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$89+ Cheap flights from San Jose (SJC) to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Oct 12 — Oct 191
Sun 10/12
Sun 10/19
1 adult, Economy
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Cheap flight deals from San Jose to Illinois

Keep the following information in mind while searching for San Jose to Illinois flight deals. Data was last updated September 12, 2025.

Round-trip from

$204
(Southwest)

One-way from

$89
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$394

Good round-trip deal

$301 or less

Good one-way deal

$169 or less
From San Jose to Illinois
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One-way flight from San Jose to Illinois
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Highest demand for flights based on searches. 9% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from San Jose to Illinois.
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Price to beat on a one-way flight from San Jose to Illinois.
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Find flight deals from San Jose to Illinois

Cheapest flights from San Jose to Illinois
Explore the most affordable flight options available from San Jose to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2025.

This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/188:40 amSJC - STL
1 stop7h 50mSouthwest
Wed 11/191:45 pmSTL - SJC
1 stop6h 15mSouthwest
Deal found 9/10$204
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:45 amSJC - ORD
1 stop9h 10mUnited Airlines
Thu 10/307:35 pmORD - SJC
Nonstop4h 53mUnited Airlines
Deal found 9/11$207
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:35 amSJC - ORD
1 stop8h 24mMultiple Airlines
Fri 10/39:54 pmORD - SJC
1 stop14h 51mMultiple Airlines
Deal found 9/12$208
This Orbitz deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:25 pmSJC - ORD
1 stop9h 34mMultiple Airlines
Mon 9/299:00 amORD - SJC
1 stop13h 00mMultiple Airlines
Deal found 9/12$210
This Frontier deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:25 pmSJC - ORD
1 stop9h 34mFrontier
Mon 9/296:00 amORD - SJC
1 stop7h 30mFrontier
Deal found 9/12$211
This Alaska Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/283:00 pmSJC - ORD
1 stop6h 59mAlaska Airlines
Sat 11/152:54 pmORD - SJC
1 stop9h 43mAlaska Airlines
Deal found 9/12$212
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:00 amSJC - MDW
1 stop7h 00mSouthwest
Sun 11/97:50 amMDW - SJC
Nonstop4h 45mSouthwest
Deal found 9/11$213
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/111:40 amSJC - ORD
1 stop22h 11mMultiple Airlines
Mon 10/66:10 amORD - SJC
1 stop7h 20mMultiple Airlines
Deal found 9/12$213
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/84:30 pmSJC - STL
1 stop5h 40mSouthwest
Sat 10/111:55 pmSTL - SJC
1 stop6h 45mSouthwest
Deal found 9/12$214
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:35 amSJC - ORD
1 stop12h 57mMultiple Airlines
Tue 9/306:44 pmORD - SJC
2 stops18h 01mMultiple Airlines
Deal found 9/11$214
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:20 amSJC - MDW
1 stop6h 55mSouthwest
Sat 11/14:10 pmMDW - SJC
Nonstop4h 30mSouthwest
Deal found 9/10$215
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/294:16 pmSJC - ORD
2 stops16h 24mMultiple Airlines
Thu 10/210:42 amORD - SJC
1 stop26h 48mMultiple Airlines
Deal found 9/11$215

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Illinois 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, Cheapflights users made 2,558,603 searches. Data last updated September 12, 2025.
Use the filters below to find and compare flights from San Jose to Illinois that are best for you.

Fly from

San Jose

Fly to

Illinois

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 10/25

1:30 pm-11:59 pm

1 stop8h 29m

Chicago O'Hare Intl

Wed 10/29

9:20 am-2:23 pm

1 stop7h 03m

$212

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Wed 10/8

4:30 pm-12:10 am

1 stop5h 40m

Lambert-St Louis

Sat 10/11

1:55 pm-6:40 pm

1 stop6h 45m

$214

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 10/28

10:25 am-6:59 pm

1 stop6h 34m

Chicago O'Hare Intl

Wed 11/19

8:00 am-4:38 pm

2 stops10h 38m

$220

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 11/15

3:00 pm-11:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Wed 11/19

8:00 am-4:38 pm

2 stops10h 38m

$220

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Sun 10/19

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Sat 10/25

2:15 pm-6:50 pm

1 stop6h 35m

$226

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 10/27

7:47 pm-6:22 am

1 stop8h 35m

Chicago O'Hare Intl

Sat 11/15

2:54 pm-10:37 pm

1 stop9h 43m

$228

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 10/25

1:30 pm-11:59 pm

1 stop8h 29m

Chicago O'Hare Intl

Thu 10/30

9:20 am-2:23 pm

1 stop7h 03m

$228

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 10/18

1:30 pm-11:59 pm

1 stop8h 29m

Chicago O'Hare Intl

Tue 10/21

6:00 am-11:44 am

1 stop7h 44m

$228

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 11/13

11:51 am-9:40 pm

1 stop7h 49m

Chicago O'Hare Intl

Mon 11/17

3:25 pm-10:57 am

1 stop21h 32m

$231

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 10/30

12:38 pm-11:59 pm

1 stop9h 21m

Chicago O'Hare Intl

Tue 11/4

8:59 pm-12:01 pm

1 stop17h 02m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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Best time to book a flight from San Jose to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from San Jose with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Jose to Illinois

What is the cheapest month to book a flight from San Jose to Illinois?

Currently, August is the cheapest month in which you can book a flight from San Jose to Illinois (average of $245). Flying from San Jose to Illinois in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SJC to IL?

Find hourly flight availability from San Jose to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 12, 2025.

When flying from San Jose to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated September 12, 2025.
Read through reviews of airlines operating flights from San Jose to Illinois, such as Southwest, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,936 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,176 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Jose to Illinois?

    For a flight from San Jose to Illinois, you will be flying from San Jose. San Jose (SJC) is just 2.9 mi from the center of the city.

  • How long is the flight from San Jose to Illinois?

    Alaska Airlines, Southwest, and Delta can get you from San Jose to Illinois in just under 5h 40m. Your travel time can differ by up to 3h 35m. The distance from San Jose to Illinois is about 1710 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from San Jose to Illinois?

    The most popular route from San Jose to Illinois is San Jose - Chicago O'Hare Intl. You may also consider San Jose - Chicago Midway or San Jose - Lambert-St Louis.

  • What are the cheapest flights from San Jose to Illinois?

    While on average a flight from San Jose to Illinois is generally $460, our data shows the cheapest flight currently is $175. When looking at the most popular route, (San Jose - Chicago O'Hare Intl), you can expect to pay $173 for that flight.

  • Can I find deals for flights from San Jose to Illinois that include hotel bookings?

    Yes. In addition to deals on San Jose to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Illinois.

  • Can I find deals for business class flights from San Jose to Illinois?

    Yes. Cheapflights offers flight deals from San Jose to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Jose to Illinois?

    Currently, August is the cheapest month in which you can book a flight from San Jose to Illinois (average of $245). Flying from San Jose to Illinois in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for San Jose to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from San Jose to Illinois

Discover the top 7 airlines that operate flights from San Jose to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$232FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$155Average$217FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$212Average$491FlexibilityNo cancel feeOn-time69%
DeltaCheapest$236Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$253Average$568FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$331Average$498FlexibilityNo cancel feeOn-time63%

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