How many flights depart from Caribbean to Chicago on average per day?

20 flights are operational daily from Caribbean to Chicago as of March 2026. The most popular departure time for this route is 4:00PM, with 71% of flights per day taking off in the afternoon.

What airlines fly to Chicago?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Caribbean according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Caribbean to Chicago on average per week?

146 flights are operational weekly from Caribbean to Chicago as of March 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.

What is the cheapest airline that flies from Caribbean to Chicago?

Frontier, Southwest, and Delta are the most popular carriers operating from Caribbean to Chicago

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?

There are 7 operators available for flights from Caribbean to Chicago as of March 2026.

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.

$109 Cheap Flights from Caribbean to Chicago in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Caribbean to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:10 pm - 12:25 am

SJU

ORD

5h 15mnonstop

7:20 am - 12:47 am

ORD

SJU

16h 27m

1 stop

$167Frontier

Thu, Aug 27 - Sat, Aug 29

8:10 pm - 12:25 am

SJU

ORD

5h 15mnonstop

5:14 pm - 7:10 pm

ORD

SJU

24h 56m

1 stop

$168Frontier

Thu, Jun 4 - Sun, Jun 7

8:10 pm - 12:25 am

SJU

ORD

5h 15mnonstop

10:09 am - 3:59 pm

ORD

SJU

4h 50mnonstop

$181Multiple Airlines

Thu, Aug 27 - Tue, Sep 1

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

8:05 am - 12:13 pm

ORD

MBJ

4h 08mnonstop

$241American Airlines

Fri, Apr 24 - Wed, Apr 29

2:23 pm - 7:10 pm

MBJ

ORD

4h 47mnonstop

5:00 am - 1:58 pm

ORD

MBJ

8h 58m

1 stop

$246American Airlines

Tue, Jun 2 - Tue, Aug 25

7:30 am - 4:12 pm

SJU

MDW

9h 42m

1 stop

10:55 am - 8:30 pm

MDW

SJU

8h 35m

1 stop

$246Delta

Fri, May 8 - Tue, May 12

4:12 pm - 6:44 pm

MBJ

ORD

26h 32m

1 stop

6:15 pm - 1:30 pm

ORD

MBJ

19h 15m

1 stop

$251United Airlines

Fri, Apr 24 - Wed, Apr 29

4:35 pm - 11:17 pm

STT

ORD

7h 42m

1 stop

4:36 pm - 1:26 pm

ORD

STT

19h 50m

2 stops

$292Spirit Airlines

Wed, Mar 25 - Wed, Apr 8

4:35 pm - 11:50 am

STT

ORD

20h 15m

2 stops

4:36 pm - 1:26 pm

ORD

STT

19h 50m

2 stops

$318Spirit Airlines

Wed, Mar 25 - Wed, Apr 8

1:50 pm - 5:59 pm

PUJ

ORD

5h 09mnonstop

9:30 am - 3:12 pm

ORD

PUJ

4h 42mnonstop

$326United Airlines

Fri, May 1 - Tue, May 5

Frontier flights from Caribbean to Chicago

Our best Frontier deals on Caribbean to Chicago flight tickets

Frontier

Aug 27

SJU8:10 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD12:25 amChicago O'Hare Intl

Aug 29

ORD7:20 amChicago O'Hare Intl

16h 27m

1 stop

SJU12:47 amSan Juan Luis Munoz Marin Intl

$167

Frontier

Jun 4

SJU8:10 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD12:25 amChicago O'Hare Intl

