$82+ Cheap flights from Midway (MDW) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SJU
Jul 16 — Jul 231

How far in advance should I book a flight from Chicago Midway Airport to Caribbean?

Users have found that booking a flight from Chicago Midway Airport to Caribbean at least 32 days early can save you up to 14% on average compared to booking a flight this week. If booking 32 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Caribbean for as little as $256 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $304 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago Midway Airport to Caribbean?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, October can be a great choice for travel to Caribbean. Flights to Caribbean from Chicago Midway Airport in October are about $328 on average during October, but can be found for as low as $90.

What is the cheapest time of day to fly from MDW to CB?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Caribbean as you normally would.

Cheap Midway to Caribbean flights in July & August 2024

Find cheap flight options from Midway to Caribbean specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,800,118 searches. Prices were last updated on July 11, 2024.
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2711:51 amMDW - SJU
1 stop13h 10mFrontier
Sat 8/310:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 7/11$166
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/284:46 pmMDW - SJU
1 stop10h 35mFrontier
Thu 9/510:50 amSJU - MDW
1 stop11h 09mFrontier
Deal found 7/9$168
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/31:58 pmMDW - SJU
1 stop10h 02mFrontier
Thu 8/157:19 pmSJU - MDW
1 stop12h 52mFrontier
Deal found 7/10$169
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - SJU
1 stop6h 35mFrontier
Sat 8/310:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 7/11$170
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 8/18:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 7/11$171
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/89:04 pmMDW - SJU
1 stop27h 59mFrontier
Mon 8/1210:04 pmSJU - MDW
1 stop11h 01mFrontier
Deal found 7/10$172
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/79:31 amMDW - SJU
1 stop16h 41mFrontier
Mon 8/1210:04 pmSJU - MDW
1 stop11h 01mFrontier
Deal found 7/10$173
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/19:04 pmMDW - SJU
1 stop27h 59mFrontier
Mon 8/54:12 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 7/10$174
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/89:04 pmMDW - SJU
1 stop18h 48mFrontier
Sun 8/113:28 amSJU - MDW
1 stop8h 02mFrontier
Deal found 7/10$175

Midway to Caribbean 2024 flight deals

Discover exclusive flight deals for travel between Midway and Caribbean in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,800,118 searches. Data last updated July 11, 2024.
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/44:46 pmMDW - SJU
1 stop10h 35mFrontier
Fri 9/203:08 amSJU - MDW
1 stop7h 05mFrontier
Deal found 7/11$163
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/44:46 pmMDW - SJU
1 stop10h 35mFrontier
Sat 9/219:42 amSJU - MDW
1 stop10h 36mFrontier
Deal found 7/11$164
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2110:59 amMDW - SJU
1 stop12h 21mFrontier
Fri 9/271:25 amSJU - MDW
1 stop9h 44mFrontier
Deal found 7/11$165
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/44:46 pmMDW - SJU
1 stop10h 35mFrontier
Mon 9/91:25 amSJU - MDW
1 stop9h 44mFrontier
Deal found 7/11$166
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1410:00 amMDW - SJU
1 stop10h 18mFrontier
Fri 9/203:08 amSJU - MDW
1 stop7h 05mFrontier
Deal found 7/10$167
This Frontier deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/284:46 pmMDW - SJU
1 stop10h 35mFrontier
Thu 9/510:50 amSJU - MDW
1 stop11h 09mFrontier
Deal found 7/9$168
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/31:58 pmMDW - SJU
1 stop10h 02mFrontier
Thu 8/157:19 pmSJU - MDW
1 stop12h 52mFrontier
Deal found 7/10$169
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2412:34 pmMDW - SJU
1 stop20h 11mFrontier
Sun 9/291:25 amSJU - MDW
1 stop9h 44mFrontier
Deal found 7/10$170
This mytrip.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 8/18:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 7/11$171

Midway to Caribbean flights leaving soon

Find last-minute flight options from Midway to Caribbean for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,800,118 searches. Data last updated July 11, 2024.
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/179:31 amMDW - SJU
1 stop16h 41mFrontier
Thu 8/85:27 amSJU - MDW
1 stop10h 23mFrontier
Deal found 7/10$207
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2011:51 amMDW - SJU
1 stop13h 10mFrontier
Thu 7/258:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 7/10$215
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/179:31 amMDW - SJU
1 stop16h 41mFrontier
Thu 7/258:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 7/10$216
This Gotogate deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/229:31 amMDW - PUJ
1 stop22h 49mFrontier
Tue 7/3010:35 amPUJ - MDW
1 stop23h 01mFrontier
Deal found 7/10$219
This Frontier deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/182:36 pmMDW - SJU
1 stop11h 36mFrontier
Sat 7/2710:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 7/10$223
This Gotogate deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/229:31 amMDW - PUJ
1 stop22h 49mFrontier
Thu 8/19:50 amPUJ - MDW
1 stop23h 46mFrontier
Deal found 7/10$224
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/196:11 pmMDW - SJU
1 stop6h 52mFrontier
Fri 8/210:15 pmSJU - MDW
1 stop10h 30mFrontier
Deal found 7/10$225
This Frontier deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/212:30 pmMDW - SJU
1 stop11h 42mFrontier
Sat 7/2710:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 7/11$229
This Gotogate deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/237:37 pmMDW - PUJ
1 stop12h 43mFrontier
Thu 8/19:50 amPUJ - MDW
1 stop23h 46mFrontier
Deal found 7/10$230

