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Cheap flights from Caribbean to Chicago from $95

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 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
JetBlue Logo
7:45 am - 6:05 pm
ORD
-
SJU
8h 20m1 stop
$165JetBlue
ven., janv. 23 - dim., janv. 25
JetBlue Logo
12:15 pm - 10:59 pm
SJU
-
ORD
11h 44m1 stop
JetBlue Logo
1:45 pm - 10:47 pm
ORD
-
SJU
8h 02m1 stop
$168JetBlue
mer., avr. 15 - sam., avr. 18
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
JetBlue Logo
10:15 am - 7:26 pm
ORD
-
SJU
7h 11m1 stop
$169JetBlue
ven., janv. 16 - lun., janv. 19
Spirit Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
Spirit Airlines Logo
9:23 am - 6:58 pm
ORD
-
SJU
7h 35m1 stop
$176Spirit Airlines
ven., janv. 23 - lun., janv. 26
Frontier Logo
4:36 pm - 10:41 am
SJU
-
ORD
20h 05m1 stop
Frontier Logo
9:25 am - 11:59 pm
ORD
-
SJU
12h 34m1 stop
$177Frontier
mer., janv. 21 - sam., janv. 24
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
8:00 am - 1:27 pm
MDW
-
SJU
27h 27m1 stop
$180Frontier
sam., févr. 7 - sam., févr. 14
Spirit Airlines Logo
4:40 pm - 11:47 pm
AUA
-
ORD
9h 07m1 stop
Spirit Airlines Logo
5:15 am - 3:35 pm
ORD
-
AUA
8h 20m1 stop
$220Spirit Airlines
jeu., févr. 5 - lun., févr. 9
American Airlines Logo
1:13 pm - 6:04 pm
STT
-
ORD
5h 51mnonstop
American Airlines Logo
5:00 am - 1:02 pm
ORD
-
STT
7h 02m1 stop
$505American Airlines
mer., mars 25 - lun., mars 30
American Airlines Logo
12:02 pm - 9:31 pm
STT
-
ORD
10h 29m1 stop
American Airlines Logo
5:00 am - 1:02 pm
ORD
-
STT
7h 02m1 stop
$519American Airlines
lun., mars 16 - jeu., mars 19
United Airlines Logo
2:35 pm - 11:08 pm
STT
-
ORD
9h 33m1 stop
United Airlines Logo
9:30 pm - 1:08 pm
ORD
-
STT
14h 38m2 stops
$543United Airlines
mer., mars 25 - lun., mars 30

JetBlue flights from Caribbean to Chicago

Our best JetBlue deals on Caribbean to Chicago flight tickets
JetBlue
Jan 23
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
Jan 25
ORD7:45 amChicago O'Hare Intl
8h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
$165
Find similar
JetBlue
Apr 15
SJU12:15 pmSan Juan Luis Munoz Marin Intl
11h 44m
1 stop
ORD10:59 pmChicago O'Hare Intl
Apr 18
ORD1:45 pmChicago O'Hare Intl
8h 02m
1 stop
SJU10:47 pmSan Juan Luis Munoz Marin Intl
$168
Find similar
JetBlue
Jan 16
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
Jan 19
ORD10:15 amChicago O'Hare Intl
7h 11m
1 stop
SJU7:26 pmSan Juan Luis Munoz Marin Intl
$169
Find similar

Spirit Airlines flights from Caribbean to Chicago

Our best Spirit Airlines deals on Caribbean to Chicago flight tickets
Spirit Airlines
Jan 23
SJU1:22 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD4:37 pmChicago O'Hare Intl
Jan 26
ORD9:23 amChicago O'Hare Intl
7h 35m
1 stop
SJU6:58 pmSan Juan Luis Munoz Marin Intl
$176
Find similar
Spirit Airlines
Dec 25
SJU6:28 pmSan Juan Luis Munoz Marin Intl
8h 02m
1 stop
ORD12:30 amChicago O'Hare Intl
Jan 1
ORD7:20 amChicago O'Hare Intl
16h 52m
1 stop
SJU2:12 amSan Juan Luis Munoz Marin Intl
$186
Find similar
Spirit Airlines
Jan 23
SJU1:22 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD4:37 pmChicago O'Hare Intl
Jan 25
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
$187
Find similar

momondo Fare Finder

 
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, momondo users made 832,500 searches. Data last updated décembre 23, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

ven. 1/23

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

dim. 1/25

7:45 am-6:05 pm

1 stop8h 20m

$165

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mer. 4/15

12:15 pm-10:59 pm

1 stop11h 44m

Chicago O'Hare Intl

sam. 4/18

1:45 pm-10:47 pm

1 stop8h 02m

$168

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

ven. 1/16

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

lun. 1/19

10:15 am-7:26 pm

1 stop7h 11m

$169

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

ven. 1/23

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

lun. 1/26

9:23 am-6:58 pm

1 stop7h 35m

$176

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mer. 1/21

4:36 pm-10:41 am

1 stop20h 05m

Chicago O'Hare Intl

sam. 1/24

9:25 am-11:59 pm

1 stop12h 34m

$177

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sam. 2/7

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

sam. 2/14

8:00 am-1:27 pm

1 stop27h 27m

$180

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

jeu. 2/5

4:40 pm-11:47 pm

1 stop9h 07m

Chicago O'Hare Intl

lun. 2/9

5:15 am-3:35 pm

1 stop8h 20m

$220

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

mer. 3/25

1:13 pm-6:04 pm

Nonstop5h 51m

Chicago O'Hare Intl

lun. 3/30

5:00 am-1:02 pm

1 stop7h 02m

$505

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

lun. 3/16

12:02 pm-9:31 pm

1 stop10h 29m

Chicago O'Hare Intl

jeu. 3/19

5:00 am-1:02 pm

1 stop7h 02m

$519

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

mer. 3/25

2:35 pm-11:08 pm

1 stop9h 33m

Chicago O'Hare Intl

lun. 3/30

9:30 pm-1:08 pm

2 stops14h 38m

$543

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 February is, on average, the cheapest month to fly to Chicago from Caribbean, with most prices found around $260. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Caribbean to Chicago during May average around $269.

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 Friday when prices can be found for as low as $384. 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 $544.

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 $257. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $477.

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?

You are more likely to see cheaper flights to Chicago from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $336 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Caribbean for as low as $286 on momondo.

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 10% 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

$166

Fastest flight time

3h 56m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Caribbean in the past 72 hours is $166. The best round-trip flight deal from Caribbean to Chicago found on momondo in the last 72 hours is $195.
The fastest flight from Caribbean to Chicago takes 3h 56m
Direct flights go from Caribbean to Chicago every day.
There are 3 airports in Chicago. From Caribbean there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • 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
JetBluePriceFrom $120Free CancellationRating
7.2
2,898 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $138Free CancellationRating
6.3
8,194 reviews
Search Spirit Airlines flights
FrontierPriceFrom $138Free CancellationRating
5.8
3,074 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.9
8,015 reviews
Search Delta flights
American AirlinesPriceFrom $258Free CancellationRating
7.2
11,051 reviews
Search American Airlines flights
United AirlinesPriceFrom $271Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,255 reviews
Search Southwest flights

Traveling to a place near Chicago?

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

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport