Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 12/6
5:03 pm-12:20 am
1 stop9h 17m
Chicago Midway
Mon 12/9
7:25 am-1:57 am
1 stop16h 32m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/23
4:50 pm-6:01 pm
1 stop27h 11m
Chicago Midway
Mon 1/27
6:15 am-3:19 pm
2 stops31h 04m
Santo DomingoChicago
SDQ - MDW
SDQMDW
Santo Domingo Las Americas
Thu 2/20
4:00 pm-7:15 pm
1 stop29h 15m
Chicago Midway
Mon 3/3
12:29 pm-2:40 pm
1 stop24h 11m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/12
6:10 am-2:15 pm
1 stop10h 05m
Chicago Midway
Mon 12/16
11:55 am-12:45 am
2 stops10h 50m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 1/15
7:30 am-4:21 pm
1 stop10h 51m
Chicago Midway
Wed 1/22
12:44 pm-11:45 pm
1 stop9h 01m
Punta CanaChicago
PUJ - MDW
PUJMDW
Punta Cana
Tue 1/14
4:50 pm-10:20 pm
1 stop7h 30m
Chicago Midway
Tue 1/21
6:00 am-3:25 pm
1 stop7h 25m
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Mon 1/13
8:00 am-6:14 pm
2 stops11h 14m
Chicago Midway
Mon 1/20
12:44 pm-8:52 pm
1 stop7h 08m
NassauChicago
NAS - MDW
NASMDW
Nassau Intl
Wed 2/5
3:06 pm-10:20 pm
1 stop8h 14m
Chicago Midway
Sun 2/9
6:00 am-4:01 pm
1 stop9h 01m
Santo DomingoChicago
SDQ - MDW
SDQMDW
Santo Domingo Las Americas
Mon 1/27
12:51 pm-4:16 pm
2 stops29h 25m
Chicago Midway
Mon 2/3
4:41 pm-3:54 pm
3 stops21h 13m
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Wed 12/4
2:00 pm-9:15 pm
1 stop8h 15m
Chicago Midway
Fri 12/6
8:35 pm-2:05 pm
2 stops16h 30m
Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $160). Flying from Caribbean Islands to Chicago Midway Airport in October is currently the most expensive (average of $232). 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.
When flying from Caribbean Islands to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Boarding
Comfort
Entertainment
Food
Overall
Crew
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$120 | Average$253 | FlexibilityNo cancel fee | On-time62% |
Delta | Cheapest$249 | Average$479 | FlexibilityNo cancel fee | On-timeN/A |
Southwest | Cheapest$267 | Average$384 | FlexibilityNo cancel fee | On-time63% |