Round-trip from | $298 (Frontier) |
---|---|
One-way from | $116 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $351 |
Good round-trip deal | $397 or less |
Good one-way deal | $285 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
vie. 5/2
1:19 pm-10:01 pm
1 stop7h 42m
San Juan Luis Munoz Marin Intl
dom. 5/4
9:58 pm-5:28 pm
1 stop20h 30m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
sáb. 5/3
6:04 am-3:32 pm
1 stop8h 28m
Punta Cana
mar. 5/6
12:55 pm-10:22 pm
1 stop10h 27m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
vie. 7/4
9:55 am-3:25 pm
Nonstop4h 30m
Punta Cana
mié. 7/9
3:45 pm-7:35 pm
Nonstop4h 50m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
sáb. 5/17
1:35 pm-10:25 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
sáb. 5/24
1:00 pm-5:20 pm
Nonstop5h 20m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
mié. 5/14
10:25 am-7:48 pm
1 stop8h 23m
San Juan Luis Munoz Marin Intl
mié. 5/28
6:15 am-11:53 am
1 stop6h 38m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
dom. 6/8
9:12 pm-11:47 am
1 stop13h 35m
Punta Cana
sáb. 6/14
3:55 pm-8:45 am
1 stop17h 50m
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
sáb. 5/31
10:25 am-12:19 am
2 stops12h 54m
Santo Domingo Las Americas
sáb. 6/7
7:05 am-4:21 pm
2 stops10h 16m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
lun. 5/26
9:12 pm-10:50 am
1 stop12h 38m
Punta Cana
vie. 5/30
12:25 pm-7:55 pm
1 stop8h 30m
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
dom. 6/1
4:06 pm-9:02 am
1 stop15h 56m
Santo Domingo Las Americas
dom. 6/8
9:53 am-8:17 pm
1 stop11h 24m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
mar. 5/6
6:20 am-1:55 pm
1 stop7h 35m
Montego Bay Sangster Intl
sáb. 5/10
1:50 pm-6:05 pm
Nonstop4h 15m
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 December is currently the most expensive (average of $336). 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).
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$133 | Average$394 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$174 | Average$280 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$325 | Average$716 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$342 | Average$711 | FlexibilityNo cancel fee | On-time63% |