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Cheap Flights from Chicago to Oakland, CA, United States - CHI to OAK

Popular flights from Chicago to Oakland

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
May 10, 2016 May 18, 2016 $234
May 11, 2016 May 18, 2016 $234
American Airlines
Departure Date Return Date Lowest Price
May 10, 2016 May 17, 2016 $207
Spirit Airlines
Departure Date Return Date Lowest Price
May 6, 2016 May 8, 2016 $147
May 6, 2016 May 9, 2016 $147
United Airlines
Departure Date Return Date Lowest Price
May 11, 2016 May 14, 2016 $191
May 11, 2016 May 16, 2016 $191

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 $184.

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 $182 $255
7-14 days $147 $212
14-21 days $187 $240
21-30 days $187 $240
30-60 days $202 $223
60-90 days $207 $240
90+ days $182 $235

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
$237 $182 $182 $182 $147 $162 $196

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
April Chicago Oakland Spirit 4/30/16 5/1/16 0 $217
May Chicago Oakland Spirit 5/6/16 5/8/16 0 $147
June Chicago Oakland Spirit 6/21/16 6/27/16 0 $202
July Chicago Oakland Spirit 7/12/16 7/19/16 0 $207
August Chicago Oakland Spirit 8/27/16 9/3/16 0 $183
September Chicago Oakland Spirit 9/19/16 9/30/16 0 $182
October Chicago Oakland Spirit 10/1/16 10/11/16 0 $182
November Chicago Oakland Spirit 11/3/16 11/6/16 0 $187

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
1 2 3 4 5 6 7
$147
8 9 10 11 12 13 14
$147 $187
15 16 17 18 19 20 21
$187 $206
22 23 24 25 26 27 28
$206 $247
29 30 31 1 2 3 4
$247 $229
5 6 7 8 9 10 11
$229

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 $238.

The average price for non-stop flights from Chicago to Oakland is $246.

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 $113.

The average price for round trip flights from Chicago to Oakland is $230.

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 37 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)

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 SLC X X X X X X X
Delta SLC / LAX 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 SLC 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 $167
Chicago to San Jose American, Alaska, United $226
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $138
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $85
Chicago to Sacramento American, Alaska, United $280
Chicago to New York American, Alaska, JetBlue, Spirit, United $97

Cheap Domestic Flights to Oakland - OAK

FlightsAirlineLowest Price
Indianapolis to Oakland American, Alaska, United $420
Milwaukee to Oakland American, Alaska, United $392
Madison to Oakland American, Alaska, United $580
Grand Rapids to Oakland American, Alaska, United $655
Ft Wayne to Oakland American, Alaska, United $576
Moline to Oakland American, Alaska, United $601
Peoria to Oakland American, United $500
South Bend to Oakland United $2,583
Green Bay to Oakland American, Alaska, United $609
Toledo to Oakland American $547
Lansing to OaklandCheck Dates
Bloomington - Normal to Oakland American $530
Appleton to Oakland Alaska, United $1,578
Kalamazoo to Oakland American, United $640
Springfield to Oakland American, United Check Dates
Champaign to Oakland American $659
Milwaukee to San Francisco American, Alaska, Frontier, United $248
Indianapolis to San Francisco American, Alaska, Frontier, United $265
Grand Rapids to San Francisco American, Alaska, United $308
Madison to San Francisco American, Alaska, Frontier, United $264
Lansing to San Francisco Alaska, United $368
Moline to San Francisco American, Alaska, United $298
Bloomington - Normal to San Francisco American $407
South Bend to San Francisco United $354
Cheap Flights from Chicago to Oakland, CA, United States, from $147 Round trip from CHI to OAK