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O'Hare Intl

$74+ Cheap flights from San Jose, CA (SJC) to O'Hare Intl (ORD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Mar 25 — Apr 11
Wed 3/25
Wed 4/1
1 adult, Economy
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Find cheap flights from San Jose to O'Hare Intl with Cheapflights

1. Tell us where you want to go

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3. Compare prices and book

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Cheapflights Tip: The best prices from San Jose to Chicago O'Hare Intl are usually found in September or April, booked 76 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from San Jose to O'Hare Intl

Cheapest flights from San Jose to O'Hare Intl
Explore the most affordable flight options available from San Jose to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:44 pm
SJC
-
ORD
1 stop7h 15m
Alaska Airlines
Fri 5/152:10 pm
ORD
-
SJC
1 stop10h 49m
Alaska Airlines
Deal found 2/21$256
This Alaska Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:44 pm
SJC
-
ORD
1 stop8h 59m
Alaska Airlines
Thu 5/212:10 pm
ORD
-
SJC
1 stop10h 49m
Alaska Airlines
Deal found 2/21$257
This CheapOair deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:21 am
SJC
-
ORD
2 stops11h 38m
Alaska Airlines
Mon 4/277:59 pm
ORD
-
SJC
1 stop15h 45m
Alaska Airlines
Deal found 2/21$258
This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:20 pm
SJC
-
ORD
2 stops17h 44m
Multiple Airlines
Wed 5/276:20 am
ORD
-
SJC
1 stop9h 22m
Multiple Airlines
Deal found 2/22$259
This Alaska Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:44 pm
SJC
-
ORD
1 stop7h 15m
Alaska Airlines
Thu 4/303:52 pm
ORD
-
SJC
1 stop9h 03m
Alaska Airlines
Deal found 2/22$260
This Alaska Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:45 pm
SJC
-
ORD
1 stop9h 14m
Alaska Airlines
Tue 3/173:07 pm
ORD
-
SJC
1 stop9h 49m
Alaska Airlines
Deal found 2/23$262
This CheapOair deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:00 am
SJC
-
ORD
1 stop14h 59m
Alaska Airlines
Mon 3/237:59 pm
ORD
-
SJC
1 stop19h 59m
Alaska Airlines
Deal found 2/19$263
This Frontier deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:42 pm
SJC
-
ORD
1 stop8h 26m
Frontier
Mon 3/3012:35 pm
ORD
-
SJC
1 stop7h 32m
Frontier
Deal found 2/21$264
This CheapOair deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:35 pm
SJC
-
ORD
1 stop18h 46m
Alaska Airlines
Mon 4/207:59 pm
ORD
-
SJC
1 stop15h 59m
Alaska Airlines
Deal found 2/23$267
This Alaska Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:45 pm
SJC
-
ORD
1 stop9h 14m
Alaska Airlines
Tue 3/248:20 am
ORD
-
SJC
1 stop7h 38m
Alaska Airlines
Deal found 2/19$270
This Alaska Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:59 pm
SJC
-
ORD
1 stop8h 56m
Alaska Airlines
Tue 6/99:00 am
ORD
-
SJC
1 stop7h 13m
Alaska Airlines
Deal found 2/22$272

Find flight deals from San Jose to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$256
(Alaska Airlines)

One-way from

$74
(Trip.com)

Popular in

November

Cheapest in

September

Average price

$427

Good round-trip deal

$348 or less

Good one-way deal

$229 or less
Provider with most accurate pricing for San Jose-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Jose-Chicago O'Hare Intl flights.
Search Deals
From San Jose to Chicago O'Hare Intl
Search Deals
One-way flight from San Jose to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from San Jose to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from San Jose to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 23, 2026.
Use the filters below to find and compare flights from San Jose to Chicago O'Hare Intl Airport that are best for you.

