$119 Find Cheap Flights from Oakland to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Illinois departing on 6/2. 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 Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Illinois, as well as popular online travel agencies
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Cheap Flights from Oakland to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$306
Moline
Moline2 stops$678
St. Louis
St. Louis1 stop$357
Chicago
Chicago1 stop$306
Moline
Moline2 stops$678
St. Louis
St. Louis1 stop$357

Book Cheap Oakland to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Illinois 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 Oakland to Illinois

Tue, Jun 9 - Sat, Jul 4
Delta Logo
12:33 pm - 9:57 pm
OAK
-
ORD
7h 24m
1 stop
Delta Logo
7:45 am - 11:53 am
ORD
-
OAK
6h 08m
1 stop
$306Delta
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
6:15 am - 5:10 pm
OAK
-
MDW
8h 55m
2 stops
Southwest Logo
6:50 am - 1:10 pm
MDW
-
OAK
8h 20m
1 stop
$307Southwest
Tue, May 26 - Wed, Jun 10
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
7:37 pm - 11:54 pm
ORD
-
OAK
6h 17m
1 stop
$308Delta
Fri, May 29 - Mon, Jun 1
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
9:50 pm - 12:25 am
MDW
-
OAK
4h 35mnonstop
$309Southwest
Fri, May 29 - Tue, Jun 2
Southwest Logo
9:30 pm - 5:25 am
OAK
-
MDW
5h 55m
1 stop
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
$310Southwest
Tue, Aug 18 - Thu, Aug 20
Southwest Logo
6:55 pm - 4:30 am
OAK
-
MDW
7h 35m
1 stop
Southwest Logo
2:05 pm - 7:45 pm
MDW
-
OAK
7h 40m
2 stops
$311Southwest
Wed, Aug 12 - Mon, Aug 17
Delta Logo
1:15 pm - 9:58 pm
OAK
-
ORD
6h 43m
1 stop
Delta Logo
3:50 pm - 11:49 pm
ORD
-
OAK
9h 59m
2 stops
$311Delta
Thu, May 28 - Tue, Jun 9
Alaska Airlines Logo
6:02 am - 6:50 pm
OAK
-
ORD
10h 48m
1 stop
Alaska Airlines Logo
9:00 am - 11:50 pm
ORD
-
OAK
16h 50m
1 stop
$314Alaska Airlines
Mon, May 25 - Tue, Jun 2
Alaska Airlines Logo
6:02 am - 1:14 pm
OAK
-
ORD
29h 12m
1 stop
Alaska Airlines Logo
9:00 am - 2:14 pm
ORD
-
OAK
7h 14m
1 stop
$317Alaska Airlines
Tue, Sep 8 - Tue, Sep 22
Alaska Airlines Logo
11:55 am - 11:41 pm
OAK
-
ORD
9h 46m
1 stop
Alaska Airlines Logo
7:59 pm - 10:44 am
ORD
-
OAK
16h 45m
1 stop
$319Alaska Airlines
Booking Insights

KAYAK's insights & trends for Oakland to Illinois flights

Get data-powered insights and trends into flights from Oakland to Illinois to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Oakland, California to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Oakland, California to Illinois departing in June.

What is the cheapest Oakland to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Oakland found in the last 72 hours was to Chicago, at $343 round-trip. The most popular route is from Oakland (OAK) to Chicago Midway Airport (MDW), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $343.

What is the cheapest time of day to fly to Illinois?

The average price for all round-trip flights from Oakland to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $338 on average. Morning departures are around 41% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $791.

Can I save money by flying with a layover from Oakland to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $421 on average.

What is the cheapest month to fly from Oakland to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oakland to Illinois is April, when tickets cost $93 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $274 and $271 respectively.

Good to know

Low seasonFebruary
Cheapest flight$119
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Oakland to Chicago Midway Airport

FAQs - booking Illinois flights

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

    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 Oakland to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland to 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 Oakland to Illinois?

    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 from Oakland to Illinois with an airline and back with another airline.

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

    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 from Oakland to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Oakland to the following destinations at these prices or less: Chicago $224 one-way - $421 round-trip

Reviews of the top 4 airlines serving from Oakland to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Oakland to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Oakland to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4314 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Agent could not provide me a boarding pass for the second leg of my flights - yet with a partner airline. Not understood.

I had to change my flight last minute due to a medical emergency. Their agent was compassionate and extremely helpful. This airlines really cares about making travel, for fun, work, or an emergency a customer-focused experience. Thank you!

More efficient with checking lines and boarding/checking bags when needed.

They were really helpful with every question and my kids had never been on a plane and the staff made them feel comfortable

The flight would have been very good , if not dor the constantly screaming baby in the row behind me. Is there a way to isolate people traveling with infants? This is not the first time this has happened to me.

No headphones provided. No gf food. Only 1 beverage cart run sAN to HNL. Rarely saw crew members

I was on flight #3022 departed from San Diego, California to Medford, Oregon. I had Denise & Damaris as my flight attendants. I didn’t have much interaction with Damaris, but I did with Denise who had, this calm, cool collective voice when she spoke about the emergency exit plans before takeoff. I travel often and I’ve never met a flight attendant that can put you at ease. I felt she respects and takes pride in her position and more airlines need to adopt the integrity and respect that she has for Alaska Airlines. Debbie

They treat me well because of my one world status. Crew is attentive and professional. One of the best airlines out there.

This was my first time flying first class. I was really disappointed with the food option and lack of entertainment. I wasn’t given an option of what to eat. The breakfast was less than desirable. It was a bowl of some type of granola cereal, dried fruit, almond butter and 3 biscuits that we pretty much tasteless. There was so much fiber in that meal I was afraid I would poop myself in the flight. There was absolutely ZERO entertainment available. No tv screen to watch a movie or listen to music. No charging port for my phone. I recently flew Delta Airlines Comfort class and I had a tv screen with numerous options of music to listen to and movies to watch. Also I had a charging port for my phone. I expected more quality from first class. Please understand I am not some prima donna that feels entitled. But the price I paid for first class wasn’t worth what I experienced.

Crew were bad Didn’t help with luggage When asked for a glass of wine, I was told that they will serve later , which they didn’t to Me and didn’t serve anyone else in First class . Didn’t offer any snacks , Chips or Nuts to anyone . Flight was not crowded either. Worst Service/ or No Service !

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Everything you need to know for your flight from Oakland to Illinois

Information on your arrival and departure airports