$65 Find Cheap Flights from Illinois to Caribbean Islands

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Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$65
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 28% 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 Punta Cana Airport (PUJ), with an average flight price of $216.

  • 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 $391. 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 $300 on average. Morning departures are around 4% 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 $438.

  • What is the cheapest flight to Caribbean Islands?

    The cheapest ticket to Caribbean Islands from Illinois found in the last 72 hours was to San Juan Luis Munoz Marin Intl Airport, at $208 round-trip. The most popular route is Chicago Midway Airport (MDW) to Punta Cana (PUJ) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $237.

  • 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 14m, covering a distance of 1989 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 (26% of total searches to Caribbean Islands). The next most popular destinations are Montego Bay (16%) and Oranjestad (10%). Searches for flights to Saint Thomas Island (9%), to Nassau (6%) and to Providenciales (4%) are also popular.

Book cheap flights from Illinois to Caribbean Islands

Recent round-trip flight deals

10/23Thu
1 stopFrontier
8h 05mORD-SJU
10/26Sun
1 stopFrontier
9h 49mSJU-ORD
$153
10/23Thu
1 stopFrontier
7h 00mMDW-SJU
10/26Sun
1 stopFrontier
13h 03mSJU-MDW
$159
7/31Thu
1 stop
8h 17mORD-SJU
8/8Fri
nonstop
5h 16mSJU-ORD
$194
7/22Tue
1 stopSpirit Airlines
7h 59mORD-SJU
8/7Thu
1 stopSpirit Airlines
16h 14mSJU-ORD
$203
9/12Fri
1 stop
9h 41mORD-SJU
9/16Tue
1 stop
7h 39mSJU-ORD
$216
7/21Mon
1 stopSpirit Airlines
15h 04mORD-SJU
8/2Sat
1 stopSpirit Airlines
15h 34mSJU-ORD
$220
8/9Sat
1 stopAmerican Airlines
6h 15mORD-PUJ
8/13Wed
1 stopAmerican Airlines
11h 46mPUJ-ORD
$285
8/7Thu
1 stopAmerican Airlines
15h 31mORD-PUJ
8/21Thu
nonstopAmerican Airlines
5h 00mPUJ-ORD
$304
11/4Tue
1 stopDelta
10h 46mMDW-SJU
11/11Tue
1 stopDelta
9h 54mSJU-MDW
$327
10/31Fri
1 stopDelta
10h 46mMDW-SJU
11/12Wed
1 stopDelta
9h 54mSJU-MDW
$337

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Recent one-way flight deals

8/31Sun
1 stopFrontier
8h 16mORD-SJU
$65
10/25Sat
1 stopFrontier
7h 05mMDW-SJU
$65
7/20Sun
1 stopSpirit Airlines
15h 04mORD-SJU
$92
11/15Sat
nonstopArajet
4h 45mORD-PUJ
$108
11/15Sat
nonstopArajet
4h 45mORD-PUJ
$109
8/24Sun
1 stopSpirit Airlines
11h 31mORD-SJU
$111
8/12Tue
1 stop
8h 44mORD-SJU
$114
7/15Tue
1 stop
9h 22mORD-SJU
$121
8/12Tue
nonstopAmerican Airlines
4h 40mORD-PUJ
$126
8/4Mon
1 stopAmerican Airlines
16h 15mORD-PUJ
$131

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Last minute flights from Illinois to Caribbean Islands

Last minute flight, train and bus deals

7/8Tue
multi-stop
13h 40mORD-SJU
7/31Thu
multi-stop
16h 14mSJU-ORD
$266
7/7Mon
multi-stop
9h 13mORD-SJU
7/14Mon
nonstop
5h 16mSJU-ORD
$269
7/8Tue
multi-stopFrontier
13h 40mORD-SJU
7/14Mon
multi-stopFrontier
7h 40mSJU-ORD
$284
7/4Fri
multi-stopFrontier
12h 08mORD-SJU
7/11Fri
multi-stopFrontier
13h 39mSJU-ORD
$286
7/8Tue
nonstopSpirit Airlines
4h 44mORD-SJU
7/11Fri
multi-stopSpirit Airlines
11h 41mSJU-ORD
$301
7/8Tue
nonstopSpirit Airlines
4h 44mORD-SJU
7/12Sat
nonstopSpirit Airlines
5h 16mSJU-ORD
$314
7/7Mon
multi-stopAmerican Airlines
14h 43mORD-PUJ
7/10Thu
multi-stopAmerican Airlines
12h 52mPUJ-ORD
$350
7/8Tue
multi-stopAmerican Airlines
15h 39mORD-PUJ
7/30Wed
nonstopAmerican Airlines
5h 05mPUJ-ORD
$379
7/8Tue
multi-stopSouthwest
10h 25mMDW-SJU
7/22Tue
multi-stopSouthwest
9h 20mSJU-MDW
$468
7/8Tue
multi-stopSouthwest
11h 05mMDW-SJU
7/29Tue
multi-stopSouthwest
9h 45mSJU-MDW
$493

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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 $279
Business Class flights to Caribbean Islandsfrom $298
Prem Econ Class flights to Caribbean Islandsfrom $108
Economy Class flights to Caribbean Islandsfrom $25

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