$137 Find Cheap Flights from San Jose to Illinois - Compare and Save

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 8/14. 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.
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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$330
Moline
Moline1 stop$349
Peoria
Peoria1 stop$389
Bloomington
Bloomington2 stops$394
Champaign
Champaign2 stops$470
Springfield
Springfield2 stops$582
St. Louis
St. Louis1 stop$237
Paducah
Paducah1 stop$902
Chicago
Chicago1 stop$330
Moline
Moline1 stop$349
Peoria
Peoria1 stop$389
Bloomington
Bloomington2 stops$394
Champaign
Champaign2 stops$470
Springfield
Springfield2 stops$582
St. Louis
St. Louis1 stop$237
Paducah
Paducah1 stop$902

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

Tue, Sep 1 - Sat, Sep 5
Delta Logo
1:24 pm - 11:26 pm
SJC
-
STL
8h 02m
1 stop
Delta Logo
11:13 am - 5:34 pm
STL
-
SJC
8h 21m
1 stop
$237Delta
Wed, Aug 26 - Thu, Aug 27
Southwest Logo
9:55 am - 5:55 pm
SJC
-
STL
6h 00m
1 stop
Southwest Logo
5:30 pm - 10:15 pm
STL
-
SJC
6h 45m
1 stop
$239Southwest
Wed, Aug 26 - Thu, Aug 27
Southwest Logo
12:00 pm - 10:35 pm
SJC
-
STL
8h 35m
1 stop
Southwest Logo
3:45 pm - 9:25 pm
STL
-
SJC
7h 40m
2 stops
$244Southwest
Thu, Sep 17 - Sun, Sep 20
Frontier Logo
9:10 am - 11:51 am
SJC
-
STL
24h 41m
1 stop
Frontier Logo
12:46 pm - 1:29 pm
STL
-
SJC
26h 43m
1 stop
$252Frontier
Sat, Aug 1 - Fri, Aug 7
Frontier Logo
2:12 pm - 6:15 pm
SJC
-
STL
26h 03m
1 stop
Frontier Logo
7:10 pm - 1:17 pm
STL
-
SJC
20h 07m
1 stop
$253Frontier
Tue, Sep 15 - Thu, Sep 17
American Airlines Logo
2:36 pm - 11:43 pm
SJC
-
STL
7h 07m
1 stop
American Airlines Logo
5:43 am - 10:53 am
STL
-
SJC
7h 10m
1 stop
$258American Airlines
Wed, Sep 2 - Sun, Sep 6
United Airlines Logo
8:45 am - 4:34 pm
SJC
-
STL
5h 49m
1 stop
United Airlines Logo
4:40 pm - 8:57 pm
STL
-
SJC
6h 17m
1 stop
$279United Airlines
Sun, Aug 23 - Mon, Aug 24
Alaska Airlines Logo
10:12 am - 7:21 pm
SJC
-
ORD
7h 09m
1 stop
Alaska Airlines Logo
6:01 am - 10:59 am
ORD
-
SJC
6h 58m
1 stop
$333Alaska Airlines
Tue, Aug 25 - Sat, Aug 29
United Airlines Logo
6:20 am - 12:45 pm
SJC
-
ORD
4h 25mnonstop
United Airlines Logo
8:03 pm - 10:50 pm
ORD
-
SJC
4h 47mnonstop
$337United Airlines
Thu, Jul 23 - Wed, Jul 29
American Airlines Logo
2:23 pm - 11:40 pm
SJC
-
PIA
7h 17m
1 stop
American Airlines Logo
6:25 am - 6:37 pm
PIA
-
SJC
14h 12m
2 stops
$389American 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 August.

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 5 days was to Chicago, at $322 round-trip. The most popular route is from San Jose (SJC) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $322.

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 $446 on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $543.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $614 on average.

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 April and December, when the average cost of round-trip tickets is $265 and $258 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 Thursday, 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 38% 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$137
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from San Jose to St. Louis

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 $255 one-way - $469 round-trip; Chicago $253 one-way - $446 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 12631 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.0Entertainment
7.0Food
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 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.

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

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

Staff at Gate desk were helpful. My connecting flight from the first part of my trip Kona to Seattle was late. I had to run through SeaTac Seattle to catch my flight to San Jose. They made an exception to let me board. On my return trip San Jose to San Diego and San Diego to Honolulu the same thing happened. One flight arrived late and I had to run through the terminal to catch my connection. There are no Gluten-free & Vegan options meals and snacks to purchase.

Short flight was fine, but no entertainment and bathrooms broken.

My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

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.

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

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.

Forget beverage, they didn't even have water for half the passangers?

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Flight was not full! Had a whole row to myself.

Wifi didn’t work, no service, seats are hard as rocks

It was as good as it could be. Flying is not a pleasant experience these days.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

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

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

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.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

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

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.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

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.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

A good, solid, no frills experience. Departed and arrived on time, staff were pleasant and attentive. Loved the Bluetooth connectivity on the SJC to IAH leg. Being able to watch movies and listen to them with my noise cancelling headphones was lovely. Missed that on the IAH to LHR leg (so I put the wired buds on and my over ear Quiet Comforts over those).

The flight from LA to Chicago was smooth and service was very good overall.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

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.

Was not able to watch most shows on the entertainment site. They would not load

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

Apart from the delay due to unforeseen circumstances. The leg from sjc to dfw was fine. It was the leg from dfw to orf that we encountered issues mainly due to the flight attendant crew not being friendly. We had two small children and we needed some assistance to warm up milk so the baby would sleep. The crew just didn’t get it and made things very difficult. One made a remark that the baby’s dirty diaper smell was a “gift” to the plane in a rude way. Normally I’d brush that off as a funny comment if the rest of the trip the attendants were helpful or understanding of the difficulty we faced. But that wasn’t the case. We were met with rudeness on the second leg. Whereas on the first leg the crew were so nice and helpful.

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

Information on your arrival and departure airports