SJC - ORD

$64 Find Cheap Flights from San Jose to Chicago O'Hare Airport

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 O'Hare Intl departing on 6/1. 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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These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Chicago.
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Cheap Flights from San Jose to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to O'Hare Intl 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.

Recent round-trip flight deals from San Jose to O'Hare Intl

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Jose to O'Hare Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
4:28 pm - 5:25 amSJC-ORD
10h 57m1 stop
Spirit Airlines Logo
11:50 am - 11:29 pmORD-SJC
13h 39m1 stop
$141Spirit Airlines
Find Deal
Tue, May 20 - Wed, May 21
Spirit Airlines Logo
6:00 am - 5:25 amSJC-ORD
21h 25m1 stop
Spirit Airlines Logo
9:02 pm - 11:29 pmORD-SJC
28h 27m1 stop
$156Spirit Airlines
Find Deal
Sat, May 17 - Tue, May 20
Frontier Logo
12:13 pm - 11:59 pmSJC-ORD
9h 46m1 stop
Frontier Logo
6:00 am - 11:18 amORD-SJC
7h 18m1 stop
$238Frontier
Find Deal
Thu, Jun 5 - Sun, Jun 8
Frontier Logo
2:33 pm - 8:53 pmSJC-ORD
28h 20m1 stop
Frontier Logo
6:00 am - 11:18 amORD-SJC
7h 18m1 stop
$241Frontier
Find Deal
Thu, May 29 - Thu, Jun 5
Delta Logo
6:30 am - 2:28 pmSJC-ORD
5h 58m1 stop
Delta Logo
7:15 pm - 11:41 pmORD-SJC
6h 26m1 stop
$299Delta
Find Deal
Wed, Jun 4 - Wed, Jun 4
Alaska Airlines Logo
6:45 am - 11:56 pmSJC-ORD
15h 11m2 stops
Alaska Airlines Logo
8:00 am - 8:14 pmORD-SJC
14h 14m1 stop
$300Alaska Airlines
Find Deal
Tue, May 27 - Tue, Jun 3
Delta Logo
7:00 am - 6:20 pmSJC-ORD
9h 20m2 stops
Delta Logo
2:25 pm - 10:06 pmORD-SJC
9h 41m1 stop
$302Delta
Find Deal
Tue, May 20 - Wed, May 21
Alaska Airlines Logo
7:03 am - 10:30 pmSJC-ORD
13h 27m1 stop
Alaska Airlines Logo
10:00 am - 7:15 pmORD-SJC
11h 15m1 stop
$304Alaska Airlines
Find Deal
Tue, Jun 17 - Tue, Jun 24
United Airlines Logo
2:30 pm - 10:41 pmSJC-ORD
6h 11m1 stop
United Airlines Logo
7:59 pm - 10:39 pmORD-SJC
4h 40mnonstop
$341United Airlines
Find Deal
Wed, Jun 4 - Mon, Jun 9
United Airlines Logo
6:35 am - 12:57 pmSJC-ORD
4h 22mnonstop
United Airlines Logo
7:59 pm - 10:39 pmORD-SJC
4h 40mnonstop
$351United Airlines
Find Deal
Thu, Jun 5 - Sat, Jun 7
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KAYAK's insights & trends for San Jose to O'Hare Intl flights

Get data-powered insights and trends into flights from San Jose to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from San Jose to Chicago O'Hare Airport?

The average price of all round-trip flights from San Jose to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

When flying from San Jose to Chicago O'Hare Airport, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to San Jose, you’ll find the best rates on Wednesdays and the most expensive ones on Sundays.

What is the cheapest month to fly from San Jose to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Chicago O'Hare Intl Airport, 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 Chicago O'Hare Intl Airport is September, where tickets cost $360 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $523 and $512 respectively.

Can I save money by flying with a layover from San Jose to Chicago O'Hare Intl Airport?

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 $745, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from San Jose to Chicago O'Hare Intl Airport?

