$84 Find Cheap Flights from Oakland to Illinois - Compare and Save

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Cheap Flights from Oakland to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Chicago
Chicago1 stop$205
Moline
Moline2 stops$669
Peoria
Peoria1 stop$479
Chicago
Chicago1 stop$205
Moline
Moline2 stops$669
Peoria
Peoria1 stop$479
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?

Flight prices are below average for this route right now.

Flights to Illinois from Oakland, California usually cost between $507 and $520 in December.
The lowest price found in the past 5 days was $205 on Frontier (Dec 2-Dec 16).

What is the cheapest Oakland to Illinois flight route?

The cheapest ticket to Illinois from Oakland found in the last 5 days was to Chicago, at $349 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 5 days was $349.

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

The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $472 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?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $429 on average.

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

The cheapest month for flights from Oakland to Illinois is February, when tickets cost $335 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $542 and $538 respectively.

Good to know

Low season

February

Cheapest flight

$84
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Oakland to Chicago O'Hare 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 $266 one-way - $431 round-trip

Reviews of the top 4 airlines serving from Oakland to Illinois

 
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.
7.9
Alaska AirlinesOverall score based on 13135 reviews
7.0Entertainment
8.1Boarding
7.0Food
8.5Crew
7.8Comfort
Airline reviews

I always have flown Alaska Airlines because I never had an issues. Their customers service is incredible and an amazing communication.

8.0 ExcellentAnonymous, Jul 2026
Read more Alaska Airlines reviews

I always have flown Alaska Airlines because I never had an issues. Their customers service is incredible and an amazing communication.

Flight was canceled in good weather due to mechanical issue. Rebooked to flight to different airport in area that landed 7 hours after initially planned arrival. We had to jump through hoops to get taxi reimbursement given flight landed in different airport at 12:45 am.

My travel mate needed wheel chair assistance getting on and off, and it was excellent. Thank you!

Affirmed my disability by allowing me to board when most accessible. Very parable, helpful and friendly staff. Smooth flight overall! I always fly Alaska when possible! Thank you!

In both halves of the trip (going and returning) there were problems. Not exactly Alaska's fault, but still really difficult. Outgoing flight was canceled and rebooked twice due to a total ground stop of all Alaska's flights. This required me to change airports with minimal notice and I almost missed my flight transferring to the other airport (which was roughly an hour and a half away). On the return, the first leg was delayed by an hour, and the second leg was delayed by nearly 3 hours. This was a rough set of flights and the communication about all of these changes was minimal. Crew did their best however, so no fault there. Other thing to remember is there is no food on Alaska flights unless you pre-order. Take that into account when you choose airlines.

The setting on the loudspeaker was painful and the crew member who did the talking spoke very quickly and repetitively, with extra little jokes that were distracting and mostly unfunny. I doubt that the main messages penetrated the noise.

The Alaska app and website were not fully operational. I had to spend about 15 minutes at the counter doing things that should have been completed online. The agent was very nice and helpful, however.

Good. They checked my bag FOR FREE so I didnt have to try to hoist it up into the overhead compartment. Also, they served free beverages, which I appreciated.

From my interactions with the Oakland airport staff through TSA through the gate agents to the flight crew on Hawaiian they were just so kind professional and helpful.. the only thing I would add would be the they need more help and TSA and on the Hawaiian airlines flight it would be so much nicer for them to play beautiful Hawaiian music on the way over there.. they didn't start playing it until right before we landed..

Staff was very friendly. Flight was on time and arrived early. Flight was comfortable.

Friendly crew. Snacks were carb-heavy. Flight was quite delaye

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Southwest Airlines is behind the times with a woefully inefficient service animal policy that leads to major inconsistency and stress for passengers and crew alike. Despite so many attempts to share feedback and request better support, they bungled it once again and provoked a panic attack in the process, with no apologies or acknowledgment that their crew was failing to adhere to their own inadequate policies. WiFi didn’t work, flight was delayed by an hour, it was about what I’ve come to expect from Southwest these days.

Flights were full but SWA still managed to get everyone loaded and depart on time. No snack or beverage service on the first leg due to turbulance. Seats were clean but very little cushioning. Reasonable amount of leg room.

Our flight to Oakland was great bc the plane was new but it was delayed by 15min not bad at all. Over all it was an 8/10

Our flight to Vegas was delayed by almost two hours - I appreciated the updates but it was a bummer of a start to a celebratory trip. The delays meant we missed our dinner reservations we made a month ago so that was disappointing. Once we got to the gate, though, the crew did all they could to make up for the lost time and to keep it efficient and enjoyable, so I appreciate their efforts!!

Requested an aisle seat at the gate and got it. The staff so friendly

Flight was very delayed so I was able to get on an earlier flight via stand-by. Crew communicated effectively around delay and worked to make customers comfortable. Wifi was ok, streaming TV was great. App functionality broke down once I was moved to stand-by on earlier flight.

Sat in the tarmac at O’Hare for 65 minutes. This is a regular occurrence for delta at O’Hare

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Cramped seating for me. Luckily it wasn’t a long flight

Better management of the boarding process. Is there any way you could forward all the window seats first? That's the Way Reno Air used to do it, and they had the fastest boarding in the industry!

We were delay because so many bags needed to be gate checked and it was disappointing not to have outlets in the seats for such a long flight.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

More options for your flight from Oakland to Illinois

Complete your trip to Illinois with a hotel stay or car rental