$89 Find Cheap Flights from Illinois to Caribbean Islands

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Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$89
Best time to beat the crowds with an average 16% 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 $246.

  • 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 $395. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $447 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 $301 on average. Morning departures are around 6% 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 $441.

  • 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 $244 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 $253.

  • 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 5 weeks before departure.

  • How long is the flight to Caribbean Islands?

    An average nonstop flight from Illinois to Caribbean Islands takes 5h 58m, covering a distance of 1987 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 25m.

  • What are the most popular destinations in Caribbean Islands?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (22% of total searches to Caribbean Islands). The next most popular destinations are Montego Bay (20%) and Saint Thomas Island (10%). Searches for flights to Oranjestad (10%), to Nassau (6%) and to Providenciales (5%) are also popular.

Book cheap flights from Illinois to Caribbean Islands

Recent round-trip flight deals

9/3Wed
nonstopSpirit Airlines
4h 41mORD-SJU
9/11Thu
1 stopSpirit Airlines
11h 42mSJU-ORD
$203
8/3Sun
1 stopSpirit Airlines
14h 35mORD-SJU
8/8Fri
1 stopSpirit Airlines
16h 14mSJU-ORD
$204
12/5Fri
1 stopFrontier
6h 54mMDW-SJU
12/10Wed
1 stopFrontier
7h 33mSJU-MDW
$220
9/8Mon
1 stopDelta
8h 27mORD-SJU
9/13Sat
1 stopDelta
10h 01mSJU-ORD
$243
9/8Mon
1 stopDelta
9h 36mMDW-SJU
9/12Fri
1 stopDelta
9h 38mSJU-MDW
$243
11/18Tue
nonstopArajet
4h 45mORD-PUJ
11/23Sun
nonstopArajet
5h 10mPUJ-ORD
$249
8/16Sat
1 stopFrontier
11h 07mORD-SJU
8/28Thu
1 stopFrontier
9h 33mSJU-ORD
$251
12/2Tue
nonstopArajet
4h 45mORD-PUJ
12/7Sun
nonstopArajet
5h 10mPUJ-ORD
$253
10/1Wed
1 stop
15h 27mORD-SJU
10/4Sat
1 stop
16h 57mSJU-ORD
$260
7/28Mon
1 stop
12h 31mORD-SJU
8/9Sat
1 stop
15h 34mSJU-ORD
$263

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Recent one-way flight deals

9/13Sat
1 stopSpirit Airlines
15h 27mORD-SJU
$89
7/22Tue
1 stopSpirit Airlines
7h 59mORD-SJU
$93
12/6Sat
1 stopFrontier
6h 54mMDW-SJU
$94
8/24Sun
1 stopFrontier
7h 11mMDW-SJU
$104
11/29Sat
nonstopArajet
4h 45mORD-PUJ
$114
11/16Sun
nonstopArajet
4h 45mORD-PUJ
$118
9/8Mon
1 stopDelta
9h 51mORD-SJU
$122
10/28Tue
1 stopDelta
9h 18mMDW-SJU
$122
8/24Sun
nonstopAmerican Airlines
4h 40mORD-PUJ
$155
8/25Mon
nonstopAmerican Airlines
4h 40mORD-PUJ
$163

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Last minute flights from Illinois to Caribbean Islands

Last minute flight, train and bus deals

7/22Tue
multi-stopSpirit Airlines
7h 59mORD-SJU
8/1Fri
multi-stopSpirit Airlines
16h 14mSJU-ORD
$207
7/22Tue
multi-stopSpirit Airlines
7h 59mORD-SJU
8/1Fri
nonstopSpirit Airlines
5h 16mSJU-ORD
$221
7/22Tue
multi-stopSpirit Airlines
7h 59mORD-SJU
7/24Thu
nonstopSpirit Airlines
5h 16mSJU-ORD
$225
7/22Tue
multi-stop
7h 59mORD-SJU
7/31Thu
multi-stop
19h 28mSJU-ORD
$245
7/19Sat
multi-stop
16h 31mORD-SJU
7/31Thu
multi-stop
11h 41mSJU-ORD
$251
7/18Fri
multi-stopFrontier
12h 31mORD-SJU
7/24Thu
multi-stopFrontier
10h 14mSJU-ORD
$286
7/18Fri
multi-stopFrontier
14h 57mMDW-SJU
7/23Wed
multi-stopFrontier
12h 21mSJU-MDW
$286
7/21Mon
multi-stopCopa Airlines
8h 58mORD-PUJ
7/29Tue
multi-stopCopa Airlines
11h 25mPUJ-ORD
$391
7/19Sat
multi-stopAmerican Airlines
17h 15mORD-PUJ
7/24Thu
nonstopAmerican Airlines
5h 04mPUJ-ORD
$434
7/22Tue
nonstopAmerican Airlines
4h 10mORD-MBJ
7/25Fri
multi-stopAmerican Airlines
13h 57mMBJ-ORD
$440

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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 $280
Business Class flights to Caribbean Islandsfrom $313
Prem Econ Class flights to Caribbean Islandsfrom $108
Economy Class flights to Caribbean Islandsfrom $25

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