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Cheap flights from Chicago (CHI) to Caribbean Islands from $81

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. 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.
CHI — SJU
May 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
1 adult, Economy
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How far in advance should I book a flight from Chicago to Caribbean Islands?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 57 days in advance, which can save you up to 20% on flights from Chicago to Caribbean Islands compared to booking the week you need them. Waiting 57 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $258. For sooner than that we have options available in the next 3 days from $280.

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

Our data shows that October tends to be the cheapest month to fly to Caribbean Islands from Chicago. Users have commonly found prices around $318 for the month, but tickets can be as low as $90. Due to multiple factors, prepare for potentially higher prices in March.

When is the cheapest time to fly from Chicago to Caribbean Islands (CHI - EPX)?

When flying from Chicago to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Spirit Airlines flights from Chicago to Caribbean Islands

Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Caribbean Islands. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Find some of the cheapest Spirit Airlines flights traveling from Chicago to Caribbean Islands. Come back soon if you're not finding the exact deal you're looking for.
Tue 8/205:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$114
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$127
Thu 5/309:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$129
Wed 9/1110:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Sat 9/2112:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/14$131
Tue 9/1010:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Tue 9/1712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$135
Tue 8/2010:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Tue 8/274:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/15$137
Mon 9/166:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Sat 9/2112:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/15$148
Tue 8/207:03 amORD - SJU
2 stops10h 54mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$152
Thu 5/3010:03 amORD - SJU
1 stop7h 54mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$153

Cheap Delta flights from Chicago to Caribbean Islands

Explore cheap flight options specifically provided by Delta for the route between Chicago and Caribbean Islands. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
To aid your search, here are some of the cheapest Delta flights we've found from Chicago to Caribbean Islands. Ensure the flight price, dates, time, and airline match your criteria before you book.
Wed 6/127:00 amORD - NAS
1 stop6h 40mDelta
Tue 6/183:55 pmNAS - ORD
1 stop7h 51mDelta
Deal found 5/16$351
Fri 7/123:47 pmMDW - SJU
1 stop6h 12mDelta
Sat 7/276:10 amSJU - MDW
1 stop9h 47mDelta
Deal found 5/15$373
Sat 5/255:57 pmORD - SXM
1 stop18h 43mDelta
Thu 5/303:10 pmSXM - ORD
1 stop18h 07mDelta
Deal found 5/15$857

Cheap Chicago to Caribbean Islands flights in May & June 2024

Find cheap flight options from Chicago to Caribbean Islands specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 2024.
Check out some of the best flight deals from Chicago to Caribbean Islands in 2024. For more flight deals, be sure to check back very soon.
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$184
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/15$185
Tue 6/118:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Deal found 5/15$187
Sat 6/111:05 amORD - SJU
1 stop12h 42mMultiple Airlines
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mMultiple Airlines
Deal found 5/15$188
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Tue 7/239:15 pmSJU - ORD
1 stop13h 08mSpirit Airlines
Deal found 5/15$189
Sun 6/26:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/15$191
Sat 6/111:05 amORD - SJU
1 stop12h 42mMultiple Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mMultiple Airlines
Deal found 5/15$192
Thu 5/309:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Tue 6/412:32 pmSJU - ORD
1 stop10h 24mSpirit Airlines
Deal found 5/15$193
Tue 6/45:41 pmORD - STT
1 stop14h 59mSpirit Airlines
Tue 6/1110:30 amSTT - ORD
1 stop6h 58mSpirit Airlines
Deal found 5/15$194

Chicago to Caribbean Islands 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Caribbean Islands in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Check out some of the best flight deals from Chicago to Caribbean Islands in 2024. For more flight deals, be sure to check back very soon.
Tue 7/27:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Tue 7/99:06 pmSJU - ORD
1 stop13h 17mSpirit Airlines
Deal found 5/15$183
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$184
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/15$185
Tue 8/207:03 amORD - SJU
2 stops10h 54mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/15$186
Wed 8/2811:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$187
Sat 6/111:05 amORD - SJU
1 stop12h 42mMultiple Airlines
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mMultiple Airlines
Deal found 5/15$188
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Tue 7/239:15 pmSJU - ORD
1 stop13h 08mSpirit Airlines
Deal found 5/15$189
Mon 9/165:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Sat 9/216:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$190
Sun 6/26:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/15$191

