Round-trip from | $296 (Frontier) |
---|---|
One-way from | $132 (Trip.com) |
Popular in | December |
Cheapest in | August |
Average price | $430 |
Good round-trip deal | $408 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 4/25
6:15 am-3:22 pm
1 stop8h 07m
San Juan Luis Munoz Marin Intl
Fri 5/2
6:00 am-5:28 pm
1 stop12h 28m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 4/20
6:04 am-1:15 pm
1 stop6h 11m
Punta Cana
Thu 4/24
12:55 pm-10:22 pm
1 stop10h 27m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/26
6:04 am-2:19 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 5/3
3:34 pm-10:22 pm
1 stop7h 48m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/26
6:35 am-6:50 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Sat 5/3
1:00 pm-5:20 pm
Nonstop5h 20m
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 5/3
9:52 am-12:50 am
2 stops13h 58m
Santo Domingo Las Americas
Sat 5/10
7:05 am-9:14 pm
2 stops15h 09m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 5/11
8:30 am-1:34 pm
1 stop28h 04m
Punta Cana
Thu 5/15
2:59 pm-11:39 pm
1 stop9h 40m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 5/30
9:12 pm-11:24 am
1 stop13h 12m
Simpson Bay Princess Juliana
Sat 6/14
12:36 pm-8:17 pm
1 stop8h 41m
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Mon 5/12
6:15 am-11:55 pm
2 stops16h 40m
Santo Domingo Las Americas
Mon 5/19
8:00 am-11:47 pm
2 stops16h 47m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 5/1
6:30 pm-1:08 pm
1 stop18h 38m
Montego Bay Sangster Intl
Sun 5/4
2:28 pm-1:34 pm
1 stop23h 06m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 4/28
5:45 am-2:35 pm
1 stop8h 50m
Montego Bay Sangster Intl
Wed 5/7
12:35 pm-10:05 pm
1 stop9h 30m
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).
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$133 | Average$377 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$174 | Average$278 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$325 | Average$752 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$342 | Average$728 | FlexibilityNo cancel fee | On-time63% |