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

Spirit Airlines, Frontier, and Arajet are the most popular carriers operating from Caribbean Islands to Chicago

What airlines fly to Chicago?

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Caribbean Islands according to our data. Spirit 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 6 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 Islands to Chicago on average per day?

As of July 2025, there are 13 flights per day flying from Caribbean Islands to Chicago. The most common time of day flights depart is 3:00PM, with 78% of flights taking off in the afternoon.

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

As of July 2025, 96 flights take off from Caribbean Islands and land in Chicago each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.

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

Prices for flights from Caribbean Islands to Chicago are refreshed on a daily basis.

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

The number of operators available for flights from Caribbean Islands to Chicago is 6 as of July 2025.

How old do you have to be to fly from Caribbean Islands 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 Islands to Chicago.

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

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$90 Cheap Flights from Caribbean Islands to Chicago in 2025

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 Islands to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

10:16 pm - 9:22 amSJU-ORD

12h 06m1 stop

6:56 am - 3:10 pmORD-SJU

7h 14m1 stop

$179Spirit Airlines

Find Deal

Fri, Aug 15 - Mon, Aug 18

12:06 pm - 5:55 pmSJU-ORD

6h 49m1 stop

12:55 pm - 6:34 pmORD-SJU

4h 39mnonstop

$186Spirit Airlines

Find Deal

Thu, Oct 16 - Sat, Oct 18

3:21 pm - 11:09 pmSJU-MDW

8h 48m1 stop

6:10 am - 3:15 pmMDW-SJU

7h 05m1 stop

$234Frontier

Find Deal

Sat, Nov 1 - Sat, Nov 15

3:39 am - 9:51 amSJU-MDW

7h 12m1 stop

10:51 am - 11:59 pmMDW-SJU

12h 08m1 stop

$237Frontier

Find Deal

Fri, Sep 12 - Sat, Sep 20

3:21 pm - 7:36 pmPUJ-ORD

5h 15mnonstop

5:20 am - 3:29 pmORD-PUJ

9h 09m1 stop

$337American Airlines

Find Deal

Thu, Oct 9 - Wed, Oct 15

2:40 pm - 9:26 pmPUJ-MDW

7h 46m1 stop

6:00 am - 2:32 pmMDW-PUJ

7h 32m1 stop

$350Delta

Find Deal

Fri, Sep 5 - Sun, Sep 14

2:40 pm - 10:37 pmPUJ-ORD

8h 57m1 stop

7:20 am - 2:32 pmORD-PUJ

6h 12m1 stop

$350Delta

Find Deal

Fri, Sep 5 - Sun, Sep 14

3:30 pm - 7:30 pmPUJ-ORD

5h 00mnonstop

7:02 am - 2:25 pmORD-PUJ

6h 23m1 stop

$367American Airlines

Find Deal

Thu, Aug 28 - Thu, Sep 4

12:10 pm - 7:56 amPUJ-ORD

20h 46m1 stop

9:23 am - 3:05 pmORD-PUJ

4h 42mnonstop

$372United Airlines

Find Deal

Thu, Aug 14 - Mon, Aug 18

1:50 pm - 5:44 pmPUJ-ORD

4h 54mnonstop

9:20 pm - 12:40 pmORD-PUJ

14h 20m1 stop

$375United Airlines

Find Deal

Sat, Sep 27 - Wed, Oct 22

Spirit Airlines flights from Caribbean Islands to Chicago

Our best Spirit Airlines deals on Caribbean Islands to Chicago flight tickets

Spirit Airlines

Aug 15

SJU10:16 pmSan Juan Luis Munoz Marin Intl

12h 06m

1 stop

ORD9:22 amChicago O'Hare Intl

Aug 18

ORD6:56 amChicago O'Hare Intl

7h 14m

1 stop

SJU3:10 pmSan Juan Luis Munoz Marin Intl

$179

Find similar

Spirit Airlines

Oct 16

SJU12:06 pmSan Juan Luis Munoz Marin Intl

6h 49m

1 stop

ORD5:55 pmChicago O'Hare Intl

Oct 18

ORD12:55 pmChicago O'Hare Intl

4h 39m

SJU6:34 pmSan Juan Luis Munoz Marin Intl

$186

Find similar

Spirit Airlines

Aug 15

SJU10:16 pmSan Juan Luis Munoz Marin Intl

12h 06m

1 stop

ORD9:22 amChicago O'Hare Intl

Aug 18

ORD12:55 pmChicago O'Hare Intl

4h 45m

SJU6:40 pmSan Juan Luis Munoz Marin Intl

$189

Find similar

Frontier flights from Caribbean Islands to Chicago

Our best Frontier deals on Caribbean Islands to Chicago flight tickets

Frontier

Nov 1

SJU3:21 pmSan Juan Luis Munoz Marin Intl

8h 48m

1 stop

MDW11:09 pmChicago Midway

Nov 15

MDW6:10 amChicago Midway

7h 05m

1 stop

SJU3:15 pmSan Juan Luis Munoz Marin Intl

$234

Find similar

Frontier

Sep 12

SJU3:39 amSan Juan Luis Munoz Marin Intl

7h 12m

1 stop

MDW9:51 amChicago Midway

Sep 20

MDW10:51 amChicago Midway

12h 08m

1 stop

SJU11:59 pmSan Juan Luis Munoz Marin Intl

$237

Find similar

Frontier

Aug 13

SJU8:15 amSan Juan Luis Munoz Marin Intl

12h 21m

1 stop

MDW7:36 pmChicago Midway

Aug 16

MDW9:12 pmChicago Midway

10h 52m

1 stop

SJU9:04 amSan Juan Luis Munoz Marin Intl

$238

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Mon 8/18

6:56 am-3:10 pm

1 stop7h 14m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/16

12:06 pm-5:55 pm

1 stop6h 49m

Chicago O'Hare Intl

Sat 10/18

12:55 pm-6:34 pm

Nonstop4h 39m

$186

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/1

3:21 pm-11:09 pm

1 stop8h 48m

Chicago Midway

Sat 11/15

6:10 am-3:15 pm

1 stop7h 05m

$234

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/12

3:39 am-9:51 am

1 stop7h 12m

Chicago Midway

Sat 9/20

10:51 am-11:59 pm

1 stop12h 08m

$237

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 10/9

3:21 pm-7:36 pm

Nonstop5h 15m

Chicago O'Hare Intl

Wed 10/15

5:20 am-3:29 pm

1 stop9h 09m

$337

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 9/5

2:40 pm-9:26 pm

1 stop7h 46m

Chicago Midway

Sun 9/14

6:00 am-2:32 pm

1 stop7h 32m

$350

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 9/5

2:40 pm-10:37 pm

1 stop8h 57m

Chicago O'Hare Intl

Sun 9/14

7:20 am-2:32 pm

1 stop6h 12m

$350

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/28

3:30 pm-7:30 pm

Nonstop5h 00m

Chicago O'Hare Intl

Thu 9/4

7:02 am-2:25 pm

1 stop6h 23m

$367

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 8/14

12:10 pm-7:56 am

1 stop20h 46m

Chicago O'Hare Intl

Mon 8/18

9:23 am-3:05 pm

Nonstop4h 42m

$372

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 9/27

1:50 pm-5:44 pm

Nonstop4h 54m

Chicago O'Hare Intl

Wed 10/22

9:20 pm-12:40 pm

1 stop14h 20m

$375

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 Islands 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 January is, on average, the cheapest month to fly to Chicago from Caribbean Islands, with most prices found around $232. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Caribbean Islands to Chicago during May average around $270.

