Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San Jose, California to Chicago from $62

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Jose, California to Chicago departing on 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from San Jose, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:42 pm - 6:08 am
SJC
-
ORD
8h 26m
1 stop
Frontier Logo
4:28 pm - 6:07 pm
ORD
-
SJC
27h 39m
2 stops
$189Frontier
Mon, Mar 23 - Wed, Mar 25
Multiple Airlines Logo
10:34 am - 9:03 pm
SJC
-
ORD
8h 29m
1 stop
Multiple Airlines Logo
8:20 am - 8:40 am
ORD
-
SJC
26h 20m
2 stops
$201Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
7:02 pm - 4:49 am
SJC
-
ORD
7h 47m
1 stop
Frontier Logo
8:55 pm - 6:07 pm
ORD
-
SJC
23h 12m
1 stop
$214Frontier
Mon, Mar 9 - Wed, Mar 11
Frontier Logo
7:42 pm - 6:08 am
SJC
-
ORD
8h 26m
1 stop
Frontier Logo
8:55 pm - 6:07 pm
ORD
-
SJC
23h 12m
1 stop
$229Frontier
Mon, Mar 23 - Wed, Mar 25
Frontier Logo
8:32 pm - 5:39 am
SJC
-
ORD
7h 07m
1 stop
Frontier Logo
12:50 pm - 7:37 pm
ORD
-
SJC
8h 47m
1 stop
$230Frontier
Mon, Apr 6 - Mon, Apr 13
Multiple Airlines Logo
10:34 am - 6:08 am
SJC
-
ORD
17h 34m
1 stop
Multiple Airlines Logo
3:07 pm - 10:56 pm
ORD
-
SJC
9h 49m
1 stop
$233Multiple Airlines
Thu, Mar 5 - Tue, Mar 10
Frontier Logo
8:32 pm - 5:39 am
SJC
-
ORD
7h 07m
1 stop
Frontier Logo
12:50 pm - 7:37 pm
ORD
-
SJC
8h 47m
1 stop
$235Frontier
Fri, Apr 10 - Mon, Apr 13
Alaska Airlines Logo
7:00 am - 11:59 pm
SJC
-
ORD
14h 59m
1 stop
Alaska Airlines Logo
3:07 pm - 10:56 pm
ORD
-
SJC
9h 49m
1 stop
$237Alaska Airlines
Wed, Mar 4 - Tue, Mar 10
Alaska Airlines Logo
7:00 am - 6:46 pm
SJC
-
ORD
9h 46m
1 stop
Alaska Airlines Logo
3:43 pm - 11:37 pm
ORD
-
SJC
9h 54m
1 stop
$239Alaska Airlines
Sat, May 16 - Tue, May 19
Frontier Logo
10:34 am - 9:03 pm
SJC
-
ORD
8h 29m
1 stop
Frontier Logo
6:34 pm - 7:55 am
ORD
-
SJC
15h 21m
1 stop
$241Frontier
Thu, Feb 19 - Thu, Feb 26

Alaska Airlines flights from San Jose, California to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on San Jose, California to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Mar 4
SJC7:00 amSan Jose
14h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Mar 10
ORD3:07 pmChicago O'Hare Intl
9h 49m
1 stop
SJC10:56 pmSan Jose
$237
Alaska Airlines
May 16
SJC7:00 amSan Jose
9h 46m
1 stop
ORD6:46 pmChicago O'Hare Intl
May 19
ORD3:43 pmChicago O'Hare Intl
9h 54m
1 stop
SJC11:37 pmSan Jose
$239
Alaska Airlines
Mar 11
SJC2:36 pmSan Jose
7h 20m
1 stop
ORD11:56 pmChicago O'Hare Intl
Mar 17
ORD3:07 pmChicago O'Hare Intl
9h 49m
1 stop
SJC10:56 pmSan Jose
$247

Frontier flights from San Jose, California to Chicago O'Hare Intl Airport

Our best Frontier deals on San Jose, California to Chicago O'Hare Intl Airport flight tickets
Frontier
Mar 23
SJC7:42 pmSan Jose
8h 26m
1 stop
ORD6:08 amChicago O'Hare Intl
Mar 25
ORD4:28 pmChicago O'Hare Intl
27h 39m
2 stops
SJC6:07 pmSan Jose
$189
Frontier
Mar 9
SJC7:02 pmSan Jose
7h 47m
1 stop
ORD4:49 amChicago O'Hare Intl
Mar 11
ORD8:55 pmChicago O'Hare Intl
23h 12m
1 stop
SJC6:07 pmSan Jose
$214
Frontier
Mar 23
SJC7:42 pmSan Jose
8h 26m
1 stop
ORD6:08 amChicago O'Hare Intl
Mar 25
ORD8:55 pmChicago O'Hare Intl
23h 12m
1 stop
SJC6:07 pmSan Jose
$229

momondo Fare Finder

 
Customize your flight search to find flights from San Jose, California to Chicago O'Hare Intl Airport 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, momondo users made 832,500 searches. Data last updated January 22, 2026.
Use the filters below to find and compare flights from San Jose, California to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 3/23

