CHI - SJC

$66 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 6/2. 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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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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Flights Deals

Cheap Flights from Chicago to San Jose

 
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.

Recent round-trip flight deals from Chicago to San Jose

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to San Jose.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
9:02 pm - 10:05 amORD-SJC
15h 03m1 stop
Spirit Airlines Logo
4:33 pm - 5:25 amSJC-ORD
10h 52m1 stop
$112Spirit Airlines
Find Deal
Thu, May 29 - Sun, Jun 1
Spirit Airlines Logo
11:50 am - 11:29 pmORD-SJC
13h 39m1 stop
Spirit Airlines Logo
4:33 pm - 5:25 amSJC-ORD
10h 52m1 stop
$121Spirit Airlines
Find Deal
Wed, May 28 - Sun, Jun 1
Frontier Logo
2:44 pm - 11:18 amMDW-SJC
22h 34m1 stop
Frontier Logo
2:30 pm - 2:56 pmSJC-MDW
22h 26m1 stop
$213Frontier
Find Deal
Sat, Jun 7 - Sun, Jun 8
Frontier Logo
2:44 pm - 11:18 amMDW-SJC
22h 34m1 stop
Frontier Logo
2:30 pm - 2:56 pmSJC-MDW
22h 26m1 stop
$218Frontier
Find Deal
Sat, Jun 7 - Sun, Jun 8
Delta Logo
2:25 pm - 10:06 pmORD-SJC
9h 41m1 stop
Delta Logo
2:20 pm - 12:03 amSJC-ORD
7h 43m1 stop
$296Delta
Find Deal
Wed, Jun 4 - Tue, Jun 10
Delta Logo
1:47 pm - 8:33 pmMDW-SJC
8h 46m1 stop
Delta Logo
10:25 pm - 9:41 amSJC-MDW
9h 16m1 stop
$299Delta
Find Deal
Tue, Jun 10 - Tue, Jun 17
United Airlines Logo
7:59 pm - 10:39 pmORD-SJC
4h 40mnonstop
United Airlines Logo
6:35 am - 12:57 pmSJC-ORD
4h 22mnonstop
$311United Airlines
Find Deal
Tue, May 27 - Tue, Jun 3
United Airlines Logo
7:59 pm - 10:39 pmORD-SJC
4h 40mnonstop
United Airlines Logo
7:00 am - 3:05 pmSJC-ORD
6h 05m1 stop
$317United Airlines
Find Deal
Tue, May 27 - Tue, Jun 3
Southwest Logo
8:35 am - 1:25 pmMDW-SJC
6h 50m1 stop
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$321Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 11
Southwest Logo
7:30 am - 1:45 pmMDW-SJC
8h 15m2 stops
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$326Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 11
Expert advice

Expert advice for your flight from Chicago to San Jose

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


United's Priority Boarding puts you in Zone 2, avoiding carry-on gate-check issues.

Southwest

Southwest offers two free checked bags up to 50 pounds each, ideal for families.


Set an alarm to check in 24 hours beforehand for a better boarding position.

Read more about Southwestby Blane Bachelor
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
Useful Info

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.

What is the cheapest Chicago to San Jose flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to San Jose.

Our data shows that the cheapest route for a return flight from Chicago to San Jose cost $308 and was between Chicago O'Hare Intl Airport (ORD) and San Jose (SJC). On average, the best prices are found if you fly from Chicago Midway Airport (MDW) to San Jose (SJC). The average price for a return flight for this route is $308.

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 Sunday is the most expensive. Flying from San Jose back to Chicago, the best deals are generally found on Wednesday, with Sunday 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 $293 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $453 and $447 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 $200 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonJanuary
High seasonDecember
Cheapest flight$66
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 7% increase in price.
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 $66 for a one-way ticket and $112 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, 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?

    Star Alliance is the only airline alliance operating flights between Chicago and San Jose.

  • 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 Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to San Jose are Southwest and Delta. With an average price for the route of $444 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 $371 and an overall rating of 8.0.

  • 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 $175 or less one-way and $371 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?

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
See more direct flights

Top 5 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 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

It was a perfect flight in all aspects! Both legs!

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

It was a perfect flight in all aspects! Both legs!

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Seats are much much more comfortable than United, which is what I usually fly

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

Only one side of the heafphone jack work. Crew was friendly and helpful.

Great. Flight departed early and arrived early. Deplaning and baggage claim ww were quick.

They separated our seats and moved us to the back of the plane. Hundreds of dollars and thousands of miles used and this was my platinum member experience.

AC barely worked on a 50 minute flight. It was very warm the whole flight. Flight was very bumpy and hard landing.

Got on the plane and then needed to deboard the plane because they didn’t have any pilots?

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

Rough day of travel all the way around. Wrong info given to us multiple times and mistakes in their booking making our trip 10 hours longer than planned. I’m bummed because I fly Delta all the time and love them. Mistakes happen. Just bummed that this was a rare trip our whole family was traveling together.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Unclear pricing; ended up being charged an extra $52 just to get onboard

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

would be great to get basic water, soda at least and stop charging for carry ons

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Your crew is a representation of your Standards and Values. The crew from Seattle to LAX, was very disappointing. The crew was more interested in hanging out at the lobby area. Talking, laughing loudly and eating all the snacks. They did not do regular rounds to see if customers needed anything. This was a huge disappointment. I will no longer be flying with your airlines moving forward.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

- flight attendants not very friendly. - Paid for WiFi and plane didn’t have it working , never got a refund.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Everything went as planned. Crew was great. Seats were still not that comfortable.

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

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

Information on your arrival and departure airports

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