$125 Cheap Flights from San Jose (SJC) to Chicago (ORD)

View $125 flight on Sat, Jul 18, 2026Opens in a new window

Popular airlines from Norman Y. Mineta San Jose Intl. Airport (SJC) to Chicago O'Hare Intl. Airport (ORD)

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

Prices were available within the past 7 days and start at $125 for one-way flights and $234 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jul 18 - Wed, Jul 22
SJC
San Jose
ORD
Chicago
$234 Roundtrip, found 9 hours ago
$234
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Jul 18 from San Jose to Chicago, returning Wed, Jul 22, priced at $234 found 9 hours ago
Frontier Airlines
Thu, Jun 25 - Mon, Jun 29
SJC
San Jose
ORD
Chicago
$250 Roundtrip, just found
$250
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jun 25 from San Jose to Chicago, returning Mon, Jun 29, priced at $250 just found
Frontier Airlines
Sat, Jul 25 - Sat, Aug 1
SJC
San Jose
ORD
Chicago
$254 Roundtrip, found 1 hour ago
$254
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jul 25 from San Jose to Chicago, returning Sat, Aug 1, priced at $254 found 1 hour ago
Alaska Airlines
Tue, Jun 2 - Wed, Jun 10
SJC
San Jose
ORD
Chicago
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Jun 2 from San Jose to Chicago, returning Wed, Jun 10, priced at $257 found 3 days ago
United
Tue, Sep 22 - Wed, Sep 30
SJC
San Jose
ORD
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 22 from San Jose to Chicago, returning Wed, Sep 30, priced at $257 found 1 day ago
Frontier Airlines
Sat, Jul 18 - Mon, Jul 20
SJC
San Jose
ORD
Chicago
$258 Roundtrip, found 4 days ago
$258
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jul 18 from San Jose to Chicago, returning Mon, Jul 20, priced at $258 found 4 days ago
Frontier Airlines
Fri, Jul 17 - Wed, Jul 22
SJC
San Jose
ORD
Chicago
$260 Roundtrip, found 9 hours ago
$260
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Fri, Jul 17 from San Jose to Chicago, returning Wed, Jul 22, priced at $260 found 9 hours ago
Frontier Airlines
Thu, Aug 6 - Thu, Aug 13
SJC
San Jose
ORD
Chicago
$264 Roundtrip, just found
$264
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Aug 6 from San Jose to Chicago, returning Thu, Aug 13, priced at $264 just found
American Airlines
Wed, Aug 5 - Wed, Aug 12
SJC
San Jose
ORD
Chicago
$277 Roundtrip, just found
$277
Roundtrip
just found
Select American Airlines flight, departing Wed, Aug 5 from San Jose to Chicago, returning Wed, Aug 12, priced at $277 just found
Delta
Wed, May 27 - Wed, Jun 10
SJC
San Jose
ORD
Chicago
$277 Roundtrip, found 6 days ago
$277
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, May 27 from San Jose to Chicago, returning Wed, Jun 10, priced at $277 found 6 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $507
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $507

Frequently asked questions

How much does a flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $125 and cheap return flights from $234 San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights usually range from $189 to $963, and return flights typically cost between $387 and $1353. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is the cheapest month to fly from San Jose (SJC) to Chicago (ORD), with average return fares around $379. This is about 18% lower than the average price throughout the year, as travel demand tends to decrease after the summer. Other affordable months to consider are May and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are 2 airlines offering direct flights from SJC to ORD:

  • United operates around 11 direct flights from SJC to ORD every week
  • American Airlines operates around 14 direct flights from SJC to ORD every week

What is the cheapest airline that flies from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
American Airlines is one of the cheapest airlines offering nonstop flights from San Jose, CA (SJC) to Chicago, IL (ORD), with round-trip tickets starting from around $508. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. Alaska Airlines offers the most daily flights from San Jose to Chicago, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly from San Jose to Chicago is in September or August. September typically has return flights priced around $379, making it a budget-friendly option, while August is also popular. These months offer a good mix of price and flight options for your travel plans.*Prices based on flights available on Expedia in the last year.
How many flights per day from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 1 nonstop flights per day from Norman Y. Mineta San Jose Intl. (SJC) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from San Jose, CA (SJC) to Chicago, IL (ORD) usually leaves at around 5:45 AM, operated by Delta. This flight is part of a seasonal service active during the summer months, allowing you to arrive in Chicago early and maximize your day. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
For flights from Norman Y. Mineta San Jose Intl. (SJC) to O'Hare Intl. (ORD), the most popular departure times are from 6am to 9am. About 44% of travelers choose this time window. Major carriers like United Airlines and American Airlines operate flights during this period. This timing is popular because it allows you to arrive in Chicago by mid-morning, ready to start your day.
How long does it take to fly from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from SJC to ORD takes around 4 hours 20 minutes, with the route covering approximately 1,825 miles. Flights with a layover typically take 4 hours longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly first class between SJC and ORD. First class cabins are available on:

  • American Airlines
  • Delta Air Lines
  • United Airlines

How do I earn miles on a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Norman Y. Mineta San Jose Intl. (SJC)?
From Norman Y. Mineta San Jose Intl. (SJC), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like San Diego Intl. (SAN), John Wayne (SNA), Los Angeles Intl. (LAX) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Southwest Airlines, United
Roundtrip price
$234
Distance
1824 mi
Average flight time
7 hours 11 mins

Book with confidence

San Jose to Chicago Flights

The cheapest times to fly from San Jose to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Jose to Chicago are during the month of July. You can find some of the cheapest flights from San Jose to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Jose to Chicago

Sunday is one of the best days to book for cheap flights from San Jose to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Jose to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Jose to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $125 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Jose to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Jose to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

San Jose to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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