopCopa Airlines
18h 58mORD-PUJ
7/22Tue
multi-stopCopa Airlines
11h 25mPUJ-ORD
$391
7/17Thu
multi-stopAmerican Airlines
16h 38mORD-PUJ
7/24Thu
nonstopAmerican Airlines
5h 04mPUJ-ORD
$434
7/17Thu
multi-stopAmerican Airlines
17h 04mORD-PUJ
7/24Thu
nonstopAmerican Airlines
5h 04mPUJ-ORD
$442
7/13Sun
multi-stopJetBlue
9h 19mORD-MBJ
7/22Tue
multi-stopJetBlue
10h 53mMBJ-ORD
$521
7/15Tue
multi-stopCopa Airlines
9h 07mORD-PUJ
7/17Thu
multi-stopCopa Airlines
12h 42mPUJ-ORD
$553
7/14Mon
multi-stopJetBlue
30h 54mORD-AUA
7/16Wed
multi-stopJetBlue
11h 13mAUA-ORD
$895

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Caribbean Islandsfrom $279
Business Class flights to Caribbean Islandsfrom $313
Prem Econ Class flights to Caribbean Islandsfrom $108
Economy Class flights to Caribbean Islandsfrom $25

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.