$73 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 9/22. 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

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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Best Illinois Flight Deals from Oakland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$167
Moline
Moline1 stop$234
Peoria
Peoria2 stops$290
Bloomington
Bloomington2 stops$759
St. Louis
St. Louis3 stops$316
Chicago
Chicago1 stop$167
Moline
Moline1 stop$234
Peoria
Peoria2 stops$290
Bloomington
Bloomington2 stops$759
St. Louis
St. Louis3 stops$316

Cheap Flights from Oakland to Illinois

 
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 6 - Wed, Aug 20
Spirit Airlines Logo
6:00 am - 2:13 pmOAK-ORD
6h 13m1 stop
Spirit Airlines Logo
6:21 pm - 7:18 amORD-OAK
14h 57m1 stop
$167Spirit Airlines
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Thu, Jul 10 - Mon, Jul 14
Spirit Airlines Logo
2:38 pm - 6:03 amOAK-ORD
13h 25m2 stops
Spirit Airlines Logo
3:18 pm - 11:33 pmORD-OAK
10h 15m1 stop
$175Spirit Airlines
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Fri, Jul 4 - Sat, Jul 12
Southwest Logo
12:45 pm - 10:20 pmOAK-ORD
7h 35m1 stop
Southwest Logo
6:55 pm - 11:15 pmORD-OAK
6h 20m1 stop
$208Southwest
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Fri, Aug 15 - Tue, Aug 19
Southwest Logo
11:30 am - 11:40 pmOAK-ORD
10h 10m2 stops
Southwest Logo
1:30 pm - 6:25 pmORD-OAK
6h 55m1 stop
$232Southwest
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Wed, Sep 10 - Sun, Sep 14
 Logo
7:48 pm - 11:46 amOAK-MLI
13h 58m1 stop
 Logo
12:36 pm - 11:39 pmMLI-OAK
13h 03m1 stop
Tue, Jul 22 - Tue, Jul 29
Delta Logo
4:55 pm - 7:49 amOAK-ORD
12h 54m2 stops
Delta Logo
7:20 pm - 11:55 pmORD-OAK
6h 35m1 stop
$262Delta
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Tue, Sep 2 - Fri, Oct 3
Alaska Airlines Logo
7:58 pm - 7:03 amOAK-ORD
9h 05m1 stop
Alaska Airlines Logo
3:20 pm - 11:59 pmORD-OAK
10h 39m1 stop
$277Alaska Airlines
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Thu, Aug 7 - Mon, Aug 11
 Logo
1:22 pm - 11:55 amOAK-PIA
20h 33m2 stops
 Logo
12:45 pm - 11:33 pmPIA-OAK
12h 48m1 stop
Mon, Jun 30 - Fri, Jul 4
Delta Logo
12:30 pm - 10:09 pmOAK-ORD
7h 39m1 stop
Delta Logo
7:40 am - 11:50 amORD-OAK
6h 10m1 stop
$318Delta
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Mon, Jul 14 - Thu, Jul 17
Alaska Airlines Logo
7:58 pm - 5:40 amOAK-ORD
7h 42m1 stop
Alaska Airlines Logo
6:00 am - 1:43 pmORD-OAK
9h 43m1 stop
$327Alaska Airlines
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Useful Info

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 $278 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 $278.

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.

No, with an average price for the route of $432, prices are generally cheapest when you fly direct.

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 $235 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $407 and $397 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.


Good to know

Low seasonFebruary
High seasonMay
Cheapest flight$73
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 8% increase in price.
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 13% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $538.

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 $229 one-way - $407 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
8.5Crew
7.1Entertainment
8.1Boarding
7.8Comfort
7.1Food
Airline reviews

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.

8.0 ExcellentAnonymous, Jun 2025OAK - SEA
Read more Alaska Airlines reviews

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.

Flying on Hawaiian Airlines was good. But, getting a boarding pass was a hassle. I booked what I thought was an Alaska Airlines flight that was actually a Hawaiian Airlines flight. I couldn't check in online. I had to wait for the Hawaiian Airlines counter to open so I could get my boarding pass which was a requirement for me to get in The Club or the Centurion Lounge. (I had no check in luggage so I didn't expect to have to physically check in.) The Alaska Airlines staff blamed the FAA for the problem.

Staff are helpful and patient. I don’t appreciate the almost 5 hours delay and also the delay of our luggage and being switched from one carousel to another to pick them up.

Staff were great but we were delayed on the tarmac for over an hour.

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

Thank you still providing bags for vomit. My son had a migraine and needed a bag to vomit in and it was right there behind the seat in front of us. Thank you!

We waited over an hour for our luggage to arrive at the carousel in Seattle.

The plane was delayed a bit. It wasn't a huge problem though, as we were heading back home.

Flight was great. Boarding was crazy because another flight was boarding late next to ours so everyone was standing and in the way.

Comfortable seat, a little delay, very informative. Love Wi-Fi

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.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

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.

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.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

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

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

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.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

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