$217 Find Cheap Flights from San José to Illinois - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals
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?

Flight prices are typical for this route right now.

Flights to Illinois from San José usually cost between $359 and $576 in October.
The lowest price found in the past 5 days was $365 on Frontier (Oct 10-Oct 16).

What is the cheapest San José to Illinois flight route?

The cheapest ticket to Illinois from San José found in the last 5 days was to Chicago, at $227 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 $227.

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

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $463 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 $465.

Can I save money by flying with a layover from San José to Illinois?

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?

The cheapest month for flights from San José to Illinois is January, when tickets cost $385 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $640 and $561 respectively.

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

If your flying dates are flexible, you should consider flying to Illinois on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday 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 get a below average price on the flight from San José to Illinois, you should book around 3 weeks before departure, which saves you about 5% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low season

April

Cheapest flight

$217
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from San José to Chicago Midway 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.

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

 
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.
8.0
SouthwestOverall score based on 4200 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

The flight was fine. Seats were very comfortable. Attendants were very friendly -

10.0 ExcellentMaggie, Jul 2026
Read more Southwest reviews

The flight was fine. Seats were very comfortable. Attendants were very friendly -

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.

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

Flight Crew Review The crew was absolutely amazing from start to finish! They were friendly, professional, attentive, and genuinely made the flight feel comfortable and enjoyable. Every interaction was pleasant, and they went above and beyond to make sure passengers were taken care of. You could really tell that they cared about providing great service. I truly appreciate their kindness and professionalism and would be happy to fly with this crew again!

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

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

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

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

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Terrible experience flying with American Airlines. Too many delays and cancellations.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

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.

Better seats, allow us to upgrade, terrible website, poor telephone service, better equipment

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

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

More options for your flight from San José to Illinois

Complete your trip to Illinois with a hotel stay or car rental