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Cheap flights from San Jose, California to Chicago from $124

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 12/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from San Jose, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
6:03 pm - 6:21 amSJC-ORD
10h 18m2 stops
Alaska Airlines Logo
8:55 am - 2:32 pmORD-SJC
7h 37m1 stop
$301Alaska Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 17
Multiple Airlines Logo
7:48 pm - 6:05 amSJC-ORD
8h 17m1 stop
Multiple Airlines Logo
10:07 pm - 6:14 pmORD-SJC
22h 07m2 stops
$302Multiple Airlines
Find Deal
Sun, Dec 21 - Sun, Jan 11
Delta Logo
7:15 am - 5:15 pmSJC-ORD
8h 00m1 stop
Delta Logo
7:50 am - 3:54 pmORD-SJC
10h 04m1 stop
$303Delta
Find Deal
Fri, Dec 5 - Mon, Dec 15
Delta Logo
7:15 am - 9:52 pmSJC-ORD
12h 37m2 stops
Delta Logo
7:30 am - 4:20 pmORD-SJC
10h 50m2 stops
$304Delta
Find Deal
Fri, Jan 30 - Mon, Feb 2
Alaska Airlines Logo
12:35 pm - 11:50 pmSJC-ORD
9h 15m1 stop
Alaska Airlines Logo
10:00 am - 10:59 pmORD-SJC
14h 59m2 stops
$306Alaska Airlines
Find Deal
Thu, Dec 4 - Tue, Dec 16
Hawaiian Airlines Logo
8:00 pm - 8:02 pmSJC-ORD
22h 02m1 stop
Hawaiian Airlines Logo
8:39 am - 2:16 pmORD-SJC
7h 37m1 stop
$307Hawaiian Airlines
Find Deal
Tue, Dec 30 - Tue, Jan 6
Delta Logo
7:15 am - 9:40 pmSJC-ORD
12h 25m2 stops
Delta Logo
7:50 am - 3:54 pmORD-SJC
10h 04m1 stop
$308Delta
Find Deal
Sat, Dec 6 - Thu, Dec 18
Multiple Airlines Logo
4:40 pm - 6:25 amSJC-ORD
35h 45m2 stops
Multiple Airlines Logo
9:06 pm - 2:32 pmORD-SJC
19h 26m1 stop
$309Multiple Airlines
Find Deal
Mon, Dec 1 - Wed, Dec 17
Alaska Airlines Logo
7:00 am - 11:50 pmSJC-ORD
14h 50m1 stop
Alaska Airlines Logo
8:58 pm - 11:16 amORD-SJC
16h 18m1 stop
$312Alaska Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 20
Alaska Airlines Logo
7:00 am - 11:59 pmSJC-ORD
14h 59m1 stop
Alaska Airlines Logo
8:58 pm - 11:11 amORD-SJC
16h 13m1 stop
$313Alaska Airlines
Find Deal
Thu, Dec 18 - Mon, Jan 5

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
Dec 6
SJC9:49 amSan Jose
12h 10m
2 stops
ORD11:59 pmChicago O'Hare Intl
Dec 16
ORD8:55 amChicago O'Hare Intl
11h 47m
1 stop
SJC6:42 pmSan Jose
$301
Find similar
Alaska Airlines
Dec 13
SJC3:09 pmSan Jose
6h 41m
1 stop
ORD11:50 pmChicago O'Hare Intl
Dec 15
ORD8:55 amChicago O'Hare Intl
7h 37m
1 stop
SJC2:32 pmSan Jose
$309
Find similar
Alaska Airlines
Dec 17
SJC12:35 pmSan Jose
9h 15m
1 stop
ORD11:50 pmChicago O'Hare Intl
Dec 24
ORD6:00 amChicago O'Hare Intl
19h 59m
1 stop
SJC11:59 pmSan Jose
$320
Find similar

