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

Popular flights from Oakland to Chicago

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
Aug 31, 2016 Sep 7, 2016 $270
American Airlines
Departure Date Return Date Lowest Price
Aug 31, 2016 Sep 10, 2016 $267
JetBlue Airways
Departure Date Return Date Lowest Price
Aug 6, 2016 Aug 13, 2016 $723
Spirit Airlines
Departure Date Return Date Lowest Price
May 21, 2016 May 25, 2016 $187
United Airlines
Departure Date Return Date Lowest Price
Aug 31, 2016 Sep 10, 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 $237.

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 $312 $345
7-14 days $192 $245
14-21 days $187 $240
21-30 days $262 $290
30-60 days $242 $260
60-90 days $227 $260
90+ days $225 $259

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
$242 $192 $247 $247 $267 $187 $277

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 Spirit 5/21/16 5/25/16 0 $187
June Oakland Chicago Spirit 6/20/16 6/22/16 0 $242
July Oakland Chicago Spirit 7/12/16 7/19/16 0 $227
August Oakland Chicago Spirit 8/3/16 8/10/16 0 $227
September Oakland Chicago Spirit 9/14/16 9/18/16 0 $225
October Oakland Chicago Spirit 10/1/16 10/8/16 0 $227
November Oakland Chicago Spirit 11/1/16 11/7/16 0 $227
December Oakland Chicago American 12/16/16 1/1/17 2 $461

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
1 2 3 4 5 6 7
$322
8 9 10 11 12 13 14
$322 $352
15 16 17 18 19 20 21
$352 $267
22 23 24 25 26 27 28
$267 $332
29 30 31 1 2 3 4
$332 $287
5 6 7 8 9 10 11
$287

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 $467.

The average price for non-stop flights from Oakland to Chicago is $345.

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 09:01 09:01

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 $157.

The average price for round trip flights from Oakland to Chicago is $423.

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 14 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: Los Angeles, CA and Minneapolis - St Paul, MN

Airlines Flying from Oakland to Chicago (OAK to CHI)

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 SLC / DTW 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 MCI 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 $396
Oakland to New York American, Alaska, JetBlue, Spirit, United $323

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Chicago American, Alaska, JetBlue, Frontier, United, Virgin America $192
Sacramento to Chicago American, Alaska, JetBlue, United $280
San Jose to Chicago American, Alaska, JetBlue, United $240
Fresno to Chicago American, Alaska, United $334
Reno to Chicago American, Alaska, United $339
Monterey to Chicago American, Alaska, United $397
San Luis Obispo to Chicago American, United $470
Modesto to ChicagoCheck Dates
Chico to ChicagoCheck Dates
Redding to Chicago Alaska, United $565
Santa Rosa to Chicago American, Alaska $499
San Francisco to New York American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $259
San Francisco to Atlanta American, Alaska, Frontier, United $208
San Francisco to Milwaukee American, Alaska, Frontier, United $261
San Francisco to Detroit American, Alaska, Frontier, United $261
San Francisco to Indianapolis American, Alaska, Frontier, United $336
Sacramento to Milwaukee American, Alaska, United $334
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 $248
San Francisco to Los Angeles American, Alaska, United, Virgin America $116
San Francisco to Madison American, Alaska, Frontier, United $351
San Jose to Milwaukee American, Alaska, United $358
San Jose to New York American, Alaska, JetBlue, United $310
Sacramento to Atlanta American, Alaska, United $347
San Francisco to St Louis American, Alaska, United $322
Sacramento to New York American, Alaska, JetBlue, United $284
San Francisco to Denver American, Alaska, Frontier, United, Virgin America $136

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Toronto American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, WestJet, Great Lakes $408
Cheap Flights from Oakland to Chicago, IL, United States, from $187 Round trip from OAK to CHI