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Fly from
Fly to
Budget
$128 - $924
Route
Depart
Return
Price
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 11/9
1 stop11h 55m
San Juan Luis Munoz Marin Intl
Sat 11/16
1 stop13h 04m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 11/24
2 stops28h 18m
San Juan Luis Munoz Marin Intl
Sun 12/8
1 stop14h 32m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 1/12
2 stops18h 56m
Punta Cana
Sat 1/18
1 stop13h 33m
Chicago MidwayMontego Bay Sangster Intl
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 12/6
1 stop18h 02m
Montego Bay Sangster Intl
Tue 12/10
1 stop22h 25m
Chicago MidwaySanto Domingo Las Americas
MDW - SDQ
MDWSDQ
Chicago Midway
Wed 1/8
2 stops20h 14m
Santo Domingo Las Americas
Tue 2/25
2 stops25h 42m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 12/9
1 stop8h 24m
Punta Cana
Thu 12/12
1 stop10h 01m
Chicago MidwayMontego Bay Sangster Intl
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 11/13
1 stop26h 53m
Montego Bay Sangster Intl
Sat 11/16
2 stops18h 49m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/11
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Sat 1/18
Nonstop5h 15m
Chicago MidwaySanto Domingo Las Americas
MDW - SDQ
MDWSDQ
Chicago Midway
Fri 1/31
1 stop6h 27m
Santo Domingo Las Americas
Wed 2/5
1 stop7h 54m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 11/17
2 stops22h 55m
Punta Cana
Sat 11/23
1 stop10h 19m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 12/2
3 stops28h 24m
Punta Cana
Wed 12/11
2 stops29h 32m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Sat 11/30
1 stop6h 52m
Simpson Bay Princess Juliana
Sat 12/7
1 stop8h 34m
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $254). Flying from Chicago Midway Airport to Caribbean in March is currently the most expensive (average of $335). 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.
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.
In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.
If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$127 | Average$374 | FlexibilityNo cancel fee | On-time62% |
Spirit Airlines | Cheapest$187 | Average$272 | FlexibilityNo cancel fee | On-time65% |
Southwest | Cheapest$267 | Average$566 | FlexibilityNo cancel fee | On-time63% |
Delta | Cheapest$365 | Average$692 | FlexibilityNo cancel fee | On-timeN/A |