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Cheap flights from Chicago (CHI) to Caribbean Islands from $62

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 5/29. 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 11 — May 181
From?
To?
Sat 5/11
Sat 5/18
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 Frontier flights from Chicago to Caribbean Islands

Explore cheap flight options specifically provided by Frontier 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 2,689,106 searches. Data last updated May 6, 2024.
Find some of the cheapest Frontier flights traveling from Chicago to Caribbean Islands. Come back soon if you're not finding the exact deal you're looking for.
Wed 5/1512:28 pmMDW - SJU
1 stop9h 38mFrontier
Wed 5/229:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/5$177
Mon 5/135:47 amORD - PUJ
Nonstop4h 41mFrontier
Wed 5/1512:43 pmPUJ - ORD
Nonstop5h 29mFrontier
Deal found 5/5$179
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Tue 5/212:51 pmSJU - MDW
1 stop7h 40mFrontier
Deal found 5/4$187
Mon 5/137:17 pmMDW - SJU
1 stop12h 17mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/5$188
Sun 5/125:47 amORD - PUJ
Nonstop4h 41mFrontier
Wed 5/1512:43 pmPUJ - ORD
Nonstop5h 29mFrontier
Deal found 5/5$189
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Tue 5/213:00 amSJU - MDW
1 stop28h 54mFrontier
Deal found 5/5$192
Sun 5/125:47 amORD - PUJ
Nonstop4h 41mFrontier
Fri 5/174:52 pmPUJ - ORD
1 stop9h 16mFrontier
Deal found 5/5$202
Sun 5/197:49 amMDW - SJU
1 stop25h 58mFrontier
Mon 5/202:48 amSJU - MDW
1 stop29h 06mFrontier
Deal found 5/4$208
Mon 5/207:23 pmMDW - PUJ
1 stop13h 19mFrontier
Tue 5/216:16 pmPUJ - MDW
1 stop25h 11mFrontier
Deal found 5/5$212

Cheap American Airlines flights from Chicago to Caribbean Islands

Explore cheap flight options specifically provided by American 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 2,689,106 searches. Data last updated May 6, 2024.
To aid your search, here are some of the cheapest American Airlines flights we've found from Chicago to Caribbean Islands. Ensure the flight price, dates, time, and airline match your criteria before you book.
Mon 5/138:30 amORD - PUJ
Nonstop4h 35mAmerican Airlines
Thu 5/163:09 pmPUJ - ORD
Nonstop5h 05mAmerican Airlines
Deal found 5/5$237
Thu 5/165:15 amORD - SJU
1 stop14h 00mAmerican Airlines
Mon 5/2012:45 amSJU - ORD
1 stop9h 40mAmerican Airlines
Deal found 5/5$246
Sat 5/1112:40 pmORD - SJU
1 stop7h 20mAmerican Airlines
Sat 5/1112:45 amSJU - ORD
1 stop11h 25mAmerican Airlines
Deal found 5/5$260
Thu 5/96:30 amORD - SJU
1 stop12h 45mAmerican Airlines
Fri 5/1012:45 amSJU - ORD
1 stop12h 47mAmerican Airlines
Deal found 5/5$265
Fri 5/1011:50 amORD - SJU
1 stop9h 55mAmerican Airlines
Sat 5/1112:45 amSJU - ORD
1 stop11h 25mAmerican Airlines
Deal found 5/5$266
Wed 5/158:23 amORD - SJU
Nonstop4h 40mAmerican Airlines
Mon 5/2012:45 amSJU - ORD
1 stop9h 40mAmerican Airlines
Deal found 5/5$272
Mon 5/135:15 amORD - PUJ
1 stop7h 10mAmerican Airlines
Wed 5/153:09 pmPUJ - ORD
Nonstop5h 05mAmerican Airlines
Deal found 5/5$282
Sun 9/18:34 amORD - PUJ
Nonstop4h 35mAmerican Airlines
Thu 9/56:21 pmPUJ - ORD
1 stop17h 33mAmerican Airlines
Deal found 5/5$291
Mon 9/168:20 pmORD - PUJ
1 stop13h 42mAmerican Airlines
Fri 9/206:21 pmPUJ - ORD
1 stop15h 41mAmerican Airlines
Deal found 5/5$295

