$92+ Cheap flights from Caribbean to O'Hare Intl (ORD)
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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Caribbean to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Caribbean to O'Hare Intl
Cheapest flights from Caribbean to O'Hare IntlExplore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 26, 2026.
Explore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 26, 2026.
This Trip.com deal was found by Cheapflights users on 1/25. 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.
This Trip.com deal was found by Cheapflights users on 1/25. 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.
This Trip.com deal was found by Cheapflights users on 1/26. 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.
This Trip.com deal was found by Cheapflights users on 1/25. 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.
This Trip.com deal was found by Cheapflights users on 1/25. 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.
This Trip.com deal was found by Cheapflights users on 1/25. 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.
This Trip.com deal was found by Cheapflights users on 1/24. 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.
This Trip.com deal was found by Cheapflights users on 1/23. 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.
This JetBlue deal was found by Cheapflights users on 1/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This eDestinos deal was found by Cheapflights users on 1/24. 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.
This Travelocity deal was found by Cheapflights users on 1/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flight deals from Caribbean to O'Hare Intl
Keep the following information in mind while searching for Caribbean to O'Hare Intl flight deals. Data was last updated enero 26, 2026.
Round-trip from | $120 (Trip.com) |
|---|---|
One-way from | $92 (Travelocity) |
Popular in | December |
Cheapest in | February |
Average price | $301 |
Good round-trip deal | $160 or less |
Good one-way deal | $187 or less |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Caribbean to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
vie. 5/1
11:59 pm-9:48 am
1 stop10h 49m
Chicago O'Hare Intl
lun. 5/4
3:15 pm-2:07 am
1 stop9h 52m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mié. 4/29
11:59 pm-9:48 am
1 stop10h 49m
Chicago O'Hare Intl
lun. 5/4
3:15 pm-2:07 am
1 stop9h 52m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
lun. 5/4
11:25 pm-8:51 am
1 stop10h 26m
Chicago O'Hare Intl
jue. 5/7
10:35 am-9:01 pm
1 stop9h 26m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
sáb. 5/2
11:59 pm-9:48 am
1 stop10h 49m
Chicago O'Hare Intl
mié. 5/6
3:15 pm-12:07 am
1 stop7h 52m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
jue. 2/12
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
dom. 2/15
12:17 pm-6:49 pm
Nonstop4h 32m
Saint Thomas IslandChicago
STT - ORD
STTORD
Saint Thomas Island Cyril E King
mar. 2/24
3:36 pm-11:47 pm
2 stops10h 11m
Chicago O'Hare Intl
mar. 3/3
8:16 pm-2:31 pm
2 stops16h 15m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
jue. 4/9
11:00 am-9:33 pm
1 stop11h 33m
Chicago O'Hare Intl
lun. 4/13
10:00 am-10:01 pm
1 stop11h 01m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
vie. 2/27
5:10 am-11:54 am
1 stop8h 44m
Chicago O'Hare Intl
lun. 3/2
12:41 pm-12:29 am
1 stop9h 48m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mié. 4/22
11:07 am-6:15 pm
1 stop8h 08m
Chicago O'Hare Intl
sáb. 4/25
12:22 pm-5:54 pm
Nonstop4h 32m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mar. 4/21
11:25 pm-8:51 am
1 stop10h 26m
Chicago O'Hare Intl
sáb. 4/25
8:31 am-6:30 pm
1 stop8h 59m
Best time to book a flight from Caribbean to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Caribbean with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Caribbean to Chicago O'Hare Intl Airport
What is the cheapest month to book a flight from Caribbean to Chicago O'Hare Intl Airport?
Currently, February is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $118). Flying from Caribbean to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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 CB to ORD?
Find hourly flight availability from Caribbean to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated enero 26, 2026.
A simple way to save on the total cost of your ticket is to fly from Caribbean to Chicago O'Hare Intl Airport in the evening. If you’re flexible enough to do this you can expect to save up to 54% on your trip compared to booking a flight in the afternoon.
What is the cheapest day to fly from Caribbean to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Caribbean to O'Hare Intl. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Caribbean to Chicago O'Hare Intl Airport 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.
Weekly flight availability from Caribbean to Chicago O'Hare Intl Airport
Explore weekly flight availability from Caribbean to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated enero 26, 2026.
The most flights from 0CB to ORD are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (10 on average).
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated enero 26, 2026.
Get a feel of what it's like to fly with United Airlines, American Airlines, and JetBlue from Caribbean to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Gerry,Jan 2026
YVR - DEN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Gerry,Jan 2026
YVR - DEN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Gerry,Jan 2026
YVR - DEN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Gerry,Jan 2026
YVR - DEN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Gerry,Jan 2026
YVR - DEN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Gerry,Jan 2026
YVR - DEN
Related info for your journey
Find useful and relevant information for your journey from Caribbean to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBrowse thousands of different options on Cheapflights for your next trip
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Alternative routes for Caribbean to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Caribbean to O'Hare Intl
Discover the top 6 airlines that operate flights from Caribbean to O'Hare Intl. 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 enero 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$626 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$316 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$351 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$525 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$557 | FlexibilityNo cancel fee | On-time71% |