Cheap flights from Caribbean Islands to Chicago from $87
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean Islands to Chicago departing on 6/3. 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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How to get the cheapest flight ticket from Caribbean Islands to Chicago
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
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Caribbean Islands, with most prices found around $232. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Caribbean Islands to Chicago during August average around $271.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Caribbean Islands to Chicago for around $455.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Caribbean Islands to Chicago during this time can be as low as $243. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $476.
What is the cheapest Caribbean Islands to Chicago flight route?
Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Caribbean Islands - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Caribbean Islands when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $305 when searching 4 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Caribbean Islands for as low as $235 on momondo.
What cabin class options are available on Caribbean Islands to Chicago flights?
There are 4 cabin classes available to choose from on Caribbean Islands to Chicago 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 Caribbean Islands to Chicago?
Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from Caribbean Islands to Chicago
What airlines fly to Chicago?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Caribbean Islands according to our data. Spirit Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Caribbean Islands to Chicago on average per day?
As of May 2025, there are 12 flights per day flying from Caribbean Islands to Chicago. The most common time of day flights depart is 3:00PM, with 71% of flights taking off in the afternoon.
How many flights depart from Caribbean Islands to Chicago on average per week?
As of May 2025, 84 flights take off from Caribbean Islands and land in Chicago each week. The most common flight departure day for this route is Sat, with 17% of weekly flights taking off on this day.
Cheap Caribbean Islands to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Caribbean Islands to Chicago
When did momondo last update prices for flights from Caribbean Islands to Chicago?
Prices for flights from Caribbean Islands to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Caribbean Islands to Chicago?
The number of operators available for flights from Caribbean Islands to Chicago is 6 as of May 2025.
How old do you have to be to fly from Caribbean Islands to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean Islands to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Caribbean Islands to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Caribbean Islands to Chicago is Boeing 737-800 (19.63% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (10.07%), Airbus A320neo (8.28%), and Airbus A321neo (8.20%).
Best airlines flying from Caribbean Islands to Chicago
Compare and see reviews for airlines that fly from Caribbean Islands to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $137 | Free Cancellation | Rating 5.9 3,286 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 6.3 7,984 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 7.4 8,724 reviews | |||
| PriceFrom $257 | Free Cancellation | Rating 8.0 4,290 reviews | |||
| PriceFrom $323 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Caribbean Islands to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Caribbean Islands to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Caribbean Islands to Chicago with flexible booking policies on momondo?
Flights from Caribbean Islands to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Caribbean Islands to Chicago?
Once you have performed a search for Caribbean Islands to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Caribbean Islands to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Caribbean Islands and alert you when they change.