Jun 7

ORD5:14 pmChicago O'Hare Intl

24h 56m

1 stop

SJU7:10 pmSan Juan Luis Munoz Marin Intl

$168

Frontier

May 8

SJU3:19 pmSan Juan Luis Munoz Marin Intl

25h 06m

1 stop

ORD3:25 pmChicago O'Hare Intl

May 11

ORD7:15 pmChicago O'Hare Intl

21h 15m

1 stop

SJU5:30 pmSan Juan Luis Munoz Marin Intl

$183

American Airlines flights from Caribbean to Chicago

Our best American Airlines deals on Caribbean to Chicago flight tickets

American Airlines

Apr 24

MBJ1:15 pmMontego Bay Sangster Intl

4h 40m

ORD5:55 pmChicago O'Hare Intl

Apr 29

ORD8:05 amChicago O'Hare Intl

4h 08m

MBJ12:13 pmMontego Bay Sangster Intl

$241

American Airlines

May 7

SJU11:59 pmSan Juan Luis Munoz Marin Intl

8h 32m

1 stop

ORD7:31 amChicago O'Hare Intl

May 10

ORD8:31 amChicago O'Hare Intl

4h 47m

SJU2:18 pmSan Juan Luis Munoz Marin Intl

$242

American Airlines

Jun 2

MBJ2:23 pmMontego Bay Sangster Intl

4h 47m

ORD7:10 pmChicago O'Hare Intl

Aug 25

ORD5:00 amChicago O'Hare Intl

8h 58m

1 stop

MBJ1:58 pmMontego Bay Sangster Intl

$246

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/27

8:10 pm-12:25 am

Nonstop5h 15m

Chicago O'Hare Intl

Sat 8/29

7:20 am-12:47 am

1 stop16h 27m

$167

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 6/4

8:10 pm-12:25 am

Nonstop5h 15m

Chicago O'Hare Intl

Sun 6/7

5:14 pm-7:10 pm

1 stop24h 56m

$168

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/27

8:10 pm-12:25 am

Nonstop5h 15m

Chicago O'Hare Intl

Tue 9/1

10:09 am-3:59 pm

Nonstop4h 50m

$181

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 4/24

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Wed 4/29

8:05 am-12:13 pm

Nonstop4h 08m

$241

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/2

2:23 pm-7:10 pm

Nonstop4h 47m

Chicago O'Hare Intl

Tue 8/25

5:00 am-1:58 pm

1 stop8h 58m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

7:30 am-4:12 pm

1 stop9h 42m

Chicago Midway

Tue 5/12

10:55 am-8:30 pm

1 stop8h 35m

$246

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 4/24

4:12 pm-6:44 pm

1 stop26h 32m

Chicago O'Hare Intl

Wed 4/29

6:15 pm-1:30 pm

1 stop19h 15m

$251

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Wed 4/8

4:36 pm-1:26 pm

2 stops19h 50m

$292

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:50 am

2 stops20h 15m

Chicago O'Hare Intl

Wed 4/8

4:36 pm-1:26 pm

2 stops19h 50m

$318

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/1

1:50 pm-5:59 pm

Nonstop5h 09m

Chicago O'Hare Intl

Tue 5/5

9:30 am-3:12 pm

Nonstop4h 42m

$326

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 $218. 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 $267.

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 $380. 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 $571.

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 $267. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $488.

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 $326 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 7% 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	$175
Fastest flight time	3h 43m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Caribbean in the past 72 hours is $175. The best round-trip flight deal from Caribbean to Chicago found on momondo in the last 72 hours is $286.

The fastest flight from Caribbean to Chicago takes 3h 43m

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?
There are 7 operators available for flights from Caribbean to Chicago as of March 2026.
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?
Based on momondo bookings for flights between Caribbean and Chicago, the leading plane model is Airbus A321neo, making up 33.48% of the total bookings. Other popular models include Airbus A318/A319/A320/A321 with 18.42%, Airbus A320 (sharklets) with 10.10%, and Boeing 737 MAX 8 with 8.87%.

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
Delta	PriceFrom $116	Free Cancellation	Rating 7.9 8,237 reviews	Search Delta flights
Spirit Airlines	PriceFrom $124	Free Cancellation	Rating 6.3 8,487 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $131	Free Cancellation	Rating 7.2 2,894 reviews	Search JetBlue flights
Frontier	PriceFrom $138	Free Cancellation	Rating 5.7 3,040 reviews	Search Frontier flights
United Airlines	PriceFrom $257	Free Cancellation	Rating 7.4 9,375 reviews	Search United Airlines flights
American Airlines	PriceFrom $258	Free Cancellation	Rating 7.1 11,369 reviews	Search American Airlines flights
Southwest	PriceFrom $292	Free Cancellation	Rating 8.0 4,306 reviews	Search Southwest flights

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Wed 4/1

Wed 4/8

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Caribbean

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Caribbean to Chicago from $109

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 4/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Caribbean to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Caribbean to Chicago

Our best Frontier deals on Caribbean to Chicago flight tickets

American Airlines flights from Caribbean to Chicago

Our best American Airlines deals on Caribbean to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Caribbean to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Caribbean to Chicago

What is the cheapest month to fly to Chicago?

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

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

What is the cheapest Caribbean to Chicago flight route?

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

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

Can stopping save me money on Caribbean to Chicago flights?

What is the cheapest airline that flies from Caribbean to Chicago?

What airlines fly to Chicago?

How many flights depart from Caribbean to Chicago on average per day?

How many flights depart from Caribbean to Chicago on average per week?

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

Fastest flight time

Direct flights

Airports in Chicago

Best airlines flying from Caribbean to Chicago

Compare and see reviews for airlines that fly from Caribbean to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Caribbean

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year