SJC - ORD

$86 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 4/21. 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
$277
Overall average: $497
Alaska Airlines
Tue 3/31Mon 4/6
SJC - ORD • 1 stop
Cheapest non-stop
$282
Typical prices: $307-$470
United Airlines
Fri 4/17Wed 4/22
SJC - ORD • Non-stop
Advice from real travelers
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
Cheapest • from $277 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with United Airlines. Average duration is 4h 23m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 6h 15m (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 32% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
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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

Tue, Mar 31 - Mon, Apr 6
Alaska Airlines Logo
6:15 am - 11:59 pm
SJC
-
ORD
15h 44m
1 stop
Alaska Airlines Logo
4:10 pm - 10:10 pm
ORD
-
SJC
8h 00m
1 stop
$277Alaska Airlines
Tue, Apr 7 - Thu, Apr 16
Alaska Airlines Logo
8:39 pm - 7:02 pm
SJC
-
ORD
20h 23m
1 stop
Alaska Airlines Logo
4:10 pm - 10:10 pm
ORD
-
SJC
8h 00m
1 stop
$278Alaska Airlines
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
12:57 pm - 11:27 pm
SJC
-
ORD
8h 30m
1 stop
Multiple Airlines Logo
5:15 am - 11:59 am
ORD
-
SJC
8h 44m
1 stop
$279Multiple Airlines
Thu, Apr 16 - Sat, Apr 18
Frontier Logo
8:11 pm - 6:08 am
SJC
-
ORD
7h 57m
1 stop
Frontier Logo
7:21 pm - 7:27 pm
ORD
-
SJC
26h 06m
1 stop
$280Frontier
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
8:11 pm - 11:27 pm
SJC
-
ORD
25h 16m
2 stops
Multiple Airlines Logo
5:15 am - 7:27 pm
ORD
-
SJC
16h 12m
1 stop
$281Multiple Airlines
Thu, Apr 16 - Sat, Apr 18
Alaska Airlines Logo
2:35 pm - 11:59 pm
SJC
-
ORD
7h 24m
1 stop
Alaska Airlines Logo
6:00 am - 1:35 pm
ORD
-
SJC
9h 35m
1 stop
$282Alaska Airlines
Tue, Jun 9 - Wed, Jun 17
Alaska Airlines Logo
2:34 pm - 11:59 pm
SJC
-
ORD
7h 25m
1 stop
Alaska Airlines Logo
6:22 am - 11:24 am
ORD
-
SJC
7h 02m
1 stop
$283Alaska Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
11:00 am - 10:20 pm
SJC
-
ORD
9h 20m
1 stop
American Airlines Logo
5:00 am - 10:07 am
ORD
-
SJC
7h 07m
1 stop
$285American Airlines
Tue, Jun 2 - Tue, Jun 16
Alaska Airlines Logo
12:59 pm - 1:14 pm
SJC
-
ORD
22h 15m
1 stop
Alaska Airlines Logo
6:22 am - 11:24 am
ORD
-
SJC
7h 02m
1 stop
$286Alaska Airlines
Tue, Apr 14 - Thu, Apr 16
Southwest Logo
11:15 am - 10:55 pm
SJC
-
ORD
9h 40m
2 stops
Southwest Logo
3:45 pm - 11:30 pm
ORD
-
SJC
9h 45m
1 stop
$287Southwest
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.

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 September, where tickets cost $353 (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 $533 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 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 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$86
Best time to beat the crowds with an average 12% drop 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 $86 for a one-way ticket and $277 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, Hawaiian Airlines, American Airlines, JetBlue, Lufthansa, 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Southwest and Delta. With an average price for the route of $493 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $409 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 $193 or less one-way and $377 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.
8.0
SouthwestOverall score based on 4318 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

8.0 ExcellentTobin, Mar 2026
SJC - BUR
Read more Southwest reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

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.

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.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Got on the plane and sat there for an hour before departure.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

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

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports