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.
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.
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.
Fly from
Fly to
Budget
$130 - $351
Route
Depart
Return
Price
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Fri 6/21
1 stop9h 19m
San Juan Luis Munoz Marin Intl
Tue 6/25
1 stop10h 02m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/22
1 stop16h 58m
San Juan Luis Munoz Marin Intl
Tue 6/25
1 stop11h 50m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 6/23
1 stop11h 42m
San Juan Luis Munoz Marin Intl
Tue 7/2
1 stop10h 02m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 6/25
1 stop6h 32m
San Juan Luis Munoz Marin Intl
Tue 7/2
1 stop10h 02m
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 stop10h 23m
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 stop8h 18m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 6/26
1 stop17h 41m
San Juan Luis Munoz Marin Intl
Tue 7/2
1 stop10h 02m
Chicago MidwaySanto Domingo Las Americas
MDW - SDQ
MDWSDQ
Chicago Midway
Sun 7/14
1 stop28h 31m
Santo Domingo Las Americas
Tue 7/16
2 stops16h 20m
Chicago MidwayNassau Intl
MDW - NAS
MDWNAS
Chicago Midway
Tue 7/9
1 stop9h 48m
Nassau Intl
Tue 7/16
1 stop9h 26m
No data available for this route at this time. Please check back soon.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$119 | Average$349 | FlexibilityNo cancel fee | On-time62% |
Spirit Airlines | Cheapest$168 | Average$268 | FlexibilityNo cancel fee | On-time65% |
Delta | Cheapest$358 | Average$727 | FlexibilityNo cancel fee | On-timeN/A |
Alaska Airlines | Cheapest$503 | Average$503 | FlexibilityNo cancel fee | On-time75% |
0%of flight departures | Early morningMidnight to 6 am |
---|---|
100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |