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Cheap flights from Caribbean to Chicago from $51

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Chicago departing on 12/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Caribbean to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Caribbean to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Caribbean to Chicago.

Cheap last minute flights

Planning a quick getaway from Caribbean to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Caribbean to Chicago

Find recent round-trip train or bus tickets from Caribbean to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$106Spirit Airlines
Find Deal
Thu, Jan 23 - Mon, Jan 27
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$116Spirit Airlines
Find Deal
Fri, Jan 17 - Mon, Jan 20
3:54 am - 9:54 amSJU-ORD
8h 00m1 stop
4:41 pm - 6:30 amORD-SJU
11h 49m1 stop
$152Frontier
Find Deal
Fri, Dec 20 - Mon, Jan 6
8:10 pm - 10:19 amSJU-ORD
16h 09m1 stop
2:19 pm - 12:41 amORD-SJU
8h 22m1 stop
$158Frontier
Find Deal
Sat, Dec 21 - Thu, Jan 2
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
$261American Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
12:50 pm - 6:02 pmSJU-ORD
7h 12m1 stop
8:05 am - 8:55 pmORD-SJU
10h 50m1 stop
$270American Airlines
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Fri, Dec 6 - Sun, Dec 8
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$298United Airlines
Find Deal
Thu, Jan 16 - Fri, Jan 24
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
8:50 am - 10:22 pmORD-SJU
11h 32m1 stop
$300United Airlines
Find Deal
Wed, Jan 15 - Mon, Jan 20
6:15 am - 11:59 amSJU-MDW
7h 44m1 stop
1:05 pm - 10:09 pmMDW-SJU
8h 04m1 stop
$354Delta
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Thu, Mar 6 - Tue, Mar 11
7:30 am - 4:12 pmSJU-MDW
10h 42m1 stop
6:00 am - 5:15 pmMDW-SJU
9h 15m1 stop
$369Delta
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Sat, Dec 7 - Tue, Dec 10
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
$51Spirit Airlines
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Sat, Dec 21
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$54Spirit Airlines
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Fri, Dec 13
3:54 am - 9:24 amSJU-ORD
7h 30m1 stop
$62Frontier
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Tue, Dec 17
7:16 pm - 10:28 amSJU-ORD
17h 12m1 stop
$69Frontier
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Mon, Dec 16
2:05 am - 9:35 amSJU-ORD
9h 30m1 stop
$105United Airlines
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Fri, Jan 24
2:05 am - 9:40 amSJU-ORD
9h 35m1 stop
$117United Airlines
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Mon, Jan 13
7:30 am - 4:21 pmSJU-MDW
10h 51m1 stop
$162Delta
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Wed, Jan 15
2:30 pm - 10:04 pmSJU-ORD
9h 34m2 stops
$194American Airlines
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Tue, Feb 11
1:50 pm - 8:59 pmPUJ-ORD
9h 09m1 stop
$199Delta
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Thu, Dec 26
4:44 pm - 8:48 amPUJ-ORD
17h 04m1 stop
$203American Airlines
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Thu, Mar 20
5:40 am - 9:04 amSJU-ORD
5h 24mnonstop
2:10 pm - 7:57 pmORD-SJU
4h 47mnonstop
$311Spirit Airlines
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Fri, Nov 29 - Tue, Apr 29
4:00 pm - 7:26 pmSJU-ORD
5h 26mnonstop
6:15 am - 12:12 amORD-SJU
16h 57m1 stop
$316Spirit Airlines
Find Deal
Fri, Nov 29 - Tue, Apr 29
9:00 am - 2:43 pmSJU-ORD
7h 43m1 stop
5:00 am - 1:46 pmORD-SJU
6h 46m1 stop
$414American Airlines
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Thu, Nov 28 - Sat, Nov 30
5:50 am - 2:43 pmSJU-ORD
10h 53m2 stops
12:03 pm - 12:42 amORD-SJU
10h 39m1 stop
$424American Airlines
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Thu, Nov 28 - Fri, Nov 29
2:05 am - 9:44 amSJU-ORD
9h 39m1 stop
1:55 pm - 2:40 pmORD-SJU
22h 45m2 stops
$458United Airlines
Find Deal
Wed, Nov 27 - Thu, Nov 28
2:05 am - 9:44 amSJU-ORD
9h 39m1 stop
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$500United Airlines
Find Deal
Wed, Nov 27 - Sat, Nov 30
2:26 pm - 9:36 pmSJU-ORD
9h 10m1 stop
5:40 am - 5:15 pmORD-SJU
9h 35m1 stop
$518Delta
Find Deal
Fri, Nov 29 - Sat, Dec 7
2:26 pm - 9:36 pmSJU-ORD
9h 10m1 stop
12:00 pm - 11:22 pmORD-SJU
9h 22m1 stop
$548Delta
Find Deal
Fri, Nov 29 - Wed, Dec 4
6:00 am - 5:01 pmSJU-MDW
13h 01m1 stop
8:27 pm - 10:48 amMDW-SJU
12h 21m1 stop
$608Frontier
Find Deal
Fri, Nov 29 - Mon, Dec 2
3:59 am - 1:27 pmSJU-ORD
11h 28m1 stop
6:30 pm - 1:29 amORD-SJU
28h 59m1 stop
$707Frontier
Find Deal
Wed, Nov 27 - Thu, Nov 28
4:43 pm - 8:13 pmSJU-ORD
5h 30mnonstop
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$116Spirit Airlines
Find Deal
Fri, Dec 20 - Tue, Jan 7
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$118Spirit Airlines
Find Deal
Thu, Jan 16 - Fri, Jan 24
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$119Spirit Airlines
Find Deal
Thu, Jan 16 - Fri, Jan 24
3:05 pm - 7:25 pmSJU-ORD
5h 20mnonstop
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
$206American Airlines
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Thu, May 1 - Tue, May 6
5:00 pm - 8:31 pmPUJ-ORD
5h 31mnonstop
6:20 am - 12:49 pmORD-PUJ
4h 29mnonstop
$287Frontier
Find Deal
Wed, Dec 25 - Wed, Jan 1
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
$341American Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
4:30 pm - 7:40 pmPUJ-ORD
5h 10mnonstop
10:43 am - 5:11 pmORD-PUJ
4h 28mnonstop
$374United Airlines
Find Deal
Sat, Dec 21 - Tue, Jan 14
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$378United Airlines
Find Deal
Sat, Dec 7 - Tue, Dec 10
5:00 pm - 8:15 pmSJU-MDW
5h 15mnonstop
8:05 am - 1:40 pmMDW-SJU
4h 35mnonstop
$473Southwest
Find Deal
Sat, Mar 1 - Sun, Mar 9
6:54 pm - 10:11 pmPUJ-ORD
5h 17mnonstop
6:10 am - 1:00 pmORD-PUJ
4h 50mnonstop
$511Frontier
Find Deal
Thu, Jan 16 - Thu, Jan 23