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

Our best Delta deals on San Jose, California to Chicago O'Hare Intl Airport flight tickets
Delta
Feb 20
SJC7:15 amSan Jose
12h 37m
2 stops
ORD9:52 pmChicago O'Hare Intl
Feb 24
ORD7:40 amChicago O'Hare Intl
11h 14m
2 stops
SJC4:54 pmSan Jose
$304
Find similar
Delta
Dec 6
SJC7:15 amSan Jose
12h 25m
2 stops
ORD9:40 pmChicago O'Hare Intl
Dec 18
ORD7:50 amChicago O'Hare Intl
10h 04m
1 stop
SJC3:54 pmSan Jose
$308
Find similar
Delta
Dec 6
SJC4:35 pmSan Jose
14h 05m
2 stops
ORD8:40 amChicago O'Hare Intl
Dec 14
ORD7:50 amChicago O'Hare Intl
13h 28m
2 stops
SJC7:18 pmSan Jose
$314
Find similar

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 November 17, 2025.
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

Sat 12/6

6:03 pm-6:21 am

2 stops10h 18m

Chicago O'Hare Intl

Wed 12/17

8:55 am-2:32 pm

1 stop7h 37m

$301

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sun 12/21

7:48 pm-6:05 am

1 stop8h 17m

Chicago O'Hare Intl

Sun 1/11

10:07 pm-6:14 pm

2 stops22h 07m

$302

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 12/5

7:15 am-5:15 pm

1 stop8h 00m

Chicago O'Hare Intl

Mon 12/15

7:50 am-3:54 pm

1 stop10h 04m

$303

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 1/30

7:15 am-9:52 pm

2 stops12h 37m

Chicago O'Hare Intl

Mon 2/2

7:30 am-4:20 pm

2 stops10h 50m

$304

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 12/4

12:35 pm-11:50 pm

1 stop9h 15m

Chicago O'Hare Intl

Tue 12/16

10:00 am-10:59 pm

2 stops14h 59m

$306

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 12/30

8:00 pm-8:02 pm

1 stop22h 02m

Chicago O'Hare Intl

Tue 1/6

8:39 am-2:16 pm

1 stop7h 37m

$307

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 12/6

7:15 am-9:40 pm

2 stops12h 25m

Chicago O'Hare Intl

Thu 12/18

7:50 am-3:54 pm

1 stop10h 04m

$308

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 12/1

4:40 pm-6:25 am

2 stops35h 45m

Chicago O'Hare Intl

Wed 12/17

9:06 pm-2:32 pm

1 stop19h 26m

$309

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 12/6

7:00 am-11:50 pm

1 stop14h 50m

Chicago O'Hare Intl

Sat 12/20

8:58 pm-11:16 am

1 stop16h 18m

$312

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 12/18

7:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Mon 1/5

8:58 pm-11:11 am

1 stop16h 13m

$313

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between San Jose, California and Chicago O'Hare Intl Airport?

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 $411.

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 Tuesday when prices can be found for as low as $474. 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 $582.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $298 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $660. 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 $468 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 November 2025, prices for San Jose, California to Chicago O'Hare Intl Airport flights are approximately 55% 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

$224

Fastest flight time

4h 13m

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 $224. 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 $382.
The fastest flight from San Jose, California to Chicago O'Hare Intl Airport takes 4h 13m
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 6h 10m, 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 $98Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $125Free CancellationRating
6.3
8,144 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $170Free CancellationRating
8.0
11,309 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $200Free CancellationRating
7.2
11,046 reviews
Search American Airlines flights
DeltaPriceFrom $256Free CancellationRating
7.9
8,006 reviews
Search Delta flights
United AirlinesPriceFrom $300Free CancellationRating
7.4
9,014 reviews
Search United Airlines flights
SouthwestPriceFrom $370Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

  • United Airlines Flights From San Jose, California to Chicago O'Hare Intl Airport

    United Airlines flies from San Jose, California to Chicago O'Hare Intl Airport around 4 times per week, with 9,014 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from San Jose, California to Chicago O'Hare Intl Airport in the last 72 hours was $300 (round-trip), much lower than the average airfare cost of $520 for United Airlines flights on this route.

Traveling to a place near Chicago?

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

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.

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