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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 C$170 (departure 29 October).

Prices updated on 23 October at 11:04

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
C$197
Frontier Airlines
F9 3647 Best price
17:15
O'Hare International Airport (ORD)
Thu, 29 Oct
18h 8min
1 stop
09:23
Oakland (OAK)
Fri, 30 Oct +1
C$170
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
C$185
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
C$184
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
C$234
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
C$206
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
C$204
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
C$337
Frontier Airlines
F9 2445
14:40
O'Hare International Airport (ORD)
Mon, 1 Mar
10h 57min
1 stop
23:37
San Francisco (SFO)
Mon, 1 Mar
C$216
Alaska Airlines
AS 1447
22:54
O'Hare International Airport (ORD)
Tue, 1 June
9h 39min
1 stop
06:33
Norman Y. Mineta San Jose (SJC)
Wed, 2 June +1
C$266
Alaska Airlines
AS 1723
16:00
O'Hare International Airport (ORD)
Thu, 1 July
6h 43min
1 stop
20:43
San Francisco (SFO)
Thu, 1 July
C$257

Low price calendar

From
To
Lowest price of the month Thu, 29 Oct · One way from C$170

Prices as of 23 October, 11:05 Moscow time

Cheap flights Chicago to Oakland

Frontier Airlines
Frontier Airlines
Mon, Thu
Price from
C$170
Southwest Airlines
Southwest Airlines
Mon, Thu, Fri, Sat
Price from
C$184

Which airlines offer the cheapest flights from Chicago to Oakland?

Based on collected data, the cheapest flights are offered by Frontier Airlines with an average ticket price of C$193.

  • Frontier Airlines Average price: C$193 · Flights: 2 · Direct: 0
  • Southwest Airlines Average price: C$219 · Flights: 6 · Direct: 5
  • Allegiant Air Average price: C$234 · Flights: 1 · Direct: 0
  • Alaska Airlines Average price: C$261 · 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 Thu (4), the fewest on Wed (0).

  • Mon Flights: 3 · Direct: 1
  • Tue Flights: 1 · Direct: 0
  • Wed —
  • Thu Flights: 4 · Direct: 2
  • Fri Flights: 2 · Direct: 1
  • Sat Flights: 1 · Direct: 1
  • Sun —

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Popular destinations to Oakland

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from
C$31
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from
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from
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from
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Flights from Chicago to cities near Oakland

Cheaper than Oakland right now: San Francisco — from C$83, C$87 less. The cities are 18 km apart.

City Distance Direct Flights Airlines Price from
OaklandOAK — 5114 direct from C$184
San FranciscoSFO 18 km 15426 C$87 cheaper direct from C$151
SacramentoSAC 109 km 084
RenoRNO 291 km 043

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

Cheap flights Chicago to Oakland

Price from
C$170
Average price
C$216
Flight time
4 hours 45 minutes
Distance
2 961 km
Рейсов в неделю
5
Airlines
4
Most frequent flight
WN 1364

Prices as of 23 October, 11:04 Moscow time

Airports on the Chicago — Oakland route

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

Departure airports · Chicago

Arrival airports · Oakland

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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 C$184.
The average ticket price Chicago Oakland is C$216. The cheapest ticket costs C$170, 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 23 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 10 hours.
Flights from Chicago to Oakland depart from these airports: Chicago Midway International Airport (MDW), 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 C$177. The average price is C$200. 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.