Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Caribbean to Chicago from $113

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 5/14. 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

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

Find the cheapest flights from Caribbean to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:58 am - 7:41 am
SJU
-
MDW
22h 43m
1 stop
Frontier Logo
8:41 am - 1:15 pm
MDW
-
SJU
27h 34m
1 stop
$196Frontier
Sat, May 2 - Mon, May 4
Frontier Logo
3:43 pm - 10:14 pm
SJU
-
MDW
7h 31m
1 stop
Frontier Logo
8:39 am - 2:01 am
MDW
-
SJU
16h 22m
1 stop
$204Frontier
Sat, May 2 - Sun, May 3
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
8:39 am - 9:54 am
MDW
-
SJU
24h 15m
1 stop
$206Frontier
Fri, May 1 - Sun, May 3
Frontier Logo
8:59 am - 3:57 pm
SJU
-
MDW
7h 58m
1 stop
Frontier Logo
6:00 am - 2:07 pm
MDW
-
SJU
7h 07m
1 stop
$211Frontier
Fri, May 8 - Sat, May 16
Southwest Logo
5:00 am - 12:20 pm
SJU
-
MDW
8h 20m
2 stops
Southwest Logo
2:55 pm - 11:50 pm
MDW
-
SJU
7h 55m
1 stop
$226Southwest
Thu, Aug 20 - Thu, Aug 27
Delta Logo
12:55 pm - 10:28 pm
SJU
-
MDW
10h 33m
1 stop
Delta Logo
12:53 pm - 10:17 pm
MDW
-
SJU
8h 24m
1 stop
$241Delta
Wed, May 6 - Tue, May 12
Delta Logo
4:32 pm - 8:47 am
MBJ
-
MDW
16h 15m
2 stops
Delta Logo
6:00 am - 11:29 am
MDW
-
MBJ
5h 29m
1 stop
$408Delta
Fri, May 1 - Mon, May 4
Southwest Logo
12:15 pm - 7:00 pm
MBJ
-
MDW
6h 45m
1 stop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$422Southwest
Thu, May 7 - Tue, Jul 7
Multiple Airlines Logo
7:15 am - 10:02 pm
NAS
-
MDW
15h 47m
2 stops
Multiple Airlines Logo
4:52 pm - 4:25 pm
MDW
-
NAS
22h 33m
1 stop
$516Multiple Airlines
Fri, May 15 - Mon, May 18
Multiple Airlines Logo
7:15 am - 10:02 pm
NAS
-
MDW
15h 47m
2 stops
Multiple Airlines Logo
6:00 am - 7:15 pm
MDW
-
NAS
12h 15m
2 stops
$577Multiple Airlines
Thu, May 14 - Tue, May 19

Southwest flights from Caribbean to Chicago Midway Airport

Our best Southwest deals on Caribbean to Chicago Midway Airport flight tickets
Southwest
Aug 20
SJU5:00 amSan Juan Luis Munoz Marin Intl
8h 20m
2 stops
MDW12:20 pmChicago Midway
Aug 27
MDW2:55 pmChicago Midway
7h 55m
1 stop
SJU11:50 pmSan Juan Luis Munoz Marin Intl
$226
Southwest
Aug 21
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 40m
1 stop
MDW12:40 pmChicago Midway
Aug 30
MDW5:00 amChicago Midway
7h 00m
1 stop
SJU1:00 pmSan Juan Luis Munoz Marin Intl
$246
Southwest
May 6
SJU5:35 amSan Juan Luis Munoz Marin Intl
9h 10m
1 stop
MDW1:45 pmChicago Midway
May 10
MDW7:35 amChicago Midway
6h 05m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
$261

Delta flights from Caribbean to Chicago Midway Airport

Our best Delta deals on Caribbean to Chicago Midway Airport flight tickets
Delta
May 6
SJU12:55 pmSan Juan Luis Munoz Marin Intl
10h 33m
1 stop
MDW10:28 pmChicago Midway
May 12
MDW12:53 pmChicago Midway
8h 24m
1 stop
SJU10:17 pmSan Juan Luis Munoz Marin Intl
$241
Delta
May 2
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 56m
1 stop
MDW4:26 pmChicago Midway
May 6
MDW10:41 amChicago Midway
8h 45m
1 stop
SJU8:26 pmSan Juan Luis Munoz Marin Intl
$271
Delta
May 2
SJU6:15 amSan Juan Luis Munoz Marin Intl
11h 11m
1 stop
MDW4:26 pmChicago Midway
May 6
MDW6:00 amChicago Midway
9h 23m
1 stop
SJU4:23 pmSan Juan Luis Munoz Marin Intl
$286

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 April 21, 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

Sat 5/2

9:58 am-7:41 am

1 stop22h 43m

Chicago Midway

Mon 5/4

8:41 am-1:15 pm

1 stop27h 34m

$196

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/2

3:43 pm-10:14 pm

1 stop7h 31m

Chicago Midway

Sun 5/3

8:39 am-2:01 am

1 stop16h 22m

$204

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Sun 5/3

8:39 am-9:54 am

1 stop24h 15m

$206

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

8:59 am-3:57 pm

1 stop7h 58m

Chicago Midway

Sat 5/16

6:00 am-2:07 pm

1 stop7h 07m

$211

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/20

5:00 am-12:20 pm

2 stops8h 20m

Chicago Midway

Thu 8/27

2:55 pm-11:50 pm

1 stop7h 55m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 5/6

12:55 pm-10:28 pm

1 stop10h 33m

Chicago Midway

Tue 5/12

12:53 pm-10:17 pm

1 stop8h 24m

$241

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 5/1

4:32 pm-8:47 am

2 stops16h 15m

Chicago Midway

Mon 5/4

6:00 am-11:29 am

1 stop5h 29m

$408
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 5/7

12:15 pm-7:00 pm

1 stop6h 45m

Chicago Midway

Tue 7/7

10:05 am-1:55 pm

Nonstop3h 50m

$422

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Fri 5/15

7:15 am-10:02 pm

2 stops15h 47m

Chicago Midway

Mon 5/18

4:52 pm-4:25 pm

1 stop22h 33m

$516

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Thu 5/14

7:15 am-10:02 pm

2 stops15h 47m

Chicago Midway

Tue 5/19

6:00 am-7:15 pm

2 stops12h 15m

$577

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 Caribbean to Chicago Midway flight route?

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

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

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

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

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

Best Price Found

$279

Fastest flight time

4h 45m

Direct flights

Mon, Tue, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Caribbean in the past 72 hours is $279. The best round-trip flight deal from Caribbean to Chicago Midway Airport found on momondo in the last 72 hours is $462.
The fastest flight from Caribbean to Chicago Midway Airport takes 4h 45m
Direct flights go from Caribbean to Chicago Midway Airport on Monday, Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
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 $281Free CancellationRating
8.0
4,331 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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
Thu 5/21
Thu 5/28
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago