Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Caribbean to Chicago from $118

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 8/20. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Caribbean to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$236Southwest
Mon, Aug 31 - Mon, Sep 7
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$246Delta
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
2:15 pm - 11:25 pm
MDW
-
SJU
8h 10m
1 stop
$256Southwest
Fri, Aug 21 - Sun, Aug 23
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
$266Delta
Wed, Aug 19 - Mon, Aug 24
Southwest Logo
8:55 pm - 8:55 am
SJU
-
MDW
13h 00m
1 stop
Southwest Logo
8:05 pm - 9:10 am
MDW
-
SJU
12h 05m
1 stop
$286Southwest
Fri, Aug 7 - Sun, Aug 9
Southwest Logo
8:55 pm - 8:55 am
SJU
-
MDW
13h 00m
1 stop
Southwest Logo
2:55 pm - 11:50 pm
MDW
-
SJU
7h 55m
1 stop
$296Southwest
Fri, Aug 14 - Mon, Aug 17
Southwest Logo
8:55 pm - 11:25 am
SJU
-
MDW
15h 30m
2 stops
Southwest Logo
8:05 pm - 9:10 am
MDW
-
SJU
12h 05m
1 stop
$301Southwest
Thu, Aug 6 - Sun, Aug 9
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$435Frontier
Fri, Jul 17 - Tue, Aug 18
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
$455Frontier
Fri, Jul 31 - Fri, Aug 7
Multiple Airlines Logo
1:45 pm - 9:40 am
GCM
-
MDW
19h 55m
1 stop
Multiple Airlines Logo
12:11 pm - 11:35 am
MDW
-
GCM
23h 24m
2 stops
$831Multiple Airlines
Sat, Jul 25 - Sat, Aug 1

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Southwest flights from Caribbean to Chicago Midway Airport

Our best Southwest deals on Caribbean to Chicago Midway Airport flight tickets
Southwest
Aug 25
SJU8:20 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW2:45 pmChicago Midway
Aug 31
MDW5:00 amChicago Midway
7h 45m
1 stop
SJU1:45 pmSan Juan Luis Munoz Marin Intl
$236
Southwest
Aug 21
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 40m
1 stop
MDW12:40 pmChicago Midway
Aug 23
MDW8:05 pmChicago Midway
12h 05m
1 stop
SJU9:10 amSan Juan Luis Munoz Marin Intl
$256
Southwest
Aug 7
SJU8:55 pmSan Juan Luis Munoz Marin Intl
13h 00m
1 stop
MDW8:55 amChicago Midway
Aug 9
MDW8:05 pmChicago Midway
12h 05m
1 stop
SJU9:10 amSan Juan Luis Munoz Marin Intl
$286

Delta flights from Caribbean to Chicago Midway Airport

Our best Delta deals on Caribbean to Chicago Midway Airport flight tickets
Delta
Aug 26
SJU2:59 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
MDW10:36 pmChicago Midway
Aug 29
MDW6:05 amChicago Midway
9h 33m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
$246
Delta
Aug 19
SJU2:59 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
MDW10:36 pmChicago Midway
Aug 24
MDW6:05 amChicago Midway
9h 33m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
$266
Delta
Aug 12
SJU7:00 amSan Juan Luis Munoz Marin Intl
10h 15m
1 stop
MDW4:15 pmChicago Midway
Aug 18
MDW6:05 amChicago Midway
9h 33m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
$306

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to Chicago Midway Airport 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 June 17, 2026.
Use the filters below to find and compare flights from Caribbean to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 8/31

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Mon 9/7

3:15 pm-11:05 pm

1 stop6h 50m

$236

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/26

2:59 pm-10:36 pm

1 stop8h 37m

Chicago Midway

Sat 8/29

6:05 am-4:38 pm

1 stop9h 33m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/21

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Sun 8/23

2:15 pm-11:25 pm

1 stop8h 10m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/19

12:56 pm-10:36 pm

1 stop10h 40m

Chicago Midway

Mon 8/24

6:05 am-1:42 pm

1 stop6h 37m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/7

8:55 pm-8:55 am

1 stop13h 00m

Chicago Midway

Sun 8/9

8:05 pm-9:10 am

1 stop12h 05m

$286

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/14

8:55 pm-8:55 am

1 stop13h 00m

Chicago Midway

Mon 8/17

2:55 pm-11:50 pm

1 stop7h 55m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/6

8:55 pm-11:25 am

2 stops15h 30m

Chicago Midway

Sun 8/9

8:05 pm-9:10 am

1 stop12h 05m

$301
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 7/17

1:32 pm-10:03 pm

1 stop8h 31m

Chicago Midway

Tue 8/18

6:00 am-12:21 pm

1 stop6h 21m

$435

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 7/31

1:32 pm-10:03 pm

1 stop8h 31m

Chicago Midway

Fri 8/7

6:05 am-12:27 pm

1 stop6h 22m

$455

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 7/25

1:45 pm-9:40 am

1 stop19h 55m

Chicago Midway

Sat 8/1

12:11 pm-11:35 am

2 stops23h 24m

$831

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Caribbean to Chicago Midway Airport

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 Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Caribbean, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Caribbean during the month December is also very affordable. Most momondo users find prices during this month for around $104.

What is the cheapest Caribbean to Chicago Midway flight route?

Fly from Montego Bay Sangster Intl to Chicago Midway for the best Caribbean - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on Caribbean to Chicago Midway Airport 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 Midway Airport flights?

You could potentially save up to 14% on your flight if you consider stops on a Caribbean to Chicago Midway Airport flight.

Cheap Caribbean to Chicago Midway Airport flight deals and tips

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

Fastest flight time

4h 45m

Direct flights

Every day
The fastest flight from Caribbean to Chicago Midway Airport takes 4h 45m
Direct flights go from Caribbean to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Caribbean to Chicago Midway Airport

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

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Caribbean to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport 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 to Chicago Midway Airport?

Best airlines flying from Caribbean to Chicago Midway Airport

Compare and see reviews for airlines that fly from Caribbean to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $326Free CancellationRating
7.9
4,235 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
Portage
Saint Joseph
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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Caribbean to Chicago for you.

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

Yes. All flights to Chicago from Caribbean on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Caribbean to Chicago.

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 Midway Airport 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
Fri 7/17
Fri 7/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago