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
$213 - $414
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop7h 23m
Chicago Midway
Mon 6/10
1 stop17h 41m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 5/29
1 stop10h 08m
Chicago Midway
Mon 6/3
1 stop12h 21m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop8h 32m
Chicago Midway
Wed 6/19
1 stop17h 41m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 5/28
1 stop7h 40m
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 5/28
1 stop28h 54m
Chicago Midway
Mon 6/3
1 stop12h 21m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 5/28
1 stop14h 10m
Chicago Midway
Mon 6/3
1 stop12h 21m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 6/9
1 stop13h 41m
Chicago Midway
Wed 6/12
1 stop12h 07m
Punta CanaChicago Midway
PUJ - MDW
PUJMDW
Punta Cana
Thu 7/4
1 stop12h 23m
Chicago Midway
Fri 7/12
1 stop14h 36m
Nassau IntlChicago Midway
NAS - MDW
NASMDW
Nassau Intl
Tue 7/9
1 stop7h 26m
Chicago Midway
Mon 7/15
1 stop16h 00m
No data available for this route at this time. Please check back soon.
Food
Overall
Comfort
Entertainment
Crew
Boarding
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.
Food
Overall
Comfort
Entertainment
Crew
Boarding
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.
Food
Overall
Comfort
Entertainment
Crew
Boarding
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.
Food
Overall
Comfort
Entertainment
Crew
Boarding
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.
Food
Overall
Comfort
Entertainment
Crew
Boarding
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.
0%of flight departures | Early morningMidnight to 6 am |
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0%of flight departures | Morning6 am to noon |
100%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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