One-way flights to Caribbean from Midway

Search for one-way flight options from Midway to Caribbean. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,800,118 searches. Data last updated July 11, 2024.
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/93:28 pmMDW - SJU
1 stop8h 57mFrontier
Deal found 7/10$82
This Frontier deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/243:36 pmMDW - SJU
1 stop8h 54mFrontier
Deal found 7/10$84
This Trip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - SJU
1 stop6h 35mFrontier
Deal found 7/10$87
This Trip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/109:31 amMDW - SJU
1 stop16h 41mFrontier
Deal found 7/10$88
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/89:04 pmMDW - SJU
1 stop27h 59mFrontier
Deal found 7/10$89
This mytrip.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1211:25 amMDW - SJU
1 stop22h 27mFrontier
Deal found 7/9$91
This Trip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/19:04 pmMDW - SJU
1 stop27h 59mFrontier
Deal found 7/10$93
This mytrip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/87:59 pmMDW - SJU
1 stop12h 11mFrontier
Deal found 7/10$99
This eDestinos deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/126:15 amMDW - SJU
2 stops28h 29mMultiple Airlines
Deal found 7/9$101

Find flights from Midway to Caribbean within your budget

Customize your flight search to find flights from Midway to Caribbean 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, Cheapflights users made 2,800,118 searches. Data last updated July 11, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$163 - $320

Route

Depart

Return

Price

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/4

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Fri 9/20

1 stop7h 05m

$163

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/4

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Sat 9/21

1 stop10h 36m

$164

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/23

1 stop12h 11m

San Juan Luis Munoz Marin Intl

Mon 9/30

1 stop9h 57m

$165

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/4

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Mon 9/9

1 stop9h 44m

$166

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 9/5

1 stop12h 21m

San Juan Luis Munoz Marin Intl

Mon 9/9

1 stop9h 57m

$167

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/28

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Thu 9/5

1 stop11h 09m

$168

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/3

1 stop10h 02m

San Juan Luis Munoz Marin Intl

Thu 8/15

1 stop12h 52m

$169

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Fri 8/23

1 stop13h 47m

San Juan Luis Munoz Marin Intl

Tue 8/27

2 stops29h 10m

$317

Chicago MidwaySanto Domingo Las Americas

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 10/5

1 stop6h 47m

Santo Domingo Las Americas

Tue 10/8

1 stop7h 48m

$320

Flights are sorted by cheapest first

Deals found on 7/11

No data available for this route at this time. Please check back soon.

Best time to book a flight from Midway to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated July 11, 2024.
8.0
Very good
9,842 reviews

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Overall

8.0

Food

7.4

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

8.0
Very good
9,842 reviews
8.0
Very good
9,842 reviews

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Overall

8.0

Food

7.4

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

7.5
Good
2,230 reviews
8.0
Very good
9,842 reviews

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Overall

8.0

Food

7.4

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

7.4
Good
2,771 reviews
8.0
Very good
9,842 reviews

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Overall

8.0

Food

7.4

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

6.2
Okay
3,868 reviews
8.0
Very good
9,842 reviews

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

8.0

Overall

8.0

Food

7.4

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Related info for your journey

Find useful and relevant information for your journey from Midway to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • Can I find flights from Chicago Midway Airport to Caribbean for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Caribbean for under $200. The cheapest flight booked recently is on Frontier for just $163, but on average you can expect to pay $173.

  • Are there last-minute flights available from Chicago Midway Airport to Caribbean for under $300?

    There are currently 20+ open flights from Chicago Midway Airport to Caribbean within the next 7 days for less than $300.

  • What are the most popular routes from Chicago Midway Airport to Caribbean?

  • What are the cheapest flights from Chicago Midway Airport to Caribbean?

    While on average a flight from Chicago Midway Airport to Caribbean is generally $162, our data shows the cheapest flight currently is $58. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $165 for that flight.

  • What does MDW to SJU mean?

    This is defined as Chicago Midway Airport (MDW) and San Juan Luis Munoz Marin Intl Airport (SJU). Codes like San Juan Luis Munoz Marin Intl Airport are often used to just call airports uniquely. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Santo Domingo Las Americas Airport (SDQ), Punta Cana Airport (PUJ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI).

  • Can I find deals for flights from Midway to Caribbean that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Caribbean flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Caribbean flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midway to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Caribbean.

  • Can I find deals for business class flights from Midway to Caribbean?

    Yes. Cheapflights offers flight deals from Midway to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Caribbean that allow pets onboard?

    Many airlines flying from Midway to Caribbean offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Caribbean?

    Yes, you can often find last-minute deals on Midway to Caribbean flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Caribbean flight deals updated?

    The Chicago Midway Airport to Caribbean flight deals you see on this page were last updated on 7/11.

  • What are the most popular airlines that fly from Chicago Midway Airport to Caribbean?

  • What is the cheapest month to book a flight from Chicago Midway Airport to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $246). Flying from Chicago Midway Airport to Caribbean in March is currently the most expensive (average of $337). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Midway to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Midway to Caribbean

Discover the top 4 airlines that operate flights from Midway to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,800,118 searches. Data last updated July 11, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$117Average$350FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$178Average$267FlexibilityNo cancel feeOn-time65%
DeltaCheapest$367Average$699FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$503Average$503FlexibilityNo cancel feeOn-time75%

Search flights from Midway to Caribbean by cabin class

Find flights from Midway to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Midway to Caribbean

Find hourly flight availability from Midway to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 11, 2024.
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0%of flight departuresEvening6 pm to midnight
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