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 $343. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Caribbean Islands to Chicago for around $479.

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 Islands to Chicago during this time can be as low as $243. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $482.

What is the cheapest Caribbean Islands to Chicago flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Caribbean Islands - 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 Islands when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Caribbean Islands for as low as $254 on momondo.

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

There are 4 cabin classes available to choose from on Caribbean Islands 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 Islands to Chicago flights?

No. A direct flight is the cheapest option for a flight between Caribbean Islands to Chicago.

Cheap Caribbean Islands to Chicago flight deals and tips

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

Best Price Found	$90
Fastest flight time	3h 56m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Caribbean Islands in the past 72 hours is $90. The best round-trip flight deal from Caribbean Islands to Chicago found on momondo in the last 72 hours is $179.

The fastest flight from Caribbean Islands to Chicago takes 3h 56m

Direct flights go from Caribbean Islands to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Caribbean Islands to Chicago?
Prices for flights from Caribbean Islands to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Caribbean Islands to Chicago?
The number of operators available for flights from Caribbean Islands to Chicago is 6 as of July 2025.
How old do you have to be to fly from Caribbean Islands 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 Islands to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Caribbean Islands to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Caribbean Islands to Chicago is Boeing 737-800 (19.98% of total bookings). The next most popular plane models are Airbus A321neo (10.01%), Boeing 737-900 (8.26%), and Boeing 737 MAX 8 (7.77%).

Best airlines flying from Caribbean Islands to Chicago

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $130	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $137	Free Cancellation	Rating 6.3 8,049 reviews	Search Spirit Airlines flights
Delta	PriceFrom $162	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
United Airlines	PriceFrom $219	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Southwest	PriceFrom $257	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
American Airlines	PriceFrom $329	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Caribbean Islands to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Caribbean Islands 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 Islands to Chicago?

Once you have performed a search for Caribbean Islands to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Caribbean Islands and alert you when they 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

Tue 8/5

Tue 8/12

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

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $39

Flights to Los Angelesfrom $37

Flights to Miamifrom $58

Flights to Orlandofrom $54

Flights to Las Vegasfrom $35

Flights to San Franciscofrom $49

Flights to Washington, D.C.from $49

Flights to Bostonfrom $77

Flights to Atlantafrom $29

Flights to Dallasfrom $55

Flights to Seattlefrom $93

Flights to Denverfrom $49

Cheap flights from Caribbean Islands to Chicago from $90

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 Islands to Chicago departing on 10/16. 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 Islands to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Caribbean Islands to Chicago

Our best Spirit Airlines deals on Caribbean Islands to Chicago flight tickets

Frontier flights from Caribbean Islands to Chicago

Our best Frontier deals on Caribbean Islands to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Caribbean Islands 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 Islands, with most prices found around $232. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Caribbean Islands to Chicago during May average around $270.

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?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Caribbean Islands to Chicago during this time can be as low as $243. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $482.

What is the cheapest Caribbean Islands to Chicago flight route?

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

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

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

There are 4 cabin classes available to choose from on Caribbean Islands 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 Islands to Chicago flights?

No. A direct flight is the cheapest option for a flight between Caribbean Islands to Chicago.

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

Spirit Airlines, Frontier, and Arajet are the most popular carriers operating from Caribbean Islands to Chicago

What airlines fly to Chicago?

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

As of July 2025, there are 13 flights per day flying from Caribbean Islands to Chicago. The most common time of day flights depart is 3:00PM, with 78% of flights taking off in the afternoon.

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

As of July 2025, 96 flights take off from Caribbean Islands and land in Chicago each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.

Cheap Caribbean Islands to Chicago flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

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

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

Best airlines flying from Caribbean Islands to Chicago

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

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

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