Round-trip from | $256 (Southwest) |
---|---|
One-way from | $109 (Priceline) |
Popular in | January |
Cheapest in | November |
Average price | $486 |
Good round-trip deal | $375 or less |
Good one-way deal | $185 or less |
Fly from
Fly to
Route
Depart
Return
Price
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 10/2
3:50 pm-11:30 pm
1 stop5h 40m
Chicago Midway
Sun 10/5
5:45 pm-8:20 pm
Nonstop4h 35m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 8/13
9:00 am-9:44 pm
2 stops10h 44m
Chicago Midway
Sat 8/16
4:25 pm-10:18 pm
1 stop7h 53m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 7/24
12:18 pm-8:54 pm
1 stop6h 36m
Chicago Midway
Thu 7/31
8:38 pm-1:17 pm
2 stops18h 39m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 7/20
12:18 pm-8:54 pm
1 stop6h 36m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 8/11
6:00 pm-8:50 am
2 stops12h 50m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 8/20
3:00 pm-11:00 pm
1 stop6h 00m
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 9/26
6:00 am-8:52 pm
1 stop12h 52m
To ensure you get the cheapest price possible for a flight from San Jose to Chicago Midway Airport, you should look to book at least 23 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, April is the cheapest month in which you can book a flight from San Jose to Chicago Midway Airport (average of $160). Flying from San Jose to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Jose to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight in the morning.
Comfort
Entertainment
Crew
Boarding
Food
Overall
Reviews
Merlyn,Feb 2025
LAX - SMF
Comfort
Entertainment
Crew
Boarding
Food
Overall
Reviews
Merlyn,Feb 2025
LAX - SMF
Comfort
Entertainment
Crew
Boarding
Food
Overall
Reviews
Merlyn,Feb 2025
LAX - SMF
Comfort
Entertainment
Crew
Boarding
Food
Overall
Reviews
Merlyn,Feb 2025
LAX - SMF
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$132 | Average$252 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$287 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$358 | Average$484 | FlexibilityNo cancel fee | On-time63% |