CHI - SJC

$99 Find Cheap Flights from Chicago to San Jose

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Jose departing on 5/29. 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 San Jose

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

Cheapest round-trip
$276
Typical prices: $540-$351
Frontier
Fri 6/12Fri 6/19
ORD - SJC • 1 stop
Cheapest non-stop
$322
Southwest
Wed 7/1Wed 7/8
MDW - SJC • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus adds 6 inches of legroom.
Midway's compact terminal is easy to navigate.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $276 (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 Southwest and United Airlines. Average duration is 4h 42m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 4% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $293 (round-trip)
Shortest trip • 6h 31m (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 62% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 48% price drop
Most popular
Good to know
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+1
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Flight Deals
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Flight Deals

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

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

Fri, Jun 12 - Fri, Jun 19
Frontier Logo
9:13 pm - 7:37 pm
ORD
-
SJC
24h 24m
1 stop
Frontier Logo
8:25 pm - 6:19 am
SJC
-
ORD
7h 54m
1 stop
$276Frontier
Sat, May 23 - Tue, Jun 9
Alaska Airlines Logo
9:00 am - 2:13 pm
ORD
-
SJC
7h 13m
1 stop
Alaska Airlines Logo
7:06 am - 6:50 pm
SJC
-
ORD
9h 44m
1 stop
$280Alaska Airlines
Thu, Jun 18 - Sun, Jun 21
Frontier Logo
9:13 pm - 7:37 pm
ORD
-
SJC
24h 24m
1 stop
Frontier Logo
2:12 pm - 5:32 am
SJC
-
ORD
13h 20m
1 stop
$281Frontier
Sat, May 23 - Fri, May 29
Frontier Logo
8:46 pm - 11:59 am
ORD
-
SJC
17h 13m
1 stop
Frontier Logo
12:57 pm - 6:34 am
SJC
-
ORD
15h 37m
1 stop
$282Frontier
Wed, May 27 - Wed, Jun 3
United Airlines Logo
7:50 pm - 10:35 pm
ORD
-
SJC
4h 45mnonstop
United Airlines Logo
1:10 pm - 12:45 am
SJC
-
ORD
9h 35m
1 stop
$283United Airlines
Wed, May 27 - Wed, Jun 3
United Airlines Logo
7:50 pm - 10:35 pm
ORD
-
SJC
4h 45mnonstop
United Airlines Logo
1:10 pm - 12:45 am
SJC
-
ORD
9h 35m
1 stop
$288United Airlines
Wed, May 27 - Wed, Jun 3
Southwest Logo
5:15 pm - 10:00 pm
MDW
-
SJC
6h 45m
1 stop
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
$292Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
5:30 pm - 11:00 pm
MDW
-
SJC
7h 30m
2 stops
Southwest Logo
11:40 am - 8:40 pm
SJC
-
MDW
7h 00m
1 stop
$307Southwest
Wed, May 20 - Tue, Jun 9
Delta Logo
6:23 am - 5:02 pm
MDW
-
SJC
12h 39m
2 stops
Delta Logo
6:35 am - 4:16 pm
SJC
-
MDW
7h 41m
1 stop
$313Delta
Wed, May 20 - Wed, Jun 10
Delta Logo
6:23 am - 5:02 pm
MDW
-
SJC
12h 39m
2 stops
Delta Logo
8:19 pm - 8:37 am
SJC
-
MDW
10h 18m
2 stops
$318Delta
Booking Insights

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

Get data-powered insights and trends into flights from Chicago to San Jose to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to San Jose, California?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to San Jose, California departing in June.

What is the cheapest Chicago to San Jose flight route?

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

The cheapest return flight from Chicago to San Jose costs $275 on the route between Chicago Midway Airport (MDW) and San Jose (SJC). Over the past month, this route was, on average, 4% cheaper than other Chicago-San Jose routes. It is also the most popular route.

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San Jose, 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 Chicago to San Jose is October, where tickets cost $80 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $297 and $207 respectively.

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

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 1 stop layover the cheapest option at $416 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San Jose, 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 Chicago to San Jose, you should book around 4 weeks before departure, which saves you about 62% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to San Jose

 
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 seasonJanuary
Cheapest flight$106
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago O'Hare Airport to San Jose

When to book flights from Chicago to San Jose

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

  • Are SJC and SJO the same airport?

    No. SJC is located in San Jose, California, in Silicon Valley. SJO is also a San Jose airport, but in Central America. SJO is the code for the Juan Santamaría International Airport located in San Jose, the capitol city of Costa Rica. These two airports are very easy to confuse when you are booking your ticket, so be extra careful.

