$93 Find Cheap Flights from Illinois to Caribbean

1 adult
1 adult, Economy

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

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

Save 20% or moreCompare multiple travel sites with one search.

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

Free to useThere are no hidden charges or fees.

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

Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$93
Best time to beat the crowds with an average 18% 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

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Caribbean 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?

    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 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?

    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 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?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean is Punta Cana Airport (PUJ), with an average flight price of $189.

  • What is the cheapest day to fly to Caribbean?

    Based on KAYAK data, the cheapest day to fly to Caribbean is Monday where round-trip tickets can be as cheap as $386. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $444 on average.

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

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $300 on average. Morning departures are around 3% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $434.

  • What is the cheapest flight to Caribbean?

    The cheapest ticket to Caribbean from Illinois found in the last 72 hours was to San Juan Luis Munoz Marin Intl Airport, at $198 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 $226.

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

    The cheapest month for flights from Illinois to Caribbean is December, when tickets cost $597 (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?

    To get a below average price on the flight from Illinois to Caribbean, 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?

    An average nonstop flight from Illinois to Caribbean takes 6h 05m, 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 18m.

  • What are the most popular destinations in Caribbean?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (22% of total searches to Caribbean). The next most popular destinations are Montego Bay (21%) and Saint Thomas Island (10%). Searches for flights to Oranjestad (10%), to Nassau (6%) and to Providenciales (4%) are also popular.

Book cheap flights from Illinois to Caribbean

Recent round-trip flight deals

7/5Sat
1 stopFrontier
11h 07mORD-SJU
7/12Sat
1 stopFrontier
9h 21mSJU-ORD
$185
7/7Mon
1 stopFrontier
7h 06mORD-SJU
7/12Sat
1 stopFrontier
9h 21mSJU-ORD
$203
7/5Sat
1 stop
16h 35mORD-SJU
7/12Sat
1 stop
9h 21mSJU-ORD
$206
6/28Sat
1 stop
11h 00mORD-SJU
7/9Wed
1 stop
15h 21mSJU-ORD
$208
7/1Tue
1 stopSpirit Airlines
13h 45mORD-SJU
7/15Tue
1 stopSpirit Airlines
15h 21mSJU-ORD
$217
7/15Tue
1 stopSpirit Airlines
9h 25mORD-SJU
7/22Tue
1 stopSpirit Airlines
15h 21mSJU-ORD
$236
12/2Tue
nonstopArajet
4h 45mORD-PUJ
12/7Sun
nonstopArajet
5h 10mPUJ-ORD
$237
11/29Sat
nonstopArajet
4h 45mORD-PUJ
12/6Sat
nonstopArajet
5h 10mPUJ-ORD
$244
7/12Sat
nonstopSouthwest
4h 30mMDW-PUJ
7/16Wed
nonstopSouthwest
4h 50mPUJ-MDW
$260
7/1Tue
1 stopSouthwest
11h 50mMDW-SJU
7/4Fri
2 stopsSouthwest
8h 40mSJU-MDW
$327

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/25Wed
1 stopFrontier
14h 07mORD-SJU
$93
8/12Tue
1 stopSpirit Airlines
9h 25mORD-SJU
$94
7/29Tue
nonstopAmerican Airlines
4h 35mORD-PUJ
$121
7/15Tue
nonstopSouthwest
4h 30mMDW-PUJ
$121
7/29Tue
1 stopAmerican Airlines
7h 45mORD-PUJ
$125
7/15Tue
nonstopUnited Airlines
4h 42mORD-PUJ
$126
6/21Sat
nonstopSouthwest
4h 30mMDW-PUJ
$136
8/31Sun
1 stopDelta
6h 30mORD-PUJ
$156
7/28Mon
1 stopDelta
6h 27mMDW-PUJ
$156
10/17Fri
1 stopUnited Airlines
16h 00mORD-PUJ
$171

Search by stops

Search by airline

Search by price

Last minute flights from Illinois to Caribbean

Last minute flight, train and bus deals

6/20Fri
multi-stopFrontier
12h 08mORD-SJU
6/26Thu
multi-stopFrontier
8h 46mSJU-ORD
$230
6/19Thu
multi-stopFrontier
26h 16mMDW-SJU
6/22Sun
multi-stopFrontier
23h 47mSJU-MDW
$230
6/21Sat
multi-stop
11h 00mORD-SJU
6/28Sat
nonstop
5h 16mSJU-ORD
$259
6/21Sat
multi-stop
11h 00mORD-SJU
7/13Sun
multi-stop
11h 41mSJU-ORD
$269
6/20Fri
nonstopSpirit Airlines
4h 44mORD-SJU
6/28Sat
nonstopSpirit Airlines
5h 16mSJU-ORD
$332
6/21Sat
nonstopSpirit Airlines
4h 44mORD-SJU
6/28Sat
nonstopSpirit Airlines
5h 16mSJU-ORD
$333
6/17Tue
multi-stopAmerican Airlines
17h 03mORD-PUJ
6/19Thu
multi-stopAmerican Airlines
11h 16mPUJ-ORD
$355
6/17Tue
multi-stopAmerican Airlines
7h 31mORD-PUJ
6/24Tue
nonstopAmerican Airlines
5h 05mPUJ-ORD
$369
6/21Sat
nonstopSouthwest
4h 30mMDW-PUJ
6/24Tue
multi-stopSouthwest
7h 35mPUJ-MDW
$505
6/20Fri
multi-stopSouthwest
9h 50mMDW-SJU
6/24Tue
multi-stopSouthwest
6h 50mSJU-MDW
$535

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Caribbean

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 Caribbeanfrom $657
Business Class flights to Caribbeanfrom $991
Prem Econ Class flights to Caribbeanfrom $781
Economy Class flights to Caribbeanfrom $198

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