
Round-trip from | $199 (Priceline) |
|---|---|
One-way from | $100 (Frontier) |
Popular in | December |
Cheapest in | April |
Average price | $592 |
Good round-trip deal | $381 or less |
Good one-way deal | $292 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 2/28
8:00 am-2:53 am
1 stop16h 53m
San Juan Luis Munoz Marin Intl
Sat 3/7
12:07 pm-11:32 pm
1 stop13h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 2/6
1:00 pm-3:26 pm
1 stop24h 26m
San Juan Luis Munoz Marin Intl
Sat 2/14
8:02 pm-2:26 pm
1 stop20h 24m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 1/25
3:15 pm-12:40 am
1 stop7h 25m
San Juan Luis Munoz Marin Intl
Fri 1/30
6:10 am-11:35 am
1 stop7h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 2/19
6:15 am-12:39 pm
1 stop28h 24m
San Juan Luis Munoz Marin Intl
Sun 2/22
3:53 am-8:32 pm
1 stop18h 39m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sat 2/14
6:00 am-3:20 pm
1 stop7h 20m
Simpson Bay Princess Juliana
Sat 2/28
4:30 pm-11:25 pm
1 stop8h 55m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/28
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/24
9:45 am-9:30 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Thu 2/26
5:30 am-1:30 pm
2 stops10h 00m
ChicagoSaint Thomas Island
MDW - STT
MDWSTT
Chicago Midway
Sun 1/11
4:21 pm-2:52 pm
1 stop20h 31m
Saint Thomas Island Cyril E King
Thu 1/15
3:57 pm-9:09 am
1 stop19h 12m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 12/15
7:10 am-9:30 pm
1 stop12h 20m
San Juan Luis Munoz Marin Intl
Wed 12/17
8:55 am-4:35 pm
1 stop9h 40m
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $131). Flying from Chicago Midway Airport to Caribbean in June is currently the most expensive (average of $298). 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.
It’s typically best to fly out from Chicago Midway Airport to Caribbean in the evening. Doing so could potentially save you 46% on the flight price compared to flying in the morning, which is usually more expensive.
Travelers seeking maximum savings on their Chicago Midway Airport to Caribbean flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$375 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$271 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$325 | Average$665 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$381 | Average$688 | FlexibilityNo cancel fee | On-time63% |