$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 4/15. 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
Chicagononstop$243
St. Louis
St. Louis1 stop$317
Chicago
Chicagononstop$243
St. Louis
St. Louis1 stop$317

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

mar., avr. 7 - mar., avr. 14
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
$243Southwest
sam., avr. 11 - sam., avr. 18
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:55 pm - 8:30 pm
MDW
-
OAK
4h 35mnonstop
$245Southwest
mer., avr. 15 - mer., avr. 22
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
$251Southwest
mar., avr. 7 - mar., avr. 14
Southwest Logo
8:50 pm - 5:40 am
OAK
-
MDW
6h 50m
1 stop
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
$252Southwest
sam., avr. 11 - sam., avr. 18
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
6:45 am - 12:10 pm
MDW
-
OAK
7h 25m
1 stop
$255Southwest
mer., mai 6 - mar., mai 12
Southwest Logo
1:50 pm - 10:55 pm
OAK
-
ORD
7h 05m
1 stop
Southwest Logo
4:50 pm - 10:35 pm
ORD
-
OAK
7h 45m
1 stop
$257Southwest
sam., mai 2 - mar., mai 5
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
6:00 am - 1:15 pm
ORD
-
OAK
9h 15m
1 stop
$261Alaska Airlines
sam., mai 2 - mer., mai 6
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
6:00 am - 1:15 pm
ORD
-
OAK
9h 15m
1 stop
$265Alaska Airlines
mar., mai 5 - sam., mai 9
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
8:50 am - 2:38 pm
ORD
-
OAK
7h 48m
1 stop
$273Alaska Airlines
mar., mars 31 - sam., avr. 4
Multiple Airlines Logo
6:40 pm - 1:20 pm
OAK
-
BRL
16h 40m
2 stops
Multiple Airlines Logo
9:10 am - 11:43 pm
BRL
-
OAK
16h 33m
2 stops
$881Multiple 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.

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 $363 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.

Good to know

Low seasonFebruary
Cheapest flight$119
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Oakland to Chicago Midway Airport

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 $192 one-way - $347 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 4319 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

8.0 ExcellentTobin, Mar 2026
SJC - BUR
Read more Southwest reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

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

After landing in Seattle, 3 hours waiting to find parking space do to driving problems. Very uncomfortable.

My only complaint was how far it was from plane to baggage claim

I had a problem with my reservation and no one could help me understand what happened. I booked my flight months ago and received a confirmation email. In the confirmation email, it said that the flight would depart at 3:15 p.m. A few hours before the flight, I tried to go online and check in, and suddenly it said that the flight was leaving an hour earlier. I had to rush to get to the airport and almost didn't make it. No one could help me understand why this happened, and I'm really concerned that it might happen in the future. I would appreciate some support in this matter.

They cancelled the flight and provided no support to find another way home or how to get a refund. Links provided didn’t work and phone wait times were over eight hours. Battery on my phone couldn’t last long enough.

It was a super old plane so the first class experience was just not luxurious

signage from the upper area to the tram down 2 escalator!

You sent me an email saying boarding was at 9:29 and AA sent one that was 8:29 on Sunday morning. I had to call AA to get that it was indeed 8:29.

Not bad. Due to not buying a seat, on the way back, my seat was not assigned till 2 hrs before the flight left. Got me worried I wouldn’t have a seat.

Great flights, little turbulence, pilots kept stewardesses seated & safe, all staff friendly & professional

There is no entertainment on the plane. The snack is minimal. The crew was nice and professional.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

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

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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

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.

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

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.

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

Information on your arrival and departure airports