When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 16 days in advance, which can save you up to 85% on flights from Caribbean to Chicago Midway Airport compared to booking the week you need them. Waiting 16 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $238. For sooner than that we have options available in the next 3 days from $311.
January can be a great time to fly to Chicago Midway Airport from Caribbean with a flight ticket averaging about $270. Cheapflights users have found deals in the month of January for as cheap as $122. The most expensive prices can be found in the month of March.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean to Chicago Midway Airport as you normally would.
Fly from
Fly to
Budget
$215 - $485
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/31
1 stop7h 05m
Chicago Midway
Sat 6/1
1 stop8h 24m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop13h 28m
Chicago Midway
Tue 6/11
1 stop6h 32m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/6
1 stop11h 50m
Chicago Midway
Mon 6/10
1 stop17h 41m
Punta CanaChicago Midway
PUJ - MDW
PUJMDW
Punta Cana
Tue 7/9
1 stop23h 01m
Chicago Midway
Mon 7/15
1 stop15h 14m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 6/21
1 stop12h 53m
Chicago Midway
Mon 6/24
1 stop7h 45m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 6/11
1 stop10h 02m
Chicago Midway
Mon 6/17
1 stop17h 41m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 6/10
1 stop23h 00m
Chicago Midway
Fri 6/14
1 stop22h 27m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 8/17
1 stop9h 59m
Chicago Midway
Mon 8/19
1 stop10h 58m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/6
3 stops23h 29m
Chicago Midway
Mon 6/10
3 stops24h 52m
No data available for this route at this time. Please check back soon.
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
9%of flight departures | Morning6 am to noon |
90%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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