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 2,689,106 searches. Prices were last updated on May 6, 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.
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Wed 5/229:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/5$148
Tue 5/286:40 pmORD - STT
1 stop13h 54mSpirit Airlines
Tue 6/410:26 amSTT - ORD
1 stop8h 14mSpirit Airlines
Deal found 5/5$174
Sat 5/185:45 pmMDW - SJU
1 stop8h 35mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/5$176
Fri 5/177:23 pmMDW - SJU
1 stop15h 38mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/5$177
Tue 5/145:41 pmORD - SJU
1 stop16h 51mMultiple Airlines
Sat 5/186:18 pmSJU - ORD
1 stop7h 40mMultiple Airlines
Deal found 5/5$181
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/5$182
Wed 5/2911:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Deal found 5/5$183
Wed 6/1210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop21h 22mSpirit Airlines
Deal found 5/5$184
Sat 5/189:08 pmMDW - SJU
1 stop10h 15mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/6$184

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 2,689,106 searches. Data last updated May 6, 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.
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Wed 5/229:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/5$148
Tue 5/286:40 pmORD - STT
1 stop13h 54mSpirit Airlines
Tue 6/410:26 amSTT - ORD
1 stop8h 14mSpirit Airlines
Deal found 5/5$174
Sat 5/185:45 pmMDW - SJU
1 stop8h 35mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/5$176
Fri 5/177:23 pmMDW - SJU
1 stop15h 38mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/5$177
Mon 5/135:47 amORD - PUJ
Nonstop4h 41mFrontier
Wed 5/1512:43 pmPUJ - ORD
Nonstop5h 29mFrontier
Deal found 5/5$179
Tue 5/145:41 pmORD - SJU
1 stop16h 51mMultiple Airlines
Sat 5/186:18 pmSJU - ORD
1 stop7h 40mMultiple Airlines
Deal found 5/5$181
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/5$182
Wed 5/2911:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Deal found 5/5$183
Wed 6/1210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop21h 22mSpirit Airlines
Deal found 5/5$184

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 2,689,106 searches. Data last updated May 6, 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 5/2811:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Fri 5/316:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/5$181
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/5$182
Wed 6/59:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Mon 6/106:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/5$196
Wed 6/59:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Mon 6/106:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/5$197
Wed 6/510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Mon 6/104:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/5$200
Sun 5/269:37 amORD - SJU
Nonstop4h 54mSpirit Airlines
Sat 6/16:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/5$201
Wed 6/1210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 6/186:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/5$202
Sun 5/269:37 amORD - SJU
Nonstop4h 54mSpirit Airlines
Sat 6/16:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/5$209
Sat 6/85:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Wed 6/126:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/5$212

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 2,689,106 searches. Data last updated May 6, 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.
Wed 5/1512:28 pmMDW - SJU
1 stop9h 38mFrontier
Wed 5/229:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/5$177
Mon 5/135:47 amORD - PUJ
Nonstop4h 41mFrontier
Wed 5/1512:43 pmPUJ - ORD
Nonstop5h 29mFrontier
Deal found 5/5$179
Tue 5/145:41 pmORD - SJU
1 stop16h 51mMultiple Airlines
Sat 5/186:18 pmSJU - ORD
1 stop7h 40mMultiple Airlines
Deal found 5/5$181
Wed 5/155:00 amORD - SJU
2 stops20h 10mSpirit Airlines
Tue 5/2112:32 pmSJU - ORD
1 stop21h 13mSpirit Airlines
Deal found 5/5$182
Tue 5/146:40 pmORD - SJU
1 stop15h 52mMultiple Airlines
Fri 5/173:15 amSJU - ORD
1 stop22h 43mMultiple Airlines
Deal found 5/5$183
Tue 5/149:25 pmORD - SJU
2 stops13h 07mSpirit Airlines
Wed 5/227:57 pmSJU - ORD
2 stops20h 11mSpirit Airlines
Deal found 5/5$184
Tue 5/149:15 pmORD - SJU
1 stop20h 42mSpirit Airlines
Sat 5/186:14 pmSJU - ORD
1 stop14h 59mSpirit Airlines
Deal found 5/4$185
Tue 5/149:15 pmORD - SJU
1 stop20h 42mSpirit Airlines
Sat 5/186:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/4$186
Wed 5/155:00 amORD - SJU
1 stop11h 28mSpirit Airlines
Tue 5/211:30 amSJU - ORD
2 stops23h 22mSpirit Airlines
Deal found 5/5$187