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 Chicago O'Hare Intl Airport, 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 Chicago O'Hare Intl Airport, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$64
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from San Jose to Chicago O'Hare Airport

When to book flights from San Jose to O'Hare Intl

Are your dates flexible? Find out the best times to travel from San Jose to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking San Jose to Chicago O'Hare Airport flights

  • What is the cheapest flight from San Jose to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from San Jose to Chicago O'Hare Intl Airport was $64 for a one-way ticket and $141 for a round-trip.

  • Do I need a passport to fly between San Jose and Chicago O'Hare Airport?

    A passport is not required to fly from San Jose to Chicago O'Hare Airport.

  • Which airlines offer Wi-Fi service onboard planes from San Jose to Chicago O'Hare Airport?

    All the following airlines offer inflight Wi-Fi service on the San Jose to Chicago O'Hare Airport flight route: JetBlue, Alaska Airlines, Delta, Air Canada, American Airlines, Finnair, Iberia, and United Airlines.

  • Which aircraft models fly most regularly from San Jose to Chicago O'Hare Airport?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the San Jose to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from San Jose to Chicago O'Hare Airport?

    Star Alliance is the only airline alliance operating flights between San Jose and Chicago O'Hare Airport.

  • On which days can I fly direct from San Jose to Chicago O'Hare Airport?

    There are nonstop flights from San Jose to Chicago O'Hare Airport on a daily basis.

  • Which is the best airline for flights from San Jose to Chicago, Delta or Southwest?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Delta and Southwest. With an average price for the route of $351 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $522 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from San Jose to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from San Jose 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 Chicago O'Hare Airport?

    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 to Chicago O'Hare Airport with an airline and back to San Jose with another airline. Booking your flights between San Jose and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Jose to Chicago O'Hare Airport?

    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 to Chicago O'Hare Airport from San Jose up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from San Jose to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $200 or less one-way and $403 or less round-trip.

Prefer to fly direct from San Jose to Chicago O'Hare Airport?

Find which airlines fly direct from San Jose Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

San Jose to Chicago O'Hare Intl

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to San Jose

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 5 airlines serving from San Jose to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Chicago. 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 O'Hare Intl? 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 4294 reviews
8.0Comfort
8.6Crew
7.1Food
8.2Boarding
7.6Entertainment
Airline reviews

It was a perfect flight in all aspects! Both legs!

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

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.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Delta flight was on time, seats were comfortable, and crew was nice.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

Horrible. Grateful to be alive but spent 13 hours at airport only to return back to my familys house and flight changed to next day. They tried to fix a part on plane, had no back up plane and after 10 hours , reattempted the flight and it STILL wasn't fixed. We got a meal voucher and rescheduled flight but there should be some other compensation for the 15 hours spent in airport

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

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Last minute 2-3 hr delay in flight schedule; no explanation Unexpected extra $52 charge What's the benefit of choosing a cheap airline if you trick people last minute and force them to pay extra last minute? Did not appreciate being cornered.

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

It’s ridiculous to pay for carry-on luggage. I also wasn’t given an option to specify I have carry on bag at time of ticket purchase. I also could not specify I have carry on luggage at time of online check-in.

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Frontier had yet another flight cancellation. Have never made a complete round trip with this airline without at least one leg getting cancelled. Miserable flights - dirty, uncomfortable planes that apparently always have issues since I've had multiple delays and cancellations with them.

Flight was delayed 3 times, would have been nice to have received text message instead of email notifications. Frontier app wasn’t even updated accordingly, no gate number disclosed. No agent at front desk of gate to inform of delay. Very confused and left if the dark

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

They changed the timing , first delayed by 4 hours then went back to 40 mins late, we had to run back to airport to not miss our flight. This is ridiculous

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

It was a redeye flight, so every passenger just wanted to sleep, but through the entire flight, the flight crew made announcements over the loudspeaker at maximum volume every few minutes making sleep impossible. For example: it’s 2am, and the crew decides to give an extremely detailed announcement about snacks and beverages for sale. And 3am is the perfect time to wake up everyone with a lengthy announcement about how to get a coffee refill and how to take advantage of new offer from frontier for a credit card.

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