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Cheap flights from San Jose, California to Chicago from $83

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 4/21. 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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0 bags

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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
5:03 pm - 1:13 pm
SJC
-
ORD
18h 10m
1 stop
Alaska Airlines Logo
7:59 pm - 9:44 am
ORD
-
SJC
15h 45m
1 stop
$268Alaska Airlines
Fri, May 1 - Mon, May 4
Alaska Airlines Logo
10:21 am - 11:59 pm
SJC
-
ORD
11h 38m
2 stops
Alaska Airlines Logo
3:52 pm - 10:55 pm
ORD
-
SJC
9h 03m
1 stop
$269Alaska Airlines
Wed, May 6 - Fri, May 8
Alaska Airlines Logo
3:15 pm - 11:39 pm
SJC
-
ORD
6h 24m
1 stop
Alaska Airlines Logo
2:20 pm - 7:11 pm
ORD
-
SJC
6h 51m
1 stop
$270Alaska Airlines
Mon, Jul 20 - Sat, Jul 25
Delta Logo
9:37 am - 6:04 pm
SJC
-
ORD
6h 27m
1 stop
Delta Logo
7:15 am - 3:00 pm
ORD
-
SJC
9h 45m
1 stop
$271Delta
Thu, Apr 16 - Tue, Apr 21
Alaska Airlines Logo
2:35 pm - 11:59 pm
SJC
-
ORD
7h 24m
1 stop
Alaska Airlines Logo
4:10 pm - 10:10 pm
ORD
-
SJC
8h 00m
1 stop
$273Alaska Airlines
Mon, Apr 13 - Thu, Apr 16
Alaska Airlines Logo
8:39 pm - 2:21 pm
SJC
-
ORD
15h 42m
1 stop
Alaska Airlines Logo
4:10 pm - 10:10 pm
ORD
-
SJC
8h 00m
1 stop
$274Alaska Airlines
Tue, Apr 7 - Tue, Apr 21
Alaska Airlines Logo
7:11 am - 7:00 pm
SJC
-
ORD
9h 49m
1 stop
Alaska Airlines Logo
6:22 am - 11:24 am
ORD
-
SJC
7h 02m
1 stop
$275Alaska Airlines
Wed, Jun 17 - Sat, Jun 27
Delta Logo
1:40 pm - 9:50 pm
SJC
-
ORD
6h 10m
1 stop
Delta Logo
6:24 am - 5:02 pm
ORD
-
SJC
12h 38m
2 stops
$276Delta
Sat, May 16 - Tue, May 19
Multiple Airlines Logo
6:39 pm - 11:27 pm
SJC
-
ORD
26h 48m
1 stop
Multiple Airlines Logo
5:15 am - 7:27 pm
ORD
-
SJC
16h 12m
1 stop
$277Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
Frontier Logo
6:39 pm - 5:50 am
SJC
-
ORD
9h 11m
1 stop
Frontier Logo
7:21 pm - 7:27 pm
ORD
-
SJC
26h 06m
1 stop
$278Frontier
Fri, Apr 17 - Sun, Apr 19

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
Apr 17
SJC6:39 pmSan Jose
9h 11m
1 stop
ORD5:50 amChicago O'Hare Intl
Apr 19
ORD7:21 pmChicago O'Hare Intl
26h 06m
1 stop
SJC7:27 pmSan Jose
$278
Frontier
Jun 5
SJC12:57 pmSan Jose
15h 10m
1 stop
ORD6:07 amChicago O'Hare Intl
Jun 11
ORD9:07 pmChicago O'Hare Intl
16h 55m
1 stop
SJC12:02 pmSan Jose
$301
Frontier
Mar 29
SJC8:20 pmSan Jose
7h 48m
1 stop
ORD6:08 amChicago O'Hare Intl
Apr 3
ORD12:50 pmChicago O'Hare Intl
8h 47m
1 stop
SJC7:37 pmSan Jose
$405

