$67 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 4/20. 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, 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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Flight Deals

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$256
Moline
Moline1 stop$334
Peoria
Peoria1 stop$513
Bloomington
Bloomington2 stops$340
Champaign
Champaign1 stop$546
Springfield
Springfield2 stops$830
St. Louis
St. Louis1 stop$230
Paducah
Paducah1 stop$795
Chicago
Chicago1 stop$256
Moline
Moline1 stop$334
Peoria
Peoria1 stop$513
Bloomington
Bloomington2 stops$340
Champaign
Champaign1 stop$546
Springfield
Springfield2 stops$830
St. Louis
St. Louis1 stop$230
Paducah
Paducah1 stop$795

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

Mon, Mar 2 - Fri, Mar 6
Frontier Logo
9:35 am - 9:13 pm
SJC
-
STL
9h 38m
1 stop
Frontier Logo
12:14 pm - 6:07 pm
STL
-
SJC
7h 53m
1 stop
$230Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
10:34 am - 9:26 pm
SJC
-
STL
8h 52m
1 stop
Frontier Logo
12:14 pm - 6:07 pm
STL
-
SJC
7h 53m
1 stop
$244Frontier
Tue, Apr 28 - Sat, May 2
Delta Logo
11:00 pm - 9:56 am
SJC
-
MDW
8h 56m
1 stop
Delta Logo
5:40 am - 12:21 pm
MDW
-
SJC
8h 41m
1 stop
$280Delta
Tue, Apr 28 - Sat, May 2
Delta Logo
11:00 pm - 9:56 am
SJC
-
MDW
8h 56m
1 stop
Delta Logo
9:46 am - 7:01 pm
MDW
-
SJC
11h 15m
2 stops
$285Delta
Wed, Mar 18 - Wed, Mar 25
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
Southwest Logo
6:05 am - 12:05 pm
MDW
-
SJC
8h 00m
1 stop
$287Southwest
Mon, Mar 16 - Tue, Mar 24
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
Southwest Logo
9:00 pm - 11:45 pm
MDW
-
SJC
4h 45mnonstop
$290Southwest
Tue, Mar 17 - Tue, Mar 24
United Airlines Logo
3:49 pm - 11:34 pm
SJC
-
STL
5h 45m
1 stop
United Airlines Logo
3:30 pm - 10:59 pm
STL
-
SJC
9h 29m
1 stop
$317United Airlines
Tue, Mar 17 - Tue, Mar 24
American Airlines Logo
6:00 am - 5:13 pm
SJC
-
STL
9h 13m
2 stops
American Airlines Logo
2:31 pm - 6:45 pm
STL
-
SJC
6h 14m
1 stop
$322American Airlines
Mon, Mar 9 - Wed, Mar 11
American Airlines Logo
4:20 pm - 11:59 pm
SJC
-
STL
5h 39m
1 stop
American Airlines Logo
7:58 am - 3:50 pm
STL
-
SJC
9h 52m
1 stop
$358American Airlines
Sat, May 16 - Mon, May 18
United Airlines Logo
6:30 am - 5:47 pm
SJC
-
CMI
9h 17m
1 stop
United Airlines Logo
7:13 pm - 12:00 pm
CMI
-
SJC
18h 47m
2 stops
$546United 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 April.

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 $281 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 $309.

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 $448, 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 February, when tickets cost $393 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $543 and $472 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 33% 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$67
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.

  • 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 $433 on average. Morning departures are around 11% more expensive than evening flights, 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 $556.

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 $213 one-way - $394 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.
8.0
Alaska AirlinesOverall score based on 11895 reviews
7.0Entertainment
7.8Comfort
8.5Crew
8.1Boarding
7.1Food
Airline reviews

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.

4.0 OkayJerry, Jan 2026
SAN - ORD
Read more Alaska Airlines reviews

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.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

One the nicest and great air crews I’ve experienced and I’ve flown a lot

Why was I charged for a glass of wine on one flight and not on another? Why no movie or TVs? It was a long flight.

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

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.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Got on the plane and sat there for an hour before departure.

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.

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

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

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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

Information on your arrival and departure airports