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$82+ Cheap flights from Chicago (CHI) to Caribbean

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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
jul. 30 — ago. 61
From?
To?
mar. 7/30
mar. 8/6
1 adult, Economy
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How far in advance should I book a flight from Chicago to Caribbean?

Travelers have found it’s best to book a flight 32 days in advance to save up to 11% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 32 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Caribbean 1-2 weeks in advance for as low as $256, or $312 for flights within the next 24 hours.

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

January is one of the best times of the year to fly to Caribbean from Chicago. Prices for January average $328 per person but you can even find prices for as low as $110. The most expensive prices can be found in the month of March. Opting for a January flight can save you 55% on your journey compared to booking in March

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

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

Cheap Chicago to Caribbean flights in July & August 2024

Find cheap flight options from Chicago to Caribbean specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on julio 25, 2024.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
mié. 8/2110:46 amSJU - ORD
1 stop10h 22mSpirit Airlines
Deal found 7/24$140
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/37:06 pmORD - SJU
1 stop6h 30mSpirit Airlines
sáb. 8/1012:18 pmSJU - ORD
1 stop8h 41mSpirit Airlines
Deal found 7/24$143
This eDestinos deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/67:01 amORD - SJU
1 stop11h 33mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$148
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/15:42 pmORD - SJU
1 stop7h 12mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$149
This FareScan deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
mié. 8/146:00 amSJU - ORD
2 stops18h 17mSpirit Airlines
Deal found 7/24$152
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/57:01 amORD - SJU
1 stop11h 33mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$153
This FareScan deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/69:15 pmORD - SJU
1 stop20h 53mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$155
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
mar. 8/208:50 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 7/24$156
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/137:32 amORD - SJU
1 stop10h 36mMultiple Airlines
lun. 8/193:03 amSJU - ORD
1 stop20h 25mMultiple Airlines
Deal found 7/24$157

Chicago to Caribbean 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Caribbean in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated julio 25, 2024.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
mié. 8/2110:46 amSJU - ORD
1 stop10h 22mSpirit Airlines
Deal found 7/24$140
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/37:06 pmORD - SJU
1 stop6h 30mSpirit Airlines
sáb. 8/1012:18 pmSJU - ORD
1 stop8h 41mSpirit Airlines
Deal found 7/24$143
This eDestinos deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/67:01 amORD - SJU
1 stop11h 33mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$148
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/15:42 pmORD - SJU
1 stop7h 12mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$149
This FareScan deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
mié. 8/146:00 amSJU - ORD
2 stops18h 17mSpirit Airlines
Deal found 7/24$152
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/57:01 amORD - SJU
1 stop11h 33mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$153
This eDestinos deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/137:00 amORD - SJU
1 stop13h 56mSpirit Airlines
lun. 9/1610:46 pmSJU - ORD
1 stop12h 12mSpirit Airlines
Deal found 7/24$154
This FareScan deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/69:15 pmORD - SJU
1 stop20h 53mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$155
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
mar. 8/208:50 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 7/24$156

Chicago to Caribbean flights leaving soon

Find last-minute flight options from Chicago to Caribbean 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 2,752,877 searches. Data last updated julio 25, 2024.
This Cheapflightsfares deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/15:42 pmORD - SJU
1 stop8h 15mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/25$158
This Cheapflightsfares deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/15:42 pmORD - SJU
1 stop17h 46mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/25$172
This FareScan deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/310:26 pmORD - SJU
Nonstop4h 45mSpirit Airlines
jue. 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/25$177
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/89:04 pmMDW - SJU
1 stop10h 22mFrontier
mié. 8/143:03 amSJU - MDW
1 stop7h 27mFrontier
Deal found 7/25$177
This Cheapflightsfares deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/15:42 pmORD - SJU
1 stop8h 15mSpirit Airlines
jue. 8/87:30 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Deal found 7/25$180
This Trip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/309:59 pmORD - SJU
1 stop14h 08mSpirit Airlines
mar. 8/69:15 pmSJU - ORD
1 stop12h 59mSpirit Airlines
Deal found 7/25$183
This eDestinos deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/309:59 pmORD - SJU
1 stop14h 08mSpirit Airlines
lun. 8/58:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Deal found 7/24$188
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/89:04 pmMDW - SJU
1 stop10h 22mFrontier
vie. 8/167:10 amSJU - MDW
1 stop12h 09mFrontier
Deal found 7/25$192
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/89:04 pmMDW - SJU
1 stop12h 33mFrontier
jue. 8/153:03 amSJU - MDW
1 stop10h 42mFrontier
Deal found 7/25$193

