OAK

$109 Find Cheap Flights from Illinois to Oakland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Oakland departing on 4/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$227
Southwest
Sat 3/7Sat 3/7
MDW - OAK • 1 stop
Cheapest non-stop
$248
Southwest
Wed 3/25Tue 3/31
MDW - OAK • Non-stop
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We hope you love your trip to Oakland!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Illinois to Oakland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Illinois to Oakland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Illinois to Oakland

Sat, Mar 7 - Sat, Mar 7
Southwest Logo
5:45 pm - 10:15 pm
MDW
-
OAK
6h 30m
1 stop
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
$227Southwest
Wed, Mar 25 - Tue, Mar 31
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
Southwest Logo
6:00 am - 3:10 pm
OAK
-
MDW
7h 10m
2 stops
$233Southwest
Wed, Mar 18 - Wed, Mar 25
Delta Logo
7:05 pm - 11:46 pm
ORD
-
OAK
6h 41m
1 stop
Delta Logo
12:35 pm - 9:34 pm
OAK
-
ORD
6h 59m
1 stop
$237Delta
Sat, Mar 7 - Sat, Mar 7
Southwest Logo
6:25 am - 11:40 am
MDW
-
OAK
7h 15m
1 stop
Southwest Logo
5:40 pm - 4:05 am
OAK
-
MDW
8h 25m
1 stop
$237Southwest
Tue, Mar 10 - Tue, Mar 17
Delta Logo
3:59 pm - 11:46 pm
ORD
-
OAK
9h 47m
2 stops
Delta Logo
12:35 pm - 9:34 pm
OAK
-
ORD
6h 59m
1 stop
$242Delta
Wed, Mar 18 - Sat, Mar 21
Southwest Logo
5:55 am - 12:40 pm
MDW
-
OAK
8h 45m
2 stops
Southwest Logo
5:40 pm - 1:55 am
OAK
-
MDW
6h 15m
1 stop
$242Southwest
Thu, Feb 26 - Thu, Mar 5
Hawaiian Airlines Logo
3:54 pm - 10:49 pm
ORD
-
OAK
8h 55m
1 stop
Hawaiian Airlines Logo
6:15 am - 4:33 pm
OAK
-
ORD
8h 18m
1 stop
$264Hawaiian Airlines
Tue, Feb 3 - Thu, Feb 5
Alaska Airlines Logo
8:00 am - 4:23 pm
ORD
-
OAK
10h 23m
1 stop
Alaska Airlines Logo
8:10 am - 2:38 pm
OAK
-
ORD
28h 28m
1 stop
$270Alaska Airlines
Wed, Feb 11 - Wed, Feb 18
Alaska Airlines Logo
8:00 am - 4:23 pm
ORD
-
OAK
10h 23m
1 stop
Alaska Airlines Logo
6:15 am - 4:33 pm
OAK
-
ORD
8h 18m
1 stop
$279Alaska Airlines
Fri, Feb 20 - Mon, Feb 23
Hawaiian Airlines Logo
7:00 am - 10:49 pm
STL
-
OAK
17h 49m
1 stop
Hawaiian Airlines Logo
6:15 am - 11:59 pm
OAK
-
STL
15h 44m
1 stop
$303Hawaiian Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago Midway Airport to Oakland

FAQs for booking flights from Illinois to Oakland

  • How does KAYAK find such low prices on flights from Illinois to Oakland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Oakland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Oakland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Oakland from Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Oakland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Oakland with an airline and back to Illinois with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Oakland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Oakland from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Oakland

Information on the airport you'll fly into in Oakland

Oakland (OAK)