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Cheap flights from Chicago Midway Airport to Caribbean Islands from $88

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Caribbean Islands departing on 1/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Caribbean Islands

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Caribbean Islands that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Caribbean Islands.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Caribbean Islands? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Caribbean Islands, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Caribbean Islands

Find recent round-trip train or bus tickets from Chicago Midway Airport to Caribbean Islands.

All round-trip flight deals to Caribbean Islands

The cheapest plane tickets to Caribbean Islands found on KAYAK recently.
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
3:59 am - 9:31 amSJU-MDW
7h 32m1 stop
$174Frontier
Find Deal
Sun, Dec 15 - Thu, Dec 19
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
11:45 am - 11:41 amSJU-MDW
25h 56m1 stop
$175Frontier
Find Deal
Sun, Dec 8 - Thu, Dec 12
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
6:00 am - 1:06 pmSJU-MDW
9h 06m1 stop
$176Frontier
Find Deal
Mon, Dec 16 - Fri, Dec 20
1:20 pm - 12:40 amMDW-SJU
9h 20m1 stop
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$200Southwest
Find Deal
Wed, Jan 15 - Thu, Jan 23
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
6:40 pm - 11:29 pmSJU-MDW
30h 49m2 stops
Mon, Dec 9 - Fri, Dec 13
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
3:20 am - 5:37 pmSJU-MDW
16h 17m2 stops
Mon, Dec 9 - Thu, Dec 12
1:20 pm - 12:40 amMDW-SJU
9h 20m1 stop
6:00 am - 4:50 pmSJU-MDW
12h 50m2 stops
$220Southwest
Find Deal
Wed, Jan 15 - Wed, Jan 22
6:00 am - 2:22 pmMDW-PUJ
6h 22m1 stop
3:53 pm - 9:49 pmPUJ-MDW
7h 56m1 stop
$343Delta
Find Deal
Mon, Feb 10 - Thu, Feb 13
6:00 am - 4:42 pmMDW-PUJ
8h 42m1 stop
3:47 pm - 10:20 pmPUJ-MDW
8h 33m1 stop
$353Delta
Find Deal
Sat, Jan 11 - Wed, Jan 15
6:00 am - 2:25 pmMDW-PUJ
6h 25m1 stop
3:50 pm - 10:06 pmPUJ-MDW
8h 16m1 stop
$473KLM
Find Deal
Tue, Dec 10 - Fri, Dec 13
5:30 am - 12:44 amMDW-SJU
17h 14m1 stop
$88Frontier
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Fri, Jan 17
12:36 pm - 2:32 amMDW-SJU
11h 56m1 stop
$89Frontier
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Thu, Dec 12
5:45 am - 5:35 pmMDW-SJU
9h 50m1 stop
$100Southwest
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Wed, Jan 22
5:45 am - 5:35 pmMDW-SJU
9h 50m1 stop
$110Southwest
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Wed, Jan 22
7:15 am - 1:22 pmMDW-SJU
28h 07m2 stops
Sat, Dec 14
7:15 am - 11:38 pmMDW-SJU
14h 23m1 stop
Sat, Dec 14
6:00 am - 2:22 pmMDW-PUJ
6h 22m1 stop
$160Delta
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Mon, Jan 6
6:00 am - 2:25 pmMDW-PUJ
6h 25m1 stop
$170Delta
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Sat, Jan 4
10:19 am - 1:53 pmMDW-MBJ
26h 34m2 stops
$446WestJet
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Wed, Jan 22
12:43 pm - 2:48 pmMDW-UVF
24h 05m2 stops
$457WestJet
Find Deal
Mon, Nov 25
7:42 am - 7:17 pmMDW-SJU
9h 35m1 stop
8:22 pm - 1:31 pmSJU-MDW
19h 09m1 stop
$325Frontier
Find Deal
Mon, Nov 18 - Mon, Nov 25
8:31 pm - 11:23 amMDW-SJU
12h 52m1 stop
3:59 am - 7:55 amSJU-MDW
29h 56m1 stop
$375Frontier
Find Deal
Mon, Nov 18 - Sun, Nov 24
3:25 pm - 12:45 amMDW-SJU
7h 20m1 stop
6:10 am - 2:50 pmSJU-MDW
10h 40m1 stop
$404Southwest
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Tue, Nov 19 - Tue, Nov 26
6:00 am - 4:40 pmMDW-PUJ
8h 40m1 stop
2:03 pm - 9:46 pmPUJ-MDW
9h 43m1 stop
$408Delta
Find Deal
Sun, Nov 17 - Wed, Nov 20
12:25 pm - 12:30 amMDW-SJU
10h 05m2 stops
11:40 am - 7:20 pmSJU-MDW
9h 40m2 stops
$424Southwest
Find Deal
Sat, Nov 16 - Mon, Nov 18
8:31 pm - 11:00 amMDW-NAS
13h 29m1 stop
12:00 pm - 7:55 amNAS-MDW
20h 55m1 stop
Mon, Nov 18 - Wed, Nov 20
8:31 pm - 2:30 pmMDW-SDQ
15h 59m1 stop
6:42 pm - 5:35 pmSDQ-MDW
24h 53m2 stops
Mon, Nov 18 - Mon, Nov 25
10:41 am - 11:22 pmMDW-SJU
10h 41m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$469Delta
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Tue, Nov 19 - Thu, Nov 28
9:30 am - 3:38 pmMDW-AUA
28h 08m2 stops
4:30 pm - 1:35 pmAUA-MDW
23h 05m2 stops
$1,397WestJet
Find Deal
Sun, Nov 17 - Tue, Nov 19
12:43 pm - 2:34 pmMDW-PUJ
23h 51m2 stops
5:00 pm - 9:32 amPUJ-MDW
42h 32m2 stops
$3,236WestJet
Find Deal
Mon, Nov 18 - Wed, Nov 20
8:35 am - 2:15 pmMDW-SJU
4h 40mnonstop
1:00 pm - 5:20 pmSJU-MDW
5h 20mnonstop
$430Southwest
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Sat, May 3 - Sat, May 10
9:35 am - 4:00 pmMDW-PUJ
4h 25mnonstop
5:00 pm - 8:00 pmPUJ-MDW
5h 00mnonstop
$499Southwest
Find Deal
Sat, Jan 25 - Sat, Feb 1
9:35 am - 4:00 pmMDW-PUJ
4h 25mnonstop
5:00 pm - 8:00 pmPUJ-MDW
5h 00mnonstop
$515Southwest
Find Deal
Sat, Jan 25 - Sat, Feb 1
8:45 am - 3:20 pmMDW-SJU
4h 35mnonstop
5:05 pm - 9:35 pmSJU-MDW
5h 30mnonstop
$525Southwest
Find Deal
Sat, Mar 8 - Sat, Mar 15
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$551Southwest
Find Deal
Sat, Feb 1 - Sat, Feb 8
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$573Southwest
Find Deal
Sat, Jan 25 - Sat, Feb 1
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$621Southwest
Find Deal
Sat, Feb 8 - Sat, Feb 15
9:35 am - 4:00 pmMDW-PUJ
4h 25mnonstop
4:25 pm - 7:30 pmPUJ-MDW
5h 05mnonstop
$687Southwest
Find Deal
Sat, Feb 8 - Sat, Feb 15
9:05 am - 3:30 pmMDW-PUJ
4h 25mnonstop
3:55 pm - 8:10 pmPUJ-MDW
5h 15mnonstop
$702Southwest
Find Deal
Thu, Mar 6 - Sun, Mar 9
9:05 am - 3:30 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$735Southwest
Find Deal
Thu, Mar 6 - Mon, Mar 10

