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Did you mean flights from Chicago to Oakland?

Cheap Flights from Oakland to Chicago, IL, United States - OAK to CHI Last modified: Jul 28, 2016 2:13 AM

Popular flights from Oakland to Chicago Last modified: Jul 28, 2016 2:13 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.

American
OAKCHI
Sun 10/30
nonstop
CHIOAK
Sat 11/5
nonstop
$190
Select
Spirit
OAKCHI
Mon 8/22
nonstop
CHIOAK
Thu 8/25
nonstop
$197
Select
Spirit
OAKCHI
Mon 8/22
nonstop
CHIOAK
Sat 8/27
nonstop
$197
Select
Spirit
OAKCHI
Tue 8/23
nonstop
CHIOAK
Thu 8/25
nonstop
$197
Select
Spirit
OAKCHI
Tue 8/23
nonstop
CHIOAK
Fri 8/26
nonstop
$197
Select
Spirit
OAKCHI
Tue 8/23
nonstop
CHIOAK
Wed 8/31
nonstop
$197
Select
United
OAKCHI
Wed 8/24
nonstop
CHIOAK
Sat 8/27
nonstop
$223
Select
Alaska
OAKCHI
Tue 9/27
1 stop
CHIOAK
Wed 10/5
1 stop
$266
Select
Alaska
OAKCHI
Tue 10/4
1 stop
CHIOAK
Tue 10/11
1 stop
$266
Select
Alaska
OAKCHI
Thu 10/6
1 stop
CHIOAK
Tue 10/11
1 stop
$266
Select
Alaska
OAKCHI
Sat 10/15
1 stop
CHIOAK
Wed 10/19
1 stop
$266
Select
Alaska
OAKCHI
Tue 10/18
1 stop
CHIOAK
Tue 10/25
1 stop
$266
Select
JetBlue
OAKCHI
Fri 9/9
1 stop
CHIOAK
Tue 9/20
1 stop
$537
Select

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

We have collected flight cost data from across the web for travel from Oakland to Chicago, and have found the average flight price for this trip to be $197.

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

Airlines can adjust prices for plane tickets from Oakland to Chicago 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 Oakland to Chicago

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

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $357 $340
7-14 days $277 $276
14-21 days $237 $270
21-30 days $197 $250
30-60 days $197 $250
60-90 days $197 $230
90+ days $190 $234

Cheapest Day To Fly from Oakland to Chicago

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

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$197 $197 $197 $197 $197 $197 $197

Lowest Fares Chart By Month from Oakland to Chicago

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

Month Origin Destination Carrier Depart Date Return Date Stops Price
July Oakland Chicago Spirit 7/30/16 8/3/16 1 $460
August Oakland Chicago Spirit 8/22/16 8/25/16 0 $197
September Oakland Chicago Spirit 9/4/16 9/7/16 0 $197
October Oakland Chicago American 10/30/16 11/5/16 0 $190
November Oakland Chicago Spirit 11/3/16 11/6/16 0 $197
December Oakland Chicago Spirit 12/14/16 12/20/16 0 $237
January Oakland Chicago Alaska 1/17/17 1/25/17 1 $266
February Oakland Chicago Spirit 2/2/17 2/6/17 1 $344

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

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 Oakland to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
31 1 2 3 4 5 6
$277
7 8 9 10 11 12 13
$277 $357
14 15 16 17 18 19 20
$357 $277
21 22 23 24 25 26 27
$277 $217
28 29 30 31 1 2 3
$217 $327
4 5 6 7 8 9 10
$327

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

Your Oakland to Chicago 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 Oakland to Chicago is $324.

The average price for non-stop flights from Oakland to Chicago is $252.

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

Nonstop Flight Details from Oakland to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
Spirit 1 1 1 1 1 1 1 08:57 08:57

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

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 Oakland to Chicago. 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 Oakland to Chicago is $192.

The average price for round trip flights from Oakland to Chicago is $301.

Oakland to Chicago Flight Questions

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

Question: How long is a direct flight from Oakland to Chicago?
Answer: The average Oakland to Chicago flight time is 4 hours and 12 minutes.
Question: How many miles are there between Oakland and Chicago?
Answer: The distance from Oakland to Chicago is 1830 miles.
Question: How common are direct flights from Oakland to Chicago?
Answer: There are 7 direct flights from Oakland to Chicago.
Question: What is the most popular airline for non-stop flights from Oakland to Chicago?
Answer: Spirit Airlines provides 100% of the non-stop flights between Oakland and Chicago.
Question: What are the most popular connecting cities when flying from Oakland to Chicago?
Answer: Salt Lake City, UT

Airlines Flying from Oakland to Chicago (OAK to CHI) Number of flights searched: 219Last modified: Jul 28, 2016 2:13 AM

Below are the different airlines that fly from Oakland to Chicago 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 Oakland to Chicago.

Oakland to Chicago
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 LAX / 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 RNO X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Oakland and Chicago, 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 Oakland - OAK

FlightsAirlineLowest Price
Oakland to Milwaukee American, Alaska, United $370
Oakland to New York American, Alaska, JetBlue, Spirit, United $348

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Chicago American, Alaska, JetBlue, Frontier, United, Virgin America $127
Sacramento to Chicago American, Alaska, JetBlue, United $264
San Jose to Chicago American, Alaska, JetBlue, United $231
Fresno to Chicago American, Alaska, United $282
Reno to Chicago American, Alaska, United $284
Monterey to Chicago American, Alaska, United $398
San Luis Obispo to Chicago American, Alaska, United $398
Modesto to ChicagoCheck Dates
Chico to ChicagoCheck Dates
Redding to Chicago Alaska, United $465
Santa Rosa to Chicago American, Alaska $598
San Francisco to New York American, Alaska, JetBlue, Frontier, Hawaiian, Sun Country, United, Virgin America $286
San Francisco to Atlanta American, Alaska, Frontier, United $197
San Francisco to Milwaukee American, Alaska, Frontier, United $244
San Francisco to Detroit American, Alaska, Frontier, United $244
San Francisco to Indianapolis American, Alaska, Frontier, United $244
Sacramento to Milwaukee American, Alaska, United $374
San Francisco to Dallas - Ft Worth American, Alaska, Frontier, United, Virgin America $207
San Francisco to Minneapolis - St Paul American, Alaska, Frontier, Sun Country, United $239
San Francisco to Los Angeles American, Alaska, United, Virgin America $112
San Francisco to Madison American, Alaska, Frontier, United $284
San Jose to Milwaukee American, Alaska, United $324
San Jose to New York American, Alaska, JetBlue, United $326
Sacramento to Atlanta American, Alaska, United $389
San Francisco to St Louis American, Alaska, Frontier, United $244
Sacramento to New York American, Alaska, JetBlue, United $310
San Francisco to Denver American, Alaska, Frontier, United, Virgin America $147

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Toronto American, Air Canada, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America, WestJet $360
Cheap Flights from Oakland to Chicago, IL, United States, from $190 Round trip from OAK to CHI