Spirit Airlines flights from Caribbean to Chicago

Our best Spirit Airlines deals on Caribbean to Chicago flight tickets
Spirit Airlines
Jan 23
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Jan 27
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Jan 17
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Jan 20
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Jan 17
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Jan 24
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl

United Airlines flights from Caribbean to Chicago

Our best United Airlines deals on Caribbean to Chicago flight tickets
United Airlines
Dec 3
SJU2:05 amSan Juan Luis Munoz Marin Intl
8h 54m
1 stop
ORD8:59 amChicago O'Hare Intl
Dec 7
ORD2:50 pmChicago O'Hare Intl
7h 46m
1 stop
SJU12:36 amSan Juan Luis Munoz Marin Intl
United Airlines
Jan 16
SJU2:05 amSan Juan Luis Munoz Marin Intl
10h 39m
1 stop
ORD10:44 amChicago O'Hare Intl
Jan 24
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
United Airlines
Jan 15
SJU2:05 amSan Juan Luis Munoz Marin Intl
10h 39m
1 stop
ORD10:44 amChicago O'Hare Intl
Jan 20
ORD8:50 amChicago O'Hare Intl
11h 32m
1 stop
SJU10:22 pmSan Juan Luis Munoz Marin Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Caribbean to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Caribbean, with most prices found around $193. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Caribbean to Chicago during August average around $259.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Caribbean to Chicago for around $399.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Caribbean to Chicago during this time can be as low as $238. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $382.

What is the cheapest Caribbean to Chicago flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Caribbean - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Caribbean is 15 days out, which is when prices tend to be around $286. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $141.

What cabin class options are available on Caribbean to Chicago flights?

There are 4 cabin classes available to choose from on Caribbean to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Caribbean to Chicago flights?

You could potentially save up to 49% on your flight if you consider stops on a Caribbean to Chicago flight.

Cheap Caribbean to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Caribbean to Chicago

Best Price Found

$51

Fastest flight time

3h 45m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Caribbean in the past 72 hours is $51. The best round-trip flight deal from Caribbean to Chicago found on momondo in the last 72 hours is $106.
The fastest flight from Caribbean to Chicago takes 3h 45m
Direct flights go from Caribbean to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • When did momondo last update prices for flights from Caribbean to Chicago?

    Prices for flights from Caribbean to Chicago are updated daily.

  • How many operators does momondo search for flights from Caribbean to Chicago?

  • How old do you have to be to fly from Caribbean to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Caribbean to Chicago?


Best airlines flying from Caribbean to Chicago

Compare and see reviews for airlines that fly from Caribbean to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $120Free CancellationRating
6.1
3,524 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,173 reviews
Search Spirit Airlines flights
DeltaPriceFrom $182Free CancellationRating
8.0
8,736 reviews
Search Delta flights
United AirlinesPriceFrom $195Free CancellationRating
7.4
9,153 reviews
Search United Airlines flights
SouthwestPriceFrom $220Free CancellationRating
8.1
4,982 reviews
Search Southwest flights
American AirlinesPriceFrom $306Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Copa AirlinesPriceFrom $400Free CancellationRating
7.7
1,776 reviews
Search Copa Airlines flights
JetBluePriceFrom $467Free CancellationRating
7.4
3,364 reviews
Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from Caribbean to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Caribbean to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Caribbean to Chicago with flexible booking policies on momondo?

Flights from Caribbean to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Caribbean to Chicago?

Once all potential Caribbean to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Caribbean to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Caribbean. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago