$171 Find Cheap Flights from San José 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 José to Illinois departing on 10/22. 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 José to Illinois.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José to Illinois.
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Cheap Flights from San José to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$378
St. Louis
St. Louis2 stops$567
Chicago
Chicago1 stop$378
St. Louis
St. Louis2 stops$567

Book Cheap San José 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 José 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 José to Illinois

Wed, Oct 7 - Wed, Oct 14
Southwest Logo
9:00 am - 8:30 pm
SJO
-
MDW
10h 30m
1 stop
Southwest Logo
6:05 am - 12:05 pm
MDW
-
SJO
7h 00m
1 stop
$378Southwest
Thu, Sep 17 - Tue, Sep 22
Southwest Logo
1:40 pm - 10:15 pm
SJO
-
MDW
7h 35m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$383Southwest
Fri, Aug 28 - Sun, Aug 30
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$390JetBlue
Fri, Aug 28 - Sun, Aug 30
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$397JetBlue
Fri, Aug 28 - Sun, Aug 30
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$400JetBlue
Fri, Aug 28 - Mon, Aug 31
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$403JetBlue
Thu, Jul 23 - Tue, Jul 28
United Airlines Logo
12:44 pm - 11:44 pm
SJO
-
STL
10h 00m
1 stop
United Airlines Logo
6:14 am - 10:39 pm
STL
-
SJO
17h 25m
1 stop
$569United Airlines
Wed, Jul 22 - Tue, Jul 28
United Airlines Logo
12:30 am - 9:26 pm
SJO
-
STL
19h 56m
2 stops
United Airlines Logo
6:14 am - 12:21 pm
STL
-
SJO
7h 07m
1 stop
$574United Airlines
Wed, Nov 25 - Mon, Nov 30
Delta Logo
7:00 am - 11:39 pm
SJO
-
STL
16h 39m
1 stop
Delta Logo
6:00 am - 1:05 pm
STL
-
SJO
7h 05m
1 stop
$645Delta
Wed, Nov 25 - Mon, Nov 30
American Airlines Logo
6:22 am - 9:08 pm
SJO
-
STL
14h 46m
2 stops
American Airlines Logo
9:38 am - 10:59 pm
STL
-
SJO
13h 21m
1 stop
$654American Airlines
Booking Insights

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

Get data-powered insights and trends into flights from San José 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 José 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 José to Illinois departing in August.

What is the cheapest San José 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 José found in the last 5 days was to Chicago, at $424 round-trip. The most popular route is from San José (SJO) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $424.

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

The average price for all round-trip flights from San José 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 $464 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 $467.

Can I save money by flying with a layover from San José 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 $528, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San José 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 José to Illinois is April, when tickets cost $103 (return) on average. On the other hand, the most expensive months are July and January, when the average cost of round-trip tickets is $291 and $195 respectively.

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

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

If your flying dates are flexible, you should consider flying to Illinois on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from San José to Illinois. For your return ticket, we recommend flying on a Tuesday and avoiding Saturdays for the best deals.

How far in advance should I book a flight from San José 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 José 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 José to Illinois, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$171
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from San José to Chicago O'Hare Airport

FAQs - booking Illinois flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San José 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 José 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 José 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 José 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 José to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between San José and Illinois per day?

    There is a maximum of 1 nonstop flight a day that takes off from San José and lands in Illinois, with an average flight time of 5h 35m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 1 flights.

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

 
See real verified KAYAK customer reviews for airlines flying from San José 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 José 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
SouthwestOverall score based on 4246 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

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

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

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.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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

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.

I am very please with the service received from Southwest. Although there was a refuel stop in Fl before we got the Baltimore. The service and kindness of the staff was excellent.

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

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

stood in line to check in luggage for nearly an hour. very poor service and not excusable

Same as the previous flight as far as comfort and food. Entertainment didn’t have a watchable screen so everything would need to be watched on your own device in which they didn’t have a charging port that accommodated my iPhone. Seats were very uncomfortable. Staff was very friendly.

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

Copa stranded us ans then tried to charge us thousands to leave Panama.

Friendly flight team and seamless travel from one stop to next.

I would like a glass of wine or some kind of alcoholic drink.

