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Did you mean flights from Chicago to Oakland?

Flights from Oakland to Chicago, United States Last modified: Dec 3, 2016 2:20 -05:00

Oakland to Chicago Last modified: Dec 3, 2016 2:20 -05:00Prices shown were found by travelers like you over the past 30 days

We've scanned 27,007,995,372 round trip itineraries and found the cheapest flights from Oakland to Chicago. American & Alaska frequently offer the best deals on Oakland to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

American
OAKCHI
Thu 1/12
nonstop
CHIOAK
Mon 1/16
nonstop
$282
Alaska
OAKCHI
Wed 1/11
1 stop
CHIOAK
Thu 1/19
1 stop
$310
Spirit
OAKCHI
Fri 12/9
1 stop
CHIOAK
Mon 12/12
1 stop
$334
JetBlue
OAKCHI
Fri 1/27
1 stop
CHIOAK
Mon 1/30
1 stop
$434

How Much is a Flight from Oakland to Chicago? Prices shown were found by travelers like you over the past 30 days

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 $288.

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? Prices shown were found by travelers like you over the past 30 days

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 $0 $334
7-14 days $2,341 $284
14-21 days $536 $375
21-30 days $0 $414
30-60 days $282 $284
60-90 days $0 $284
90+ days $227 $310

Cheapest Day To Fly from Oakland to Chicago Prices shown were found by travelers like you over the past 30 days

We've examined 27,015,131,706 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
$294 $284 $284 $282 $284 $294 $294

Compare Flight Prices from Oakland to Chicago by Month Prices shown were found by travelers like you over the past 30 days

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
December Oakland Chicago American 12/13/16 12/14/16 1 $284
January Oakland Chicago American 1/12/17 1/16/17 0 $282
February Oakland Chicago American 2/1/17 2/4/17 1 $284
March Oakland Chicago Alaska 3/22/17 3/28/17 1 $310
April Oakland Chicago Spirit 4/27/17 4/30/17 0 $247
May Oakland Chicago Spirit 5/2/17 5/9/17 0 $227
June Oakland Chicago Spirit 6/14/17 6/20/17 0 $347
July Oakland Chicago Spirit 7/18/17 8/1/17 0 $347

Cheap Last Minute Flights from Oakland to Chicago Prices shown were found by travelers like you over the past 30 days

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
4 5 6 7 8 9 10
$334
11 12 13 14 15 16 17
$334 $394
18 19 20 21 22 23 24
$394 $908
25 26 27 28 29 30 31
$908 $544
1 2 3 4 5 6 7
$544 $298
8 9 10 11 12 13 14
$298

Connecting Flights vs Direct Flights from Oakland to Chicago Prices shown were found by travelers like you over the past 30 days

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 $342.

The average price for direct flights from Oakland to Chicago is $316.

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
Southwest 4 4 4 4 4 2 3 05:45 15:20

One Way Flights vs Round Trip Flights from Oakland to Chicago Prices shown were found by travelers like you over the past 30 days

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 not available.

The average price for round trip flights from Oakland to Chicago is $313.

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 5 minutes.
Question: How far is Chicago from Oakland?
Answer: The distance from Oakland to Chicago is 1,838 miles (2,957 kilometers).
Question: How common are direct flights from Oakland to Chicago?
Answer: There are 25 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 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

Airlines in Oakland flying to Chicago Last modified: Dec 3, 2016 2:20 -05:00Number of routes searched: 250Number of itineraries searched: 152,971

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 -
Alaska -
Spirit -
United -
Virgin America -
American DEN
American DSM
American DTW
American LAX
Alaska PDX
Alaska SEA
Alaska SAN
Alaska SNA
JetBlue BOS
JetBlue JFK
Delta ATL
Delta SLC
Delta DTW
Delta MSP
Delta CVG
Frontier DEN
Spirit DFW
Spirit LAS
Spirit MSY
United DEN
United DFW
United EWR
United IAH
Virgin America LAX

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 Last modified: Dec 3, 2016 2:20 -05:00Prices shown were found by travelers like you over the past 30 days

Cheap International Flights to Chicago - CHI Last modified: Dec 3, 2016 2:20 -05:00Prices shown were found by travelers like you over the past 30 days

FlightsLowest Price
San Francisco to Toronto$367
Cheap Flights from Oakland to Chicago