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Cheap flights from Midway (MDW) to Caribbean from $96

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 7/9. 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
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
1 adult, Economy
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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 57 days early can save you up to 25% on average compared to booking a flight this week. If booking 57 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Caribbean for as little as $258 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 $283 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 $319 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 June & July 2024

Find cheap flight options from Midway to Caribbean specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 7/1110:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$191
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Thu 7/1810:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$201
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Thu 7/115:27 amSJU - MDW
1 stop17h 19mFrontier
Deal found 6/6$212
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Wed 7/103:03 amSJU - MDW
1 stop7h 17mFrontier
Deal found 6/6$213
Sat 6/297:49 amMDW - SJU
1 stop23h 51mFrontier
Tue 7/98:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$216
Mon 7/295:14 pmMDW - SJU
1 stop7h 51mFrontier
Tue 8/68:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$227
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Sat 7/1310:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 6/6$230
Sat 6/2211:51 amMDW - SJU
1 stop13h 08mFrontier
Wed 6/2610:15 pmSJU - MDW
1 stop12h 16mFrontier
Deal found 6/5$231
Thu 6/135:57 pmMDW - SDQ
1 stop13h 41mFrontier
Mon 6/179:58 amSDQ - MDW
1 stop14h 41mFrontier
Deal found 6/6$232

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 3,050,429 searches. Data last updated June 6, 2024.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 7/1110:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$191
Thu 8/12:36 pmMDW - SJU
1 stop11h 36mFrontier
Wed 8/74:01 pmSJU - MDW
2 stops30h 59mFrontier
Deal found 6/6$196
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Thu 7/1810:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$201
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Thu 7/115:27 amSJU - MDW
1 stop17h 19mFrontier
Deal found 6/6$212
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Wed 7/103:03 amSJU - MDW
1 stop7h 17mFrontier
Deal found 6/6$213
Sat 6/297:49 amMDW - SJU
1 stop23h 51mFrontier
Tue 7/98:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$216
Mon 7/295:14 pmMDW - SJU
1 stop7h 51mFrontier
Tue 8/68:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$227
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Sat 7/1310:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 6/6$230
Thu 8/83:45 pmMDW - SJU
1 stop13h 05mFrontier
Thu 8/157:00 amSJU - MDW
1 stop7h 59mFrontier
Deal found 6/6$231

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 3,050,429 searches. Data last updated June 6, 2024.
Tue 6/117:36 pmMDW - SJU
1 stop6h 32mFrontier
Tue 7/2311:15 amSJU - MDW
1 stop8h 18mFrontier
Deal found 6/6$221
Thu 6/135:57 pmMDW - SDQ
1 stop13h 41mFrontier
Mon 6/179:58 amSDQ - MDW
1 stop14h 41mFrontier
Deal found 6/6$232
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Tue 6/1811:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 6/6$245
Tue 6/117:36 pmMDW - SJU
1 stop6h 32mFrontier
Tue 6/1811:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 6/6$246
Wed 6/128:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1811:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 6/4$247
Tue 6/117:36 pmMDW - SJU
1 stop6h 32mFrontier
Sun 6/168:41 pmSJU - MDW
1 stop11h 50mFrontier
Deal found 6/6$251
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Mon 6/176:00 amSJU - MDW
1 stop17h 58mFrontier
Deal found 6/6$258
Fri 6/145:12 pmMDW - SJU
1 stop7h 47mFrontier
Tue 6/1811:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 6/6$259
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Sun 6/169:45 amSJU - MDW
1 stop15h 39mFrontier
Deal found 6/5$261

