$111 Find Cheap Flights from San Jose 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 San Jose to Illinois departing on 5/28. 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 San Jose to Illinois.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Illinois.
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Cheap Flights from San Jose to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$272
Moline
Moline1 stop$349
Peoria
Peoria1 stop$349
Bloomington
Bloomington2 stops$478
Champaign
Champaign2 stops$486
Springfield
Springfield2 stops$661
St. Louis
St. Louis1 stop$232
Paducah
Paducah2 stops$1,020
Chicago
Chicago1 stop$272
Moline
Moline1 stop$349
Peoria
Peoria1 stop$349
Bloomington
Bloomington2 stops$478
Champaign
Champaign2 stops$486
Springfield
Springfield2 stops$661
St. Louis
St. Louis1 stop$232
Paducah
Paducah2 stops$1,020

Book Cheap San Jose 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 San Jose 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 San Jose to Illinois

Thu, May 28 - Wed, Jun 3
Frontier Logo
8:21 am - 8:26 pm
SJC
-
STL
10h 05m
1 stop
Frontier Logo
6:51 pm - 1:17 pm
STL
-
SJC
20h 26m
1 stop
$232Frontier
Sun, May 24 - Sun, May 31
Frontier Logo
2:12 pm - 8:11 pm
SJC
-
STL
27h 59m
1 stop
Frontier Logo
9:06 pm - 1:17 pm
STL
-
SJC
18h 11m
1 stop
$241Frontier
Wed, May 27 - Wed, Jun 3
Alaska Airlines Logo
2:00 pm - 1:14 pm
SJC
-
ORD
21h 14m
1 stop
Alaska Airlines Logo
7:40 am - 1:40 pm
ORD
-
SJC
8h 00m
1 stop
$272Alaska Airlines
Wed, Jun 10 - Tue, Jun 23
Southwest Logo
2:10 pm - 11:50 pm
SJC
-
MDW
7h 40m
1 stop
Southwest Logo
5:30 am - 9:40 am
MDW
-
SJC
6h 10m
1 stop
$277Southwest
Tue, Jun 2 - Wed, Jun 3
Alaska Airlines Logo
1:14 pm - 10:59 pm
SJC
-
ORD
7h 45m
1 stop
Alaska Airlines Logo
2:10 pm - 7:22 pm
ORD
-
SJC
7h 12m
1 stop
$277Alaska Airlines
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
9:45 am - 7:30 pm
SJC
-
MDW
7h 45m
2 stops
Southwest Logo
6:45 am - 1:05 pm
MDW
-
SJC
8h 20m
1 stop
$282Southwest
Tue, Jun 2 - Wed, Jun 3
Delta Logo
1:40 pm - 9:50 pm
SJC
-
ORD
6h 10m
1 stop
Delta Logo
5:19 pm - 11:41 pm
ORD
-
SJC
8h 22m
2 stops
$282Delta
Tue, Jul 14 - Tue, Jul 28
Delta Logo
8:19 pm - 8:37 am
SJC
-
MDW
10h 18m
2 stops
Delta Logo
11:05 am - 7:32 pm
MDW
-
SJC
10h 27m
2 stops
$298Delta
Tue, Aug 11 - Thu, Aug 20
United Airlines Logo
2:09 pm - 10:52 pm
SJC
-
PIA
6h 43m
1 stop
United Airlines Logo
5:31 pm - 10:41 pm
PIA
-
SJC
7h 10m
1 stop
$349United Airlines
Thu, May 21 - Mon, May 25
United Airlines Logo
2:32 pm - 1:08 pm
SJC
-
PAH
20h 36m
2 stops
United Airlines Logo
2:17 pm - 12:03 pm
PAH
-
SJC
23h 46m
1 stop
$1,020United Airlines
Booking Insights

KAYAK's insights & trends for San Jose to Illinois flights

Get data-powered insights and trends into flights from San Jose 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 San Jose, California to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Jose, California to Illinois departing in May.

What is the cheapest San Jose to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from San Jose found in the last 72 hours was to Chicago, at $270 round-trip. The most popular route is from San Jose (SJC) to Chicago Midway Airport (MDW), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $270.

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

The average price for all round-trip flights from San Jose 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 afternoon, when round-trip flights cost $442 on average. The most expensive time of day to fly to Illinois is generally at night, which is peak travel time and where the average cost of a ticket is $517.

Can I save money by flying with a layover from San Jose 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 $513, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Jose to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose 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 San Jose to Illinois is March, when tickets cost $95 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $258 and $208 respectively.

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

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

For San Jose to Illinois, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Illinois back to San Jose, the best deals are generally found on Wednesday, with Sunday being the most expensive.

How far in advance should I book a flight from San Jose 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 San Jose 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 San Jose to Illinois, you should book around 4 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$111
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from San Jose to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from San Jose 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 San Jose to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose 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 San Jose 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 San Jose 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 San Jose 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 San Jose 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 San Jose to the following destinations at these prices or less: Chicago $203 one-way - $434 round-trip; Chicago $300 one-way - $456 round-trip

Reviews of the top 5 airlines serving from San Jose to Illinois

 
See real verified KAYAK customer reviews for airlines flying from San Jose 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 San Jose 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 12336 reviews
8.5Crew
7.0Entertainment
7.1Food
8.1Boarding
7.8Comfort
Airline reviews

No complimentary snacks or food. Had to buy drinks and food.

4.0 OkayAnonymous, Mar 2026
SJC - SEA
Read more Alaska Airlines reviews

No complimentary snacks or food. Had to buy drinks and food.

in-flight wifi was not working well. also the cabin temperature was a bit hot.

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

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.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

I wasn’t able to check in prior to arriving at the airport, I was told by the agent I may not get a seat on the plane as others were waiting for seats, I sat there for 2 hours before being assigned a seat, very stressful. The plane was delayed. Overall not a great travel experience for a 44 minute flight.

Larger seats and more room would elevate the experience. Otherwise, it was good!

Check in went pretty well and you didn't lose my bag. After I got a drink from the drink cart they charged me for it, and at the crazy overpriced airport rates. Never had that happen before, is that an american thing? what madness.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Boarding was quick and efficient. We arrived at our destination early.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Everything you need to know for your flight from San Jose to Illinois

Information on your arrival and departure airports