CHI - SJC

$119 Find Cheap Flights from Chicago to San Jose - 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 Chicago to San Jose departing on 8/22. 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
$242
Typical prices: $333-$395
Southwest
Wed 9/9Fri 9/11
MDW - SJC • Non-stop
Cheapest one-way
$119
Typical prices: $159-$320
United Airlines
Sat 8/22
ORD - SJC • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest Cash + Points adds booking flexibility; Rapid Rewards has no blackout dates.
United Economy Plus adds up to 6 inches more legroom; Priority Boarding helps bin space.
Expert advice
Expert advice
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Nonstop flights
You can fly direct with Southwest and United Airlines. Average duration is 4h 32m
Direct flights
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Top routes
Cheapest • 8% average savings
Most popular
Insights
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Top layover airports
Cheapest • Avg $266 (round-trip)
Shortest trip • 6h 32m (one-way)
Insights
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Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 65% compared to booking last minute.
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When to travel
Cheapest • 15% price drop
Most popular
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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

Wed, Sep 9 - Fri, Sep 11
Southwest Logo
8:30 pm - 11:05 pm
MDW
-
SJC
4h 35mnonstop
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
$242Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
2:05 pm - 6:20 pm
MDW
-
SJC
6h 15m
1 stop
Southwest Logo
7:10 am - 1:15 pm
SJC
-
MDW
4h 05mnonstop
$243Southwest
Sat, Sep 12 - Wed, Sep 16
United Airlines Logo
8:59 am - 11:45 am
ORD
-
SJC
4h 46mnonstop
United Airlines Logo
12:51 pm - 10:46 pm
SJC
-
ORD
7h 55m
1 stop
$247United Airlines
Thu, Sep 10 - Sat, Oct 24
United Airlines Logo
5:55 am - 1:04 pm
ORD
-
SJC
9h 09m
1 stop
United Airlines Logo
2:08 pm - 8:35 pm
SJC
-
ORD
4h 27mnonstop
$247United Airlines
Thu, Aug 20 - Wed, Aug 26
Alaska Airlines Logo
6:01 am - 10:59 am
ORD
-
SJC
6h 58m
1 stop
Alaska Airlines Logo
8:29 am - 7:21 pm
SJC
-
ORD
8h 52m
1 stop
$247Alaska Airlines
Thu, Aug 20 - Wed, Aug 26
Alaska Airlines Logo
2:18 pm - 7:09 pm
ORD
-
SJC
6h 51m
1 stop
Alaska Airlines Logo
8:29 am - 7:21 pm
SJC
-
ORD
8h 52m
1 stop
$249Alaska Airlines
Mon, Aug 17 - Mon, Aug 24
Multiple Airlines Logo
6:20 am - 11:24 am
ORD
-
SJC
7h 04m
1 stop
Multiple Airlines Logo
8:14 pm - 6:17 am
SJC
-
ORD
8h 03m
1 stop
$249Multiple Airlines
Thu, Aug 20 - Mon, Aug 31
Frontier Logo
9:20 pm - 7:19 pm
ORD
-
SJC
23h 59m
1 stop
Frontier Logo
8:14 pm - 6:17 am
SJC
-
ORD
8h 03m
1 stop
$250Frontier
Sat, Sep 12 - Sat, Sep 19
American Airlines Logo
5:00 am - 10:53 am
ORD
-
SJC
7h 53m
1 stop
American Airlines Logo
12:02 pm - 9:09 pm
SJC
-
ORD
7h 07m
1 stop
$256American Airlines
Mon, Aug 24 - Mon, Aug 31
American Airlines Logo
5:00 am - 11:57 am
ORD
-
SJC
8h 57m
1 stop
American Airlines Logo
12:42 pm - 11:30 pm
SJC
-
ORD
8h 48m
1 stop
$257American Airlines
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 September.

Flight prices are below average for this route right now.

Flights to San Jose, California from Chicago usually cost between $382 and $539 in September.
The lowest price found in the past 5 days was $243 on Southwest (Sep 10-Sep 17).

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 $237 on the route between Chicago O'Hare Intl Airport (ORD) and San Jose (SJC). Over the past month, this route was, on average, 8% cheaper than other Chicago-San Jose routes. The most popular route is between Chicago Midway Airport (MDW) and San Jose (SJC).

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, Thursday 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 Monday 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 $392 (return) on average. On the other hand, the most expensive months are February and November, where the average cost of round-trip tickets is $582 and $562 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.

No, with an average price for the route of $422, prices are generally cheapest when you fly direct.

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 65% 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 season

January

Cheapest flight

$119
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago Midway 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 5 days, the lowest price for a flight from Chicago to San Jose was $119 for a one-way ticket and $242 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, 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 $478 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 $392 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 $188 or less one-way and $375 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

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

Information on your arrival and departure airports