$115 Find Cheap Flights from Caribbean Islands to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 4/28. 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.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Caribbean Islands to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean Islands to Chicago

Thu, Apr 23 - Mon, Apr 27
Frontier Logo
3:03 pm - 10:39 pm
SJU
-
ORD
8h 36m
1 stop
Frontier Logo
5:50 am - 2:08 pm
ORD
-
SJU
7h 18m
1 stop
$159Frontier
Mon, Apr 13 - Sat, Apr 18
Spirit Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
6:40 am - 12:58 am
ORD
-
SJU
17h 18m
1 stop
$163Spirit Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
3:23 pm - 10:39 pm
SJU
-
ORD
8h 16m
1 stop
Multiple Airlines Logo
7:50 am - 12:58 am
ORD
-
SJU
16h 08m
1 stop
$173Multiple Airlines
Thu, Apr 16 - Mon, Apr 27
Multiple Airlines Logo
11:30 am - 11:59 pm
SJU
-
ORD
13h 29m
1 stop
Multiple Airlines Logo
7:50 am - 12:58 am
ORD
-
SJU
16h 08m
1 stop
$175Multiple Airlines
Sat, Apr 25 - Sun, Aug 23
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$281American Airlines
Sat, May 16 - Mon, May 18
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
United Airlines Logo
9:56 pm - 1:30 pm
ORD
-
MBJ
15h 34m
1 stop
$286United Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
5:00 am - 1:25 pm
ORD
-
MBJ
8h 25m
1 stop
$291American Airlines
Wed, Apr 29 - Wed, May 6
United Airlines Logo
4:12 pm - 11:43 pm
MBJ
-
ORD
7h 31m
1 stop
United Airlines Logo
11:00 am - 3:10 pm
ORD
-
MBJ
28h 10m
1 stop
$292United Airlines
Mon, May 11 - Wed, Sep 9
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
Delta Logo
10:35 am - 12:57 am
MDW
-
SDQ
13h 22m
2 stops
$560Delta
Mon, May 11 - Wed, Sep 9
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
Delta Logo
10:35 am - 12:57 am
MDW
-
SDQ
13h 22m
2 stops
$561Delta
Useful Info

Good to know

Low seasonMarch
Cheapest flight$115
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs for booking flights from Caribbean Islands to Chicago

  • How does KAYAK find such low prices on flights from Caribbean Islands to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean Islands to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean Islands to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean Islands to Chicago

 
Need help choosing which airline to fly with from Caribbean Islands to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8369 reviews
7.2Food
7.9Comfort
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

10.0 ExcellentViraj, Apr 2026
JFK - SFO
Read more Delta reviews

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Our recent international travel was from Newark, NJ to Grenada via Atlanta. During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta as it did not wait for arriving passengers. Consequently, we were delayed by 24 hours before the next available flight was provided. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for me as a resident of New Jersey.

This was my first flight with Delta, the overall experience was good. I would definitely consider them more with my future flights.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Caribbean Islands

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.