SJC - ORD

$91 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 2/12. 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 Chicago O'Hare Intl Airport

 
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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Everything you should know

Cheapest round-trip
$353
Typical prices: $416-$547
Alaska Airlines
Mon 1/5Tue 1/6
SJC - ORD • 1 stop
Cheapest non-stop
$387
Typical prices: $466-$616
American Airlines
Fri 2/6Sun 2/8
SJC - ORD • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
SJC offers a smooth security process for quick departures.
Take the CTA Blue Line train from ORD for easy downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from $360 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 26% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
6 days a week
There are direct flights from San Jose to O'Hare Intl 6 days a week: Mon, Tue, Thu, Fri, Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to O'Hare Intl!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights from San Jose to O'Hare Intl (SJC-ORD)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Mon, Jan 5 - Tue, Jan 6
Alaska Airlines Logo
2:53 pm - 11:59 pm
SJC
-
ORD
7h 06m1 stop
Alaska Airlines Logo
8:39 am - 10:39 pm
ORD
-
SJC
16h 00m1 stop
$353Alaska Airlines
Fri, Feb 13 - Wed, Feb 18
Delta Logo
9:15 am - 8:44 pm
SJC
-
ORD
9h 29m2 stops
Delta Logo
2:20 pm - 10:05 pm
ORD
-
SJC
9h 45m1 stop
$360Delta
Mon, Jan 19 - Thu, Jan 22
Delta Logo
8:05 pm - 9:41 am
SJC
-
ORD
11h 36m2 stops
Delta Logo
7:30 am - 4:20 pm
ORD
-
SJC
10h 50m2 stops
$365Delta
Wed, Apr 29 - Mon, May 4
Alaska Airlines Logo
8:10 am - 5:53 pm
SJC
-
ORD
7h 43m1 stop
Alaska Airlines Logo
2:59 pm - 10:38 pm
ORD
-
SJC
9h 39m1 stop
$367Alaska Airlines
Fri, Feb 13 - Wed, Feb 18
Alaska Airlines Logo
7:00 am - 11:59 pm
SJC
-
ORD
14h 59m1 stop
Alaska Airlines Logo
3:07 pm - 10:56 pm
ORD
-
SJC
9h 49m1 stop
$371Alaska Airlines
Tue, Mar 3 - Thu, Mar 5
Alaska Airlines Logo
2:50 pm - 11:59 pm
SJC
-
ORD
7h 09m1 stop
Alaska Airlines Logo
3:07 pm - 10:56 pm
ORD
-
SJC
9h 49m1 stop
$375Alaska Airlines
Thu, Apr 2 - Tue, Apr 14
Alaska Airlines Logo
2:00 pm - 11:58 pm
SJC
-
ORD
7h 58m1 stop
Alaska Airlines Logo
7:55 pm - 9:48 am
ORD
-
SJC
15h 53m1 stop
$379Alaska Airlines
Mon, Jan 5 - Tue, Jan 6
Delta Logo
6:20 am - 3:19 pm
SJC
-
ORD
6h 59m1 stop
Delta Logo
7:20 am - 5:40 pm
ORD
-
SJC
12h 20m2 stops
$380Delta
Sun, Jan 4 - Tue, Jan 20
Alaska Airlines Logo
7:05 am - 5:02 am
SJC
-
ORD
19h 57m1 stop
Alaska Airlines Logo
9:00 am - 10:35 pm
ORD
-
SJC
15h 35m1 stop
$382Alaska Airlines
Mon, Jan 5 - Mon, Jan 19
Delta Logo
5:05 pm - 8:43 am
SJC
-
ORD
13h 38m2 stops
Delta Logo
7:30 am - 4:20 pm
ORD
-
SJC
10h 50m2 stops
$385Delta
Booking Insights

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.

How much is a round-trip flight from San Jose, California to Chicago O'Hare Intl Airport?

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 Chicago O'Hare Intl Airport departing in January.

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 Fridays 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 December, where tickets cost $337 (return) on average. On the other hand, the most expensive months are November and October, where the average cost of round-trip tickets is $569 and $496 respectively.

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 4 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Expert advice

Expert advice for your flight from San Jose to O'Hare Intl

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
SJC

SJC offers a smooth security process with generally shorter lines than larger airports, making it ideal for quick departures.

ORD

Take the CTA Blue Line train from ORD to downtown Chicago for a 45-minute, traffic-free commute.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Bill Fink

Bill Fink

Expert on SJC

Bill Fink

Bill Fink

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more

Good to know

Low seasonJanuary
Cheapest flight$91
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 4% 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 $91 for a one-way ticket and $353 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: Alaska Airlines, JetBlue, Hawaiian Airlines, American Airlines, Air Canada, British Airways, SWISS, and Lufthansa.

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

    The Boeing 737 MAX 8 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between San Jose and Chicago O'Hare Airport, with SkyTeam being the most commonly used for this route.

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

    You can catch a nonstop flight from San Jose to Chicago O'Hare Airport on Monday, Tuesday, Thursday, Friday, Saturday, and Sunday.

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

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Alaska Airlines and Southwest. With an average price for the route of $315 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Southwest is also a great choice for the route, with an average price of $496 and an overall rating of 7.9.

  • 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 $206 or less one-way and $524 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San Jose to Chicago O'Hare Intl.
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, American Airlines

United Airlines, American Airlines

Tuesday

United Airlines, American Airlines

United Airlines, American Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

United Airlines, American Airlines

United Airlines, American 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, American Airlines

United Airlines, American Airlines

Tuesday

United Airlines

United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

United Airlines, American Airlines

United Airlines, American Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines, American Airlines

United Airlines, American Airlines

See more direct flights

Reviews of the 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
Alaska AirlinesOverall score based on 11466 reviews
8.5Crew
7.1Food
7.8Comfort
7.0Entertainment
8.1Boarding
Airline reviews

Larger seats and more room would elevate the experience. Otherwise, it was good!

10.0 ExcellentAnonymous, Dec 2025
SJC - SEA
Read more Alaska Airlines reviews

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.

5 1/2 hour trip. Nice plane. easy boarding. Could have used a bit more beverage service but it was a red eye flight and they didn't want to wake everyone.

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.

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.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

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

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

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

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Everything you need to know for your flight from San Jose to O'Hare Intl

Information on your arrival and departure airports