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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 6/9. 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.
Frontier Logo
8:25 pm - 6:19 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
9:13 pm - 7:39 pm
ORD
-
SJC
24h 26m
1 stop
$280Frontier
Sat, Jul 4 - Wed, Jul 8
Delta Logo
11:29 am - 11:39 pm
SJC
-
ORD
10h 10m
1 stop
Delta Logo
8:36 am - 5:17 pm
ORD
-
SJC
10h 41m
2 stops
$282Delta
Wed, Jun 10 - Tue, Jun 16
Delta Logo
8:05 pm - 8:39 am
SJC
-
ORD
10h 34m
2 stops
Delta Logo
7:45 am - 5:12 pm
ORD
-
SJC
11h 27m
2 stops
$288Delta
Tue, Jun 2 - Wed, Aug 19
Multiple Airlines Logo
8:25 pm - 6:19 am
SJC
-
ORD
7h 54m
1 stop
Multiple Airlines Logo
7:59 pm - 9:26 am
ORD
-
SJC
15h 27m
1 stop
$289Multiple Airlines
Fri, Jul 3 - Tue, Jul 7
Frontier Logo
2:12 pm - 5:28 am
SJC
-
ORD
13h 16m
1 stop
Frontier Logo
7:15 am - 1:17 pm
ORD
-
SJC
8h 02m
1 stop
$290Frontier
Thu, Aug 6 - Mon, Aug 10
Alaska Airlines Logo
3:15 pm - 11:36 pm
SJC
-
ORD
6h 21m
1 stop
Alaska Airlines Logo
7:59 pm - 9:26 am
ORD
-
SJC
15h 27m
1 stop
$292Alaska Airlines
Tue, Jun 16 - Wed, Jun 24
Alaska Airlines Logo
2:00 pm - 11:55 pm
SJC
-
ORD
7h 55m
1 stop
Alaska Airlines Logo
7:00 am - 1:44 pm
ORD
-
SJC
8h 44m
1 stop
$295Alaska Airlines
Sat, Jun 6 - Wed, Aug 19
Frontier Logo
12:57 pm - 6:34 am
SJC
-
ORD
15h 37m
1 stop
Frontier Logo
8:46 pm - 11:59 am
ORD
-
SJC
17h 13m
1 stop
$299Frontier
Thu, May 28 - Sun, May 31
Frontier Logo
12:57 pm - 6:34 am
SJC
-
ORD
15h 37m
1 stop
Frontier Logo
8:46 pm - 11:59 am
ORD
-
SJC
17h 13m
1 stop
$302Frontier
Thu, May 28 - Sat, May 30
Multiple Airlines Logo
2:12 pm - 5:28 am
SJC
-
ORD
13h 16m
1 stop
Multiple Airlines Logo
7:59 pm - 9:26 am
ORD
-
SJC
15h 27m
1 stop
$304Multiple Airlines
Sat, Jul 18 - Tue, Jul 21

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
Jun 16
SJC3:15 pmSan Jose
6h 21m
1 stop
ORD11:36 pmChicago O'Hare Intl
Jun 24
ORD7:59 pmChicago O'Hare Intl
15h 27m
1 stop
SJC9:26 amSan Jose
$292
Alaska Airlines
Jun 6
SJC2:00 pmSan Jose
7h 55m
1 stop
ORD11:55 pmChicago O'Hare Intl
Aug 19
ORD7:00 amChicago O'Hare Intl
8h 44m
1 stop
SJC1:44 pmSan Jose
$295
Alaska Airlines
Jun 8
SJC2:00 pmSan Jose
7h 55m
1 stop
ORD11:55 pmChicago O'Hare Intl
Jun 16
ORD6:20 amChicago O'Hare Intl
7h 04m
1 stop
SJC11:24 amSan Jose
$305

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
Jun 10
SJC2:32 pmSan Jose
8h 12m
1 stop
ORD12:44 amChicago O'Hare Intl
Aug 19
ORD8:03 pmChicago O'Hare Intl
4h 47m
SJC10:50 pmSan Jose
$317
United Airlines
May 25
SJC8:45 amSan Jose
9h 20m
1 stop
ORD8:05 pmChicago O'Hare Intl
Jun 16
ORD7:50 pmChicago O'Hare Intl
4h 45m
SJC10:35 pmSan Jose
$524

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 May 14, 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

Sat 7/4

8:25 pm-6:19 am

1 stop7h 54m

Chicago O'Hare Intl

Wed 7/8

9:13 pm-7:39 pm

1 stop24h 26m

$280

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 6/10

11:29 am-11:39 pm

1 stop10h 10m

Chicago O'Hare Intl

Tue 6/16

8:36 am-5:17 pm

2 stops10h 41m

$282

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 6/2

8:05 pm-8:39 am

2 stops10h 34m

Chicago O'Hare Intl

Wed 8/19

7:45 am-5:12 pm

2 stops11h 27m

$288

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 7/3

8:25 pm-6:19 am

1 stop7h 54m

Chicago O'Hare Intl

Tue 7/7

7:59 pm-9:26 am

1 stop15h 27m

$289

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 8/6

2:12 pm-5:28 am

1 stop13h 16m

Chicago O'Hare Intl

Mon 8/10

7:15 am-1:17 pm

1 stop8h 02m

$290

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 6/16

3:15 pm-11:36 pm

1 stop6h 21m

Chicago O'Hare Intl

Wed 6/24

7:59 pm-9:26 am

1 stop15h 27m

$292
Quickest round-trip

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 6/6

2:00 pm-11:55 pm

1 stop7h 55m

Chicago O'Hare Intl

Wed 8/19

7:00 am-1:44 pm

1 stop8h 44m

$295

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 5/28

12:57 pm-6:34 am

1 stop15h 37m

Chicago O'Hare Intl

Sun 5/31

8:46 pm-11:59 am

1 stop17h 13m

$299

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 5/28

12:57 pm-6:34 am

1 stop15h 37m

Chicago O'Hare Intl

Sat 5/30

8:46 pm-11:59 am

1 stop17h 13m

$302

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 7/18

2:12 pm-5:28 am

1 stop13h 16m

Chicago O'Hare Intl

Tue 7/21

7:59 pm-9:26 am

1 stop15h 27m

$304

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 May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Jose, California averaging around $371.

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 $450. 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 $637.

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 $629. 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 $447 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 $215 on momondo.

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 May 2026, prices for San Jose, California to Chicago O'Hare Intl Airport flights are approximately 31% 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

$318

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 $318. 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 $448.
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
Spirit AirlinesPriceFrom $121Free CancellationRating
6.2
8,626 reviews
Search Spirit Airlines flights
FrontierPriceFrom $131Free CancellationRating
5.6
2,953 reviews
Search Frontier flights
American AirlinesPriceFrom $200Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $235Free CancellationRating
7.9
12,364 reviews
Search Alaska Airlines flights
DeltaPriceFrom $236Free CancellationRating
7.9
8,456 reviews
Search Delta flights
SouthwestPriceFrom $270Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
9,718 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 3 times per week, with 9,716 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 $278 (round-trip), much lower than the average airfare cost of $548 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
Rosemont
Naperville
Orland Park
New Buffalo
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Elgin
Tinley Park

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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