$109 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 5/2. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% 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.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Oakland to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$217
Moline
Moline2 stops$1,334
St. Louis
St. Louis1 stop$295
Chicago
Chicagononstop$217
Moline
Moline2 stops$1,334
St. Louis
St. Louis1 stop$295

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, Apr 8 - Tue, Apr 14
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$217Southwest
Wed, May 6 - Fri, May 8
Alaska Airlines Logo
7:19 pm - 7:03 pm
OAK
-
ORD
21h 44m
1 stop
Alaska Airlines Logo
3:52 pm - 2:38 pm
ORD
-
OAK
24h 46m
1 stop
$217Alaska Airlines
Wed, Apr 22 - Sat, Apr 25
Alaska Airlines Logo
7:19 pm - 11:43 pm
OAK
-
ORD
26h 24m
1 stop
Alaska Airlines Logo
8:50 am - 2:38 pm
ORD
-
OAK
7h 48m
1 stop
$220Alaska Airlines
Wed, May 13 - Wed, May 20
Alaska Airlines Logo
7:00 am - 6:46 pm
OAK
-
ORD
9h 46m
1 stop
Alaska Airlines Logo
9:00 am - 2:32 pm
ORD
-
OAK
7h 32m
1 stop
$223Alaska Airlines
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
6:40 am - 12:45 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
3:25 pm - 9:25 pm
MDW
-
OAK
8h 00m
1 stop
$227Southwest
Sat, May 2 - Mon, May 4
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
7:59 pm - 10:17 am
ORD
-
OAK
16h 18m
1 stop
$227Alaska Airlines
Tue, May 12 - Wed, May 20
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
9:00 am - 2:32 pm
ORD
-
OAK
7h 32m
1 stop
$230Alaska Airlines
Sat, Apr 11 - Mon, Apr 20
Delta Logo
5:55 am - 3:18 pm
OAK
-
ORD
7h 23m
1 stop
Delta Logo
7:12 pm - 11:54 pm
ORD
-
OAK
6h 42m
1 stop
$237Delta
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
3:40 pm - 11:45 pm
OAK
-
MDW
6h 05m
1 stop
Southwest Logo
6:00 pm - 10:50 pm
MDW
-
OAK
6h 50m
1 stop
$237Southwest
Wed, Mar 4 - Tue, Mar 10
Delta Logo
5:55 am - 6:40 pm
OAK
-
MDW
10h 45m
2 stops
Delta Logo
1:10 pm - 11:46 pm
MDW
-
OAK
12h 36m
2 stops
$247Delta
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?

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 $259 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 $259.

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 $398, 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 July, when tickets cost $302 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $631 and $568 respectively.

Good to know

Low seasonFebruary
Cheapest flight$109
Best time to beat the crowds with an average 14% 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.

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

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $363 on average. Morning departures are around 28% 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.

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 11819 reviews
7.0Entertainment
7.1Food
7.8Comfort
8.1Boarding
8.5Crew
Airline reviews

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

2.0 MediocreAnonymous, Jan 2026
STS - SAN
Read more Alaska Airlines reviews

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

I paid for wifi and it never worked... it was miserable. I couldn't access my shared files to work on the plane, it didn't work on my phone. I paid for nothing but frustration and continual refreshing, hoping it would work

The stewardess are very nice and pleasant, Someone onboard had a medical attention, and they attended that person non-stop all throughout the flight, and yet, did not forget to serve and help other passengers.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

My TSA pre check was left Off my boarding pass which was a large inconvenience.

Again, very smooth and all of the Alaska folks were great. They continue to meet all my needs.

Overall it was fine, however one of my two checked bags did not arrive and I was told it was left in Palm Springs. I don't understand how one of the two bags made it through fine but the other got lost .

The Alaska Airlines app made it very difficult to find my boarding pass. It was very frustrating to use! The flight itself was flawless.

It wasn’t great. Your app is not user friendly unless you sign up for those points. It tries to force you and won’t show you flight/trip info until you sign up. You have to somehow get into get your boarding pass because your kiosks don’t offer boarding pass information only bag check. It was not helpful or user friendly. The app is useless unless you sign up for your rewards program. My daughters info was missing even though I checked us in we had to get out of security and go back to a ticket window the woman told us that it sometimes populates incorrectly so it didn’t have her information. It populated incorrect birth date. She said this is common. Luckily we were at Palm Springs and not JFK where leaving the giant security line would have been a much bigger problem. I will avoid your airline in the future if it’s possible. Also no food availability except dry snack boxes.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

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.

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

The flight was delayed for about 2 hrs. Other than it, it was good.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

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.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

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

Information on your arrival and departure airports