SJC - ORD

$161 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 9/27. 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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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$313
Typical prices: $280-$468
United Airlines
Fri 9/11Tue 9/15
SJC - ORD • Non-stop
Cheapest non-stop
$315
Typical prices: $380-$514
United Airlines
Fri 8/21Wed 8/26
SJC - ORD • Non-stop
Top airlines
Cheapest • from $313 (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 24m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 6h 14m (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 45% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
Good to know
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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

Fri, Sep 11 - Tue, Sep 15
United Airlines Logo
2:10 pm - 8:35 pm
SJC
-
ORD
4h 25mnonstop
United Airlines Logo
1:30 pm - 8:57 pm
ORD
-
SJC
9h 27m
1 stop
$313United Airlines
Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
6:20 am - 12:45 pm
SJC
-
ORD
4h 25mnonstop
United Airlines Logo
6:00 am - 1:08 pm
ORD
-
SJC
9h 08m
1 stop
$313United Airlines
Sat, Oct 3 - Wed, Oct 7
Alaska Airlines Logo
9:15 am - 6:53 pm
SJC
-
ORD
7h 38m
1 stop
Alaska Airlines Logo
7:00 am - 2:18 pm
ORD
-
SJC
9h 18m
1 stop
$313Alaska Airlines
Mon, Sep 28 - Thu, Oct 1
Multiple Airlines Logo
1:38 pm - 5:38 am
SJC
-
ORD
14h 00m
1 stop
Multiple Airlines Logo
2:18 pm - 7:09 pm
ORD
-
SJC
6h 51m
1 stop
$313Multiple Airlines
Mon, Sep 14 - Fri, Oct 2
Multiple Airlines Logo
1:38 pm - 5:38 am
SJC
-
ORD
14h 00m
1 stop
Multiple Airlines Logo
2:18 pm - 7:09 pm
ORD
-
SJC
6h 51m
1 stop
$313Multiple Airlines
Fri, Aug 21 - Mon, Aug 24
Alaska Airlines Logo
7:29 am - 7:21 pm
SJC
-
ORD
9h 52m
1 stop
Alaska Airlines Logo
8:17 pm - 9:23 am
ORD
-
SJC
15h 06m
1 stop
$315Alaska Airlines
Sun, Sep 6 - Sat, Sep 12
Delta Logo
7:00 am - 3:51 pm
SJC
-
ORD
6h 51m
1 stop
Delta Logo
8:25 am - 7:51 pm
ORD
-
SJC
13h 26m
2 stops
$315Delta
Sun, Sep 6 - Fri, Sep 11
Delta Logo
2:20 pm - 11:48 pm
SJC
-
ORD
7h 28m
1 stop
Delta Logo
6:25 pm - 10:45 am
ORD
-
SJC
18h 20m
2 stops
$315Delta
Mon, Oct 19 - Thu, Oct 22
Frontier Logo
2:24 pm - 5:42 am
SJC
-
ORD
13h 18m
1 stop
Frontier Logo
6:50 am - 1:29 pm
ORD
-
SJC
8h 39m
1 stop
$316Frontier
Fri, Aug 28 - Tue, Sep 1
Frontier Logo
8:14 pm - 6:17 am
SJC
-
ORD
8h 03m
1 stop
Frontier Logo
9:20 pm - 12:07 pm
ORD
-
SJC
40h 47m
2 stops
$317Frontier
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 August.

Flight prices are below average for this route right now.

Flights to Chicago O'Hare Intl Airport from San Jose, California usually cost between $330 and $535 in August.
The lowest price found in the past 5 days was $313 on United Airlines (Aug 29-Sep 5).

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 Thursdays 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 $377 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $577 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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 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 season

February

Cheapest flight

$161
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 27% 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 $161 for a one-way ticket and $313 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: American Airlines, JetBlue, Alaska Airlines, Hawaiian Airlines, Air Canada, United Airlines, and Brussels 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 Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Southwest and Alaska Airlines. With an average price for the route of $493 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $343 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 $253 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 4229 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

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.

2.0 MediocreGlenn, Apr 2026
SJC - PHX
Read more Southwest reviews

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.

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

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.

Forget beverage, they didn't even have water for half the passangers?

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Flight was not full! Had a whole row to myself.

Wifi didn’t work, no service, seats are hard as rocks

I always know what to expect from Southwest - friendly crew, on time departures. I like getting free baggage. The app works great and the in-flight entertainment passes the time.

Only issue is that when you board last they make you check your carry on due to lack of space. Did not care for that.

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

My flight was several times rescheduled and then finally canceled.

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.

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.

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.

Broke the wheels of my luggage. Should be more gentle with other peoples belongings. Very upset about needing a new suitcase before Christmas.

There was no coffee on the flight. I was very surprised. I know it is a small thing, but they seemed to have run out of other drinks.

If Alaska Air is going to partner with other airlines, then it has to make the transition to the connecting flight better, especially if Alaska Air is the one that is running late. When I realized our 30 minutes of lateness due to weather was going to make getting to my connecting flight home more difficult ,I would have expected more from the crew than blank stares and "sorry". My son and I had 20 minutes to get from Gate E to the end of Gate K in the Chicago airport. My 50+ year-old body had to sprint and yell to get through the throngs and have any chance of arriving to the gate on time. In addition, the seats I had chosen when I purchased the connecting flight were changed so that my son and I placed in the last rows next to the bathrooms and were separated. There needs to be better communication between the airlines if one is going to be late. The thought of not making it home on time (we still had an 1.5 hour drive to get there) was stressful and unnecessary.

It was as good as it could be. Flying is not a pleasant experience these days.

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

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

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

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

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.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Wifi did not work. Cut off on and off every 10 min

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

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

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