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Cheap flights from Caribbean Islands to Chicago (CHI)

SJU — CHI
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
1 adult, Economy
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Find flight deals from Caribbean Islands to Chicago

Keep the following information in mind while searching for Caribbean Islands to Chicago flight deals. Data was last updated May 14, 2026.

Round-trip from

$201
(CheapOair)

One-way from

$112
(Kiwi.com)
From Caribbean Islands to Chicago (CHI)
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One-way flight from Caribbean Islands to Chicago (CHI)
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Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Chicago

What is the cheapest month to book a flight from Caribbean Islands to Chicago?

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $139). Flying from Caribbean Islands to Chicago in February is currently the most expensive (average of $221). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EPX to CHI?

Find hourly flight availability from Caribbean Islands to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 14, 2026.

It’s typically best to fly out from Caribbean Islands to Chicago in the evening. Doing so could potentially save you 47% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Caribbean Islands to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Chicago. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Caribbean Islands to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 14, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican Airlines from Caribbean Islands to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,454 reviews

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.9
Good
8,454 reviews
Delta
7.9
Good
8,454 reviews

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
9,711 reviews
Delta
7.9
Good
8,454 reviews

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,664 reviews
Delta
7.9
Good
8,454 reviews

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Caribbean Islands to Chicago?

    JetBlue, United Airlines, and Frontier can get you from Caribbean Islands to Chicago in just under 6h 20m. Your travel time can differ by up to 10h 59m. There are 1312 mi between Caribbean Islands and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean Islands to Chicago one-way?

    One-way options have recently been found by users for as low as $74 on JetBlue. Other airlines that offer cheap prices include Frontier from $95 and Spirit Airlines from $97 one-way.

  • What are the most popular routes from Caribbean Islands to Chicago?

    The most popular route from Caribbean Islands to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Punta Cana - Chicago O'Hare Intl.

  • What are the most reliable airlines from Caribbean Islands to Chicago?

    The top 3 most reliable airlines when flying from Caribbean Islands to Chicago are Air Canada (89%), United Airlines (89%) and Air New Zealand (89%).

  • What are the cheapest flights from Caribbean Islands to Chicago?

    While on average a flight from Caribbean Islands to Chicago is generally $470, our data shows the cheapest flight currently is $99. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $226 for that flight.

  • Can I find deals for flights from Caribbean Islands to Chicago that include hotel bookings?

    Yes. In addition to deals on Caribbean Islands to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean Islands to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Chicago.

  • Can I find deals for business class flights from Caribbean Islands to Chicago?

    Yes. Cheapflights offers flight deals from Caribbean Islands to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Caribbean Islands to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $139). Flying from Caribbean Islands to Chicago in February is currently the most expensive (average of $221). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Caribbean Islands to Chicago

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Top 8 airlines flying from Caribbean Islands to Chicago

Discover the top 8 airlines that operate flights from Caribbean Islands to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$566FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$119Average$254FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$120Average$265FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
ArajetCheapest$195Average$404FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$256Average$481FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$534FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$512FlexibilityNo cancel feeOn-time63%

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