OAK

$63 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 4/18. 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
$171
Southwest
Sat 4/18Tue 4/28
MDW - OAK • Non-stop
Cheapest one-way
$63
Typical prices: $159-$226
Southwest
Sat 4/18
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, Apr 18 - Tue, Apr 28
Southwest Logo
5:55 pm - 8:30 pm
MDW
-
OAK
4h 35mnonstop
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
$171Southwest
Sat, Apr 18 - Tue, Apr 28
Southwest Logo
5:55 pm - 8:30 pm
MDW
-
OAK
4h 35mnonstop
Southwest Logo
6:45 pm - 4:35 am
OAK
-
MDW
7h 50m
1 stop
$181Southwest
Sat, Mar 14 - Wed, Mar 18
Southwest Logo
9:40 pm - 12:20 am
MDW
-
OAK
4h 40mnonstop
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
$201Southwest
Sat, Mar 14 - Wed, Mar 18
Southwest Logo
9:40 pm - 12:20 am
MDW
-
OAK
4h 40mnonstop
Southwest Logo
9:10 pm - 5:00 am
OAK
-
MDW
5h 50m
1 stop
$211Southwest
Fri, Apr 24 - Mon, Apr 27
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
Alaska Airlines Logo
6:55 pm - 1:13 pm
OAK
-
ORD
16h 18m
1 stop
$223Alaska Airlines
Wed, Apr 22 - Tue, Apr 28
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
$230Alaska Airlines
Tue, Apr 21 - Mon, Apr 27
Alaska Airlines Logo
8:20 am - 10:17 am
ORD
-
OAK
27h 57m
1 stop
Alaska Airlines Logo
3:18 pm - 11:43 pm
OAK
-
ORD
6h 25m
1 stop
$233Alaska Airlines
Mon, Apr 6 - Thu, Apr 9
Delta Logo
7:10 pm - 11:46 pm
ORD
-
OAK
6h 36m
1 stop
Delta Logo
12:35 pm - 9:34 pm
OAK
-
ORD
6h 59m
1 stop
$237Delta
Tue, Mar 24 - Tue, Mar 31
Delta Logo
7:10 pm - 11:46 pm
ORD
-
OAK
6h 36m
1 stop
Delta Logo
5:55 am - 4:43 pm
OAK
-
ORD
8h 48m
2 stops
$242Delta
Sun, May 24 - Sun, May 31
Delta Logo
11:00 am - 9:32 pm
MLI
-
OAK
12h 32m
2 stops
Delta Logo
5:06 pm - 10:15 am
OAK
-
MLI
15h 09m
2 stops
$940Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$63
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly and prices are also 5% 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)