Flights from Oakland, California to Chicago, United States

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Did you mean flights from Chicago to Oakland, California?

Oakland, California to Chicago Last modified: Jul 17, 2019 2:33 -04:00

We've scanned 48,195,047,545 round trip itineraries and found the cheapest flights to Chicago. Spirit & Alaska frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Spirit
OAKCHI
Wed 8/14
nonstop
CHIOAK
Sat 8/17
nonstop
$207
Alaska
OAKCHI
Mon 8/12
nonstop
CHIOAK
Tue 8/20
nonstop
$277
American
OAKCHI
Mon 8/26
nonstop
CHIOAK
Wed 8/28
nonstop
$277
Major Airlines
OAKCHI
Wed 8/7
1 stop
CHIOAK
Sat 8/17
1 stop
$294

How Much is a Flight from Oakland, California to Chicago?

We have collected flight cost data from across the web for travel from Oakland, California to Chicago, and have found the average flight price for this trip to be $233.

Where To Buy Cheap Flights from Oakland, California 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 think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Oakland, California 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, California to Chicago?

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

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $421 $367
7-14 days $269 $318
14-21 days $274 $266
21-30 days $207 $231
30-60 days $207 $231
60-90 days $220 $231
90+ days $243 $266

Cheapest Day To Fly from Oakland, California to Chicago

We've examined 57,595,778,181 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Oakland, California to Chicago is Sunday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$233$233$233$233$233$233$233

Compare Flight Prices from Oakland, California 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, California to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
July Oakland, California Chicago Spirit 7/31/19 8/14/19 1 $269
August Oakland, California Chicago Spirit 8/7/19 8/15/19 0 $233
September Oakland, California Chicago Spirit 9/1/19 9/4/19 0 $233
October Oakland, California Chicago Spirit 10/3/19 10/5/19 0 $233
November Oakland, California Chicago Spirit 11/2/19 11/4/19 1 $266
December Oakland, California Chicago American 12/3/19 12/14/19 1 $324
January Oakland, California Chicago American 1/13/20 1/22/20 2 $337
February Oakland, California Chicago American 2/13/20 2/17/20 1 $355

Cheap Last Minute Flights from Oakland, California to Chicago

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

Next 30 Days

SunMonTueWedThuFriSat
14 15 16 17 18 19 20
$418
21 22 23 24 25 26 27
$418 $355
28 29 30 31 1 2 3
$355 $337
4 5 6 7 8 9 10
$337 $233
11 12 13 14 15 16 17
$233 $244
18 19 20 21 22 23 24
$244

Connecting Flights vs Direct Flights from Oakland, California 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, California to Chicago is $320.

The average price for direct flights from Oakland, California to Chicago is $305.

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

Weekly Direct Flights from Oakland, California to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
Spirit 1 1 1 1 1 1 1 05:50 05:50
Major Airlines 3 3 3 3 3 3 3 01:00 13:15

One Way Flights vs Round Trip Flights from Oakland, California 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, California 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, California to Chicago is $154.

The average price for round trip flights from Oakland, California to Chicago is $316.

Oakland, California to Chicago Flight Questions

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

Question: How long is the flight from Oakland, California to Chicago?
Answer: The average Oakland, California to Chicago flight time is 4 hours and 7 minutes.
Question: How far is Chicago from Oakland, California?
Answer: The distance from Oakland, California to Chicago is 1,830 miles (2,945 kilometers).
Question: How common are direct flights from Oakland, California to Chicago?
Answer: There are 28 direct flights from Oakland, California to Chicago.
Question: What are the most popular Oakland, California airlines for direct flights from Oakland, California to Chicago?
Answer: Major Airlines provides 75% of the non-stop flights between Oakland, California and Chicago.
Question: What are the most popular connecting cities when flying from Oakland, California to Chicago?
Answer: Seattle, WA

Airlines in Oakland, California flying to Chicago Last modified: Jul 17, 2019 2:33 -04:00Number of routes searched: 126Number of itineraries searched: 172,150

Wondering which airlines fly out of Oakland, California to Chicago? We've gathered the average price of Oakland, California 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, California to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
Alaska -
Spirit -
American DFW
American PDX
American PHX
American SEA
Alaska PDX
Alaska SEA
Alaska LAX
Alaska SAN
JetBlue BOS
JetBlue JFK
Major Airlines ATL
Major Airlines SLC
Spirit IAH
Spirit LAS
Spirit LAX

Oakland, California to Chicago Airports

These are the major commercial airports we're currently monitoring in Oakland, California 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 Last modified: Jul 17, 2019 2:33 -04:00

Cheap International Flights to Chicago - CHI Last modified: Jul 17, 2019 2:33 -04:00

FlightsLowest Price
San Francisco to Toronto$317

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Cheap Flights from Oakland, California to Chicago