$104 Find Cheap Flights from Chicago to Caribbean - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Caribbean departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Chicago to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$374
Santo Domingo
Santo Domingo1 stop$341
Montego Bay
Montego Baynonstop$428
Oranjestad
Oranjestad1 stop$482
Nassau
Nassau1 stop$365
Kingston
Kingston1 stop$458
Simpson Bay
Simpson Bay1 stop$419
Providenciales
Providenciales1 stop$442
George Town
George Town1 stop$394
Aguadilla
Aguadilla1 stop$362
St. John's
St. John's1 stop$557
Punta Cana
Punta Cananonstop$374
Santo Domingo
Santo Domingo1 stop$341
Montego Bay
Montego Baynonstop$428
Oranjestad
Oranjestad1 stop$482
Nassau
Nassau1 stop$365
Kingston
Kingston1 stop$458
Simpson Bay
Simpson Bay1 stop$419
Providenciales
Providenciales1 stop$442
George Town
George Town1 stop$394
Aguadilla
Aguadilla1 stop$362
St. John's
St. John's1 stop$557

Book Cheap Chicago to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Caribbean

Sun, Aug 23 - Sat, Aug 29
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$226Frontier
Tue, Aug 25 - Tue, Sep 1
Frontier Logo
8:05 am - 4:11 pm
ORD
-
SJU
31h 06m
1 stop
Frontier Logo
6:35 am - 12:50 pm
SJU
-
ORD
31h 15m
1 stop
$227Frontier
Tue, Aug 18 - Mon, Aug 31
Multiple Airlines Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Multiple Airlines Logo
5:37 pm - 12:50 pm
SJU
-
ORD
20h 13m
2 stops
$238Multiple Airlines
Wed, Aug 26 - Mon, Aug 31
Multiple Airlines Logo
8:05 am - 4:11 pm
ORD
-
SJU
31h 06m
1 stop
Multiple Airlines Logo
5:37 pm - 12:50 pm
SJU
-
ORD
20h 13m
2 stops
$248Multiple Airlines
Sun, Aug 23 - Sat, Aug 29
American Airlines Logo
5:20 pm - 11:15 pm
ORD
-
SJU
4h 55mnonstop
American Airlines Logo
12:55 am - 5:00 am
SJU
-
ORD
5h 05mnonstop
$265American Airlines
Mon, Aug 24 - Sat, Aug 29
American Airlines Logo
5:20 pm - 11:15 pm
ORD
-
SJU
4h 55mnonstop
American Airlines Logo
12:55 am - 5:00 am
SJU
-
ORD
5h 05mnonstop
$265American Airlines
Wed, Sep 2 - Wed, Sep 16
United Airlines Logo
8:55 am - 2:44 pm
ORD
-
SJU
4h 49mnonstop
United Airlines Logo
3:56 pm - 8:05 pm
SJU
-
ORD
5h 09mnonstop
$265United Airlines
Tue, Sep 22 - Tue, Sep 29
United Airlines Logo
8:55 am - 2:44 pm
ORD
-
SJU
4h 49mnonstop
United Airlines Logo
3:56 pm - 8:05 pm
SJU
-
ORD
5h 09mnonstop
$265United Airlines
Tue, Sep 8 - Wed, Sep 9
Southwest Logo
12:45 pm - 10:05 pm
MDW
-
SJU
8h 20m
2 stops
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
1 stop
$269Southwest
Tue, Sep 8 - Wed, Sep 9
Southwest Logo
12:20 pm - 9:10 pm
MDW
-
SJU
7h 50m
1 stop
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
1 stop
$269Southwest
Booking Insights

KAYAK's insights & trends for Chicago to Caribbean flights

Get data-powered insights and trends into flights from Chicago to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Chicago found in the last 5 days was to San Juan, at $161 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $161.

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

The average price for all round-trip flights from Chicago to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $365 on average. Morning departures are around 19% 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 $525.

Can I save money by flying with a layover from Chicago to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $658, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Caribbean is August, when tickets cost $442 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $611 and $598 respectively.

What’s the cheapest day of the week to fly from Chicago to Caribbean?

The average price of all round-trip flights from Chicago to Caribbean clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Tuesday and more expensive on a Friday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low season

September

Cheapest flight

$104
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago O'Hare Airport to San Juan

FAQs - booking Caribbean flights

  • Are there special amenities for travelers with infants in Chicago O'Hare International Airport ?

    There are mother’s rooms located in each terminal. They have seats, changing tables, and sinks where you can nurse or let your child nap before departure. Designated lactation pods are available in all terminals. There are vending machines that dispense formula, bottles, diapers, and wipes 24 hours a day. Their locations include Main Hall K1 and Gate G2, Concourse G in Terminal 3.

  • What are the public transport options from downtown Chicago to Chicago O'Hare International Airport (ORD)?

    Buses from Peoria Charter Coach Company operate twice a day from Union Station and Jackson & Canal to Terminal 2 with a travel time of approximately 30 minutes. Taxi services are offered by agencies such as Yellow Cab Chicago and Flash Cab, with a commute time of approximately 23 minutes. Shuttles by Jayride company provide transport services on demand, with a commute time of around 22 minutes.

  • Which airline flying from Chicago to the Caribbean provides unaccompanied minor services?

    American Airlines allow children from five to 14 years to travel alone without an adult present. However, an adult must accompany the child to the departure gate and wait until the flight has taken off. Contact information of the adult meeting the child upon arrival must be provided. An airport escort accompanies your child during flight connections and brings them to the authorized adult at the destination.

  • Which airline offering flights from Chicago to the Caribbean has favorable pet policies?

    Delta Air Line allows cats, dogs, and small household birds on board. Your pet is required to stay inside a carrier with the door securely closed for the entirety of the flight. A soft-sided carrier is recommended, with dimensions no larger than approximately 18x11x11 inches. Two pets of the same species can travel in one carrier. There are no maximum weight restrictions for pets flying in the cabin.

  • How does KAYAK find such low prices on flights from Chicago 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 Chicago to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 Chicago 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 Chicago 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 Chicago 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 Chicago to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean

  • Most airlines offering flights from Chicago to the Caribbean depart from Chicago O'Hare International Airport (ORD). American Airlines and Spirit Airlines operate from Terminal 3, while Southwest Airlines and Delta operate from Terminal 5.
  • Chicago O'Hare International Airport (ORD) is the hub for American Airlines. The airline provides multiple daily flights to several destinations in the Caribbean, such as Punta Cana and Santo Domingo.
  • Another airport choice available when departing from Chicago is Chicago Midway International Airport (MDW). This airport is recommended if you are traveling from the city, as it is a short distance from downtown with less traffic congestion. The airport also offers shorter waiting times as it is less busy compared to ORD.
  • Wheelchair assistance is offered while transiting through the airport by all airlines operating in ORD. All washrooms located in the terminals are wheelchair accessible. Braille lettering and raised numbers are installed on the elevator buttons to allow accessibility by the visually impaired.
  • Several airlines offer connecting flights from ORD to the Caribbean with layovers in different cities. Delta flies to Punta Cana International Airport (PUJ) with a layover in Atlanta, while Spirit Airlines has a layover in Fort Lauderdale for the same route. American Airlines offers two-stop flights to the Bahamas' Lynden Pindling International Airport (NAS), with layovers at New York and Miami.

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.