  • Do both Chicago airports (CHI) airports have a direct flight to San Jose?

    Yes. United Airlines, American Airlines, and Alaska Airlines are among the carriers that fly nonstop from ORD to SJC. Southwest flies nonstop from MDW to SJC. United, American, Delta, Alaska, and Spirit Airlines all operate one-stop and two-stop flights from ORD to SJC with layovers and cities such as Minneapolis (MSP), Los Angeles (LAX) and Phoenix (PHX). Delta and primarily Southwest fly one and two-stop flights to from MDW to SJC with layovers and cities such as Minneapolis (MSP), Denver (DEN), and Las Vegas (LAS).

  • Do both Chicago airports (CHI) have a USO?

    Yes. ORD has two USO lounges, and MDW has one. The lounges at ORD are located landside in Terminal 2 an airside in Terminal 3. The USO at Midway is post-security on Concourse C. Active-duty members of the US military and their families can enjoy the benefits of these lounges free of charge. Amenities include devices for connectivity and entertainment, comfy and relaxing furniture, refreshments, information, and more.

  • Does either ORD or MDW have a hotel at the airport?

    Yes, the Hilton Chicago O'Hare Airport hotel is across from Terminal 2 and connected to all the different terminals by way of an underground walkway. Amenities include an indoor pool, room service, a business center, wheelchair accessibility, and much more.

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

    In the last 3 days, the lowest price for a flight from Chicago to San Jose was $99 for a one-way ticket and $276 for a round-trip.

  • Do I need a passport to fly between Chicago and San Jose?

    No, a passport isn't needed to fly from Chicago to San Jose. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to San Jose?

    On your way to San Jose, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at San Jose.

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

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

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

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

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

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

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

    There are nonstop flights from Chicago to San Jose on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to San Jose are Southwest and Alaska Airlines. With an average price for the route of $476 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 $383 and an overall rating of 7.9.

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

    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 Chicago to San Jose.

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

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

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

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

    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 San Jose from Chicago 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 Chicago to San Jose

  • Looking for a cheap flight? 25% of our users found flights on this route for $218 or less one-way and $401 or less round-trip.
  • A hub for United Airlines in American Airlines, the Chicago O'Hare International Airport (ORD) is the primary airport for the Chicago metropolitan area. The Midway International Airport (MDW) also serves Chicago and is a hub for Southwest Airlines and a focus city for Frontier Airlines. The Norman Y. Mineta San Jose International Airport (SJC) is a focus city for Alaska Airlines.
  • If you need to reboot or get ready for a business meeting when you land at SJC, you can gain access to one of the exclusive lounges Club SJC, located at Gate 8 and Gate 15. The entry fee is about $50 and AAA members are likely to get a discount. The Gate 15 Club SJC features shower facilities.
  • If you don't want your muscles you tighten up on your flight to California, you can stretch out in the Yoga Room, which is located in both ORD and MDW. You can enjoy a low-key session of stretching by following the poses that play on wall-mounted TVs. Open daily 6 am to 10 pm, these rooms do not have changing rooms.
  • If you are a traveling mom who needs to pump or wants to breastfeed in privacy before your flight to California, you can use the facilities provided by both ORD and MDW. ORD has lactation suites and a Mother's Room in each terminal of the airport. MDW has installed a freestanding lactation suite on Concourse A and has a Mother's Room on the C Concourse.
  • At SJC has an Inter-Faith Meditation Room in Terminal B at Gate 18. ORD has an Inter-Faith Chapel in Terminal 2 and MDW has an Inter-Faith Chapel on Concourse C. These quiet places of sanctuary and reflection welcome all.

Prefer to fly direct from Chicago to San Jose?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to San Jose.
Find which airlines fly direct from Chicago to San Jose Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

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

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Jose. 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 Chicago to San Jose? 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 4314 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

8.0 ExcellentCheryl, Apr 2026
DEN - SBA
Read more Southwest reviews

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

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.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

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

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

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

3 hour delay. Had to change plans and was still delayed.

Thanks for all you do to keep us safe and on time!

Several delays without clear communication on timing. Very late beverage service during the flight.

I wasn’t aware that we needed to supply our own screens for entertainment

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

I was standing in line to use the restroom. A First Class passenger wanted to use the restroom after me, but Jaques made me wait on Flight 3418 from BOI to SJC on December 12, 2025. I felt this was inappropriate and rude.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

My flight got canceled never left san diego and miss out my fam event

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Better than expected. Staff were friendly and nice on both flights.

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

Information on your arrival and departure airports