Use the Orange Line to reach MDW quickly; it's a cost-effective and efficient option for travelers heading to the airport.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $249 (Delta) |
One-way from | $109 (Southwest) |
Popular in | November |
Cheapest in | September |
Average price | $562 |
Good round-trip deal | $537 or less |
Good one-way deal | $323 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 1/7
7:20 am-11:57 am
1 stop6h 37m
Oakland
Sat 1/17
12:38 pm-9:52 pm
1 stop7h 14m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 1/20
8:15 am-3:55 pm
1 stop9h 40m
Oakland
Fri 1/23
11:10 am-5:15 pm
Nonstop4h 05m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 1/21
6:40 pm-11:53 pm
1 stop7h 13m
Oakland
Wed 1/28
12:33 pm-9:52 pm
1 stop7h 19m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sun 1/18
8:10 am-2:55 pm
1 stop8h 45m
Oakland
Thu 1/22
9:30 am-6:50 pm
1 stop7h 20m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sun 1/18
8:10 am-2:55 pm
1 stop8h 45m
Oakland
Fri 1/23
5:25 am-2:45 pm
1 stop7h 20m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Fri 1/23
5:05 am-10:05 am
1 stop7h 00m
Oakland
Tue 1/27
11:10 am-5:15 pm
Nonstop4h 05m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Thu 2/19
3:54 pm-10:49 pm
1 stop8h 55m
Oakland
Tue 2/24
6:15 am-4:33 pm
1 stop8h 18m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Fri 1/23
8:00 am-8:40 pm
1 stop14h 40m
Oakland
Tue 1/27
8:10 am-11:50 pm
1 stop13h 40m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 1/7
1:00 pm-7:50 pm
2 stops8h 50m
Oakland
Sat 1/17
2:05 pm-10:35 pm
1 stop6h 30m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 1/28
8:00 am-4:23 pm
1 stop10h 23m
Oakland
Sat 1/31
11:08 am-11:50 pm
1 stop10h 42m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Chicago to Oakland, California, you should look to book at least 30 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, October is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $80). Flying from Chicago to Oakland, California in November is currently the most expensive (average of $207). 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 afternoon. Doing so could potentially save you 33% on the flight price compared to flying in the morning, which is usually more expensive.
Travelers seeking maximum savings on their Chicago to Oakland, California flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Denver (DEN) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Oakland, California on Cheapflights.
Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $300.
Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 9h 45m.
Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 3h 18m.
About 22% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 99 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Wednesday tends to have the lowest number of delays on this route, whereas Monday 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 24% of flights being delayed.
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Entertainment
Comfort
Crew
Overall
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$223 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$236 | Average$432 | FlexibilityNo cancel fee | On-time63% |