SJC - CHI

$144 Find Cheap Flights from San Jose to Chicago

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 Chicago departing on 7/20. 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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$329
Typical prices: $583-$384
Frontier
Mon 7/6Wed 7/15
SJC - ORD • 1 stop
Cheapest non-stop
$361
Typical prices: $537-$455
Southwest
Tue 7/14Tue 7/21
SJC - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest adds value with free carry-on; checked bags now cost extra.
United Economy Plus adds up to 6 inches of legroom over standard economy.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $329 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest and United Airlines. Average duration is 4h 08m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 5h 47m (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 39% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 45% price drop
Most popular
Good to know
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Flight Deals
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Flight Deals

Cheap Flights from San Jose to Chicago (SJC-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Chicago 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 Chicago

Mon, Jul 6 - Wed, Jul 15
Frontier Logo
8:23 pm - 6:17 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
9:13 pm - 7:28 pm
ORD
-
SJC
24h 15m
1 stop
$329Frontier
Wed, Nov 4 - Thu, Nov 12
Southwest Logo
11:10 am - 5:15 pm
SJC
-
MDW
4h 05mnonstop
Southwest Logo
9:15 pm - 11:55 pm
MDW
-
SJC
4h 40mnonstop
$330Southwest
Tue, Jul 21 - Sat, Jul 25
Multiple Airlines Logo
7:13 am - 6:57 pm
SJC
-
ORD
9h 44m
1 stop
Multiple Airlines Logo
7:15 am - 1:17 pm
ORD
-
SJC
8h 02m
1 stop
$330Multiple Airlines
Thu, Aug 6 - Wed, Aug 12
Frontier Logo
8:23 pm - 6:17 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
9:13 pm - 7:28 pm
ORD
-
SJC
24h 15m
1 stop
$332Frontier
Fri, Jul 10 - Mon, Jul 13
Multiple Airlines Logo
8:23 pm - 6:17 am
SJC
-
ORD
7h 54m
1 stop
Multiple Airlines Logo
7:59 pm - 9:26 am
ORD
-
SJC
15h 27m
1 stop
$333Multiple Airlines
Wed, Jul 8 - Fri, Jul 24
Alaska Airlines Logo
9:09 am - 6:57 pm
SJC
-
ORD
7h 48m
1 stop
Alaska Airlines Logo
6:20 am - 11:24 am
ORD
-
SJC
7h 04m
1 stop
$334Alaska Airlines
Wed, Nov 4 - Thu, Nov 12
Southwest Logo
6:00 am - 12:10 pm
SJC
-
MDW
4h 10mnonstop
Southwest Logo
7:30 am - 1:55 pm
MDW
-
SJC
8h 25m
1 stop
$335Southwest
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
Tue, Sep 1 - Sat, Sep 5
Alaska Airlines Logo
8:29 am - 7:21 pm
SJC
-
ORD
8h 52m
1 stop
Alaska Airlines Logo
6:00 am - 12:48 pm
ORD
-
SJC
8h 48m
1 stop
$340Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
Delta Logo
12:46 pm - 10:45 pm
SJC
-
MDW
7h 59m
1 stop
Delta Logo
1:00 pm - 9:49 pm
MDW
-
SJC
10h 49m
1 stop
$381Delta
Booking Insights

KAYAK's insights & trends for San Jose to Chicago flights

Get data-powered insights and trends into flights from San Jose to Chicago 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?

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 departing in July.

What is the cheapest San Jose to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from San Jose to Chicago costs $323 on the route between San Jose (SJC) and Chicago O'Hare Intl Airport (ORD). This is also the most popular route.

What’s the cheapest day of the week to fly from San Jose to Chicago?

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

For San Jose to Chicago, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to San Jose, the best deals are generally found on Thursday, with Sunday being the most expensive.

What is the cheapest month to fly from San Jose to Chicago?

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, 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 is March, where tickets cost $95 (return) on average. On the other hand, the most expensive months are April and December, where the average cost of round-trip tickets is $265 and $258 respectively.

Can I save money by flying with a layover from San Jose to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $460 on average.

How far in advance should I book a flight from San Jose to Chicago?

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, 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, you should book around 4 weeks before departure, which saves you about 39% 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 Chicago

 
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
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

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 15% drop in price.
Flight from San Jose to Chicago O'Hare Airport

When to book flights from San Jose to Chicago

Are your dates flexible? Find out the best times to travel from San Jose to Chicago 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 flights from San Jose to Chicago

  • Are there exchange rate centers at O'Hare International airport?

    Yes, there is an exchange rate center. Each terminal at O'Hare International Airport has a foreign currency exchange counter operated by Seaway Bank. Seaway is a service that assists passengers in getting ready for their trips to international locations by facilitating the acquisition of foreign currency before departure and currency exchange upon return. There are automated teller machines (ATMs) positioned throughout the airport, both before and after security checkpoints, as well as in each terminal. These ATMs are offered by both local and national financial organizations.

