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  1. Flights
  2. United States
  3. Chicago
  4. Oakland, CA - Chicago

Cheap Flights from Oakland, CA (OAK) to Chicago (CHI)

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Discover the cheapest flights from Oakland, CA to Chicago
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Tue, May 5 - Thu, May 7
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
Alaska Airlines
Alaska Airlines1 stop
CHI - OAK
207$
194$
Prime price per passenger
Tue, May 12 - Thu, May 14
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
Alaska Airlines
Alaska Airlines1 stop
CHI - OAK
214$
200$
Prime price per passenger
Wed, May 20 - Wed, May 27
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
Alaska Airlines
Alaska Airlines1 stop
CHI - OAK
226$
205$
Prime price per passenger
Wed, Mar 25 - Wed, Apr 1
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
Alaska Airlines
Alaska Airlines1 stop
CHI - OAK
239$
225$
Prime price per passenger
Wed, Apr 22 - Sat, Apr 25
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
Alaska Airlines
Alaska Airlines1 stop
CHI - OAK
255$
236$
Prime price per passenger
Wed, Apr 8 - Mon, Apr 13
Hawaiian Airlines
Hawaiian Airlines1 stop
OAK - CHI
Hawaiian Airlines
Hawaiian Airlines1 stop
CHI - OAK
474$
455$
Prime price per passenger
Mon, May 18
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
111$
105$
Prime price per passenger
Wed, May 20
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
111$
105$
Prime price per passenger
Sat, Apr 25
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
118$
111$
Prime price per passenger
Sat, May 2
Alaska Airlines
Alaska Airlines1 stop
OAK - CHI
118$
111$
Prime price per passenger
Wed, Apr 8
Hawaiian Airlines
Hawaiian Airlines1 stop
OAK - CHI
185$
171$
Prime price per passenger
Wed, Apr 1
Hawaiian Airlines
Hawaiian Airlines1 stop
OAK - CHI
211$
196$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Oakland, CA to Chicago

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available at the beginning of May. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.
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week: May 4 - May 10
Flights from just $130
$171
$209
$210
$153
$147
$147
$139
$130
$152
$182
$160
$161
MarchAprilMayJune
Flying Time6 h and 24 mWhen flying from Oakland, CA to Chicago, this can take around 6 h and 24 m in flying time, however this flight duration can vary due to other factors
Cheapest flight$105The best price for flights from Oakland, CA to Chicago offered by eDreams, which have been found by our customers in the last 3 days
Origin airportOakland International AirportWhen flying from Oakland, CA to Chicago
Peak seasonMarchMarch is the busiest time to fly from Oakland, CA to Chicago according to search data results from our customers
One-way average Price234.98A flight from Oakland, CA to Chicago at eDreams will cost around 234.98, this being based on prices of the previous 6 months of data
Best time to bookMarchFebruary is one of the most frequent times to fly to Chicago from Oakland, CA according to real data from our customers
Distance: 1841 miles
Oakland, CA airports
Oakland Intl (OAK)How far from city center: 7 miles
Chicago airports
O'hare International Airport (ORD)How far from city center: 14 miles
Midway Airport (MDW)How far from city center: 4 miles

Are you planning to travel to Chicago for vacations, business or family visits? eDreams offers you the cheapest flights and best deals departing from Oakland, CA. With our fast search engine you will get a large selection of airfares from standard and low cost airlines worldwide and easily book your tickets for this route. If you are flexible we help you identify the cheapest day to fly to Chicago and if you need to leave soon you can check our most convenient last minute fares. Read all the useful information about your next destination and proceed to the reservation, indicating your flight dates and completing your travel booking with hotels and car rental!

Frequently asked questions about flights from Oakland, CA to Chicago

What are the benefits of booking flexible flight tickets?
Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. At eDreams have you covered!
On average, how much is the price of a flight from Oakland, CA to Chicago?
When you fly from Oakland, CA to Chicago the average price is 234.98. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.
For flights from Oakland, CA to Chicago, how can I find the cheapest price?
The cheapest price for a flight from Oakland, CA to Chicago is $105. At eDreams we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.
When booking, when is the best time to get the best prices for flights from Oakland, CA to Chicago?
The most popular months to book a trip from Oakland, CA to Chicago are July, August and May, based on the searches of our customers.
When is the best time to travel from Oakland, CA to Chicago?
The best time of the year to visit Chicago depends on lots of personal preferences, especially the price. Regarding popularity, August is the best month to fly to Chicago from Oakland, CA in terms of searches from our customers, followed by July and September. If you prefer to avoid the busy season and get away from the crowds January, February and March are the months with fewer searches for Oakland, CA - Chicago.
How long does the flight from Oakland, CA to Chicago take?
Flight length from Oakland, CA to Chicago is around 6 h and 24 m on average, at an average distance of 1,841.25 mi, for flights for the route (which may have 1 or more stops in other cities in between).

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