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Cheap flights from Chicago Midway Airport to Caribbean Islands from $87

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 4/9. 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.
4:40 pm - 8:33 amMDW-SJU
14h 53m1 stop
2:12 pm - 7:35 pmSJU-MDW
30h 23m1 stop
$178Frontier
Find Deal
mar., abr. 1 - mar., abr. 8
4:40 pm - 1:50 amMDW-SJU
8h 10m1 stop
2:55 am - 7:35 pmSJU-MDW
17h 40m1 stop
$180Frontier
Find Deal
mar., abr. 1 - mar., abr. 8
4:00 pm - 11:15 pmMDW-SJU
6h 15m1 stop
12:50 pm - 10:22 pmSJU-MDW
10h 32m1 stop
$271Delta
Find Deal
sáb., abr. 26 - sáb., may. 3
4:00 pm - 11:15 pmMDW-SJU
6h 15m1 stop
7:15 am - 5:59 pmSJU-MDW
11h 44m1 stop
$296Delta
Find Deal
sáb., abr. 26 - sáb., may. 3
12:46 pm - 8:55 amMDW-STT
19h 09m1 stop
1:55 pm - 11:24 pmSTT-MDW
10h 29m1 stop
jue., abr. 3 - mar., abr. 8
10:19 am - 8:55 amMDW-STT
21h 36m1 stop
1:55 pm - 11:24 pmSTT-MDW
10h 29m1 stop
jue., abr. 3 - mar., abr. 8
8:35 am - 2:15 pmMDW-SJU
4h 40mnonstop
8:00 am - 6:25 pmSJU-MDW
11h 25m1 stop
$377Southwest
Find Deal
sáb., abr. 26 - mar., abr. 29
6:05 am - 3:10 pmMDW-SJU
8h 05m1 stop
7:20 am - 7:10 pmSJU-MDW
12h 50m2 stops
$381Southwest
Find Deal
vie., sep. 5 - mar., sep. 9
6:04 am - 2:05 pmMDW-SXM
7h 01m1 stop
1:46 pm - 12:35 pmSXM-MDW
23h 49m2 stops
$858KLM
Find Deal
dom., abr. 27 - dom., may. 4
6:04 am - 2:05 pmMDW-SXM
7h 01m1 stop
1:46 pm - 12:35 pmSXM-MDW
23h 49m2 stops
$890KLM
Find Deal
dom., abr. 27 - dom., may. 4

Southwest flights from Chicago Midway Airport to Caribbean Islands

Our best Southwest deals on Chicago Midway Airport to Caribbean Islands flight tickets
Southwest
Apr 26
MDW8:35 amChicago Midway
4h 40m
SJU2:15 pmSan Juan Luis Munoz Marin Intl
Apr 29
SJU8:00 amSan Juan Luis Munoz Marin Intl
11h 25m
1 stop
MDW6:25 pmChicago Midway
Southwest
Sep 5
MDW6:05 amChicago Midway
8h 05m
1 stop
SJU3:10 pmSan Juan Luis Munoz Marin Intl
Sep 9
SJU7:20 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW7:10 pmChicago Midway
Southwest
May 6
MDW9:40 amChicago Midway
11h 10m
1 stop
SJU9:50 pmSan Juan Luis Munoz Marin Intl
May 13
SJU11:15 amSan Juan Luis Munoz Marin Intl
10h 10m
1 stop
MDW8:25 pmChicago Midway

Frontier flights from Chicago Midway Airport to Caribbean Islands

Our best Frontier deals on Chicago Midway Airport to Caribbean Islands flight tickets
Frontier
Apr 1
MDW4:40 pmChicago Midway
14h 53m
1 stop
SJU8:33 amSan Juan Luis Munoz Marin Intl
Apr 8
SJU2:12 pmSan Juan Luis Munoz Marin Intl
30h 23m
1 stop
MDW7:35 pmChicago Midway
Frontier
Apr 1
MDW4:40 pmChicago Midway
8h 10m
1 stop
SJU1:50 amSan Juan Luis Munoz Marin Intl
Apr 8
SJU2:55 amSan Juan Luis Munoz Marin Intl
17h 40m
1 stop
MDW7:35 pmChicago Midway
Frontier
Mar 26
MDW3:14 pmChicago Midway
8h 21m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Mar 27
SJU5:30 amSan Juan Luis Munoz Marin Intl
7h 10m
1 stop
MDW11:40 amChicago Midway

See travel insights to Caribbean Islands from

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 month to fly to Caribbean Islands?

The month of May is, on average, the cheapest month to fly to Caribbean Islands from Chicago Midway Airport, with most prices found around $258. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $304.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Chicago Midway Airport to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $59. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $453. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Chicago Midway Airport to Caribbean Islands in the evening for as low as $324. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $456. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago Midway to Caribbean Islands flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Chicago Midway Airport when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $396 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Chicago Midway Airport for as low as $287 on momondo.

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

There are 1 cabin classes available to choose from on Chicago Midway to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

$87

Fastest flight time

4h 00m

Direct flights

Every day

Airports in Caribbean Islands

5 airports
The best one-way flight to Caribbean Islands from Chicago Midway Airport in the past 72 hours is $87. The best round-trip flight deal from Chicago Midway Airport to Caribbean Islands found on momondo in the last 72 hours is $178.
The fastest flight from Chicago Midway Airport to Caribbean Islands takes 4h 00m
Direct flights go from Chicago Midway Airport to Caribbean Islands every day.
There are 5 airports near Caribbean Islands: 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 $133Free CancellationRating
6.0
3,292 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $174Free CancellationRating
6.3
7,896 reviews
Search Spirit Airlines flights
DeltaPriceFrom $325Free CancellationRating
8.0
7,944 reviews
Search Delta flights
SouthwestPriceFrom $337Free CancellationRating
8.0
4,292 reviews
Search Southwest 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.


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mar. 3/18
mar. 3/25

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Popular cities in Caribbean Islands

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