Non-stop flights to Caribbean Islands from Chicago

Discover non-stop flight options from Chicago to Caribbean Islands. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Consider booking one of these non-stop flights heading from Chicago to Caribbean Islands. Users can also choose from other Chicago to Caribbean Islands flights by using the search form above.
Tue 9/1011:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 9/176:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$177
Tue 8/209:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 8/274:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/15$182
Wed 8/2811:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$187
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/14$196
Wed 9/1111:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Sat 9/216:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/14$201
Tue 8/209:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 8/274:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/15$202
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/14$204
Wed 8/289:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sat 9/76:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$213
Wed 6/510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 6/126:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/15$215

Chicago to Caribbean Islands flights leaving soon

Find last-minute flight options from Chicago to Caribbean Islands for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Have a look at some of the flights available from Chicago to Caribbean Islands departing last-minute. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/299:07 pmSJU - ORD
2 stops20h 21mSpirit Airlines
Deal found 5/14$194
Tue 5/215:56 pmORD - SJU
1 stop7h 13mMultiple Airlines
Sat 5/2512:32 pmSJU - ORD
1 stop9h 00mMultiple Airlines
Deal found 5/15$197
Sat 5/256:40 pmORD - SJU
1 stop15h 52mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$198
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/2912:32 pmSJU - ORD
3 stops22h 23mSpirit Airlines
Deal found 5/14$200
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Fri 5/319:00 pmSJU - ORD
3 stops22h 23mSpirit Airlines
Deal found 5/14$201
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Thu 5/3011:07 pmSJU - ORD
1 stop11h 48mSpirit Airlines
Deal found 5/14$204
Sat 5/2511:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$205
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Fri 5/319:00 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/14$206
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Fri 5/319:00 pmSJU - ORD
2 stops22h 23mSpirit Airlines
Deal found 5/14$210

One-way flights to Caribbean Islands from Chicago

Search for one-way flight options from Chicago to Caribbean Islands. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Users in need of a one-way flight from Chicago to Caribbean Islands can choose from these deals. Those needing a return flight from Chicago to Caribbean Islands can use the search form above.
Mon 8/126:26 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 5/14$81
Sat 8/106:59 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 5/14$82
Tue 6/47:00 amORD - SJU
2 stops10h 57mSpirit Airlines
Deal found 5/15$87
Thu 5/3010:03 amORD - SJU
1 stop7h 54mSpirit Airlines
Deal found 5/14$88
Wed 5/298:09 pmORD - SJU
1 stop21h 48mSpirit Airlines
Deal found 5/14$89
Tue 6/49:57 amORD - SJU
1 stop8h 00mSpirit Airlines
Deal found 5/15$90
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Deal found 5/15$91
Wed 10/25:00 amORD - SXM
1 stop7h 44mSpirit Airlines
Deal found 5/15$91
Wed 5/297:20 amORD - SJU
2 stops18h 45mSpirit Airlines
Deal found 5/15$95

Find flights from Chicago to Caribbean Islands within your budget

Customize your flight search to find flights from Chicago to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$114 - $351

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop13h 11m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$114

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$127

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/30

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Mon 6/3

1 stop13h 48m

$129

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/11

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Sat 9/21

1 stop9h 04m

$131

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/29

1 stop12h 52m

San Juan Luis Munoz Marin Intl

Tue 6/4

1 stop13h 54m

$171

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 7/7

Nonstop4h 44m

Punta Cana

Tue 8/6

Nonstop5h 03m

$179

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 6/1

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Tue 6/4

1 stop13h 54m

$179

Chicago O'Hare IntlNassau Intl

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Wed 6/19

1 stop7h 33m

Nassau Intl

Tue 6/25

1 stop14h 25m

$350

Chicago O'Hare IntlNassau Intl

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Wed 6/12

1 stop6h 40m

Nassau Intl

Tue 6/18

1 stop7h 51m

$351

Flights are sorted by cheapest first

Deals found on 5/15

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated May 16, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Delta and Frontier from Chicago to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,673 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

