Cheap flights from Caribbean Islands 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 Islands to Chicago?
Travelers have found it’s best to book a flight 16 days in advance to save up to 85% 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 16 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 Caribbean Islands to Chicago 1-2 weeks in advance for as low as $238, or $312 for flights within the next 24 hours.
What is the cheapest month to fly from Caribbean Islands to Chicago?
The best pricing can be found in the month of January. Prices to Chicago from Caribbean Islands average $269. You can even find prices in January for less than $269, as users have found deals to Chicago from as low as $122. The month of March appears to be one of the more expensive times to travel to Chicago from Caribbean Islands. Flying in the targeted month can save you up to 34%.
What is the cheapest time of day to fly from EPX to CHI?
When flying from Caribbean Islands 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 Islands to Chicago
Explore cheap flight options specifically provided by American Airlines for the route between Caribbean Islands 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 mayo 30, 2024.
Consider these cheap American Airlines flights we've found departing from Caribbean Islands to Chicago. Deals update often to give you more flight options matching your criteria
Cheap Spirit Airlines flights from Caribbean Islands to Chicago
Explore cheap flight options specifically provided by Spirit Airlines for the route between Caribbean Islands 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 mayo 30, 2024.
Browse through some of the cheapest Spirit Airlines flights traveling from Caribbean Islands to Chicago. Check back soon if you're not seeing flights that suit your needs.
Cheap Caribbean Islands to Chicago flights in May & June 2024
Find cheap flight options from Caribbean Islands 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 mayo 30, 2024.
Check out some of the best flight deals from Caribbean Islands to Chicago in 2024. For more flight deals, be sure to check back very soon.
Caribbean Islands to Chicago 2024 flight deals
Discover exclusive flight deals for travel between Caribbean Islands 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 mayo 30, 2024.
Check out some of the best flight deals from Caribbean Islands to Chicago in 2024. For more flight deals, be sure to check back very soon.
Non-stop flights to Chicago from Caribbean Islands
Discover non-stop flight options from Caribbean Islands 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 mayo 30, 2024.
Consider booking one of these non-stop flights heading from Caribbean Islands to Chicago. Search for alternative flights from Caribbean Islands to Chicago by utilizing the search form above.
Caribbean Islands to Chicago flights leaving soon
Find last-minute flight options from Caribbean Islands 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 mayo 30, 2024.
Have a look at some of the flights available from Caribbean Islands to Chicago departing last-minute. It's wise to confirm all flight details are correct before booking.
One-way flights to Chicago from Caribbean Islands
Search for one-way flight options from Caribbean Islands 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 mayo 30, 2024.
Users in need of a one-way flight from Caribbean Islands to Chicago can choose from these deals. Users needing a return flight from Caribbean Islands to Chicago should utilize the search form above.
Find flights from Caribbean Islands to Chicago within your budget
Customize your flight search to find flights from Caribbean Islands 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 mayo 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
mar. 9/10
Nonstop5h 14m
Chicago O'Hare Intl
mar. 9/17
1 stop10h 30m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mar. 9/10
1 stop14h 36m
Chicago O'Hare Intl
mar. 9/17
1 stop15h 56m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mié. 8/14
Nonstop5h 13m
Chicago O'Hare Intl
lun. 8/26
1 stop16h 53m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mar. 9/10
Nonstop5h 14m
Chicago O'Hare Intl
mar. 9/17
1 stop16h 53m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
jue. 9/5
1 stop14h 36m
Chicago O'Hare Intl
mar. 9/10
1 stop10h 30m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mié. 6/12
1 stop13h 23m
Chicago O'Hare Intl
dom. 6/30
1 stop25h 08m
Punta CanaChicago Midway
PUJ - MDW
PUJMDW
Punta Cana
mar. 7/9
1 stop23h 01m
Chicago Midway
lun. 7/15
1 stop15h 14m
Punta CanaChicago O'Hare Intl
PUJ - ORD
PUJORD
Punta Cana
jue. 10/24
1 stop7h 39m
Chicago O'Hare Intl
lun. 10/28
1 stop6h 40m
Punta CanaChicago O'Hare Intl
PUJ - ORD
PUJORD
Punta Cana
jue. 9/19
2 stops10h 17m
Chicago O'Hare Intl
mar. 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 Islands to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Caribbean Islands 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 mayo 30, 2024.
Read reviews from past customers who have flown American Airlines, Spirit Airlines and United Airlines from Caribbean Islands to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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 Islands 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 Islands 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 Islands to Chicago
Discover the top 7 airlines that operate flights from Caribbean Islands 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 mayo 30, 2024.
Search flights from Caribbean Islands to Chicago by cabin class
Find flights from Caribbean Islands to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Caribbean Islands to Chicago
Find hourly flight availability from Caribbean Islands 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 mayo 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 |
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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Can Cheapflights find flights from Caribbean Islands to Chicago with no change fees?
Yes, we can. To see specific flights from Caribbean Islands to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.
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