Very long delay but we just made the connection. The requested wheel chairs were not there so I had to assist/carry BOTH of my parents to the gate while carrying their bags so we could make the connection. The plane had no entertainment system and NO WIFI, legroom zero. Restrooms on ALL of flights were dirty and one restroom did not even work properly. I was surprised to see COPA like this since my flight with them in 2013 was incredible, the seats were amazing and the food options were spectacular. Of course, I see this kind of service on many airlines now, with services and hospitality at an all time low. The worse part of the trip was seeing my 90 year old parents go through hell on these flights and having to try and rush to a gate to make the next flight. Never again

Just a minor inconvinient with weather delay! but not Copa's fault

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

The flight to Houston the agents were not very helpful

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

It was good, although we could not get our preferred seats, we did enjoy the whole experience from Costa Rica. I still don't understand why our luggage is not the first to come out at the band.

Movie selection is good. Crew did not understand mileage program and were no help. Sick later. Food?

I love United was disappointed we had a two hour delay, however the Pilot did say safety first.

Since when do I have to pay for my checked bag? I have a United Explorer mileage plus silver card and I was charged for my checked bags. This also is an international flight. So I would like an explanation to be clear before I choose an airline please?

Boarding was terrible. My wife uses a wheel chair and she was in an incredibly hot closed metal cargo box for close to 20 minutes before getting on board

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

When I'm on a 5hr 22 minute flight I expect food to be purchased. Especially when American makes a very tight connection time where u have to run to make the long flight. Chips and nuts are unacceptable and being told you should be in first class to get a meal is also unacceptable. I didn't change the flight times American Airlines did.

Flight attendants on American Airlines are rude very harsh with their time of voice. Nearly identical experience as spirit airlines. However, from Spirit Airlines, you expect this level of mediocre service. You do not expect this from the big three..

The plane had maintenance issues and didn't leave after 72 hours

The staff were very nice! However when our first flight got delayed an hour, the second connection flight was not delayed and the layover was only 40 minutes. When we rushed and made it to our gate for the connection flight, the gate said it had moved to another section of the airport. We barley made it to the connection flight, and overall we were very stressed. We asked about taking a later time for the second connection flight, but the other option was much later and we would have to wait at the airport for 9+ hours. I just wish American Airlines could have moved the second connection flight to a later time too for its customers, and thank you for taking the time to read my review.

Flight was canceled and then rescheduled on another flight. Paid for first class but moved to the back of the plane. Then put up in the worst/dirtiest hotel I’ve ever stayed in. American Airlines should be ashamed of putting their passengers/customers in a place that filthy.

The flight was on time, boarding process good. Good value flight.

Flight was delayed by one hour, then another 1/2 hour then cancelled and changed till the next day. We were not allowed to get our luggage & put up in a dirty hotel. I had cockroaches in the bathroom. When I finally arrived home…i noticed the airline had damaged the zipper on my suitcase. An awful awful trip thanks to American Airlines.

The employees at the gate were not communicating, they preferred to give the upgrade to pilots and not to the elite passengers Every flight I more disappointing, clients shooed be priority instead of other employees even if they are pilots, there was plenty room for pilots in economy

Horrible experience with Avianca, they delayed their flight and when we arrived to NYC, AVIANCA took 1 hr y 30 mins to park the airplane and all passenger get off the plane, it made me lost all my trains to get back home and I came back to my place at 3 am instead of 12 am. On the top of that their plane seat are so uncomfortable and is not enough space and killed my legs and knees, Avianca used to be good when it was a Colombian company, now after Brasilian company bought them, their service quality is bad and their flights are delayed and oversold.

I handed in my suitcase in perfect condition at SAL Airport. And in MIA Airport I received it with one corner broken and the wheels bent.

I like the crew members they're very friendly. Clean plane. The flight was on time. I dont like the comfort my car seat its better that the plane seats. They charge for everything. This airline was very good. Now it's a low cost airline

6 hour flight and have to pay for everything 100 dollars to add a carry-on bag is insane

The check in is the only positive thing in Avianca. The seat is the most uncomfortable I have traveled, the distance is minimal.

Not what it used to be. The sale of food makes them look greedy!

Avianca is not what it used to be. So disappointing

It was horrible. My experience with Avianca. I didn’t know it was Pakistan international Airlines but anyway, whatever it is it is bad horrible you guys need to upgrade everything in those planes. And you guys charge $130 for a carry-on did they wanna let me in with my carry-on that I travel everywhere with the luggage you guys are such a dog thank you

The incoming plane was late and no information was shared. They even announced we would board in 10 muntes 40 minutes prior to the plane arriving, and the website said until takeoff that we had taken off an hour earlier

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

Information on your arrival and departure airports