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
Apr 16
SJC9:37 amSan Jose
6h 27m
1 stop
ORD6:04 pmChicago O'Hare Intl
Apr 21
ORD7:15 amChicago O'Hare Intl
9h 45m
1 stop
SJC3:00 pmSan Jose
$271
Delta
May 16
SJC5:50 amSan Jose
12h 24m
2 stops
ORD8:14 pmChicago O'Hare Intl
May 20
ORD2:00 pmChicago O'Hare Intl
9h 40m
1 stop
SJC9:40 pmSan Jose
$276
Delta
Jun 1
SJC8:05 pmSan Jose
10h 31m
2 stops
ORD8:36 amChicago O'Hare Intl
Jun 3
ORD8:42 amChicago O'Hare Intl
8h 50m
2 stops
SJC3:32 pmSan Jose
$281

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 March 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 5/1

5:03 pm-1:13 pm

1 stop18h 10m

Chicago O'Hare Intl

Mon 5/4

7:59 pm-9:44 am

1 stop15h 45m

$268

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 5/6

10:21 am-11:59 pm

2 stops11h 38m

Chicago O'Hare Intl

Fri 5/8

3:52 pm-10:55 pm

1 stop9h 03m

$269
Quickest round-trip

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 7/20

3:15 pm-11:39 pm

1 stop6h 24m

Chicago O'Hare Intl

Sat 7/25

2:20 pm-7:11 pm

1 stop6h 51m

$270

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 4/16

9:37 am-6:04 pm

1 stop6h 27m

Chicago O'Hare Intl

Tue 4/21

7:15 am-3:00 pm

1 stop9h 45m

$271

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 4/13

2:35 pm-11:59 pm

1 stop7h 24m

Chicago O'Hare Intl

Thu 4/16

4:10 pm-10:10 pm

1 stop8h 00m

$273

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 4/7

8:39 pm-2:21 pm

1 stop15h 42m

Chicago O'Hare Intl

Tue 4/21

4:10 pm-10:10 pm

1 stop8h 00m

$274

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 6/17

7:11 am-7:00 pm

1 stop9h 49m

Chicago O'Hare Intl

Sat 6/27

6:22 am-11:24 am

1 stop7h 02m

$275

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 5/16

1:40 pm-9:50 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 5/19

6:24 am-5:02 pm

2 stops12h 38m

$276

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 4/20

6:39 pm-11:27 pm

1 stop26h 48m

Chicago O'Hare Intl

Mon 4/27

5:15 am-7:27 pm

1 stop16h 12m

$277

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 4/17

6:39 pm-5:50 am

1 stop9h 11m

Chicago O'Hare Intl

Sun 4/19

7:21 pm-7:27 pm

1 stop26h 06m

$278

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 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 $434. 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 $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 morning is the least expensive time of day to depart. momondo users have found prices as low as $508 when looking at flights departing in the morning. Try not to purchase tickets in the evening because they tend to be around $622. 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 $460 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 $308 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 March 2026, prices for San Jose, California to Chicago O'Hare Intl Airport flights are approximately 16% cheaper 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

$223

Fastest flight time

4h 19m

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 $223. 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 $392.
The fastest flight from San Jose, California to Chicago O'Hare Intl Airport takes 4h 19m
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 19m, 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
6.3
8,532 reviews
Search Spirit Airlines flights
FrontierPriceFrom $131Free CancellationRating
5.7
3,019 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $177Free CancellationRating
7.9
12,093 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $200Free CancellationRating
7.1
11,486 reviews
Search American Airlines flights
DeltaPriceFrom $208Free CancellationRating
7.9
8,314 reviews
Search Delta flights
United AirlinesPriceFrom $291Free CancellationRating
7.4
9,455 reviews
Search United Airlines flights
SouthwestPriceFrom $362Free CancellationRating
8.0
4,324 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 5 times per week, with 9,455 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 $291 (round-trip), much lower than the average airfare cost of $511 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
Schaumburg
South Haven
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Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
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Janesville
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Elgin
Tinley Park
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.

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