Cheap flights from Chicago to Caribbean Islands from $82
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Caribbean Islands departing on 5/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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1 adult
Economy
0 bags
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One-way
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Cheap round-trip flights
These are some of the best round-trip flight deals from Chicago to Caribbean Islands that have been recently found on momondo from popular airlines, departing in the coming months.
Cheap one-way flights
Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Caribbean Islands.
Cheap last minute flights
Planning a quick getaway from Chicago to Caribbean Islands? These are the last-minute flight deals available now.
Cheap direct flights
If you prefer a non-stop journey, check out our latest direct flight deals to Caribbean Islands, so you can enjoy a seamless trip without layovers.
Spirit Airlines flights from Chicago to Caribbean Islands
Our best Spirit Airlines deals on Chicago to Caribbean Islands flight tickets
Spirit Airlines![Spirit Airlines]()
May 19![Spirit Airlines]()
May 29
ORD11:30 amChicago O'Hare Intl
4h 46m
SJU5:16 pmSan Juan Luis Munoz Marin Intl
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
May 25![Spirit Airlines]()
Jun 2
ORD8:17 amChicago O'Hare Intl
10h 45m
1 stop
SJU8:02 pmSan Juan Luis Munoz Marin Intl
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
Southwest flights from Chicago to Caribbean Islands
Our best Southwest deals on Chicago to Caribbean Islands flight tickets
Southwest![Southwest]()
May 12![Southwest]()
May 29
MDW2:40 pmChicago Midway
8h 15m
2 stops
SJU11:55 pmSan Juan Luis Munoz Marin Intl
SJU3:25 pmSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
MDW10:40 pmChicago Midway
Southwest![Southwest]()
Sep 16![Southwest]()
Sep 23
MDW7:30 amChicago Midway
6h 25m
1 stop
SJU2:55 pmSan Juan Luis Munoz Marin Intl
SJU7:20 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW7:10 pmChicago Midway
See travel insights to Caribbean Islands from
How to get the cheapest flight ticket from Chicago to Caribbean Islands
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
Prices
Airlines
Other information
What is the cheapest month to fly to Caribbean Islands?
The month of August is, on average, the cheapest month to fly to Caribbean Islands from Chicago, with most prices found around $296. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Chicago averaging around $309.
What is the cheapest day to depart on your flight to Caribbean Islands?
The cheapest day to depart from Chicago to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $365. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $421. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.
What is the cheapest time of day to depart on your flight to Caribbean Islands?
According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Chicago to Caribbean Islands in the evening for as low as $298. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $409. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Chicago to Caribbean Islands flight route?
Fly from Chicago O'Hare Intl to Punta Cana for the best Chicago - Caribbean Islands flight prices
How far in advance should I book a flight to Caribbean Islands?
You are more likely to see cheaper flights to Caribbean Islands from Chicago when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $367 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Chicago for as low as $293 on momondo.
What cabin class options are available on Chicago to Caribbean Islands flights?
There are 4 cabin classes available to choose from on Chicago to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Caribbean Islands?
Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating from Chicago to Caribbean Islands
What airlines fly to Caribbean Islands?
American Airlines, Spirit Airlines and United Airlines are the top three most popular airlines that fly to Caribbean Islands from Chicago according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 10 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Caribbean Islands on average per day?
The number of flights available between Chicago and Caribbean Islands is 10 per day as of April 2025. The most frequent departure time is 8:00AM, with 81% of daily flights leaving at noon.
How many flights depart from Chicago to Caribbean Islands on average per week?
73 flights are operational weekly from Chicago to Caribbean Islands as of April 2025. The most popular departure day for this route is Mon, with 21% of flights per week taking off on this day.
Cheap Chicago to Caribbean Islands flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Caribbean Islands
Best Price Found | $82 |
|---|---|
Fastest flight time | 3h 26m |
Direct flights | Every day |
Airports in Caribbean Islands | 4 airports |
When did momondo last update prices for flights from Chicago to Caribbean Islands?
Prices for flights from Chicago to Caribbean Islands were last updated today.
How many operators does momondo search for flights from Chicago to Caribbean Islands?
There are 10 operators available for flights from Chicago to Caribbean Islands as of April 2025.
How old do you have to be to fly from Chicago to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Caribbean Islands?
Based on momondo bookings for flights between Chicago and Caribbean Islands, the leading plane model is Boeing 737-800, making up 14.93% of the total bookings. Other popular models include Airbus A321neo with 13.38%, Airbus A320neo with 12.38%, and Boeing 737-900 with 7.94%.
Best airlines flying from Chicago to Caribbean Islands
Compare and see reviews for airlines that fly from Chicago to Caribbean Islands with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $124 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $142 | Free Cancellation | Rating 6.3 7,963 reviews | |||
| PriceFrom $193 | Free Cancellation | Rating 7.5 1,414 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,936 reviews | |||
| PriceFrom $226 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $293 | Free Cancellation | Rating 7.3 2,924 reviews | |||
| PriceFrom $335 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $335 | Free Cancellation | Rating 7.0 9,245 reviews | |||
| PriceFrom $345 | Free Cancellation | Rating 8.0 4,294 reviews | |||
| PriceFrom $397 | Free Cancellation | Rating 6.7 2,317 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Caribbean Islands?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Caribbean Islands. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Caribbean Islands with flexible booking policies on momondo?
All flight searches from Chicago to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Caribbean Islands?
momondo provides multiple filters to help you find the best flight to Caribbean Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Caribbean Islands right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Chicago and alert you when they change.
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