7:42 pm-6:08 am

1 stop8h 26m

Chicago O'Hare Intl

Wed 3/25

4:28 pm-6:07 pm

2 stops27h 39m

$189

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 2/19

10:34 am-9:03 pm

1 stop8h 29m

Chicago O'Hare Intl

Sun 2/22

8:20 am-8:40 am

2 stops26h 20m

$201

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 3/9

7:02 pm-4:49 am

1 stop7h 47m

Chicago O'Hare Intl

Wed 3/11

8:55 pm-6:07 pm

1 stop23h 12m

$214

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 3/23

7:42 pm-6:08 am

1 stop8h 26m

Chicago O'Hare Intl

Wed 3/25

8:55 pm-6:07 pm

1 stop23h 12m

$229

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 4/6

8:32 pm-5:39 am

1 stop7h 07m

Chicago O'Hare Intl

Mon 4/13

12:50 pm-7:37 pm

1 stop8h 47m

$230

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 3/5

10:34 am-6:08 am

1 stop17h 34m

Chicago O'Hare Intl

Tue 3/10

3:07 pm-10:56 pm

1 stop9h 49m

$233

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 4/10

8:32 pm-5:39 am

1 stop7h 07m

Chicago O'Hare Intl

Mon 4/13

12:50 pm-7:37 pm

1 stop8h 47m

$235

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 3/4

7:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Tue 3/10

3:07 pm-10:56 pm

1 stop9h 49m

$237

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 5/16

7:00 am-6:46 pm

1 stop9h 46m

Chicago O'Hare Intl

Tue 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$239

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 2/19

10:34 am-9:03 pm

1 stop8h 29m

Chicago O'Hare Intl

Thu 2/26

6:34 pm-7:55 am

1 stop15h 21m

$241

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from San Jose, California to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Jose, California averaging around $398.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $466. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from San Jose, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $577.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from San Jose, California in the morning is the least expensive time of day to depart. momondo users have found prices as low as $507 when looking at flights departing in the morning. Try not to purchase tickets in the evening because they tend to be around $655. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest San Jose to Chicago O'Hare Intl flight route?

Fly from San Jose to Chicago O'Hare Intl for the best San Jose - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San Jose, California when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $453 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San Jose, California for as low as $262 on momondo.

What cabin class options are available on San Jose to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on San Jose to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San Jose, California to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between San Jose, California to Chicago O'Hare Intl Airport.

How have San Jose, California to Chicago O'Hare Intl Airport flight prices changed over time?

As of January 2026, prices for San Jose, California to Chicago O'Hare Intl Airport flights are approximately 41% more expensive when compared to flights at the same time last year.

When to book flights from San Jose, California to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Jose, California to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Jose, California to Chicago O'Hare Intl Airport (SJC to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Jose, California to Chicago O'Hare Intl Airport

Best Price Found

$239

Fastest flight time

4h 18m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from San Jose, California in the past 72 hours is $239. The best round-trip flight deal from San Jose, California to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $469.
The fastest flight from San Jose, California to Chicago O'Hare Intl Airport takes 4h 18m
Direct flights go from San Jose, California to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is San Jose to Chicago O'Hare Intl by plane?

    The straight-line distance from San Jose to Chicago O'Hare Intl is 1822.3 mi. Flights usually cover this in 4h 18m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from San Jose Airport to Chicago O'Hare Intl Airport?

    Prices for flights from San Jose Airport to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from San Jose Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from San Jose Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Jose Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from San Jose, California to Chicago O'Hare Intl Airport?

  • What is the most popular airline from San Jose, California to Chicago O'Hare Intl Airport?

Best airlines flying from San Jose, California to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from San Jose, California to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $62Free CancellationRating
5.7
3,057 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $125Free CancellationRating
6.3
8,365 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $170Free CancellationRating
8.0
11,775 reviews
Search Alaska Airlines flights
DeltaPriceFrom $208Free CancellationRating
7.9
8,087 reviews
Search Delta flights
American AirlinesPriceFrom $253Free CancellationRating
7.2
11,173 reviews
Search American Airlines flights
United AirlinesPriceFrom $297Free CancellationRating
7.4
9,192 reviews
Search United Airlines flights
SouthwestPriceFrom $362Free CancellationRating
8.0
4,267 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from San Jose to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San Jose to Chicago for you.

Can I find flights from San Jose to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from San Jose with this policy.

How can momondo help me find flights from San Jose to Chicago?

momondo helps you find the best flight between San Jose and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from San Jose to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from San Jose and alert you when they change.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 2/21
Sat 2/28
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago