
Round-trip from | $196 (Frontier) |
|---|---|
One-way from | $109 (Kiwi.com) |
Popular in | July |
Cheapest in | December |
Average price | $374 |
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/4
4:31 pm-10:12 pm
1 stop7h 41m
Chicago Midway
Sun 12/7
2:59 pm-9:37 am
1 stop16h 38m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 12/5
7:00 am-11:55 am
1 stop6h 55m
Chicago Midway
Mon 12/8
6:00 am-2:14 pm
1 stop6h 14m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 1/23
6:15 am-12:01 pm
1 stop7h 46m
Chicago Midway
Tue 2/3
12:48 pm-8:57 pm
1 stop6h 09m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 11/19
6:17 pm-11:42 am
1 stop19h 25m
Chicago Midway
Sun 11/23
5:30 pm-11:44 pm
2 stops28h 14m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 11/21
9:30 pm-2:40 pm
2 stops19h 10m
Chicago Midway
Sun 11/23
5:30 pm-2:54 am
1 stop7h 24m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 11/24
7:15 am-4:52 pm
1 stop11h 37m
Chicago Midway
Wed 11/26
5:57 pm-9:40 am
1 stop13h 43m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 12/5
9:40 am-7:30 pm
1 stop11h 50m
Chicago Midway
Tue 12/9
9:20 am-11:20 pm
1 stop12h 00m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 11/25
7:30 am-3:20 pm
2 stops9h 50m
Chicago Midway
Tue 12/2
4:35 pm-12:35 am
1 stop6h 00m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 2/4
6:10 am-11:35 am
1 stop7h 25m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/11
6:38 pm-11:47 pm
1 stop7h 09m
Currently, December is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $154). 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 49% on your trip compared to booking a flight in the afternoon.
Comfort
Entertainment
Crew
Overall
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Crew
Overall
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Crew
Overall
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$394 | Average$566 | FlexibilityNo cancel fee | On-time63% |