$56 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 8/20. 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

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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
Chicago2 stops$131
Moline
Moline2 stops$335
Bloomington
Bloomington2 stops$924
St. Louis
St. Louis1 stop$311
Chicago
Chicago2 stops$131
Moline
Moline2 stops$335
Bloomington
Bloomington2 stops$924
St. Louis
St. Louis1 stop$311

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

Wed, Aug 20 - Wed, Sep 3
Spirit Airlines Logo
10:44 am - 4:50 amOAK-ORD
16h 06m2 stops
Spirit Airlines Logo
6:21 pm - 7:38 amORD-OAK
15h 17m1 stop
$131Spirit Airlines
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Wed, Oct 1 - Mon, Oct 6
Spirit Airlines Logo
6:00 am - 9:01 pmOAK-ORD
13h 01m1 stop
Spirit Airlines Logo
6:05 pm - 11:32 pmORD-OAK
7h 27m1 stop
$140Spirit Airlines
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Fri, Sep 26 - Mon, Sep 29
 Logo
6:30 am - 8:52 pmOAK-MDW
12h 22m1 stop
 Logo
7:03 pm - 11:32 pmMDW-OAK
6h 29m1 stop
Sun, Oct 19 - Sat, Oct 25
Southwest Logo
6:40 am - 12:45 pmOAK-MDW
4h 05mnonstop
Southwest Logo
3:55 pm - 6:30 pmMDW-OAK
4h 35mnonstop
$207Southwest
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Tue, Aug 26 - Sun, Aug 31
Southwest Logo
5:35 am - 2:10 pmOAK-ORD
6h 35m1 stop
Southwest Logo
1:50 pm - 10:20 pmORD-OAK
10h 30m1 stop
$213Southwest
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Wed, Oct 22 - Wed, Nov 12
Alaska Airlines Logo
7:06 pm - 5:01 amOAK-ORD
7h 55m1 stop
Alaska Airlines Logo
8:00 am - 1:55 pmORD-OAK
7h 55m1 stop
$216Alaska Airlines
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Sat, Oct 25 - Wed, Nov 12
Delta Logo
5:59 pm - 9:40 amOAK-MDW
13h 41m2 stops
Delta Logo
1:00 pm - 11:53 pmMDW-OAK
12h 53m2 stops
$267Delta
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Thu, Sep 18 - Mon, Sep 22
 Logo
6:00 am - 6:52 pmOAK-RFD
10h 52m1 stop
 Logo
10:37 am - 7:38 amRFD-OAK
23h 01m2 stops
Tue, Nov 4 - Tue, Nov 18
Delta Logo
5:55 am - 6:25 pmOAK-MDW
10h 30m2 stops
Delta Logo
1:00 pm - 11:53 pmMDW-OAK
12h 53m2 stops
$285Delta
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Wed, Oct 22 - Tue, Oct 28
Alaska Airlines Logo
6:40 am - 12:03 amOAK-STL
15h 23m1 stop
Alaska Airlines Logo
7:00 am - 1:55 pmSTL-OAK
8h 55m1 stop
$312Alaska Airlines
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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.

What is the cheapest Oakland to Illinois flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Oakland to Illinois.

The cheapest ticket to Illinois from Oakland found in the last 72 hours was to Chicago, at $264 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 $264.

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 1 stop layover the cheapest option at $494 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 September, when tickets cost $236 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $407 and $398 respectively.

What’s the cheapest day of the week to fly from Oakland to Illinois?

The average price of all round-trip flights from Oakland to Illinois clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Illinois on a Tuesday and more expensive on a Thursday. On your return trip to Oakland, you should consider flying back on a Wednesday, and avoid Fridays for better deals.

How far in advance should I book a flight from Oakland to Illinois?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Oakland to Illinois, you should book around 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonFebruary
Cheapest flight$56
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 12% 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.

  • 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 $306 on average. Morning departures are around 6% 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 $468.

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 $188 one-way - $338 round-trip

Reviews of the top 5 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
Alaska AirlinesOverall score based on 10000 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.1Food
7.1Entertainment
Airline reviews

Departing flight to San Diego was delayed. Return flight from SD to SBP was delayed. Not terrible but not ideal

4.0 OkaySean, Jul 2025SBP - SAN
Read more Alaska Airlines reviews

Departing flight to San Diego was delayed. Return flight from SD to SBP was delayed. Not terrible but not ideal

I always heard this was a terrible airline but I was happy to experience otherwise. The seats were more comfortable than delta. They did board late and gate was a little chaotic, which is to be expected for a budget airline. I would definitely do it again for that price.

My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.

Canceled flight. No communication of this prior. Rescheduled to next day. Our good seats we purchased months ago turned into last row middle. No apology, reason, nor compensation for time and $ spent.

delayed flight 3 hours, then took 45 min to get to gate and another 10 min to open door

Delayed flight both ways. Then, on the return flight, we were stuck on the tarmac for at least 30+ minutes. Idk what happened, but this was a bad experience.

The plane was put out of service and had to wait for a new plane to be assigned. No one had any information and the information on the screens was never updated. The call wait time was 2 hours and the estimated time for text assistance was 55 minutes which was a lie because after 55 minutes nothing happened. I understand that delays happen but to not have anyone available to provide any update or reassurance was just negligent. Also, what is the point of having an 800 number if no one answers it and don’t get me started on the text message system. Ridiculous!

Great flight, no bumps to speak of, pleasant crew, good inflight entertainment choices

Coffee or tea service would be nice for an evening flight, water or juice not good enough.

Very expensive for short flights. Can’t communicate with Alaska Air about passport issue at check-in. Also no replies to my text messages. Wanted to extend our vacation for two more days but this expensive flight ticket is called SAVER and I couldn’t make changes or cancel or get a credit even, so I paid another airline for the return trip. Extremely disappointed.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

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.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

Delta flight was on time, seats were comfortable, and crew was nice.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

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.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

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