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$69+ Cheap flights from San Jose, CA (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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
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 November 21, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$252
(Expedia)

One-way from

$69
(Priceline)

Popular in

June

Cheapest in

January

Average price

$411

Good round-trip deal

$382 or less

Good one-way deal

$193 or less
Provider with most accurate pricing for San Jose-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Jose-Chicago (CHI) flights.
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From San Jose to Illinois
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One-way flight from San Jose to Illinois
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 21, 2025.

This Delta deal was found by Cheapflights users on 11/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:15 amSJC - STL
2 stops9h 55mDelta
Tue 12/166:00 amSTL - SJC
2 stops11h 54mDelta
Deal found 11/18$254
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:40 amSJC - STL
2 stops11h 21mDelta
Wed 12/176:15 amSTL - SJC
2 stops11h 39mDelta
Deal found 11/21$274
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:40 amSJC - ORD
1 stop10h 19mDelta
Tue 12/168:50 amORD - SJC
2 stops9h 04mDelta
Deal found 11/20$308
This Delta deal was found by Cheapflights users on 11/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:00 amSJC - ORD
2 stops14h 59mDelta
Wed 12/246:35 amORD - SJC
2 stops15h 21mDelta
Deal found 11/18$310
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/127:45 pmSJC - MDW
2 stops11h 04mDelta
Tue 12/169:59 amMDW - SJC
2 stops14h 13mDelta
Deal found 11/20$314
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:45 pmSJC - ORD
2 stops12h 15mDelta
Tue 12/166:00 amORD - SJC
2 stops11h 54mDelta
Deal found 11/20$314
This American Airlines deal was found by Cheapflights users on 11/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/162:37 pmSJC - STL
1 stop6h 10mAmerican Airlines
Wed 12/177:38 amSTL - SJC
1 stop6h 53mAmerican Airlines
Deal found 11/21$318
This Alaska Airlines deal was found by Cheapflights users on 11/19. 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 12/1612:35 pmSJC - ORD
1 stop9h 15mAlaska Airlines
Wed 12/311:09 pmORD - SJC
1 stop22h 13mAlaska Airlines
Deal found 11/19$322
This Delta deal was found by Cheapflights users on 11/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1012:55 pmSJC - MDW
1 stop8h 52mDelta
Wed 12/171:14 pmMDW - SJC
2 stops10h 58mDelta
Deal found 11/18$323
This KAYAK deal was found by Cheapflights users on 11/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/123:09 pmSJC - ORD
1 stop6h 41mAlaska Airlines
Thu 12/188:39 amORD - SJC
1 stop7h 37mAlaska Airlines
Deal found 11/19$323
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:15 amSJC - ORD
1 stop14h 44mDelta
Thu 12/254:01 pmORD - SJC
1 stop7h 03mDelta
Deal found 11/19$328
This Alaska Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 12/116:18 amSJC - STL
1 stop15h 41mAlaska Airlines
Tue 12/167:00 amSTL - SJC
1 stop15h 00mAlaska Airlines
Deal found 11/18$331

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 November 21, 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 JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Thu 1/29

12:34 pm-9:06 pm

1 stop6h 32m

Lambert-St Louis

Tue 2/3

2:50 pm-5:08 pm

1 stop28h 18m

$252

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Thu 1/29

11:40 am-11:25 pm

2 stops9h 45m

Lambert-St Louis

Tue 2/3

6:40 am-5:40 pm

2 stops13h 00m

$254

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Thu 12/11

7:15 am-7:10 pm

2 stops9h 55m

Lambert-St Louis

Tue 12/16

6:00 am-3:54 pm

2 stops11h 54m

$254

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Sun 1/18

11:14 am-9:14 pm

1 stop8h 00m

Lambert-St Louis

Thu 1/22

10:01 pm-8:40 am

1 stop12h 39m

$268

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Mon 12/15

7:15 am-7:10 pm

2 stops9h 55m

Lambert-St Louis

Wed 12/17

12:49 pm-8:36 pm

1 stop9h 47m

$286

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Wed 1/14

11:40 am-11:25 pm

2 stops9h 45m

Lambert-St Louis

Wed 1/21

6:40 am-12:26 pm

1 stop7h 46m

$286

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Wed 1/14

9:05 am-1:54 pm

1 stop26h 49m

Lambert-St Louis

Wed 1/21

2:50 pm-9:48 am

1 stop20h 58m

$312

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 12/12

7:45 pm-8:49 am

2 stops11h 04m

Chicago Midway

Tue 12/16

9:59 am-10:12 pm

2 stops14h 13m

$314

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 1/8

11:00 am-11:50 pm

1 stop10h 50m

Chicago O'Hare Intl

Sun 1/11

3:44 pm-2:21 pm

1 stop24h 37m

$317

San JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Tue 12/16

2:37 pm-10:47 pm

1 stop6h 10m

Lambert-St Louis

Wed 12/17

7:38 am-12:31 pm

1 stop6h 53m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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, California to Illinois?

Currently, December is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $110). Flying from San Jose, California to Illinois in March is currently the most expensive (average of $194). 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 November 21, 2025.

It’s optimal to fly from San Jose, California to Illinois in the afternoon. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from San Jose, California to Illinois?

Use this chart to determine the cheapest time to fly round-trip from San Jose to Illinois. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their San Jose, California to Illinois flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 21, 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
4,252 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
9,035 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
11,048 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
8,159 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
3,102 reviews
Southwest
8.0
Very good
4,252 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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, California to Illinois?

    Departing from San Jose, California to Illinois will take you 8h. There are 1710 mi between San Jose, California and Illinois. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The most popular route from San Jose, California 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, California to Illinois?

    While on average a flight from San Jose, California to Illinois is generally $447, our data shows the cheapest flight currently is $171. When looking at the most popular route, (San Jose - Chicago O'Hare Intl), you can expect to pay $204 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, California to Illinois?

    Currently, December is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $110). Flying from San Jose, California to Illinois in March is currently the most expensive (average of $194). 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

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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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$260FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$125Average$260FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$315FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$588FlexibilityNo cancel feeOn-time71%
DeltaCheapest$256Average$385FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$287Average$457FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$331Average$505FlexibilityNo cancel feeOn-time63%

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