JetBlue
7.6
Good
4,472 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.5
Good
2,919 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Avianca
7.5
Good
3,765 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

United Airlines
7.4
Good
10,924 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

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

  • Can I find flights from Chicago to Caribbean Islands for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Caribbean Islands for under $200. The cheapest flight booked recently is on Spirit Airlines for just $114, but on average you can expect to pay $152.

  • Are there nonstop flights from Chicago to Caribbean Islands for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Caribbean Islands under $200. A good price for a nonstop flight from Chicago to Caribbean Islands is less than $213.

  • Are there last-minute flights available from Chicago to Caribbean Islands for under $200?

    There are currently 20+ open flights from Chicago to Caribbean Islands within the next 7 days for less than $200.

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

    When deciding which route to take from Chicago to Caribbean Islands consider Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana or Chicago Midway - San Juan Luis Munoz Marin Intl as they are the most popular.

  • What are the most popular airlines that fly from Chicago to Caribbean Islands?

    The most popular airlines flying from Chicago to Caribbean Islands are American Airlines, Alaska Airlines and JetBlue. Something to consider prior to booking your flight.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Caribbean Islands consider choosing Alaska Airlines (93%), American Airlines (92%) or United Airlines (83%) as they are the most reliable in getting you off to your destination on time.

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

    Looking for the cheapest flight from Chicago to Caribbean Islands? While on average our users pay $527, our data indicates the cheapest price to be $87. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $125.

  • What does ORD to SJU mean?

    ORD and SJU are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ORD to SJU refers to a flight route from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Caribbean Islands that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Caribbean Islands flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Caribbean Islands with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Caribbean Islands flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

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

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

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

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

  • Can I find deals for flights from Chicago to Caribbean Islands that allow pets onboard?

    Many airlines flying from Chicago to Caribbean Islands offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Caribbean Islands?

    Yes, you can often find last-minute deals on Chicago to Caribbean Islands flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Caribbean Islands flight deals updated?

    The Chicago to Caribbean Islands flight deals you see on this page were last updated on 5/15.

See more FAQs

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Alternative routes for Chicago to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.

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Top 10 airlines flying from Chicago to Caribbean Islands

Discover the top 10 airlines that operate flights from Chicago to Caribbean Islands. 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 2,637,452 searches. Data last updated May 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$329FlexibilityNo cancel feeOn-time62%
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Spirit AirlinesCheapest$132Average$386FlexibilityNo cancel feeOn-time65%
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DeltaCheapest$137Average$618FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapest$153Average$602FlexibilityNo cancel feeOn-time69%
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JetBlueCheapest$172Average$549FlexibilityNo cancel feeOn-time62%
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AeromexicoCheapest$262Average$548FlexibilityNo cancel feeOn-timeN/A
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Air CanadaCheapest$283Average$846FlexibilityNo cancel feeOn-time67%
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Alaska AirlinesCheapest$288Average$620FlexibilityNo cancel feeOn-time75%
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American AirlinesCheapest$291Average$611FlexibilityNo cancel feeOn-time71%
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LufthansaCheapest$405Average$452FlexibilityNo cancel feeOn-time76%
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Search flights from Chicago to Caribbean Islands by cabin class

Find flights from Chicago to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Chicago to Caribbean Islands

Find hourly flight availability from Chicago to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 16, 2024.
18%of flight departuresEarly morningMidnight to 6 am
82%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Caribbean Islands?

Deals for Chicago to Caribbean Islands flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Caribbean Islands?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Caribbean Islands.

Can Cheapflights find flights from Chicago to Caribbean Islands with no change fees?

Need flexible booking options for your flight to Caribbean Islands from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Caribbean Islands become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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