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Did you mean flights from Chicago to Oakland?

Flights from Oakland to Chicago, United States Last modified: Sep 27, 2016 2:15 AM

Oakland to Chicago Last modified: Sep 27, 2016 2:15 AM

We've scanned 23,126,175,300 round trip itineraries and found the cheapest flights from Oakland to Chicago. Spirit & American frequently offer the best deals on Oakland to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Spirit
OAKCHI
Thu 10/20
nonstop
CHIOAK
Sat 10/22
nonstop
$186
Select
Spirit
OAKCHI
Thu 10/20
nonstop
CHIOAK
Wed 11/2
nonstop
$186
Select
American
OAKCHI
Wed 10/26
1 stop
CHIOAK
Mon 10/31
1 stop
$217
Select
Alaska
OAKCHI
Thu 10/27
1 stop
CHIOAK
Sun 10/30
1 stop
$253
Select
Alaska
OAKCHI
Sat 11/5
1 stop
CHIOAK
Sun 11/6
1 stop
$253
Select
JetBlue
OAKCHI
Fri 1/20
1 stop
CHIOAK
Sat 1/28
1 stop
$429
Select

How Much is a Flight from Oakland to Chicago?

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.

Where To Buy Cheap Flights from Oakland to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we thinking FareCompare is the best place to find cheap tickets. Airlines can adjust prices for 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 found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Oakland to Chicago?

The chart below shows up-to-date information regarding how far in advance to book your flight from Oakland to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $227 $284
7-14 days $187 $260
14-21 days $187 $244
21-30 days $186 $217
30-60 days $187 $244
60-90 days $362 $244
90+ days $227 $244

Cheapest Day To Fly from Oakland to Chicago

We've examined 23,133,250,742 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Oakland to Chicago is Thursday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$207 $187 $187 $186 $212 $187 $212

Compare Flight Prices from Oakland to Chicago by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Oakland to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
September Oakland Chicago Spirit 9/30/16 10/5/16 0 $352
October Oakland Chicago Spirit 10/20/16 10/22/16 0 $186
November Oakland Chicago Spirit 11/3/16 11/8/16 0 $187
December Oakland Chicago American 12/1/16 12/4/16 1 $244
January Oakland Chicago American 1/11/17 1/18/17 1 $244
February Oakland Chicago American 2/9/17 2/12/17 1 $287
March Oakland Chicago Alaska 3/2/17 3/7/17 2 $375
April Oakland Chicago Alaska 4/20/17 4/24/17 2 $450

Cheap Last Minute Flights from Oakland to Chicago

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Oakland to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
25 26 27 28 29 30 1
$382
2 3 4 5 6 7 8
$382 $257
9 10 11 12 13 14 15
$257 $187
16 17 18 19 20 21 22
$187 $187
23 24 25 26 27 28 29
$187 $187
30 31 1 2 3 4 5
$187

Connecting Flights vs Direct Flights from Oakland to Chicago

Flights between some cities may be significantly cheaper if you choose 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 $306.

The average price for direct flights from Oakland to Chicago is $253.

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

Weekly Direct Flights from Oakland to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
Spirit 1 1 1 1 1 1 1 09:15 09:15
Southwest 4 4 4 4 4 3 4 06:30 14:35

One Way Flights vs Round Trip Flights from Oakland to Chicago

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 $337.

The average price for round trip flights from Oakland to Chicago is $288.

Oakland to Chicago Flight Questions

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

Question: How long is the flight from Oakland to Chicago?
Answer: The average Oakland to Chicago flight time is 4 hours and 6 minutes.
Question: How far is Chicago from Oakland?
Answer: The distance from Oakland to Chicago is 1,830 miles (2,945 kilometers).
Question: How common are direct flights from Oakland to Chicago?
Answer: There are 34 direct flights from Oakland to Chicago.
Question: What are the most popular Oakland airlines for direct flights from Oakland to Chicago?
Answer: Southwest Airlines provides 79% 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

Airlines in Oakland flying to Chicago Last modified: Sep 27, 2016 2:15 AMNumber of routes searched: 238Number of itineraries searched: 103,900

Wondering which airlines fly out of Oakland to Chicago? We've gathered the average price of Oakland airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Oakland to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American PHX
Spirit LAS
Delta SLC
American SEA
American PDX
Spirit MSY
American -
American DFW
Frontier DEN
Delta ATL
Alaska SAN
Alaska SNA
Delta CVG
United SMF

Oakland to Chicago Airports

These are the major commercial airports we're currently monitoring in Oakland and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Domestic Flights from Oakland - OAK

FlightsAirlineLowest Price
Flights from Oakland to Milwaukee American, Alaska, Delta $318
Flights from Oakland to New York American, Alaska, JetBlue, Delta, Spirit $297

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Flights from San Francisco to Chicago American, Alaska, JetBlue, Delta, Frontier, United, Virgin America $117
Flights from Sacramento to Chicago American, Alaska, JetBlue, United $264
Flights from San Jose to Chicago American, Alaska, JetBlue, Delta, United $215
Flights from Fresno to Chicago American, Alaska, Delta, United $290
Flights from Reno to Chicago American, Alaska, Delta, United $284
Flights from Monterey to Chicago American, Alaska, United $365
Flights from San Luis Obispo to Chicago American, Alaska, United $297
Flights from Modesto to ChicagoCheck Dates
Flights from Chico to ChicagoCheck Dates
Flights from Redding to Chicago Alaska, United $457
Flights from Santa Rosa to Chicago American, Alaska, Delta $526
Flights from San Francisco to New York American, Alaska, JetBlue, Delta, Frontier, Sun Country, United, Virgin America $267
Flights from San Francisco to Atlanta American, Alaska, Delta, Frontier, United $187
Flights from San Francisco to Milwaukee American, Alaska, Delta, Frontier, United $284
Flights from San Francisco to Detroit American, Alaska, Delta, Frontier, United $309
Flights from San Francisco to Indianapolis American, Alaska, Delta, Frontier, United $284
Flights from Sacramento to Milwaukee American, Alaska, Delta, United $363
Flights from San Francisco to Dallas - Ft Worth American, Alaska, Delta, Frontier, United, Virgin America $211
Flights from San Francisco to Minneapolis - St Paul American, Alaska, Delta, Frontier, Sun Country, United $197
Flights from San Francisco to Los Angeles American, Alaska, Delta, United, Virgin America $112
Flights from San Francisco to Madison American, Alaska, Delta, Frontier, United $310
Flights from San Jose to Milwaukee American, Alaska, Delta, United $314
Flights from San Jose to New York Alaska, JetBlue, Delta $297
Flights from Sacramento to Atlanta American, Alaska, Delta, United $367
Flights from San Francisco to St Louis American, Alaska, Delta, Frontier, United $274
Flights from Sacramento to New York American, Alaska, JetBlue, Delta, United $268
Flights from San Francisco to Denver American, Alaska, Delta, Frontier, United, Virgin America $147

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Flights from San Francisco to Toronto American, Air Canada, AeroMexico, Alaska, Copa, Delta, United, WestJet $379
Cheap Flights from Oakland to Chicago