SJC - CHI

$160 Find Cheap Flights from San Jose to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Jose to Chicago departing on 9/16. 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

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Everything you should know

Cheapest round-trip
$313
Typical prices: $346-$577
Alaska Airlines
Sat 10/3Wed 10/7
SJC - ORD • 1 stop
Cheapest non-stop
$315
Southwest
Fri 11/13Thu 11/19
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
Nonstop flights
You can fly direct with Southwest and United Airlines. Average duration is 4h 14m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 6% average savings
Most popular
Insights
Insights
Insights
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 45% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
Good to know
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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

Sat, Oct 3 - Wed, Oct 7
Alaska Airlines Logo
9:15 am - 6:53 pm
SJC
-
ORD
7h 38m
1 stop
Alaska Airlines Logo
7:00 am - 2:18 pm
ORD
-
SJC
9h 18m
1 stop
$313Alaska Airlines
Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
6:20 am - 12:45 pm
SJC
-
ORD
4h 25mnonstop
United Airlines Logo
6:00 am - 1:08 pm
ORD
-
SJC
9h 08m
1 stop
$313United Airlines
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
3:05 pm - 8:25 pm
MDW
-
SJC
7h 20m
1 stop
$313Southwest
Sat, Sep 5 - Sat, Sep 19
United Airlines Logo
2:10 pm - 8:35 pm
SJC
-
ORD
4h 25mnonstop
United Airlines Logo
3:56 pm - 8:54 pm
ORD
-
SJC
6h 58m
1 stop
$313United Airlines
Mon, Sep 28 - Thu, Oct 1
Multiple Airlines Logo
1:38 pm - 5:38 am
SJC
-
ORD
14h 00m
1 stop
Multiple Airlines Logo
2:18 pm - 7:09 pm
ORD
-
SJC
6h 51m
1 stop
$313Multiple Airlines
Thu, Sep 17 - Fri, Oct 2
Multiple Airlines Logo
1:38 pm - 5:38 am
SJC
-
ORD
14h 00m
1 stop
Multiple Airlines Logo
7:20 am - 1:45 pm
ORD
-
SJC
8h 25m
1 stop
$313Multiple Airlines
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
11:00 pm - 5:00 am
SJC
-
MDW
4h 00mnonstop
Southwest Logo
2:05 pm - 8:25 pm
MDW
-
SJC
8h 20m
2 stops
$314Southwest
Thu, Oct 15 - Tue, Oct 20
Frontier Logo
2:24 pm - 11:57 am
SJC
-
ORD
19h 33m
1 stop
Frontier Logo
6:50 am - 8:08 pm
ORD
-
SJC
15h 18m
2 stops
$314Frontier
Fri, Aug 21 - Mon, Aug 24
Alaska Airlines Logo
7:29 am - 7:21 pm
SJC
-
ORD
9h 52m
1 stop
Alaska Airlines Logo
8:17 pm - 9:23 am
ORD
-
SJC
15h 06m
1 stop
$315Alaska Airlines
Mon, Oct 19 - Thu, Oct 22
Frontier Logo
2:24 pm - 5:42 am
SJC
-
ORD
13h 18m
1 stop
Frontier Logo
6:50 am - 1:29 pm
ORD
-
SJC
8h 39m
1 stop
$316Frontier
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 September.

Flight prices are below average for this route right now.

Flights to Chicago from San Jose, California usually cost between $346 and $518 in September.
The lowest price found in the past 5 days was $313 on Southwest (Sep 5-Sep 9).

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 $277 on the route between San Jose (SJC) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 6% cheaper than other San Jose-Chicago routes. It 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 April, where tickets cost $405 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $577 and $527 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 1 stop layover the cheapest option at $395 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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Expert advice

Expert advice for your flight from San Jose to 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 season

January

Cheapest flight

$160
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from San Jose to Chicago Midway 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 $160 for a one-way ticket and $313 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, American Airlines, JetBlue, 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 $506 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 $346 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 $238 or less one-way and $393 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

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

Information on your arrival and departure airports