$117 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 5/14. 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
6:00 am - 9:17 pm
SJU
-
ORD
16h 17m
1 stop
Frontier Logo
5:50 am - 2:08 pm
ORD
-
SJU
7h 18m
1 stop
$159Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
6:09 pm - 11:13 pm
SJU
-
ORD
30h 04m
1 stop
Frontier Logo
10:22 am - 12:50 am
ORD
-
SJU
13h 28m
1 stop
$168Frontier
Sat, Apr 25 - Sat, May 2
Frontier Logo
8:00 am - 3:23 pm
SJU
-
ORD
8h 23m
1 stop
Frontier Logo
7:34 pm - 11:29 pm
ORD
-
SJU
26h 55m
1 stop
$169Frontier
Wed, Apr 8 - Tue, Apr 14
Spirit Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
7:17 am - 6:55 pm
ORD
-
SJU
10h 38m
1 stop
$183Spirit Airlines
Thu, Apr 9 - Mon, Apr 13
Spirit Airlines Logo
11:03 am - 6:31 pm
SJU
-
ORD
8h 28m
1 stop
Spirit Airlines Logo
8:56 pm - 2:29 am
ORD
-
SJU
4h 33mnonstop
$187Spirit Airlines
Sat, May 16 - Mon, May 18
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
United Airlines Logo
11:00 pm - 1:30 pm
ORD
-
MBJ
14h 30m
1 stop
$286United Airlines
Sat, May 16 - Mon, May 18
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
United Airlines Logo
11:00 pm - 1:30 pm
ORD
-
MBJ
14h 30m
1 stop
$290United Airlines
Wed, May 6 - Tue, Sep 8
American Airlines Logo
12:25 pm - 11:54 pm
MBJ
-
ORD
11h 29m
1 stop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$292American Airlines
Mon, May 11 - Wed, Sep 9
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
$560Delta
Sat, Apr 25 - Sun, May 3
Delta Logo
2:37 pm - 10:28 pm
SDQ
-
MDW
8h 51m
1 stop
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
$573Delta
Useful Info

Good to know

Low seasonMarch
Cheapest flight$117
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 8341 reviews
8.1Boarding
7.8Entertainment
7.9Comfort
7.2Food
8.5Crew
Airline reviews

I took seat 15A in anticipation of window seat, there is no window.

2.0 MediocreDileep, Mar 2026
SMF - ATL
Read more Delta reviews

I took seat 15A in anticipation of window seat, there is no window.

I lost my plane and spend 5 hours at the airport arriving at Buffalo at 1 am taxis are very expensive at that time.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

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.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint Joseph
Hammond
Portage
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Valparaiso
Chesterton
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Munster
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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.