Cheap flights from Caribbean to Chicago (CHI) from $69
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 8/28. 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.
How far in advance should I book a flight from Caribbean to Chicago?
Users have found that booking a flight from Caribbean to Chicago at least 16 days early can save you up to 85% on average compared to booking a flight this week. If booking 16 days before your flight isn’t an option for you, users have found flights from Caribbean to Chicago for as little as $238 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $312 for flights departing within the next 3 days.
What is the cheapest month to fly from Caribbean to Chicago?
Flights from Caribbean to Chicago lean towards being more expensive in March. Prices are generally better when you fly from Caribbean to Chicago in January, with the cheapest ticket starting at $122.
What is the cheapest time of day to fly from CB to CHI?
When flying from Caribbean to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Cheap American Airlines flights from Caribbean to Chicago
Explore cheap flight options specifically provided by American Airlines for the route between Caribbean and Chicago. 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 2,784,634 searches. Data last updated May 30, 2024.
Cheap Spirit Airlines flights from Caribbean to Chicago
Explore cheap flight options specifically provided by Spirit Airlines for the route between Caribbean and Chicago. 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 2,784,634 searches. Data last updated May 30, 2024.
Cheap Caribbean to Chicago flights in May & June 2024
Find cheap flight options from Caribbean to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Prices were last updated on May 30, 2024.
Caribbean to Chicago 2024 flight deals
Discover exclusive flight deals for travel between Caribbean and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated May 30, 2024.
Non-stop flights to Chicago from Caribbean
Discover non-stop flight options from Caribbean to Chicago. 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 2,784,634 searches. Data last updated May 30, 2024.
Caribbean to Chicago flights leaving soon
Find last-minute flight options from Caribbean to Chicago 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 2,784,634 searches. Data last updated May 30, 2024.
One-way flights to Chicago from Caribbean
Search for one-way flight options from Caribbean to Chicago. 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 2,784,634 searches. Data last updated May 30, 2024.
Find flights from Caribbean to Chicago within your budget
Customize your flight search to find flights from Caribbean to Chicago 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 2,784,634 searches. Data last updated May 30, 2024.
Fly from
Fly to
Budget
$119 - $320
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
Nonstop5h 14m
Chicago O'Hare Intl
Tue 9/17
1 stop10h 30m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
1 stop14h 36m
Chicago O'Hare Intl
Tue 9/17
1 stop15h 56m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/14
Nonstop5h 13m
Chicago O'Hare Intl
Mon 8/26
1 stop16h 53m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
Nonstop5h 14m
Chicago O'Hare Intl
Tue 9/17
1 stop16h 53m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/5
1 stop14h 36m
Chicago O'Hare Intl
Tue 9/10
1 stop10h 30m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop13h 23m
Chicago O'Hare Intl
Sun 6/30
1 stop25h 08m
Punta CanaChicago Midway
PUJ - MDW
PUJMDW
Punta Cana
Tue 7/9
1 stop23h 01m
Chicago Midway
Mon 7/15
1 stop15h 14m
Punta CanaChicago O'Hare Intl
PUJ - ORD
PUJORD
Punta Cana
Thu 10/24
1 stop7h 39m
Chicago O'Hare Intl
Mon 10/28
1 stop6h 40m
Punta CanaChicago O'Hare Intl
PUJ - ORD
PUJORD
Punta Cana
Thu 9/19
2 stops10h 17m
Chicago O'Hare Intl
Tue 9/24
1 stop20h 37m
No data available for this route at this time. Please check back soon.
Best time to book a flight from Caribbean to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Caribbean with our price prediction graph.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 30, 2024.
Crew
Overall
Boarding
Entertainment
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Boarding
Entertainment
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Boarding
Entertainment
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Boarding
Entertainment
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Boarding
Entertainment
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Boarding
Entertainment
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Caribbean to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Caribbean to Chicago
Discover the top 7 airlines that operate flights from Caribbean to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated May 30, 2024.
Search flights from Caribbean to Chicago by cabin class
Find flights from Caribbean to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Caribbean to Chicago
Find hourly flight availability from Caribbean to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 30, 2024.
| 7%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 8%of flight departures | Morning6 am to noon |
| 85%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
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Why should you use Cheapflights to find cheap flight tickets from Caribbean to Chicago?
Cheapflights helps you find that perfect flight to Chicago from Caribbean by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from Caribbean to Chicago with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Caribbean to Chicago, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Caribbean to Chicago become cheaper?
Yes! Start tracking prices for Caribbean to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.