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Cheap Flights from Oakland to Chicago, IL, United States - OAK to CHI Last modified: May 28, 2016 1:36 AM

Popular flights from Oakland to Chicago Last modified: May 28, 2016 1:36 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 13, 2016 Sep 20, 2016 $304
Sep 17, 2016 Sep 21, 2016 $304
American Airlines
Departure Date Return Date Lowest Price
Aug 24, 2016 Sep 7, 2016 $287
JetBlue Airways
Departure Date Return Date Lowest Price
Aug 23, 2016 Aug 31, 2016 $583
Spirit Airlines
Departure Date Return Date Lowest Price
Aug 23, 2016 Sep 3, 2016 $207
Aug 23, 2016 Aug 31, 2016 $207
Aug 24, 2016 Sep 7, 2016 $207
Aug 24, 2016 Aug 30, 2016 $207
Aug 24, 2016 Aug 27, 2016 $207
United Airlines
Departure Date Return Date Lowest Price
Jun 4, 2016 Jun 11, 2016 $267

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 $227.

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 $340 $418
7-14 days $252 $305
14-21 days $247 $280
21-30 days $247 $280
30-60 days $282 $300
60-90 days $207 $250
90+ days $207 $250

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
$252 $207 $207 $207 $207 $247 $257

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
May Oakland Chicago United 5/29/16 6/1/16 0 $340
June Oakland Chicago Spirit 6/18/16 6/22/16 0 $247
July Oakland Chicago Spirit 7/4/16 7/9/16 0 $282
August Oakland Chicago Spirit 8/23/16 8/31/16 0 $207
September Oakland Chicago Spirit 9/3/16 9/7/16 0 $207
October Oakland Chicago Spirit 10/1/16 10/4/16 0 $207
November Oakland Chicago Spirit 11/2/16 11/6/16 0 $207
December Oakland Chicago Spirit 12/14/16 1/2/17 0 $267

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
29 30 31 1 2 3 4
$287
5 6 7 8 9 10 11
$287 $352
12 13 14 15 16 17 18
$352 $267
19 20 21 22 23 24 25
$267 $307
26 27 28 29 30 1 2
$307 $362
3 4 5 6 7 8 9
$362

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 $368.

The average price for non-stop flights from Oakland to Chicago is $314.

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 $152.

The average price for round trip flights from Oakland to Chicago is $357.

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 11 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: 207Last modified: May 28, 2016 1:36 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 ATL 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 DEN 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 $392
Oakland to New York American, Alaska, JetBlue, Spirit, United $324

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Chicago American, Alaska, JetBlue, Frontier, United, Virgin America $203
Sacramento to Chicago American, Alaska, JetBlue, United $411
San Jose to Chicago American, Alaska, JetBlue, United $287
Fresno to Chicago American, Alaska, United $274
Reno to Chicago American, Alaska, United $361
Monterey to Chicago American, Alaska, United $416
San Luis Obispo to Chicago American, United $412
Modesto to ChicagoCheck Dates
Chico to ChicagoCheck Dates
Redding to Chicago Alaska, United $550
Santa Rosa to Chicago American, Alaska $620
San Francisco to New York American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $324
San Francisco to Atlanta American, Alaska, Frontier, United $208
San Francisco to Milwaukee American, Alaska, Frontier, United $278
San Francisco to Detroit American, Alaska, Frontier, United $199
San Francisco to Indianapolis American, Alaska, Frontier, United $244
Sacramento to Milwaukee American, Alaska, United $364
San Francisco to Dallas - Ft Worth American, Alaska, Frontier, United, Virgin America $107
San Francisco to Minneapolis - St Paul American, Alaska, Frontier, Sun Country, United $240
San Francisco to Los Angeles American, Alaska, United, Virgin America $132
San Francisco to Madison American, Alaska, Frontier, United $335
San Jose to Milwaukee American, Alaska, United $396
San Jose to New York American, Alaska, JetBlue, United $322
Sacramento to Atlanta American, Alaska, United $199
San Francisco to St Louis American, Alaska, JetBlue, United $302
Sacramento to New York American, Alaska, JetBlue, United $320
San Francisco to Denver American, Alaska, Frontier, United, Virgin America $141

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Toronto American, Air Canada, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America, WestJet $384
Cheap Flights from Oakland to Chicago, IL, United States, from $207 Round trip from OAK to CHI