$47 Cheap Flights from San Jose (SJC) to Chicago (ORD)

View $47 flight on Tue, Jun 3, 2025Opens in a new window

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Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $47 for one-way flights and $166 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, May 20 - Thu, May 29
SJC
San Jose
ORD
Chicago
$166 Roundtrip, found 19 hours ago
$166
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, May 20 from San Jose to Chicago, returning Thu, May 29, priced at $166 found 19 hours ago
Spirit Airlines
Wed, May 28 - Tue, Jun 10
SJC
San Jose
ORD
Chicago
$166 Roundtrip, found 2 days ago
$166
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, May 28 from San Jose to Chicago, returning Tue, Jun 10, priced at $166 found 2 days ago
Spirit Airlines
Tue, May 27 - Thu, May 29
SJC
San Jose
ORD
Chicago
$184 Roundtrip, found 10 hours ago
$184
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Tue, May 27 from San Jose to Chicago, returning Thu, May 29, priced at $184 found 10 hours ago
Frontier Airlines
Thu, May 29 - Tue, Jun 3
SJC
San Jose
ORD
Chicago
$184 Roundtrip, found 11 hours ago
$184
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, May 29 from San Jose to Chicago, returning Tue, Jun 3, priced at $184 found 11 hours ago
Spirit Airlines
Wed, May 21 - Wed, May 28
SJC
San Jose
ORD
Chicago
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, May 21 from San Jose to Chicago, returning Wed, May 28, priced at $188 found 1 day ago
Spirit Airlines
Tue, May 20 - Thu, May 29
SJC
San Jose
ORD
Chicago
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, May 20 from San Jose to Chicago, returning Thu, May 29, priced at $197 found 19 hours ago
Spirit Airlines
Tue, May 20 - Sun, May 25
SJC
San Jose
ORD
Chicago
$198 Roundtrip, found 23 hours ago
$198
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Tue, May 20 from San Jose to Chicago, returning Sun, May 25, priced at $198 found 23 hours ago
Alaska Airlines
Wed, May 28 - Thu, May 29
SJC
San Jose
ORD
Chicago
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, May 28 from San Jose to Chicago, returning Thu, May 29, priced at $265 found 1 day ago
United
Sun, May 25 - Tue, May 27
SJC
San Jose
ORD
Chicago
$311 Roundtrip, found 2 hours ago
$311
Roundtrip
found 2 hours ago
Select United flight, departing Sun, May 25 from San Jose to Chicago, returning Tue, May 27, priced at $311 found 2 hours ago
Hawaiian Airlines
Tue, Jun 10 - Tue, Jun 24
SJC
San Jose
ORD
Chicago
$312 Roundtrip, found 2 hours ago
$312
Roundtrip
found 2 hours ago
Select Hawaiian Airlines flight, departing Tue, Jun 10 from San Jose to Chicago, returning Tue, Jun 24, priced at $312 found 2 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
Roundtrip price
$165
Distance
1824 mi

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 May. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $47 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.

Frequently asked questions

How much does a flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD) cost?
Score cheap return fares from Norman Y. Mineta San Jose Intl. Airport (SJC) to O’Hare Intl. Airport (ORD) starting from $311. Book a seat and get ready for takeoff. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving SJC on May 21 2025 and touching down at ORD. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from SJC to ORD?
The cheapest flights from SJC to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
If you’re departing from Norman Y. Mineta San Jose Intl. Airport (SJC), you can hop on a direct flight to O’Hare Intl. Airport (ORD) with United Airlines.
What is the cheapest airline that flies from SJC to ORD?
Take off from SJC to ORD with United. This airline currently offers the cheapest one-way ticket for this route, starting at $156. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SJC on July 2 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
On average, there’s only 1 direct flight leaving from Norman Y. Mineta San Jose Intl. Airport (SJC) to O’Hare Intl. Airport (ORD) every day. If this doesn’t work with your itinerary, think about flights with layovers. Just filter your search on Expedia to include one stop or more to discover a better alternative.
What are the most popular departure times for flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
Flights between SJC and ORD are busiest at 6 AM. If you’d like a quieter experience and potentially cheaper prices, look for a departure that’s outside typical rush times.
What day of the week has the most flights from SJC to ORD?
Friday offers the most flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to O’Hare Intl. Airport (ORD). Consider jetting off on this day and you’ll have the best chance of finding a schedule that works for you.
What is the earliest flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
Norman Y. Mineta San Jose Intl. Airport (SJC)’s first flight to O’Hare Intl. Airport (ORD) departs at approximately 6:30AM UTC-8. With a total flight time of 4h 20m, you’ll touch down at around 12:50PM UTC-6.
How long does it take to fly from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
The average flight time from SJC to ORD is 4 hours and 20 minutes, covering a total distance of 1,850 mi.
What airline has the least delays from SJC to ORD?
With 87% of journeys generally landing on schedule, United Airlines has the best on-time performance for nonstop flights from Norman Y. Mineta San Jose Intl. Airport (SJC) to O’Hare Intl. Airport (ORD). To keep track of your flight status and get notifications about any changes, use the Expedia App.
What is the best time to fly from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
Opt for a flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O’Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the likelihood of delays. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Norman Y. Mineta San Jose Intl. Airport (SJC)?
You can touch down at O’Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when you travel to Chicago on a direct flight from Norman Y. Mineta San Jose Intl. Airport (SJC).
Is it cheaper to buy a plane ticket from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from SJC to ORD right before your trip is typically more expensive. But if you’re flexible with your travel times and dates, you could score a cheap last-minute fare.
Is it cheaper to book a SJC to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a SJC to ORD flight and hotel package with Expedia could lead to significant savings. What’s more, having everything in one place takes the hassle out of travel planning. Just secure your flights and choose from our extensive range of stays, then customize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD)?
If you reserved your SJC to ORD 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 fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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*Available to One Key members.