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 2,689,106 searches. Data last updated May 6, 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.
Wed 5/2911:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Deal found 5/4$62
Tue 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
Deal found 5/5$63
Tue 5/289:15 pmORD - SJU
1 stop20h 42mSpirit Airlines
Deal found 5/5$64
Tue 5/149:25 pmORD - SJU
2 stops13h 07mSpirit Airlines
Deal found 5/5$66
Wed 6/59:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/5$69
Tue 5/219:35 amORD - SJU
2 stops24h 57mSpirit Airlines
Deal found 5/5$70
Wed 5/295:00 amORD - SJU
2 stops21h 05mSpirit Airlines
Deal found 5/4$78
Tue 5/286:40 pmORD - SJU
2 stops31h 25mSpirit Airlines
Deal found 5/5$79
Tue 5/147:08 amORD - SJU
3 stops27h 24mSpirit Airlines
Deal found 5/5$80

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 2,689,106 searches. Data last updated May 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$174 - $409

Route

Depart

Return

Price

Chicago O'Hare IntlSaint Thomas Island Cyril E King

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 5/28

1 stop13h 54m

Saint Thomas Island Cyril E King

Tue 6/4

1 stop8h 14m

$174

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 6/1

1 stop16h 51m

San Juan Luis Munoz Marin Intl

Sat 6/8

1 stop8h 21m

$181

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/30

Nonstop4h 53m

San Juan Luis Munoz Marin Intl

Wed 6/5

Nonstop5h 09m

$182

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sun 5/19

1 stop12h 07m

San Juan Luis Munoz Marin Intl

Tue 5/21

1 stop7h 40m

$187

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/13

1 stop12h 17m

San Juan Luis Munoz Marin Intl

Wed 5/22

1 stop16h 05m

$188

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/20

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Fri 5/24

Nonstop5h 10m

$189

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sun 5/19

1 stop12h 07m

San Juan Luis Munoz Marin Intl

Tue 5/21

1 stop28h 54m

$192

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/9

1 stop12h 45m

San Juan Luis Munoz Marin Intl

Fri 5/10

1 stop12h 47m

$265

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 9/25

1 stop10h 03m

Punta Cana

Sun 9/29

1 stop18h 58m

$409

Flights are sorted by cheapest first

Deals found on 5/5

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 6, 2024.
Peruse reviews from past customers who have flown with Frontier, American Airlines and Spirit Airlines 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
8.1
Very good
10,818 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.1

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
8.1
Very good
10,818 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.1

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.

Copa Airlines
8.0
Very good
2,791 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.1

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
4,535 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.1

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
7.6
Good
2,957 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.1

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
3,843 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Crew

8.6

Overall

8.1

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 $174, but on average you can expect to pay $187.

  • 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 $212.

  • 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 American Airlines (94%), Alaska Airlines (93%) or United Airlines (84%) 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 $797, our data indicates the cheapest price to be $78. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $90.

  • 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), Nassau Intl Airport (NAS) 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 5/6.

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 2,689,106 searches. Data last updated May 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$326FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$133Average$388FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$136Average$618FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$153Average$605FlexibilityNo cancel feeOn-time69%
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JetBlueCheapest$171Average$550FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
AeromexicoCheapest$262Average$548FlexibilityNo cancel feeOn-timeN/A
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Air CanadaCheapest$283Average$846FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Alaska AirlinesCheapest$288Average$620FlexibilityNo cancel feeOn-time75%
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American AirlinesCheapest$291Average$612FlexibilityNo cancel feeOn-time71%
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LufthansaCheapest$406Average$446FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
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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 6, 2024.
8%of flight departuresEarly morningMidnight to 6 am
92%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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