Frontier flights from Chicago Midway Airport to Caribbean Islands

Our best Frontier deals on Chicago Midway Airport to Caribbean Islands flight tickets
Frontier
Dec 15
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 19
SJU3:59 amSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MDW9:31 amChicago Midway
Frontier
Dec 8
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 12
SJU11:45 amSan Juan Luis Munoz Marin Intl
25h 56m
1 stop
MDW11:41 amChicago Midway
Frontier
Dec 16
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 20
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 06m
1 stop
MDW1:06 pmChicago Midway

Southwest flights from Chicago Midway Airport to Caribbean Islands

Our best Southwest deals on Chicago Midway Airport to Caribbean Islands flight tickets
Southwest
Jan 15
MDW1:20 pmChicago Midway
9h 20m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 23
SJU2:55 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:45 pmChicago Midway
Southwest
Jan 15
MDW1:20 pmChicago Midway
9h 20m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 22
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW4:50 pmChicago Midway
Southwest
Feb 2
MDW1:20 pmChicago Midway
9h 30m
2 stops
SJU12:50 amSan Juan Luis Munoz Marin Intl
Feb 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW4:50 pmChicago Midway

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

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 airline that flies to Caribbean Islands from Chicago Midway Airport?

Spirit Airlines. Spirit Airlines, Frontier, and Delta are the most popular carriers operating from Chicago Midway Airport to Caribbean Islands

Can stopping save me money on Chicago Midway Airport to Caribbean Islands flights?

You could potentially save up to 68% on your flight if you consider stops on a Chicago Midway Airport to Caribbean Islands flight.

Cheap Chicago Midway Airport to Caribbean Islands flight deals and tips

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

Best Price Found

$88

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Caribbean Islands

7 airports
The best one-way flight to Caribbean Islands from Chicago Midway Airport in the past 72 hours is $88. The best round-trip flight deal from Chicago Midway Airport to Caribbean Islands found on momondo in the last 72 hours is $174.
The fastest flight from Chicago Midway Airport to Caribbean Islands takes 3h 55m
Direct flights go from Chicago Midway Airport to Caribbean Islands every day.
There are 7 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), Santo Domingo Las Americas (SDQ), Nassau Intl (NAS), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

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

    Prices for flights from Chicago Midway Airport to Caribbean Islands were last updated today.

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

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

    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 Chicago Midway Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

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


Best airlines flying from Chicago Midway Airport to Caribbean Islands

Compare and see reviews for airlines that fly from Chicago Midway Airport to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $128Free CancellationRating
6.1
3,551 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $199Free CancellationRating
6.3
8,167 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
DeltaPriceFrom $365Free CancellationRating
8.0
8,788 reviews
Search Delta flights

Why use momondo?

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

Finding the right flight to Caribbean Islands from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

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

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

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

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Caribbean Islands from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Caribbean Islands trip

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Popular cities in Caribbean Islands

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