One-way flights to Caribbean from Chicago

Search for one-way flight options from Chicago to Caribbean. 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 2,752,877 searches. Data last updated julio 25, 2024.
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/266:53 pmMDW - SJU
1 stop8h 22mFrontier
Deal found 7/24$82
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/225:24 pmORD - SJU
1 stop9h 57mFrontier
Deal found 7/25$84
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/2411:51 amMDW - SJU
1 stop13h 07mFrontier
Deal found 7/25$84
This FareScan deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/275:22 pmORD - SJU
2 stops29h 50mSpirit Airlines
Deal found 7/24$85
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/73:32 pmMDW - SJU
1 stop9h 22mFrontier
Deal found 7/24$85
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/87:12 pmORD - SJU
1 stop12h 14mFrontier
Deal found 7/25$86
This Trip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/76:16 pmORD - SJU
1 stop7h 03mSpirit Airlines
Deal found 7/24$87
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/89:04 pmMDW - SJU
1 stop10h 22mFrontier
Deal found 7/24$87
This FareScan deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/246:05 pmORD - SJU
1 stop29h 07mSpirit Airlines
Deal found 7/24$88

Find flights from Chicago to Caribbean within your budget

Customize your flight search to find flights from Chicago to Caribbean 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 2,752,877 searches. Data last updated julio 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$140 - $324

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/13

1 stop10h 36m

San Juan Luis Munoz Marin Intl

mié. 8/21

1 stop10h 22m

$140

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/6

1 stop11h 33m

San Juan Luis Munoz Marin Intl

jue. 8/8

1 stop12h 48m

$148

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 8/10

1 stop13h 19m

San Juan Luis Munoz Marin Intl

lun. 8/19

1 stop20h 25m

$156

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/13

1 stop10h 36m

San Juan Luis Munoz Marin Intl

lun. 8/19

1 stop20h 25m

$157

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/6

1 stop14h 16m

San Juan Luis Munoz Marin Intl

lun. 8/19

1 stop20h 25m

$158

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 8/23

1 stop20h 51m

San Juan Luis Munoz Marin Intl

vie. 8/30

1 stop7h 38m

$161

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

dom. 9/15

1 stop9h 24m

Punta Cana

mar. 9/24

2 stops20h 53m

$272

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 12/3

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

mar. 12/10

1 stop10h 48m

$281

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

sáb. 12/7

1 stop6h 58m

San Juan Luis Munoz Marin Intl

mié. 12/11

1 stop11h 44m

$324

Flights are sorted by cheapest first

Deals found on 7/24

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

Best time to book a flight from Chicago to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated julio 25, 2024.
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Delta
8.0
Very good
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Copa Airlines
7.9
Good
2,260 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

JetBlue
7.6
Good
3,996 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

LATAM Airlines
7.5
Good
2,182 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

United Airlines
7.4
Good
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Related info for your journey

Find useful and relevant information for your journey from Chicago to Caribbean. 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 for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Caribbean for under $200. The cheapest flight booked recently is on Spirit Airlines for just $140, but on average you can expect to pay $158.

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

    Cheapflights has at least 20 direct flights from Chicago to Caribbean under $200. A good price for a nonstop flight from Chicago to Caribbean is less than $209.

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

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

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

    The most popular flight routes from Chicago to Caribbean are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana and Chicago Midway - San Juan Luis Munoz Marin Intl.

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

    The top 3 most reliable airlines when flying from Chicago to Caribbean are Air Canada (85%), United Airlines (85%) and Air New Zealand (85%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $753, our data indicates the cheapest price to be $88. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $143.

  • What does ORD to SJU mean?

    Great question - ORD to SJU just means Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport. Now you’ll know what these unique codes when you look for flights! Santo Domingo Las Americas Airport (SDQ), Punta Cana Airport (PUJ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI) are other airports near this flight route and their unique identifiers/IATA codes.

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

    The amount of baggage you can bring on your Chicago to Caribbean 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 with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Caribbean 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 that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Caribbean 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 that allow pets onboard?

    Many airlines flying from Chicago to Caribbean 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?

    Yes, you can often find last-minute deals on Chicago to Caribbean 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 flight deals updated?

    The Chicago to Caribbean flight deals you see on this page were last updated on 7/24.

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

    Consider American Airlines, Alaska Airlines or JetBlue when booking your flight. These represent the most popular airlines when flying from Chicago to Caribbean.

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $245). Flying from Chicago to Caribbean in March is currently the most expensive (average of $336). 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.

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Alternative routes for Chicago to Caribbean
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

Discover the top 10 airlines that operate flights from Chicago to Caribbean. 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 2,752,877 searches. Data last updated julio 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$93Average$327FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$134Average$383FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$137Average$531FlexibilityNo cancel feeOn-time62%
DeltaCheapest$150Average$611FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$185Average$613FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$262Average$548FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$283Average$821FlexibilityNo cancel feeOn-time67%
Alaska AirlinesCheapest$288Average$620FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$304Average$603FlexibilityNo cancel feeOn-time71%
LufthansaCheapest$400Average$486FlexibilityNo cancel feeOn-time76%
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Search flights from Chicago to Caribbean by cabin class

Find flights from Chicago to Caribbean, 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

Find hourly flight availability from Chicago to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 25, 2024.
4%of flight departuresEarly morningMidnight to 6 am
96%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
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6 PM

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