
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Delta) |
One-way from | $129 (Southwest) |
Popular in | November |
Cheapest in | September |
Average price | $326 |
Good round-trip deal | $373 or less |
Good one-way deal | $221 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Tue 6/9
7:37 pm-11:54 pm
1 stop6h 17m
Oakland
Tue 6/16
12:33 pm-9:57 pm
1 stop7h 24m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Wed 7/29
9:00 pm-11:30 pm
Nonstop4h 30m
Oakland
Tue 8/4
11:55 am-9:05 pm
1 stop7h 10m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Wed 6/17
5:35 am-9:50 am
1 stop6h 15m
Oakland
Mon 6/22
4:45 pm-1:25 am
1 stop6h 40m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Thu 6/18
9:40 pm-12:10 am
Nonstop4h 30m
Oakland
Tue 6/23
11:55 pm-6:00 am
Nonstop4h 05m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Thu 9/3
7:00 am-12:49 pm
1 stop7h 49m
Oakland
Thu 9/10
3:00 pm-11:57 pm
1 stop6h 57m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Wed 8/5
8:35 pm-11:05 pm
Nonstop4h 30m
Oakland
Mon 8/10
11:55 pm-5:55 am
Nonstop4h 00m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Wed 6/24
4:40 pm-10:25 pm
1 stop7h 45m
Oakland
Sun 6/28
11:55 pm-6:00 am
Nonstop4h 05m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 5/27
7:15 pm-7:05 am
1 stop13h 50m
Oakland
Fri 5/29
6:25 am-6:50 pm
2 stops10h 25m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Thu 7/9
6:20 am-2:10 pm
1 stop9h 50m
Oakland
Thu 7/16
2:50 pm-11:36 pm
1 stop6h 46m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 6/10
6:20 am-2:10 pm
1 stop9h 50m
Oakland
Tue 7/7
7:52 am-5:00 am
1 stop19h 08m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Currently, August is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $83). Flying from Chicago to Oakland, California in December is currently the most expensive (average of $288). 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.
It’s typically best to fly out from Chicago to Oakland, California in the evening. Doing so could potentially save you 46% on the flight price compared to flying in the morning, which is usually more expensive.
About 26% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 105 minutes.
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Thursday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 30% of flights being delayed.
Food
Comfort
Boarding
Entertainment
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Entertainment
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Entertainment
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Entertainment
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Entertainment
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$434 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$264 | Average$355 | FlexibilityNo cancel fee | On-timeN/A |