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Cheap flights Chicago to Oakland

1 passenger, economy

Nonstop flights from Chicago to Oakland: Southwest Airlines. Nonstop flights per week: 5. Flight time: 4 hours 45 minutes. Distance: 2961 km. Tickets from R2 016 (departure 29 October).

Prices updated on 25 October at 11:06

See also: Oakland — ChicagoFlights from ChicagoFlights to Oakland

Cheap flights Chicago to Oakland

Compare prices, duration and stops

Southwest Airlines
WN 4280 🔥 Hot deal
10:05
Chicago Midway International Airport (MDW)
Thu, 29 Oct
4h 40min
Direct
12:45
Oakland (OAK)
Thu, 29 Oct
R2 334
Frontier Airlines
F9 3647 Best price
17:15
Chicago O'Hare International Airport (ORD)
Thu, 29 Oct
18h 8min
1 stop
09:23
Oakland (OAK)
Fri, 30 Oct +1
R2 016
Southwest Airlines
WN 4327
05:25
Chicago Midway International Airport (MDW)
Fri, 30 Oct
4h 45min
Direct
08:10
San Francisco (SFO)
Fri, 30 Oct
R2 192
Southwest Airlines
WN 4293
21:30
Chicago Midway International Airport (MDW)
Thu, 29 Oct
4h 45min
Direct
00:15
Oakland (OAK)
Fri, 30 Oct +1
R2 189
Allegiant Air
G4 158
05:53
Chicago Rockford International Airport (RFD)
Mon, 2 Nov
14h 30min
1 stop
18:23
Oakland (OAK)
Mon, 2 Nov
R2 780
Frontier Airlines
F9 3647
17:15
Chicago O'Hare International Airport (ORD)
Mon, 2 Nov
20h 38min
1 stop
11:53
Oakland (OAK)
Tue, 3 Nov +1
R3 483
Southwest Airlines
WN 2990 🔥 Hot deal
06:55
Chicago Midway International Airport (MDW)
Sat, 7 Nov
4h 40min
Direct
09:35
Oakland (OAK)
Sat, 7 Nov
R2 445
Southwest Airlines
WN 1364 🔥 Hot deal
20:45
Chicago Midway International Airport (MDW)
Mon, 16 Nov
4h 45min
Direct
23:30
Oakland (OAK)
Mon, 16 Nov
R2 423
Southwest Airlines
WN 2995
05:20
Chicago Midway International Airport (MDW)
Fri, 1 Jan
6h 45min
1 stop
10:05
San Francisco (SFO)
Fri, 1 Jan
R4 005
Frontier Airlines
F9 2445
14:40
Chicago O'Hare International Airport (ORD)
Mon, 1 Mar
10h 57min
1 stop
23:37
San Francisco (SFO)
Mon, 1 Mar
R2 567
Alaska Airlines
AS 1447
22:54
Chicago O'Hare International Airport (ORD)
Tue, 1 June
9h 39min
1 stop
06:33
Norman Y. Mineta San Jose (SJC)
Wed, 2 June +1
R3 154
Alaska Airlines
AS 1723
16:00
Chicago O'Hare International Airport (ORD)
Thu, 1 July
6h 43min
1 stop
20:43
San Francisco (SFO)
Thu, 1 July
R3 051

Low price calendar

From
To
Lowest price of the month Thu, 29 Oct · One way from R2 016

Prices as of 25 October, 11:07 Moscow time

Cheap flights Chicago to Oakland

Frontier Airlines
Frontier Airlines
Mon, Thu
Price from
R3 483

Which airlines offer the cheapest flights from Chicago to Oakland?

Based on collected data, the cheapest flights are offered by Southwest Airlines with an average ticket price of R2 598.

  • Southwest Airlines Average price: R2 598 · Flights: 6 · Direct: 5
  • Frontier Airlines Average price: R2 689 · Flights: 2 · Direct: 0
  • Allegiant Air Average price: R2 780 · Flights: 1 · Direct: 0
  • Alaska Airlines Average price: R3 103 · Flights: 2 · Direct: 0

Which airlines fly most often from Chicago to Oakland?

The most flight options on this route are offered by Southwest Airlines — options found: 6.