Fly from

San Jose

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 3/17

2:50 pm-11:59 pm

1 stop7h 09m

Chicago O'Hare Intl

Mon 3/23

7:59 pm-6:45 pm

1 stop24h 46m

$263

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 3/2

8:05 pm-2:58 pm

1 stop16h 53m

Chicago O'Hare Intl

Sat 3/7

7:00 am-1:42 pm

1 stop8h 42m

$301

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 3/2

12:45 pm-11:59 pm

1 stop9h 14m

Chicago O'Hare Intl

Tue 3/10

7:00 am-1:42 pm

1 stop8h 42m

$301

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 3/17

1:35 pm-9:34 pm

1 stop5h 59m

Chicago O'Hare Intl

Tue 3/24

1:19 pm-10:02 pm

2 stops10h 43m

$302

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 4/17

1:30 pm-9:18 pm

1 stop5h 48m

Chicago O'Hare Intl

Wed 4/22

7:35 am-12:23 pm

1 stop6h 48m

$310

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 2/26

12:45 pm-11:59 pm

1 stop9h 14m

Chicago O'Hare Intl

Sat 2/28

7:00 am-1:42 pm

1 stop8h 42m

$352

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 5/7

7:36 am-5:04 pm

1 stop7h 28m

Chicago O'Hare Intl

Sun 5/10

7:45 am-12:52 pm

1 stop7h 07m

$365

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 3/17

10:55 pm-5:14 am

Nonstop4h 19m

Chicago O'Hare Intl

Tue 3/24

7:59 pm-10:59 pm

Nonstop5h 00m

$367

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 3/17

9:40 am-6:05 pm

1 stop6h 25m

Chicago O'Hare Intl

Mon 3/23

1:19 pm-10:02 pm

2 stops10h 43m

$373

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sun 3/15

10:55 pm-10:00 am

1 stop9h 05m

Chicago O'Hare Intl

Tue 3/17

1:19 pm-10:02 pm

2 stops10h 43m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 23 results
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Compare providers for flights from San Jose to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Jose to O'Hare Intl in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Jose, California-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose, California-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Jose, California-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San Jose to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from San Jose with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Jose to Chicago O'Hare Intl Airport

How far ahead should I book a flight from San Jose, California to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from San Jose to O'Hare Intl. Price data was last updated on February 20, 2026.

Booking 45 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Jose, California to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from San Jose, California to Chicago O'Hare Intl Airport?

Currently, April is the cheapest month in which you can book a flight from San Jose, California to Chicago O'Hare Intl Airport (average of $123). Flying from San Jose, California to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $257). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

The best insider tips for San Jose to Chicago O'Hare Intl Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Jose to Chicago O'Hare Intl Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on SJC

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated February 23, 2026.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta from San Jose to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,937 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,937 reviews
Alaska Airlines
8.0
Very good
11,937 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,300 reviews
Alaska Airlines
8.0
Very good
11,937 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,236 reviews
Alaska Airlines
8.0
Very good
11,937 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,342 reviews
Alaska Airlines
8.0
Very good
11,937 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,339 reviews
Alaska Airlines
8.0
Very good
11,937 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Related info for your journey

Find useful and relevant information for your journey from San Jose to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Jose to Chicago O'Hare Intl?

    If you book a flight to Chicago O'Hare Intl from San Jose, you will be flying from San Jose, which is the city’s only airport. San Jose (SJC) is located 2.9 mi from the center of San Jose. There are 0 flights from San Jose to Chicago O'Hare Intl per day from 7 different airlines.

  • How long is the flight from San Jose, California to Chicago O'Hare Intl Airport?

    Departing from San Jose, California to Chicago O'Hare Intl Airport will take you 5h 59m. There are 1824 mi between San Jose, California and Chicago O'Hare Intl Airport. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from San Jose, California to Chicago O'Hare Intl Airport round-trip?

    Cheapflights users have booked flights from San Jose, California to Chicago O'Hare Intl Airport round-trip from $62. Other airlines that can offer you cheap pricing are Spirit Airlines, from $125, and Alaska Airlines, from $170. Users have found that Frontier is 86% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from San Jose, California to Chicago O'Hare Intl Airport one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $60. Users have also found prices from $86 and $98 on Frontier and Alaska Airlines, respectively.

  • What are the most reliable airlines from San Jose, California to Chicago O'Hare Intl Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from San Jose, California to Chicago O'Hare Intl Airport on time: American Airlines (100%), Qatar Airways (100%), United Airlines (99%).

  • What are the cheapest flights from San Jose, California to Chicago O'Hare Intl Airport?

    On average you can expect to pay $869 for a flight from San Jose, California to Chicago O'Hare Intl Airport. The cheapest flight overall is $148 while the most popular route, (San Jose - Chicago O'Hare Intl) is currently priced at $231.

  • Can I find deals for flights from San Jose to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on San Jose to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to O'Hare Intl.

  • Can I find deals for business class flights from San Jose to O'Hare Intl?

    Yes. Cheapflights offers flight deals from San Jose to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Jose, California to Chicago O'Hare Intl Airport?

    Currently, April is the cheapest month in which you can book a flight from San Jose, California to Chicago O'Hare Intl Airport (average of $123). Flying from San Jose, California to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $257). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Naperville
Hoffman Estates
Beloit
Delavan
Des Plaines
Elgin
Downers Grove
Elk Grove Village
Skokie
Oak Brook
South Holland
Libertyville
Oakbrook Terrace
Lake Geneva
Waukegan
Bridgeview
Kenosha

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Alternative routes for San Jose to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from San Jose to O'Hare Intl

Discover the top 7 airlines that operate flights from San Jose to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$244FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$125Average$239FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$315FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$410FlexibilityNo cancel feeOn-time71%
DeltaCheapest$208Average$407FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$297Average$521FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$362Average$496FlexibilityNo cancel feeOn-time63%

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