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Cheap flights from San Jose, California to Chicago from $144

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 7/20. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from San Jose, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:29 am - 7:21 pm
SJC
-
ORD
9h 52m
1 stop
Multiple Airlines Logo
9:07 pm - 12:02 pm
ORD
-
SJC
16h 55m
1 stop
$332Multiple Airlines
Fri, Aug 21 - Sun, Aug 23
Multiple Airlines Logo
8:23 pm - 6:17 am
SJC
-
ORD
7h 54m
1 stop
Multiple Airlines Logo
7:59 pm - 9:26 am
ORD
-
SJC
15h 27m
1 stop
$333Multiple Airlines
Fri, Jul 10 - Mon, Jul 13
Alaska Airlines Logo
10:03 am - 6:57 pm
SJC
-
ORD
6h 54m
1 stop
Alaska Airlines Logo
6:20 am - 11:24 am
ORD
-
SJC
7h 04m
1 stop
$334Alaska Airlines
Wed, Jul 15 - Sat, Jul 18
Alaska Airlines Logo
8:29 am - 7:21 pm
SJC
-
ORD
8h 52m
1 stop
Alaska Airlines Logo
2:18 pm - 7:09 pm
ORD
-
SJC
6h 51m
1 stop
$335Alaska Airlines
Sun, Sep 27 - Mon, Sep 28
Frontier Logo
8:23 pm - 8:52 pm
SJC
-
ORD
22h 29m
2 stops
Frontier Logo
9:20 pm - 7:28 pm
ORD
-
SJC
24h 08m
1 stop
$337Frontier
Mon, Aug 10 - Wed, Aug 19
Frontier Logo
2:12 pm - 5:37 am
SJC
-
ORD
13h 25m
1 stop
Frontier Logo
7:15 am - 1:17 pm
ORD
-
SJC
8h 02m
1 stop
$338Frontier
Thu, Jul 16 - Fri, Jul 24
United Airlines Logo
2:32 pm - 12:44 am
SJC
-
ORD
8h 12m
1 stop
United Airlines Logo
7:58 pm - 10:43 pm
ORD
-
SJC
4h 45mnonstop
$339United Airlines
Wed, Jul 22 - Wed, Jul 29
Multiple Airlines Logo
2:12 pm - 5:37 am
SJC
-
ORD
13h 25m
1 stop
Multiple Airlines Logo
6:20 am - 11:24 am
ORD
-
SJC
7h 04m
1 stop
$340Multiple Airlines
Thu, Jul 9 - Sat, Jul 11
Frontier Logo
2:12 pm - 5:37 am
SJC
-
ORD
13h 25m
1 stop
Frontier Logo
7:15 am - 1:17 pm
ORD
-
SJC
8h 02m
1 stop
$343Frontier
Fri, Jul 10 - Mon, Jul 13
Frontier Logo
8:23 pm - 6:17 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
9:13 pm - 7:28 pm
ORD
-
SJC
24h 15m
1 stop
$344Frontier
Thu, Aug 6 - Sun, Aug 9

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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
Aug 10
SJC8:23 pmSan Jose
22h 29m
2 stops
ORD8:52 pmChicago O'Hare Intl
Aug 19
ORD9:20 pmChicago O'Hare Intl
24h 08m
1 stop
SJC7:28 pmSan Jose
$337
Frontier
Jul 16
SJC2:12 pmSan Jose
13h 25m
1 stop
ORD5:37 amChicago O'Hare Intl
Jul 24
ORD7:15 amChicago O'Hare Intl
8h 02m
1 stop
SJC1:17 pmSan Jose
$338
Frontier
Jul 10
SJC2:12 pmSan Jose
13h 25m
1 stop
ORD5:37 amChicago O'Hare Intl
Jul 13
ORD7:15 amChicago O'Hare Intl
8h 02m
1 stop
SJC1:17 pmSan Jose
$343

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

Our best United Airlines deals on San Jose, California to Chicago O'Hare Intl Airport flight tickets
United Airlines
Jul 22
SJC2:32 pmSan Jose
8h 12m
1 stop
ORD12:44 amChicago O'Hare Intl
Jul 29
ORD7:58 pmChicago O'Hare Intl
4h 45m
SJC10:43 pmSan Jose
$339
United Airlines
Aug 26
SJC6:20 amSan Jose
4h 25m
ORD12:45 pmChicago O'Hare Intl
Aug 27
ORD9:00 amChicago O'Hare Intl
4h 46m
SJC11:46 amSan Jose
$346
United Airlines
Jul 22
SJC2:32 pmSan Jose
8h 12m
1 stop
ORD12:44 amChicago O'Hare Intl
Jul 28
ORD7:58 pmChicago O'Hare Intl
4h 45m
SJC10:43 pmSan Jose
$358

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 June 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

Cheapest round-trip

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 8/21

7:29 am-7:21 pm

1 stop9h 52m

Chicago O'Hare Intl

Sun 8/23

9:07 pm-12:02 pm

1 stop16h 55m

$332

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 7/10

8:23 pm-6:17 am

1 stop7h 54m

Chicago O'Hare Intl

Mon 7/13

7:59 pm-9:26 am

1 stop15h 27m

$333

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 7/15

10:03 am-6:57 pm

1 stop6h 54m

Chicago O'Hare Intl

Sat 7/18

6:20 am-11:24 am

1 stop7h 04m

$334

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sun 9/27

8:29 am-7:21 pm

1 stop8h 52m

Chicago O'Hare Intl

Mon 9/28

2:18 pm-7:09 pm

1 stop6h 51m

$335

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 8/10

8:23 pm-8:52 pm

2 stops22h 29m

Chicago O'Hare Intl

Wed 8/19

9:20 pm-7:28 pm

1 stop24h 08m

$337

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 7/16

2:12 pm-5:37 am

1 stop13h 25m

Chicago O'Hare Intl

Fri 7/24

7:15 am-1:17 pm

1 stop8h 02m

$338
Quickest round-trip

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 7/22

2:32 pm-12:44 am

1 stop8h 12m

Chicago O'Hare Intl

Wed 7/29

7:58 pm-10:43 pm

Nonstop4h 45m

$339

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 7/9

2:12 pm-5:37 am

1 stop13h 25m

Chicago O'Hare Intl

Sat 7/11

6:20 am-11:24 am

1 stop7h 04m

$340

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 7/10

2:12 pm-5:37 am

1 stop13h 25m

Chicago O'Hare Intl

Mon 7/13

7:15 am-1:17 pm

1 stop8h 02m

$343

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 8/6

8:23 pm-6:17 am

1 stop7h 54m

Chicago O'Hare Intl

Sun 8/9

9:13 pm-7:28 pm

1 stop24h 15m

$344

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Jose, California averaging around $384.

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 $467. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $707.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $448 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $640. 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 from San Jose, California 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 $461 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 $229 on momondo.

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

There are 4 cabin classes available to choose from on San Jose, California to Chicago O'Hare Intl Airport 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?

You could potentially save up to 1% on your flight if you consider stops on a San Jose, California to Chicago O'Hare Intl Airport flight.

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

As of June 2026, prices for San Jose, California to Chicago O'Hare Intl Airport flights are approximately 100% 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

$280

Fastest flight time

4h 20m

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 $280. 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 $530.
The fastest flight from San Jose, California to Chicago O'Hare Intl Airport takes 4h 20m
Direct flights go from San Jose, California to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from San Jose, California to Chicago O'Hare Intl Airport

  • 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 20m, 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 $131Free CancellationRating
5.6
2,871 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $235Free CancellationRating
7.9
12,560 reviews
Search Alaska Airlines flights
DeltaPriceFrom $236Free CancellationRating
7.8
8,422 reviews
Search Delta flights
American AirlinesPriceFrom $253Free CancellationRating
7.1
11,737 reviews
Search American Airlines flights
SouthwestPriceFrom $270Free CancellationRating
7.9
4,243 reviews
Search Southwest flights
United AirlinesPriceFrom $294Free CancellationRating
7.4
9,874 reviews
Search United Airlines 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 5 times per week, with 9,874 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 $294 (round-trip), much lower than the average airfare cost of $564 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
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Gurnee
Rosemont
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Orland Park
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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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