  • Southwest Airlines Flights: 6 · Direct: 5
  • Frontier Airlines Flights: 2 · Direct: 0
  • Alaska Airlines Flights: 2 · Direct: 0
  • Allegiant Air Flights: 1 · Direct: 0

How many flights per day operate from Chicago to Oakland?

Most flights operate on Mon (4), the fewest on Wed (0).

  • Mon Flights: 4 · Direct: 1
  • Tue Flights: 1 · Direct: 0
  • Wed —
  • Thu Flights: 4 · Direct: 2
  • Fri Flights: 2 · Direct: 1
  • Sat Flights: 1 · Direct: 1
  • Sun —

Popular destinations from Chicago

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from
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Chicago — Phoenix
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from
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Popular destinations to Oakland

All →
LAX
Los Angeles — Oakland
United States → United States
OAK
from
R370
LGB
Long Beach — Oakland
United States → United States
OAK
from
R1 108
ONT
Ontario — Oakland
United States → United States
OAK
from
R1 156
PDX
Portland — Oakland
United States → United States
OAK
from
R1 168
LAS
Las Vegas — Oakland
United States → United States
OAK
from
R1 415
SEA
Seattle — Oakland
United States → United States
OAK
from
R1 668
PAE
Everett — Oakland
United States → United States
OAK
from
R1 920
NYC
New York — Oakland
United States → United States
OAK
from
R2 167
SAN
San Diego — Oakland
United States → United States
OAK
from
R2 276

Flights from Chicago to cities near Oakland

Cheaper than Oakland right now: San Francisco — from R985, R1 031 less. The cities are 18 km apart.

City Distance Direct Flights Airlines Price from
OaklandOAK — 5114 direct from R2 189
San FranciscoSFO 18 km 15426 R1 031 cheaper direct from R1 789
SacramentoSAC 109 km 084
RenoRNO 291 km 032

Distance is a straight line between the cities. Prices are the lowest one-way fares.

Cheap flights Chicago to Oakland

Price from
R2 016
Average price
R2 506
Flight time
4 hours 45 minutes
Distance
2 961 km
Рейсов в неделю
5
Airlines
4
Most frequent flight
WN 1364

Prices as of 25 October, 11:06 Moscow time

Airports on the Chicago — Oakland route

From → to Flights Direct Airlines Price from
Chicago O'Hare International AirportORD OaklandOAK Cheapest
101
Chicago Midway International AirportMDW OaklandOAK
441
Chicago Midway International AirportMDW San FranciscoSFO
211
Chicago O'Hare International AirportORD San FranciscoSFO
202
Chicago Rockford International AirportRFD OaklandOAK
101
Chicago O'Hare International AirportORD Norman Y. Mineta San JoseSJC
101

Departure airports · Chicago

Arrival airports · Oakland

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

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30

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R149

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2 GB

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R207

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5 GB

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30

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R232

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3 GB

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30

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R265

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5 GB

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30

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R373

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Frequently Asked Questions

Yes. Nonstop flights from Chicago to Oakland are operated by: Southwest Airlines. A nonstop flight takes 4 hours 45 minutes on average. Nonstop tickets start at R2 189.
The average ticket price Chicago Oakland is R2 506. The cheapest ticket costs R2 016, operated by Frontier Airlines, flight F9 3647, departing Chicago on 29 October at 17:15, arriving Oakland on 30 October at 09:23. Prices as of 25 October.
A nonstop flight takes 4 hours 45 minutes on average. The fastest is WN 4280 Southwest Airlines: 4 hours 40 minutes. With a connection: from 6 hours 43 minutes, usually about 11 hours.
Flights from Chicago to Oakland depart from these airports: Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD). Most flights depart from Chicago Midway International Airport. Arrival: Oakland (OAK), San Francisco (SFO), Norman Y. Mineta San Jose (SJC).
Tickets from Chicago to Oakland are sold by: Southwest Airlines, Alaska Airlines, Frontier Airlines, Allegiant Air. Nonstop: Southwest Airlines.
The distance from Chicago to Oakland is 2961 km.
Tickets from Oakland to Chicago start at R2 106. The average price is R2 371. Nonstop flights are operated by: Alaska Airlines. All tickets Oakland — Chicago
Yes, the time difference is 2 hours: Chicago — UTC−5, Oakland — UTC−7. For example: Chicago 12:00 → Oakland 10:00.