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Cheap flights from Caribbean to Chicago from $117

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 8/21. 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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Cheap round-trip flights

Delta Logo
12:58 pm - 9:36 pmSJU-MDW
9h 38m1 stop
Delta Logo
6:00 am - 4:31 pmMDW-SJU
9h 31m1 stop
$233Delta
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Fri, Sep 12 - Sun, Sep 21
Delta Logo
12:58 pm - 9:36 pmSJU-MDW
9h 38m1 stop
Delta Logo
12:43 pm - 10:00 pmMDW-SJU
8h 17m1 stop
$243Delta
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Thu, Sep 11 - Tue, Sep 16
Frontier Logo
4:20 pm - 11:25 pmSJU-MDW
9h 05m1 stop
Frontier Logo
6:15 am - 3:15 pmMDW-SJU
7h 00m1 stop
$279Frontier
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Mon, Nov 10 - Sun, Nov 16
Frontier Logo
3:21 pm - 11:25 pmSJU-MDW
9h 04m1 stop
Frontier Logo
6:21 am - 3:37 pmMDW-SJU
8h 16m1 stop
$280Frontier
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Fri, Oct 10 - Mon, Oct 13
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
2:55 pm - 10:30 pmMDW-SJU
6h 35m1 stop
$327Southwest
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Thu, Sep 4 - Tue, Sep 9
Southwest Logo
7:20 am - 2:40 pmSJU-MDW
8h 20m2 stops
Southwest Logo
9:00 am - 7:45 pmMDW-SJU
9h 45m2 stops
$362Southwest
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Wed, Sep 17 - Tue, Sep 23
Logo
2:12 pm - 9:18 amSDQ-MDW
20h 06m1 stop
Logo
9:48 am - 1:07 pmMDW-SDQ
26h 19m1 stop
$441
Find Deal
Sat, Sep 13 - Fri, Sep 19
Logo
2:12 pm - 9:18 amSDQ-MDW
20h 06m1 stop
Logo
5:15 pm - 1:07 pmMDW-SDQ
18h 52m2 stops
$508
Find Deal
Sat, Sep 13 - Fri, Sep 19
WestJet Logo
10:30 am - 9:36 amMBJ-MDW
23h 06m2 stops
WestJet Logo
12:43 pm - 9:27 amMDW-MBJ
20h 44m2 stops
$1,164WestJet
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Tue, Aug 12 - Tue, Aug 19
WestJet Logo
10:30 am - 9:36 amMBJ-MDW
23h 06m2 stops
WestJet Logo
12:43 pm - 9:27 amMDW-MBJ
20h 44m2 stops
$1,185WestJet
Find Deal
Tue, Aug 19 - Wed, Aug 20

Delta flights from Caribbean to Chicago Midway Airport

Our best Delta deals on Caribbean to Chicago Midway Airport flight tickets
Delta
Sep 12
SJU12:58 pmSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
MDW9:36 pmChicago Midway
Sep 21
MDW6:00 amChicago Midway
9h 31m
1 stop
SJU4:31 pmSan Juan Luis Munoz Marin Intl
$233
Find similar
Delta
Sep 11
SJU12:58 pmSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
MDW9:36 pmChicago Midway
Sep 16
MDW12:43 pmChicago Midway
8h 17m
1 stop
SJU10:00 pmSan Juan Luis Munoz Marin Intl
$243
Find similar
Delta
Oct 24
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 53m
1 stop
MDW4:23 pmChicago Midway
Oct 29
MDW6:00 amChicago Midway
6h 23m
1 stop
SJU1:23 pmSan Juan Luis Munoz Marin Intl
$349
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Frontier flights from Caribbean to Chicago Midway Airport

Our best Frontier deals on Caribbean to Chicago Midway Airport flight tickets
Frontier
Nov 10
SJU4:20 pmSan Juan Luis Munoz Marin Intl
9h 05m
1 stop
MDW11:25 pmChicago Midway
Nov 16
MDW6:15 amChicago Midway
7h 00m
1 stop
SJU3:15 pmSan Juan Luis Munoz Marin Intl
$279
Find similar
Frontier
Oct 10
SJU3:21 pmSan Juan Luis Munoz Marin Intl
9h 04m
1 stop
MDW11:25 pmChicago Midway
Oct 13
MDW6:21 amChicago Midway
8h 16m
1 stop
SJU3:37 pmSan Juan Luis Munoz Marin Intl
$280
Find similar
Frontier
Oct 2
SJU3:16 pmSan Juan Luis Munoz Marin Intl
9h 04m
1 stop
MDW11:20 pmChicago Midway
Oct 5
MDW6:21 amChicago Midway
7h 59m
1 stop
SJU3:20 pmSan Juan Luis Munoz Marin Intl
$284
Find similar

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from Caribbean, with most prices found around $252. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Caribbean during the month October is also very affordable. Most momondo users find prices during this month for around $312.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Caribbean. The lowest ticket price found for a Friday departure recently was $154. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Caribbean because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $580.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Caribbean in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $610. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

You are more likely to see cheaper flights to Chicago Midway Airport from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $399 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Caribbean for as low as $266 on momondo.

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

There are 1 cabin classes 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?

You could potentially save up to 43% 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

Best Price Found

$117

Fastest flight time

4h 10m

Direct flights

Mon, Tue, Thu, Fri and Sun
The best one-way flight to Chicago Midway Airport from Caribbean in the past 72 hours is $117. The best round-trip flight deal from Caribbean to Chicago Midway Airport found on momondo in the last 72 hours is $233.
The fastest flight from Caribbean to Chicago Midway Airport takes 4h 10m
Direct flights go from Caribbean to Chicago Midway Airport on Monday, Tuesday, Thursday, Friday and Sunday. The only airline offering direct flights is Southwest.
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  • 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
FrontierPriceFrom $130Free CancellationRating
5.9
3,252 reviews
Search Frontier flights
SouthwestPriceFrom $312Free CancellationRating
8.0
4,239 reviews
Search Southwest flights
DeltaPriceFrom $332Free CancellationRating
8.0
7,959 reviews
Search Delta 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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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.

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