Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Flights
Hotels
1 traveler
Unsupported Browser!
Find Flights

Cheap Flights from Chicago to Oakland, CA, United States - CHI to OAK Last modified: May 26, 2016 12:52 AM

Popular flights from Chicago to Oakland Last modified: May 26, 2016 12:52 AM

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

Alaska Airlines
Departure Date Return Date Lowest Price
Sep 20, 2016 Sep 24, 2016 $280
Sep 20, 2016 Oct 1, 2016 $280
Sep 21, 2016 Sep 24, 2016 $280
American Airlines
Departure Date Return Date Lowest Price
Sep 17, 2016 Sep 21, 2016 $273
Spirit Airlines
Departure Date Return Date Lowest Price
Aug 16, 2016 Aug 23, 2016 $207
Aug 17, 2016 Aug 24, 2016 $207
Aug 23, 2016 Aug 27, 2016 $207
Aug 23, 2016 Aug 28, 2016 $207
Aug 24, 2016 Aug 29, 2016 $207
United Airlines
Departure Date Return Date Lowest Price
Sep 17, 2016 Sep 21, 2016 $257

How Much Does it Cost to Fly from Chicago to Oakland (CHI to OAK)?

We have collected flight cost data from across the web for travel from Chicago to Oakland, and have found the average flight price for this trip to be $232.

When Can I Buy the Cheapest Flight from Chicago to Oakland (CHI to OAK)?

Airlines can adjust prices for plane tickets from Chicago to Oakland based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Chicago to Oakland

The chart below shows up-to-date information regarding how far in advance a flight from Chicago to Oakland should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $272 $370
7-14 days $257 $280
14-21 days $227 $260
21-30 days $227 $260
30-60 days $232 $260
60-90 days $207 $250
90+ days $205 $250

Cheapest Day To Fly from Chicago to Oakland

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to Oakland.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$247 $207 $207 $222 $232 $222 $287

Lowest Fares Chart By Month from Chicago to Oakland

The chart below shows the lowest fare by month when flying from Chicago to Oakland.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago Oakland Spirit 5/28/16 6/5/16 0 $272
June Chicago Oakland Spirit 6/11/16 6/20/16 0 $227
July Chicago Oakland Spirit 7/8/16 7/12/16 0 $237
August Chicago Oakland Spirit 8/16/16 8/23/16 0 $207
September Chicago Oakland Spirit 9/1/16 9/5/16 0 $207
October Chicago Oakland Spirit 10/5/16 10/7/16 0 $205
November Chicago Oakland Spirit 11/3/16 11/6/16 0 $207
December Chicago Oakland Spirit 12/11/16 12/15/16 0 $207

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Oakland

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to Oakland.

Next 30 Days

SunMonTueWedThuFriSat
29 30 31 1 2 3 4
$267
5 6 7 8 9 10 11
$267 $257
12 13 14 15 16 17 18
$257 $232
19 20 21 22 23 24 25
$232 $262
26 27 28 29 30 1 2
$262 $262
3 4 5 6 7 8 9
$262

Non-Stop vs Connecting Flights from Chicago to Oakland (CHI to OAK)

Your Chicago to Oakland flight can be significantly cheaper by choosing a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Chicago to Oakland is $305.

The average price for non-stop flights from Chicago to Oakland is $305.

The chart below shows up to date information regarding non-stop flights from Chicago to Oakland.

Nonstop Flight Details from Chicago to Oakland
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
Spirit 1 1 1 1 1 1 1 13:31 13:31

Round Trip vs One Way Flights from Chicago to Oakland (CHI to OAK)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Oakland. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Oakland is $119.

The average price for round trip flights from Chicago to Oakland is $274.

Chicago to Oakland Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is a direct flight from Chicago to Oakland?
Answer: The average Chicago to Oakland flight time is 4 hours and 35 minutes.
Question: How many miles are there between Chicago and Oakland?
Answer: The distance from Chicago to Oakland is 1830 miles.
Question: How common are direct flights from Chicago to Oakland?
Answer: There are 7 direct flights from Chicago to Oakland.
Question: What is the most popular airline for non-stop flights from Chicago to Oakland?
Answer: Spirit Airlines provides 100% of the non-stop flights between Chicago and Oakland.
Question: What are the most popular connecting cities when flying from Chicago to Oakland?
Answer: Las Vegas, NV

Airlines Flying from Chicago to Oakland (CHI to OAK) Number of flights searched: 253Last modified: May 26, 2016 12:52 AM

Below are the different airlines that fly from Chicago to Oakland with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to Oakland.

Chicago to Oakland
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American PHX X X X X X X X
Alaska SEA X X X X X X X
Delta ATL X X X X X X X
Delta DTW / SLC X X X X X X X
Spirit - X X X X X X X
Spirit LAS X X X X X X X
Southwest - X X X X X X X
Southwest LAS X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and Oakland, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to San Francisco American, Alaska, Frontier, United, Virgin America $207
Chicago to San Jose American, Alaska, United $273
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $160
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $118
Chicago to Sacramento American, Alaska, United $411
Chicago to New York American, Alaska, JetBlue, Spirit, United $137

Cheap Domestic Flights to Oakland - OAK

FlightsAirlineLowest Price
Indianapolis to Oakland American, Alaska, United $404
Milwaukee to Oakland American, Alaska, United $382
Madison to Oakland American, Alaska, United $490
Grand Rapids to Oakland American, United $633
Ft Wayne to Oakland American, Alaska, United $730
Moline to Oakland American, Alaska, United $521
Peoria to Oakland American, United $482
South Bend to Oakland United $743
Green Bay to Oakland American, Alaska, United Check Dates
Toledo to OaklandCheck Dates
Lansing to Oakland American, Alaska, United $891
Bloomington - Normal to Oakland American Check Dates
Appleton to Oakland Alaska, United Check Dates
Kalamazoo to OaklandCheck Dates
Springfield to Oakland American $675
Champaign to Oakland American $525
Milwaukee to San Francisco American, Alaska, Frontier, United $244
Indianapolis to San Francisco American, Alaska, Frontier, United $244
Grand Rapids to San Francisco American, Alaska, United $339
Madison to San Francisco American, Alaska, Frontier, United $334
Lansing to San Francisco American, Alaska, United $420
Moline to San Francisco American, Alaska, United $320
Bloomington - Normal to San Francisco American $320
South Bend to San Francisco United $384
Cheap Flights from Chicago to Oakland, CA, United States, from $207 Round trip from CHI to OAK