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 1/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Oakland

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$252
Southwest
Sat 1/24Tue 1/27
MDW - OAK • Non-stop
Cheapest one-way
$109
Typical prices: $213-$328
Southwest
Tue 1/20
MDW - OAK • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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, Jan 24 - Tue, Jan 27
Southwest Logo
7:40 pm - 10:35 pmMDW-OAK
4h 55mnonstop
Southwest Logo
11:10 am - 5:15 pmOAK-MDW
4h 05mnonstop
$252Southwest
Find Deal
Sun, Jan 18 - Wed, Jan 21
Delta Logo
5:20 pm - 9:38 pmORD-OAK
6h 18m1 stop
Delta Logo
12:38 pm - 9:52 pmOAK-ORD
7h 14m1 stop
$253Delta
Find Deal
Sat, Jan 10 - Sat, Jan 17
Delta Logo
5:20 pm - 9:38 pmORD-OAK
6h 18m1 stop
Delta Logo
12:38 pm - 9:52 pmOAK-ORD
7h 14m1 stop
$256Delta
Find Deal
Wed, Dec 17 - Sat, Jan 17
Delta Logo
7:40 pm - 12:08 amORD-OAK
6h 28m1 stop
Delta Logo
12:38 pm - 9:52 pmOAK-ORD
7h 14m1 stop
$258Delta
Find Deal
Thu, Jan 15 - Tue, Jan 20
Alaska Airlines Logo
8:00 am - 8:40 pmORD-OAK
14h 40m1 stop
Alaska Airlines Logo
8:10 am - 11:50 pmOAK-ORD
13h 40m1 stop
$259Alaska Airlines
Find Deal
Sat, Jan 24 - Tue, Jan 27
Southwest Logo
7:40 pm - 10:35 pmMDW-OAK
4h 55mnonstop
Southwest Logo
2:50 pm - 10:40 pmOAK-MDW
5h 50m1 stop
$262Southwest
Find Deal
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
11:10 am - 2:05 pmMDW-OAK
4h 55mnonstop
Southwest Logo
11:10 am - 5:15 pmOAK-MDW
4h 05mnonstop
$264Southwest
Find Deal
Mon, Jan 12 - Tue, Jan 20
Delta Logo
2:20 pm - 10:53 pmORD-OAK
10h 33m2 stops
Delta Logo
5:55 am - 1:38 pmOAK-ORD
5h 43m1 stop
$265Delta
Find Deal
Thu, Jan 29 - Tue, Feb 3
Alaska Airlines Logo
8:00 am - 8:40 pmORD-OAK
14h 40m1 stop
Alaska Airlines Logo
11:43 am - 11:50 pmOAK-ORD
10h 07m1 stop
$276Alaska Airlines
Find Deal
Wed, Jan 14 - Mon, Jan 19
Alaska Airlines Logo
2:50 pm - 4:23 pmSTL-OAK
27h 33m1 stop
Alaska Airlines Logo
8:10 am - 1:54 pmOAK-STL
27h 44m1 stop
$302Alaska Airlines
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 4% increase in price.
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)