  • Can I have access to a nursing room at San Jose International Airport?

    Yes, you can access a nursing room. The Nursing Rooms may be found just inside the door of the women's toilet (with the exception of the Gate 8 site), and they are furnished with a comfy chair, sink, changing station, and outlets.

  • At O'Hare International Airport, do they provide car rental services?

    Yes, there is car rental services. You don’t have to worry when traveling to Chicago O’Hare International Airport (ORD) because there are a variety of car rental services. Car rentals provide flexible rentals with no hidden fees. Rental companies include Alamo, Goldcar, Megadrive, Europcar, Centaura. They are located inside the terminal building, usually in arrivals.

  • What services are available for passengers with reduced mobility?

    When departing from San Jose International Airport, it is feasible to request special assistance to go through security and to your gate in advance. The airport has accessible facilities as well as additional assistance for those with concealed disabilities. O'Hare International Airport, the airport of arrival, also provides accessible services like wheelchairs and adapted facilities.

  • What is the cheapest flight from San Jose to Chicago?

    In the last 5 days, the lowest price for a flight from San Jose to Chicago 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?

    No

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

    Alaska Airlines, JetBlue, American Airlines, Delta, and Hawaiian Airlines offer inflight Wi-Fi service on the San Jose to Chicago flight route.

  • Which aircraft models fly most regularly from San Jose to Chicago?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the San Jose to Chicago flight route.

  • Which airline alliances offer flights from San Jose to Chicago?

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

  • On which days can I fly direct from San Jose to Chicago?

    There are nonstop flights from San Jose to Chicago 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 $486 and an overall rating of 7.9, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $356 and an overall rating of 7.9.

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to San Jose with another airline.

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

    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 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

  • Looking for a cheap flight? 25% of our users found flights on this route for $257 or less one-way and $501 or less round-trip.
  • You can use Terminal 2 United Club at San Jose International Airport (SJC) if you want to refresh or even take a shower before starting your flight to Chicago. You may purchase a day ticket for around $50 or be invited by a member to have access to free Wi-Fi and an open bar.
  • There is Public Transit and Scheduled/Charter Buses websites for the most up-to-date schedule information on ground transportation (including Valley Transportation Authority [VTA] bus and light rail services) at San Jose International Airport.
  • Free Wi-Fi is accessible for a short period in all O'Hare International Airport (ORD) and Chicago Midway Airport (MDW) terminals. Terminal 3 of the O’Hare Airport has a Yoga Room for passengers who need to relieve tension after a flight delay.
  • At San Jose International Airport (SJC) there is discounted airport parking which one can book online before you even leave your home and there is ample space.
  • Arrive up to 2h before your domestic flight's departure time and 3h before your international flight's departure time at San Jose International Airport. Prepare in advance, a valid ID and boarding pass are required. Avoid carrying too much in your carry-on and consider checking luggage wherever possible.
  • At San Jose International Airport (SJC), there is a pet relief stations available both outside and within the airport. Constant changes are made to airline legislation regulating animals in cabins.

Prefer to fly direct from San Jose to Chicago?

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

Direct departures

San Jose to Chicago

Monday

Southwest,United Airlines

Southwest,United Airlines

Tuesday

Southwest,United Airlines

Southwest,United Airlines

Wednesday

Southwest,United Airlines

Southwest,United Airlines

Thursday

Southwest,United Airlines

Southwest,United Airlines

Friday

Southwest,United Airlines

Southwest,United Airlines

Saturday

Southwest,United Airlines

Southwest,United Airlines

Sunday

Southwest,United Airlines

Southwest,United Airlines

See more direct flights

Direct returns

Chicago to San Jose

Monday

Southwest,United Airlines

Southwest,United Airlines

Tuesday

Southwest,United Airlines

Southwest,United Airlines

Wednesday

Southwest,United Airlines

Southwest,United Airlines

Thursday

Southwest,United Airlines

Southwest,United Airlines

Friday

Southwest,United Airlines

Southwest,United Airlines

Saturday

Southwest,United Airlines

Southwest,United Airlines

Sunday

Southwest,United Airlines

Southwest,United Airlines

See more direct flights

Reviews of the top 4 airlines serving from San Jose to Chicago

 
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 Chicago? 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 12528 reviews
7.0Entertainment
8.5Crew
8.1Boarding
7.8Comfort
7.1Food
Airline reviews

My flight was several times rescheduled and then finally canceled.

2.0 MediocrePeter, Jun 2026
SAN - ORD
Read more Alaska Airlines reviews

My flight was several times rescheduled and then finally canceled.

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!

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.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

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.

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.

Everything you need to know for your flight from San Jose to Chicago

Information on your arrival and departure airports