$157 Cheap United flights San Jose (SJC) to Chicago (ORD)

View $157 flight on Thu, Sep 11, 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

$157 Cheap United flights San Jose (SJC) to Chicago (ORD)

Prices were available within the past 7 days and start at $157 for one-way flights and $313 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, Oct 2 - Sat, Oct 11
SJC
San Jose
ORD
Chicago
$313 Roundtrip, found 6 hours ago
$313
Roundtrip
found 6 hours ago
Select United flight, departing Thu, Oct 2 from San Jose to Chicago, returning Sat, Oct 11, priced at $313 found 6 hours ago
Flights from San Jose (SJC) to Chicago (ORD)
Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Hawaiian Airlines, Southwest Airlines, Spirit Airlines, United
Popular airline
Alaska Airlines
Distance
1824 mi
Average flight time
7 hours 13 mins

Frequently asked questions

How much is a United Airlines flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
Apply the "Price (lowest to highest)" filter on Expedia to look for cheap United Airlines round-trip flights from $313 from SJC to ORD. Affordable one-way options from $157 are also on offer.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from SJC to ORD with United Airlines?
United Airlines flights to Chicago are often more affordable in the low-season months of January and February. Whether you're after a return or one-way ticket, you could land a better deal then.
What is the cheapest time to book flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD) with United Airlines?
Look for affordable United Airlines flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD) one to three months prior to your day of departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and itinerary, the best day of the week to book a domestic flight is usually Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does United Airlines fly nonstop from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
United Airlines operates direct flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD), with 7 departures every week. Just choose the "Nonstop" and "Airline" filters while searching on Expedia to see all direct United Airlines flights to ORD.
How long does it take to fly from SJC to ORD with United Airlines?
Depart Norman Y. Mineta San Jose Intl. Airport (SJC) for O'Hare Intl. Airport (ORD) on a direct United Airlines flight, and you'll be in the sky for about 4h 20m.
What is the earliest United Airlines flight from SJC to ORD?
The first flight from SJC to ORD with United Airlines departs at 6:30AM UTC-8. You'll touch down at 12:50PM UTC-6. The last United Airlines flight of the day takes off at 6:30AM UTC-8 and arrives at 12:50PM UTC-6. With approximately 20% fewer cancellations for morning and mid-morning flights, setting off early is generally the smartest option.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does United Airlines fly into in Chicago?
United Airlines flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to Chicago touch down at O'Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). The primary Chicago gateway serviced by this airline is ORD. It's worth exploring flights landing at nearby airports on Expedia as they may have lower prices.
Why fly with United Airlines from SJC to ORD?
With a rewarding loyalty program, United Airlines is a top choice for many travelers departing from SJC to ORD. Plus, as a United Mileage Plus and One Key™ member booking through Expedia, you can earn OneKeyCash™* on eligible flights along with your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
What type of plane does United Airlines fly from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
Jet off on a United Airlines flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD), and you'll usually be on an Airbus A319. Bear in mind though, that the aircraft type can vary depending on operational needs.
Can I change or cancel my United Airlines flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
Changes are typically free within 24 hours of making a booking, but your airline may charge you after that time. For further information about modifying your flights, head to your "Trips," select your flight and click on "Manage Booking." If you want the freedom to change your plans without additional costs, apply the "Changes included" or "No cancel fee" filter when organizing your next break.

Explore a world of travel with Expedia

*Available to One Key members.