
Discover tips and strategies to find the most affordable flight options for your journey from San José del Cabo (SJD) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $610 (Southwest) |
One-way from | $244 (Kiwi.com) |
Popular in | August |
Cheapest in | September |
Average price | $795 |
Fly from
Fly to
Route
Depart
Return
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 10/30
11:05 am-9:50 pm
1 stop8h 45m
Chicago Midway
Fri 11/6
5:15 am-1:10 pm
1 stop8h 55m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 9/24
12:12 pm-10:44 pm
1 stop8h 32m
Chicago Midway
Sun 9/27
6:05 am-11:07 am
1 stop7h 02m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Tue 11/3
1:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Mon 11/9
6:00 am-6:34 pm
2 stops13h 34m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Sat 9/12
11:35 am-10:20 pm
1 stop8h 45m
Chicago Midway
Wed 9/16
6:00 am-12:50 pm
2 stops8h 50m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Sun 9/27
12:12 pm-10:44 pm
1 stop8h 32m
Chicago Midway
Sun 10/4
6:05 am-11:07 am
1 stop7h 02m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Wed 8/26
11:40 am-9:50 pm
2 stops8h 10m
Chicago Midway
Sat 8/29
7:20 am-12:15 pm
1 stop6h 55m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 10/9
12:15 pm-12:25 am
1 stop10h 10m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 11/13
2:45 pm-1:05 am
2 stops9h 20m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 9/10
1:45 pm-10:20 pm
1 stop6h 35m
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 9/18
10:40 am-10:20 pm
1 stop9h 40m
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