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 3,050,429 searches. Data last updated June 6, 2024.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Deal found 6/6$96
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Deal found 6/5$99
Mon 6/175:14 pmMDW - PUJ
1 stop15h 14mFrontier
Deal found 6/4$111
Wed 7/109:31 amMDW - SJU
1 stop16h 41mFrontier
Deal found 6/5$112
Mon 8/59:31 amMDW - PUJ
1 stop22h 49mFrontier
Deal found 6/4$113
Fri 6/215:12 pmMDW - SDQ
1 stop14h 26mFrontier
Deal found 6/4$113
Sun 8/49:04 pmMDW - PUJ
1 stop17h 42mFrontier
Deal found 6/5$115
Sun 8/42:30 pmMDW - PUJ
1 stop17h 50mFrontier
Deal found 6/5$120
Thu 8/222:45 pmMDW - SDQ
1 stop18h 31mFrontier
Deal found 6/5$120

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 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$221 - $622

Route

Depart

Return

Price

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 7/29

1 stop15h 14m

Punta Cana

Tue 8/6

1 stop12h 07m

$221

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 6/25

1 stop15h 26m

Punta Cana

Tue 7/2

1 stop9h 08m

$224

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 7/8

1 stop15h 14m

Punta Cana

Fri 7/12

1 stop15h 49m

$225

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 7/8

1 stop15h 14m

Punta Cana

Thu 7/18

1 stop23h 46m

$227

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/9

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Tue 7/16

1 stop24h 26m

$227

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/9

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Sat 7/13

1 stop12h 30m

$230

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/20

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Sat 8/24

1 stop8h 27m

$344

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/17

1 stop9h 13m

Montego Bay Sangster Intl

Tue 10/1

2 stops8h 04m

$366

Chicago MidwayNassau Intl

MDW - NAS

MDWNAS

Chicago Midway

Fri 7/5

1 stop5h 35m

Nassau Intl

Sun 7/7

1 stop9h 35m

$622

Flights are sorted by cheapest first

Deals found on 6/6

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 June 6, 2024.
Southwest
8.2
Very good
5,918 reviews

Food

7.3

Entertainment

7.8

Comfort

8.1

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,918 reviews
Southwest
8.2
Very good
5,918 reviews

Food

7.3

Entertainment

7.8

Comfort

8.1

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,368 reviews
Southwest
8.2
Very good
5,918 reviews

Food

7.3

Entertainment

7.8

Comfort

8.1

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

WestJet
7.5
Good
2,856 reviews
Southwest
8.2
Very good
5,918 reviews

Food

7.3

Entertainment

7.8

Comfort

8.1

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Frontier
6.2
Okay
3,985 reviews
Southwest
8.2
Very good
5,918 reviews

Food

7.3

Entertainment

7.8

Comfort

8.1

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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 $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Caribbean for under $300. The cheapest flight booked recently is on Frontier for just $221, but on average you can expect to pay $235.

  • 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?

    The most popular flight routes from Chicago Midway Airport to Caribbean are Chicago Midway - San Juan Luis Munoz Marin Intl, Chicago Midway - Punta Cana and Chicago Midway - Montego Bay Sangster Intl.

  • 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 $198 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 6/6.

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

    When booking a flight from Chicago Midway Airport to Caribbean, you may want to consider flying on Delta, Frontier or Spirit Airlines as they are the most popular for this route.

  • 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 $245). Flying from Chicago Midway Airport to Caribbean in March is currently the most expensive (average of $338). 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.

See more FAQs

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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.

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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 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$347FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$167Average$267FlexibilityNo cancel feeOn-time65%
DeltaCheapest$361Average$724FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$503Average$503FlexibilityNo cancel feeOn-time75%
Denver to Phoenix flights
Dallas to Salt Lake City flights
Tampa to Miami flights
New York to Lisbon flights
Philadelphia to Chicago flights
Boston to Pittsburgh flights
New York to Las Vegas flights
Las Vegas to Denver flights
New York to Beijing flights
USA to Morocco flights
New Orleans to Houston flights
Chicago Midway Airport to Middle East flights

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.
First Class
Business Class
Prem Econ Class
Economy 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 June 6, 2024.
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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