SJC - ORD

$144 Find Cheap Flights from San Jose to Chicago O'Hare Airport - 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 O'Hare Intl departing on 8/6. 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
$329
Typical prices: $582-$375
Frontier, Alaska Airlines
Sat 7/4Tue 7/7
SJC - ORD • 1 stop
Cheapest non-stop
$361
Typical prices: $564-$451
United Airlines
Tue 8/4Tue 8/11
SJC - ORD • Non-stop
Top airlines
Cheapest • from $330 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 4h 24m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 6h 16m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 41% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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
Booking Insights
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

Sat, Jul 4 - Tue, Jul 7
Multiple Airlines Logo
2:12 pm - 5:07 am
SJC
-
ORD
12h 55m
1 stop
Multiple Airlines Logo
7:59 pm - 9:26 am
ORD
-
SJC
15h 27m
1 stop
$329Multiple Airlines
Wed, Jul 15 - Sat, Jul 18
Alaska Airlines Logo
10:03 am - 6:57 pm
SJC
-
ORD
6h 54m
1 stop
Alaska Airlines Logo
5:59 pm - 11:55 pm
ORD
-
SJC
7h 56m
1 stop
$330Alaska Airlines
Tue, Aug 25 - Fri, Sep 11
Delta Logo
2:45 pm - 11:29 pm
SJC
-
ORD
6h 44m
1 stop
Delta Logo
5:00 pm - 10:44 pm
ORD
-
SJC
7h 44m
1 stop
$332Delta
Mon, Aug 24 - Thu, Aug 27
Delta Logo
1:46 pm - 9:30 pm
SJC
-
ORD
5h 44m
1 stop
Delta Logo
7:48 am - 12:54 pm
ORD
-
SJC
7h 06m
1 stop
$333Delta
Wed, Jul 8 - Thu, Jul 16
Alaska Airlines Logo
7:13 am - 6:57 pm
SJC
-
ORD
9h 44m
1 stop
Alaska Airlines Logo
6:20 am - 11:24 am
ORD
-
SJC
7h 04m
1 stop
$334Alaska Airlines
Mon, Aug 3 - Mon, Aug 10
Frontier Logo
8:23 pm - 6:17 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
7:15 am - 1:17 pm
ORD
-
SJC
8h 02m
1 stop
$335Frontier
Thu, Aug 6 - Fri, Aug 14
Frontier Logo
8:23 pm - 6:17 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
9:57 pm - 7:28 pm
ORD
-
SJC
23h 31m
2 stops
$336Frontier
Fri, Aug 21 - Tue, Sep 1
Delta Logo
1:46 pm - 9:30 pm
SJC
-
ORD
5h 44m
1 stop
Delta Logo
8:28 am - 5:12 pm
ORD
-
SJC
10h 44m
2 stops
$337Delta
Mon, Aug 24 - Sat, Aug 29
Delta Logo
9:34 am - 9:47 pm
SJC
-
ORD
10h 13m
2 stops
Delta Logo
7:00 am - 1:26 pm
ORD
-
SJC
8h 26m
1 stop
$338Delta
Tue, Jul 7 - Sat, Jul 11
United Airlines Logo
1:10 pm - 12:45 am
SJC
-
ORD
9h 35m
1 stop
United Airlines Logo
7:58 pm - 10:43 pm
ORD
-
SJC
4h 45mnonstop
$340United Airlines
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 July.

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 Mondays 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 May, where tickets cost $375 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $612 and $577 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 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 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.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

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.

Bill Fink

Bill Fink

Expert on SJC

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.

Good to know

Low seasonFebruary
Cheapest flight$144
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 35% 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 5 days, the lowest price for a flight from San Jose to Chicago O'Hare Intl Airport was $144 for a one-way ticket and $329 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, American Airlines, Hawaiian Airlines, Alaska Airlines, SWISS, and United Airlines.

  • 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?

    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, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Alaska Airlines and Delta. With an average price for the route of $345 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $395 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 $288 or less one-way and $530 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

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

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.
7.9
Alaska AirlinesOverall score based on 12509 reviews
7.8Comfort
7.0Food
7.0Entertainment
8.5Crew
8.1Boarding
Airline reviews

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

2.0 MediocreAnonymous, Jun 2026
SEA - ORD
Read more Alaska Airlines reviews

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

It was good. Too long for older people. Service and support was great! Friendly crew!

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'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

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.

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

Was fine, delayed and feels like southwest is always late

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.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

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

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.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Flight delayed four separate times. I’m now one hour hours late to landing.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

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

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

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

Information on your arrival and departure airports