
Round-trip from | $180 (Expedia) |
|---|---|
One-way from | $96 (Priceline) |
Popular in | July |
Cheapest in | December |
Average price | $297 |
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/29
4:22 pm-10:19 pm
1 stop7h 57m
Chicago Midway
Mon 2/2
1:00 pm-11:59 pm
1 stop8h 59m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 2/19
4:25 pm-2:26 pm
1 stop24h 01m
Chicago Midway
Mon 2/23
9:22 pm-12:43 am
1 stop25h 21m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/15
9:04 pm-9:09 am
1 stop14h 05m
Chicago Midway
Mon 1/19
6:10 am-3:27 pm
1 stop7h 17m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 1/11
10:47 pm-2:06 pm
1 stop17h 19m
Chicago Midway
Thu 1/15
11:27 am-2:48 am
1 stop13h 21m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 3/5
4:11 pm-10:29 pm
1 stop8h 18m
Chicago Midway
Wed 3/11
11:19 am-10:45 pm
1 stop10h 26m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 1/13
4:35 pm-10:19 pm
1 stop7h 44m
Chicago Midway
Wed 1/21
1:20 pm-6:58 pm
2 stops27h 38m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 1/13
6:10 am-11:35 am
1 stop7h 25m
Chicago Midway
Wed 1/21
9:50 am-11:10 pm
1 stop11h 20m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/22
6:10 am-1:55 pm
2 stops9h 45m
Chicago Midway
Sun 1/25
3:15 pm-12:40 am
1 stop7h 25m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 1/16
11:52 am-6:54 pm
1 stop9h 02m
Chicago Midway
Mon 1/19
9:09 pm-3:26 pm
2 stops16h 17m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 1/25
4:22 pm-10:19 pm
1 stop7h 57m
Chicago Midway
Sun 2/1
1:00 pm-1:08 am
1 stop10h 08m
Currently, December is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $137). Flying from San Juan to Chicago Midway Airport in March is currently the most expensive (average of $427). 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.
A simple way to save on the total cost of your ticket is to fly from San Juan to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 59% on your trip compared to booking a flight at noon.
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$419 | Average$566 | FlexibilityNo cancel fee | On-time63% |