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
$195 - $369
Route
Depart
Return
Price
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/8
1 stop16h 37m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop9h 24m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 6/13
1 stop17h 40m
Punta Cana
Thu 6/20
1 stop14h 21m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 7/8
1 stop22h 49m
Punta Cana
Thu 7/11
1 stop12h 56m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 6/24
1 stop15h 14m
Punta Cana
Thu 6/27
1 stop14h 28m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 6/25
1 stop15h 26m
Punta Cana
Thu 6/27
1 stop14h 28m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 6/5
1 stop17h 41m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop8h 32m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 9/14
1 stop12h 49m
Punta Cana
Fri 9/20
1 stop9h 01m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/13
1 stop11h 32m
San Juan Luis Munoz Marin Intl
Thu 6/20
1 stop20h 01m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/8
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Wed 8/14
1 stop8h 16m
No data available for this route at this time. Please check back soon.
Crew
Entertainment
Food
Comfort
Boarding
Overall
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.
Crew
Entertainment
Food
Comfort
Boarding
Overall
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.
Crew
Entertainment
Food
Comfort
Boarding
Overall
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.
Crew
Entertainment
Food
Comfort
Boarding
Overall
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.
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 |
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Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway to Caribbean, users can toggle the no change fees filter when performing a flight search.
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