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Cheap flights Chicago to Oakland

1 passenger, economy

Cheap flights Chicago to Oakland

Compare prices, duration and stops

Frontier Airlines
F9 2145
01:55
Chicago, O'Hare International Airport (ORD)
Tue, 15 sep
16h 56min
1 stop
18:51
Oakland (OAK)
Tue, 15 sep
242 S$
Frontier Airlines
F9 3647
18:21
Chicago, O'Hare International Airport (ORD)
Tue, 15 sep
24h 30min
1 stop
18:51
Oakland (OAK)
Wed, 16 sep +1
230 S$
Alaska Airlines
AS 1470
12:20
Chicago, O'Hare International Airport (ORD)
Thu, 17 sep
9h 13min
1 stop
21:33
Oakland (OAK)
Thu, 17 sep
171 S$
Frontier Airlines
F9 1596
15:26
Chicago, O'Hare International Airport (ORD)
Thu, 17 sep
11h 22min
1 stop
02:48
San Francisco (SFO)
Fri, 18 sep +1
274 S$
Frontier Airlines
F9 2145
01:55
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
16h 56min
1 stop
18:51
Oakland (OAK)
Sat, 19 sep
240 S$
Frontier Airlines
F9 1483
11:30
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
6h 17min
1 stop
17:47
San Francisco (SFO)
Sat, 19 sep
142 S$
Frontier Airlines
F9 3241 Best price
21:35
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
7h 53min
1 stop
05:28
San Francisco (SFO)
Sun, 20 sep +1
140 S$
Frontier Airlines
F9 2145
00:32
Chicago, O'Hare International Airport (ORD)
Sun, 20 sep
15h 50min
1 stop
16:22
Oakland (OAK)
Sun, 20 sep
227 S$
Frontier Airlines
F9 3647
18:21
Chicago, O'Hare International Airport (ORD)
Tue, 22 sep
24h 30min
1 stop
18:51
Oakland (OAK)
Wed, 23 sep +1
231 S$
Southwest Airlines
WN 4280 🔥 Hot deal
15:05
Chicago, Chicago Midway International Airport (MDW)
Thu, 29 oct
4h 40min
Direct
19:45
Oakland (OAK)
Thu, 29 oct
171 S$
Southwest Airlines
WN 2990 🔥 Hot deal
03:55
Chicago, Chicago Midway International Airport (MDW)
Sat, 7 nov
4h 40min
Direct
08:35
Oakland (OAK)
Sat, 7 nov
179 S$
Southwest Airlines
WN 1364 🔥 Hot deal
02:45
Chicago, Chicago Midway International Airport (MDW)
Tue, 17 nov
4h 45min
Direct
07:30
Oakland (OAK)
Tue, 17 nov
177 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 227 S$ · max: 274 S$
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227 S$
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231 S$
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Cheap flights Chicago to Oakland

Frontier Airlines
Frontier Airlines
Tue, Thu, Sat, Sun
Price from
S$227

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
United States → United States
ORL
from
S$27
CHI
Chicago — Orlando
United States → United States
MCO
from
S$27
CHI
Chicago — Atlanta
United States → United States
ATL
from
S$28
CHI
Chicago — Houston
United States → United States
HOU
from
S$28
CHI
Chicago — Houston
United States → United States
IAH
from
S$28
CHI
Chicago — New York
United States → United States
NYC
from
S$30
CHI
Chicago — Denver
United States → United States
DEN
from
S$30
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
S$31
CHI
Chicago — Miami
United States → United States
MIA
from
S$31

Popular destinations to Oakland

All →
SAN
San Diego — Oakland
United States → United States
OAK
from
S$33
LAS
Las Vegas — Oakland
United States → United States
OAK
from
S$38
LAX
Los Angeles — Oakland
United States → United States
OAK
from
S$42
ONT
Ontario — Oakland
United States → United States
OAK
from
S$44
PHX
Phoenix — Oakland
United States → United States
OAK
from
S$46
SEA
Seattle — Oakland
United States → United States
OAK
from
S$59
PDX
Portland — Oakland
United States → United States
OAK
from
S$96
DEN
Denver — Oakland
United States → United States
OAK
from
S$140

Cheap flights Chicago to Oakland

Interesting facts about the route

Flight time

10h 18min

Distance

2 946 km

Average price

S$203

Most frequent flight

F9 2145

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

S$11

Buy

change

2 GB

data

15

days

S$16

Buy

change

5 GB

data

30

days

S$18

Buy

change

3 GB

data

30

days

S$20

Buy

change

5 GB

data

30

days

S$29

Buy

Frequently Asked Questions

The average ticket price Chicago Oakland is S$203. The cheapest ticket costs S$171, operated by Alaska Airlines, flight 1470, departing Chicago on 17 September at 12:20, arriving Oakland on 17 September at 21:33.
The average flight time is 16 hours 56 minutes. The fastest flight takes 9 hours 13 minutes, flight 1470 operated by Alaska Airlines, departing Chicago on 17 September at 12:20, arriving Oakland on 17 September at 21:33.
Flights on the Chicago - Oakland route are operated by the following airlines: Frontier Airlines.
The distance from Chicago to Oakland is 2946 km.